From: Sam W Date: Sat, 3 Nov 2018 22:14:46 +0000 (+0000) Subject: Created separate year 1 folder for year 1 Chemistry Lab reports. X-Git-Url: https://git.dalvak.com/public/?a=commitdiff_plain;h=1f38a9e3e01940157e93a9639a4d72a22c41f124;p=chemistry%2Funiversity-chemistry-lab-reports.git Created separate year 1 folder for year 1 Chemistry Lab reports. --- diff --git a/10a/10a.bcf b/10a/10a.bcf deleted file mode 100644 index 1402288..0000000 --- a/10a/10a.bcf +++ /dev/null @@ -1,1961 +0,0 @@ - - - - - - output_encoding - ascii - - - input_encoding - ascii - - - debug - 0 - - - mincrossrefs - 2 - - - minxrefs - 2 - - - sortcase - 1 - - - sortupper - 1 - - - - - - - alphaothers - + - - - labelalpha - 0 - - - labelnamespec - shortauthor - author - shorteditor - editor - translator - - - labeltitle - 0 - - - labeltitlespec - shorttitle - title - maintitle - - - labeltitleyear - 0 - - - labeldateparts - 0 - - - labeldatespec - date - year - eventdate - origdate - urldate - nodate - - - julian - 0 - - - gregorianstart - 1582-10-15 - - - maxalphanames - 3 - - - maxbibnames - 3 - - - maxcitenames - 3 - - - maxitems - 3 - - - 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title - - - sorttitle - title - - - sortyear - year - - - volume - 0 - - - - diff --git a/10a/10a.pdf b/10a/10a.pdf deleted file mode 100644 index b5cfb33..0000000 Binary files a/10a/10a.pdf and /dev/null differ diff --git a/10a/10a.run.xml b/10a/10a.run.xml deleted file mode 100644 index ce41222..0000000 --- a/10a/10a.run.xml +++ /dev/null @@ -1,87 +0,0 @@ - - - - - - - - - - - - - - - - - - - - - - - - -]> - - - latex - - 10a.bcf - - - 10a.bbl - - - blx-dm.def - blx-compat.def - biblatex.def - verbose.bbx - authortitle.bbx - standard.bbx - verbose.cbx - biblatex.cfg - british.lbx - english.lbx - - - - biber - - biber - 10a - - - 10a.bcf - - - 10a.bbl - - - 10a.bbl - - - 10a.bcf - - - ../bibliographies/reference.bib - - - diff --git a/10a/10a.tex b/10a/10a.tex deleted file mode 100644 index 6c9aa5a..0000000 --- a/10a/10a.tex +++ /dev/null @@ -1,228 +0,0 @@ -%Document Setup. -\documentclass{article} -\usepackage{graphicx} %Allows import of images. -%\usepackage{float} -\usepackage{floatrow} %Align tables and figures side-by-side. -\usepackage[extreme,mathspacing=normal,leading=normal]{savetrees} %Reduce whitespace. -\usepackage{siunitx} %SI Units formatting. -%\usepackage{vhistory} %Revision History. -\usepackage[version=4]{mhchem} %Chemical Equations. -\usepackage{amsmath} %Mathematical alignments. -\usepackage{amssymb} %Mathematical symbols e.g. therefore. -\usepackage[parfill]{parskip} %Blank lines between paragraphs. -\usepackage[autostyle]{csquotes} -\usepackage{array} %Table centering. -\usepackage[british]{babel} %British localisation. -\usepackage[backend=biber,style=verbose]{biblatex} %Bibliography. - -\numberwithin{equation}{subsection} %Number equations based on their subsection. -\bibliography{../bibliographies/reference} %Use Bibliography of reference books. -\floatsetup[table]{style=plaintop} %Put captions on top of tables. -\floatsetup[figure]{style=plain} %Ensure figure captions are below figures. - -%Document Headings. -\begin{document} -\title{Preparation of Aspirin (10A/PA)} -\author{Sam White} -\date{28/11/2017} -%\date{\vhCurrentDate\\\vhCurrentVersion} -\maketitle - -\section{Reaction Mechanism and Overall Equation} -\begin{figure}[H] - \centering - \includegraphics[width=0.85\textwidth]{Mechanism.png} - \caption{Mechanism for the reaction where ROH is salicylic acid.\label{fig:mechanism}} -\end{figure} -\begin{figure}[H] - \centering - \includegraphics[width=0.55\textwidth]{Equation.png} - \caption{Equation for the reaction.\label{fig:equation}} -\end{figure} - -\section{Summary of Method} -Salicylic acid (\SI{3.50}{\gram}), glacial acetic acid (\SI{5}{\centi\metre\cubed}) and acetic anhydride (\SI{3}{\centi\metre\cubed}) were boiled under reflux for 10 minutes. The product was precipitated by pouring into ice-cold water (\SI{75}{\centi\metre\cubed}) and then recrystallised in a water and glacial acetic acid mixture (1:1 by volume) using ice to cool the mixture. The crude product, recrystallised product, salicylic acid and a sample of pure aspirin (each in \SI{0.5}{\centi\metre\cubed} dichloromethane) were then analysed using thin-layer chromatography (TLC) with light petroleum ether and ethyl acetate (70:30 by volume) as the TLC solvent. The melting point of the purified product was then determined. - -\section{Results and Analysis} - -{\centering Mass of purified product: \SI{3.99}{\gram} - -} - -\subsection{Thin-Layer Chromatography (TLC) Results} \label{tlc-results} -\begin{table}[H] - \centering - \begin{tabular}{|c|c|c|} - \hline - Substance & $R_{f}$ Value of First Spot & $R_{f}$ Value of Second Spot \\ - \hline - Salicylic acid & 0.64 & N/A \\ - \hline - Pure aspirin & 0.32 (Diffuse) & N/A \\ - \hline - Crude product & 0.42 & 0.58 \\ - \hline - Purified product & 0.43 & N/A \\ - \hline - \end{tabular} -\end{table} -The crude product gave two distinct spots on the TLC plate indicating the presence of two substances in the sample. The $R_{f}$ value for the first spot (at 0.42) is different to that for the aspirin, however the aspirin produced a diffuse mark on the plate (possibly since too much solution was added to the plate) with the $R_{f}$ values for the bottom and top of the mark being 0.18 and 0.45 respectively. The $R_{f}$ value for the first spot from the crude product is within this range, hence suggesting that the crude product contains aspirin. The $R_{f}$ value of 0.58 for the second spot of the crude product is close to the $R_{f}$ value of the salicylic acid which suggests the presence of salicylic acid as an impurity in the product. This indicates that the reaction did not proceed to completion since the salicylic acid was the limiting reagent (see the percentage yield calculation in section~\ref{yield-calculation}). This is expected since the reaction is reversible (see figure~\ref{fig:mechanism}), hence an equilibrium between the reactants and products will be established. - -The TLC result for the purified product only shows a single spot at almost the same position as that for the spot assigned to aspirin in the crude product. This suggests that the recrystallisation was effective at removing the salicylic acid impurity since the spot due to this impurity is no longer present. - -\subsection{Melting Point Determination} \label{melting-point} -\begin{table}[H] - \caption{Melting Point Determination Results.} - \centering - \begin{tabular}{|c|c|c|} - \hline - Run & Melting Started / \si{\celsius} & Melting Finished / \si{\celsius} \\ - \hline - 1 & 95.1 & 101.9 \\ - \hline - 2 & 88.7 & 112.0 \\ - \hline - 3 & 91.1 & 100.4 \\ - \hline - \end{tabular} -\end{table} -The expected melting point for aspirin is \SI{136}{\celsius}.\footcite[Physical Constants of Organic Compounds, 3-8]{crc-handbook} The melting temperature results show a wide temperature range of over \SI{10}{\celsius} for the melting of the product and the temperature at which the product melted is much lower than the expected value. This is likely to have occurred since the product was not completely dry (the product consisted of clumps and upon grinding with a pestle and mortar some of the product formed a thin paste instead of forming a fine powder). - -To reduce the amount of solvent contaminating the product it could have been left in the B\"{u}chner funnel for a longer period of time after the final filtration, however it is unlikely that this would result in a fully dried product since the solvent used was not particularly volatile (the boiling temperature of water is \SI{100}{\celsius} and that of acetic acid is \SI{117.9}{\celsius}\footcite[Physical Constants of Organic Compounds, 3-4]{crc-handbook}). A more effective way to dry the product would have been to leave it in a vacuum desiccator overnight, since then the ambient pressure would be reduced below the vapour pressure of the solvent, hence causing it to evaporate much faster and leave a drier product. - -\subsection{Yield Calculation} \label{yield-calculation} -The density of acetic anhydride is \SI{1.082}{\gram\per\centi\metre\cubed}.\footcite[Physical Constants of Organic Compounds, 3-4]{crc-handbook} -\begin{displaymath} - \begin{aligned} - \text{Moles of salicylic acid at start of reaction} &= \frac{\SI{3.50}{\gram}}{(7(12.011) + 6(1.008) + 3(15.999)) \text{ \si{\gram\per\mole}}} \\ - &= \frac{\SI{3.50}{\gram}}{\SI{138.122}{\gram\per\mole}} = \SI{0.0253}{\mole} \\ - \text{Moles of acetic anhydride at start of reaction} &= \frac{\SI{3.00}{\centi\metre\cubed} \times \SI{1.082}{\gram\per\centi\metre\cubed}}{(4(12.011) + 6(1.008) + 3(15.999))\text{ \si{\gram\per\mole}}} \\ - &= \frac{\SI{3.246}{\gram}}{\SI{102.089}{\gram\per\mole}} = \SI{0.0318}{\mole} - \end{aligned} -\end{displaymath} - -From the equation (see figure~\ref{fig:equation}) there is a 1:1 molar ratio between salicylic acid and acetic anhydride, hence the acetic anhydride is in excess. The equation also shows a 1:1 molar ratio between the salicylic acid and aspirin, hence the theoretical amount of aspirin produced is \SI{0.0253}{\mole}. - -\begin{displaymath} - \begin{aligned} - \therefore \text{Theoretical yield of aspirin} &= \SI{0.0253}{\mole} \times (9(12.011) + 8(1.008) + 4(15.999)) \text{ \si{\gram\per\mole}} \\ - &= \SI{0.0253}{\mole} \times \SI{180.159}{\gram\per\mole} = \SI{4.57}{\gram} \\ - \therefore \text{Percentage yield} &= \frac{\SI{3.99}{\gram}}{\SI{4.57}{\gram}} \times \SI{100}{\percent} = \SI{87.4}{\percent} - \end{aligned} -\end{displaymath} - -This is very high: this is because the aspirin was not fully dry before the mass was determined (see section~\ref{melting-point}). This yield value is much higher than expected since the reaction is reversible and hence will not proceed to completion (as shown in section~\ref{tlc-results} with the TLC results of the crude product). - -In addition there were significant transfer losses at all transfers since the product was difficult to completely remove the sides of the vessels and while washing with ice-cold water aided in the transfer of product this would have also reduced the yield since some of the product would have dissolved in the water. - -\subsection{Spectra} -\begin{table}[H] -\begin{floatrow} - \CenterFloatBoxes - \ttabbox - {\caption{IR Spectrum of Salicylic Acid.}} - {\begin{tabular}{|c|c|c|} - \hline - Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ - \hline - 1609.7 & Moderate & \ce{C=C} Absorption. \\ - \hline - 1651.5 & Moderate & \ce{C=O} Absorption. \\ - \hline - 2850.8 & Weak and Broad & \ce{O-H} Absorption in hydroxyl group. \\ - \hline - \end{tabular} - } - \killfloatstyle - \ffigbox - {\includegraphics[height=2cm]{Salicylic-acid-NMR.png}\label{fig:salicylic-acid-nmr}} - {\caption{Salicylic acid.}} -\end{floatrow} -\end{table} - -\begin{table}[H] - \caption{$^1$H NMR Spectrum of Salicylic Acid in DMSO.} - \centering - \begin{tabular}{|c|>{\centering}m{3.3cm}|>{\centering}m{2.2cm}|m{7.9cm}|} - \hline - Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ - \hline - 9.6 & Broad Singlet & Not Integrated & Proton in (6) (carboxyl group). \\ - \hline - 7.6 & Doublet of Doublets & 4.00 & Proton in (5), coupling with (4) and (3). \\ \cline{1-2} \cline{4-4} - 7.2 & Doublet of Doublets & & Proton in (2), coupling with (3) and (4). \\ \cline{1-2} \cline{4-4} - 6.6 & Triplet of Doublets (Considerable Roofing) & (Integrated together) & One proton in (3) and one in (4), coupling with (2) and (5) (and with each other). \\ - \hline - 2.4 & Singlet & 0.17 & Characteristic of \ce{DMSO} (solvent). \\ - \hline - \end{tabular} -\end{table} -\begin{table}[H] - \caption{IR Spectrum of Acetic Anhydride.} - \centering - \begin{tabular}{|c|c|c|} - \hline - Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ - \hline - 1751.0 & Strong & \ce{C=O} Absorption. \\ - \hline - 1821.9 & Strong & \ce{C=O} Absorption. \\ - \hline - \end{tabular} -\end{table} -\begin{table}[H] - \caption{$^1$H NMR Spectrum of Acetic Anhydride.} - \centering - \begin{tabular}{|c|c|c|c|} - \hline - Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ - \hline - 2.3 & Singlet & 1.00 & Six protons in equivalent environment (from the two methyl groups). \\ - \hline - \end{tabular} -\end{table} - -\begin{table}[H] -\begin{floatrow} - \CenterFloatBoxes - \ttabbox - {\caption{IR Spectrum of Product.}} - {\begin{tabular}{|c|c|c|} - \hline - Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ - \hline - 1602.5 & Moderate & \ce{C=C} Absorption. \\ - \hline - 1681.7 & Strong & \ce{C=O} Absorption. \\ - \hline - 1750.4 & Moderate & \ce{C=O} Absorption. \\ - \hline - 2835.7 & Weak and Broad & \ce{O-H} in hydroxyl group. \\ - \hline - \end{tabular} - } - \killfloatstyle - \ffigbox - {\includegraphics[height=2cm]{Aspirin-NMR.png}\label{fig:aspirin-nmr}} - {\caption{Aspirin.}} -\end{floatrow} -\end{table} - -\begin{table}[H] - \caption{$^1$H NMR Spectrum of Product.} - \centering - \begin{tabular}{|c|c|c|p{7.9cm}|} - \hline - Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ - \hline - 8.4-6.8 & Complex Multiplet & 16.21 & Protons (2), (3), (4) and (5) from aspirin and salicylic acid impurity. \\ - \hline - 2.4 & Singlet & 7.40 & Six protons from acetic anhydride impurity. \\ - \hline - 2.2 & Singlet & 3.00 & Three protons in (1) from aspirin. \\ - \hline - \end{tabular} -\end{table} - -The product used for the $^1$H NMR spectra was not pure since the spectrum contains a singlet peak from the two methyl groups in acetic anhydride and the relative area for the aromatic peaks is greater than four with a poorly defined splitting patten, hence indicating the presence of salicylic acid. Some aspirin can be seen to have been produced by the presence of the additional peak at 2.2 ppm due to the three protons in (1). The composition of the product can be determined by comparing the areas of the peaks sue to each substance and is 1.00:1.23:3.05 (aspirin:acetic anhydride:salicylic acid). This indicates that the purification steps were not very successful since the sample mostly consisted of impurities. The IR spectrum shows that aspirin was produced since the number of peaks due to carbonyl bonds increased from the one in salicylic acid to two in the product: is expected for an acylation. -\end{document} diff --git a/10a/Aspirin-NMR.png b/10a/Aspirin-NMR.png deleted file mode 100755 index b9cf6f8..0000000 Binary files a/10a/Aspirin-NMR.png and /dev/null differ diff --git a/10a/Equation.png b/10a/Equation.png deleted file mode 100755 index c18da07..0000000 Binary files a/10a/Equation.png and /dev/null differ diff --git a/10a/Mechanism.png b/10a/Mechanism.png deleted file mode 100755 index 5534a79..0000000 Binary files a/10a/Mechanism.png and /dev/null differ diff --git a/10a/Salicylic-acid-NMR.png b/10a/Salicylic-acid-NMR.png deleted file mode 100755 index 15376e2..0000000 Binary files a/10a/Salicylic-acid-NMR.png and /dev/null differ diff --git a/16a/16a.bcf b/16a/16a.bcf deleted file mode 100644 index 43cd3dc..0000000 --- a/16a/16a.bcf +++ /dev/null @@ -1,1975 +0,0 @@ - - - - - - output_encoding - 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- - - - - - - - - - - - - - - - - - - - - - - -]> - - - latex - - 16a.bcf - - - 16a.bbl - - - blx-dm.def - blx-compat.def - biblatex.def - numeric.bbx - standard.bbx - verbose-note.cbx - biblatex.cfg - british.lbx - english.lbx - - - - biber - - biber - 16a - - - 16a.bcf - - - 16a.bbl - - - 16a.bbl - - - 16a.bcf - - - ../bibliographies/reference.bib - ../bibliographies/coretextbooks.bib - specific.bib - - - diff --git a/16a/16a.tex b/16a/16a.tex deleted file mode 100644 index d4d08ec..0000000 --- a/16a/16a.tex +++ /dev/null @@ -1,130 +0,0 @@ -%Document Setup. -\documentclass{article} -\usepackage{graphicx} %Allows import of images. -%\usepackage{float} -\usepackage{floatrow} %Align tables and figures side-by-side. -\usepackage[extreme,mathspacing=normal,leading=normal]{savetrees} %Reduce whitespace. -\usepackage{siunitx} %SI Units formatting. -%\usepackage{vhistory} %Revision History. -\usepackage[version=4]{mhchem} %Chemical Equations. -\usepackage{amsmath} %Mathematical alignments. -\usepackage{amssymb} %Mathematical symbols e.g. therefore. -\usepackage[parfill]{parskip} %Blank lines between paragraphs. -\usepackage[autostyle]{csquotes} -\usepackage{array} %Table centering. -\usepackage[british]{babel} %British localisation. -\usepackage[backend=biber,citestyle=verbose-note]{biblatex} %Bibliography. - -\numberwithin{equation}{subsection} %Number equations based on their section. -\bibliography{../bibliographies/reference,../bibliographies/coretextbooks,specific} %Use Bibliography of reference books. -\floatsetup[table]{style = plaintop} %Put captions on top of tables. -\floatsetup[figure]{style = plain} %Ensure figure captions are below figures. -\sisetup{range-phrase = --,range-units = single} %Use - for ranges and only have a single unit shown after. -\sisetup{separate-uncertainty = true,multi-part-units=single} %Use \pm for uncertainties. - -%Document Headings. -\begin{document} -\title{Preparation of Cyclohexene (16A/PC)} -\author{Sam White (Author) and Mihkel Raidal} -\date{27/02/2018} -%\date{\vhCurrentDate\\\vhCurrentVersion} -\maketitle - -\section{Introduction} -The aim of this experiment was to synthesise cyclohexene through the dehydration of cyclohexanol. Phosphoric acid was used as a catalyst and can be seen to behave catalytically in the reaction mechanism (figure~\ref{fig:syn-mechanism}) since it is regenerated by the proton donation from the more acidic hydronium ion (p$K_{\text{a}}$(\ce{H3O+}) = -0.7~\footcite{burgot98}, p$K_{\text{a}}$(\ce{H3PO4}) = 2.16~\footcite[Dissociation Constants of Inorganic Acids and Bases, 5-87]{crc-handbook}) in the final step. -% -\begin{figure}[H] - \centering - \includegraphics[width=0.85\textwidth]{Synthesis-Mechanism.png} - \caption{Mechanism for the dehydration reaction.\label{fig:syn-mechanism}} -\end{figure} -% -The overall chemical equation for this reaction is given by equation~\ref{eqn:overall-reaction}. - -\begin{equation}\label{eqn:overall-reaction} - \ce{C6H11OH(l) ->[H3PO4] C6H10(l) + H2O(l)} -\end{equation} - -An azeotropic distillation was completed in this experiment with an azeotrope (a mixture of two liquids that boils at constant composition)~\footcite[pp.~53]{oxford-chemistry-dictionary} formed between the water and cyclohexene, hence depressing the boiling temperature of the mixture due to positive excess Gibbs free energy associated with the unfavourable mixing of this liquids relative to an ideal mixture.~\footcite[Azeotropes, pp.~207]{atkins-physical} This distillation removed the products of the reaction from the reaction vessel hence driving the reaction to completion. -% -\section{Experimental Method} -A mixture of concentrated (\SI{85}{\percent}) phosphoric acid (\SI{10.0}{\centi\metre\cubed}) and cyclohexanol (\SI{24.00}{\gram}) was distilled at \SIrange{85}{95}{\celsius} (with collection in a ice-cold flask) until white fumes were evolved from the mixture residue. This produced a colourless, but cloudy distillate containing \SI{3.0}{\centi\metre\cubed} of water (\SI{69}{\percent} of the theoretical maximum volume). The distillate was washed with \SI{15}{\centi\metre\cubed} of concentrated sodium chloride solution and then the organic product was dried using anhydrous calcium chloride. After drying the organic product was very slightly cloudy. A further distillation of the dry organic product was completed (boiling temperature \SI{81.5}{\celsius} compared to the literature value of \SI{82.9(2)}{\celsius})~\footcite[Physical Constants of Organic Compounds, 3-134]{crc-handbook} and \SI{3.81}{\gram} of perfectly clear cyclohexene (\SI{19.4}{\percent} yield) was collected in a ice-cold flask. -% -\subsection{Calculations} -\subsubsection{Percentage Yield} -From equation~\ref{eqn:overall-reaction}, there is a 1:1 molar ratio between the cyclohexanol and the cyclohexene. - -\begin{align*} - \text{Amount of Product Synthesised} &= \frac{\SI{3.81}{\gram}}{(6(12.011) + 10(1.008)) \text{ \si{\gram\per\mole}}} = \frac{\SI{3.81}{\gram}}{\SI{82.15}{\gram\per\mole}} = \SI{46.4e-3}{\mole} \\ - \text{Theoretical Product Yield} &= \frac{\SI{24.00}{\gram}}{(6(12.011) + 12(1.008) + 15.999) \text{ \si{\gram\per\mole}}} = \frac{\SI{24.00}{\gram}}{\SI{100.2}{\gram\per\mole}} = \SI{0.2396}{\mole} \\ - \therefore \text{Percentage Yield} &= \frac{\SI{46.4e-3}{\mole}}{\SI{0.2396}{\mole}} \times \SI{100}{\percent} = \SI{19.4}{\percent} -\end{align*} - -\subsubsection{Percentage of Water Obtained Compared to the Theoretical Maximum} -Also from equation~\ref{eqn:overall-reaction}, there is a 1:1 molar ratio between the cyclohexanol and the water. The density of water at \SI{20.0}{\celsius} is \SI{0.998}{\gram\per\centi\metre\cubed}.\footcite[Standard Density of Water, 6-7]{crc-handbook} - -\begin{align*} - \text{Theoretical Yield of Water} &= \SI{0.2396}{\mole} \times (2(1.008) + 15.999)\text{ \si{\gram\per\mole}} = \SI{4.317}{\gram} \\ - \text{Mass of Obtained Water} &= \SI{0.998}{\gram\per\centi\metre\cubed} \times \SI{3.0}{\centi\metre\cubed} = \SI{3.0}{\gram} \\ - \therefore \text{Percentage} &= \frac{\SI{3.0}{\gram}}{\SI{4.317}{\gram}} \times \SI{100}{\percent} = \SI{69}{\percent} -\end{align*} -% -\section{Analysis} -During the experiment both cyclohexanol and water impurities were removed from the product. After the first distillation the product was heavily contaminated with water and hence appeared cloudy due to the emulsion formed. Washing with concentrated sodium chloride solution removed most of this water due to the negative Gibbs free energy change associated with the further solvation of the sodium and chloride ions in the saturated solution. In addition this washing removed any cyclohexanol from the crude product since it is soluble in water,\footcite[Physical Constants of Organic Compounds, 3-134]{crc-handbook} although it is likely that little cyclohexanol was present as an impurity since it has a high boiling temperature of \SI{160.9(2)}{\celsius}.~\footcite[Physical Constants of Organic Compounds, 3-134]{crc-handbook} The subsequent drying with anhydrous calcium chloride was intended to remove any remaining water and the final distillation removed byproducts formed from side reactions (e.g. nucleophilic substitution). -% -\subsection{Tests Performed} -Three drops of a solution of bromine in dichloromethane (since cyclohexene is insoluble in water,\footcite[Physical Constants of Organic Compounds, 3-134]{crc-handbook} also a different product of (1S,2S)-2-bromocyclohexan-1-ol would result from using an aqueous bromine solution although this is inconsequential since this is also colourless) were added to approximately \SI{1}{\centi\metre\cubed} of the collected cyclohexene. This caused the bromine solution to change colour from red-orange to colourless as the reaction shown in figure~\ref{fig:electro-add-mechanism} occurred. This demonstrated the presence of the nucleophilic double bond in the cyclohexene product, hence suggesting the intended product was successfully synthesised. -% -\begin{figure}[H] - \centering - \includegraphics[width=0.5\textwidth]{Electrophillic-Addition-Mechanism.png} - \caption{Mechanism for the electrophilic addition reaction between the cyclohexene and bromine.\label{fig:electro-add-mechanism}} -\end{figure} -% -\subsection{Boiling Temperature} -The boiling temperature of the distillate collected appears to be close to the published value (\SI{1.4}{\celsius} lower) and there was no noticeable range of boiling temperatures which suggests that the cyclohexene produced was fairly pure. However the true difference in boiling temperature is slightly greater than this since the air pressure in the laboratory was greater (by approximately \SI{0.575}{\kilo\pascal}) than the air pressure for which the literature value is reported at (\SI{101.325}{\kilo\pascal}). This would have slightly elevated the boiling temperature of the product (since the vapour pressure of the liquid would have to be greater for boiling to occur) thus the true difference in boiling temperatures between pure cyclohexene and the product was instead approximately \SI{1.6}{\celsius}. The calculations used to determine these numbers are included in section \ref{sec:boiling-calculations}. - -This lower boiling temperature could be due to a combination of factors such as a slight cooling of the vapour as it travelled up the still head and the presence of impurities in the vapour. The product could have been analysed using NMR spectroscopy to definitively identify any impurities in the product, and the thermometer could have been temporarily moved to a position just above the boiling liquid during the distillation in order to obtain a more accurate value for its boiling temperature. An electronic thermometer could also have been used hence giving a more precise temperature reading and allowing the easier establishment of the range of boiling temperatures for the solution. - -However it is likely that there was still a little water impurity in the product after the drying since it was very slightly cloudy when compared to the distilled product. This may have been since the solution was not left to dry for 10 minutes as recommended in the laboratory manual due to time constraints, however a possible improvement to the method could be be grind the drying agent into a fine powder to increase its surface area and thus reduce the time required to dry the product. -% -\subsubsection{Boiling Temperature Calculations}\label{sec:boiling-calculations} -The approximate laboratory air pressure was calculated using an adjusted sea-level air pressure of approximately \SI{102.6}{\kilo\pascal}~\footcite[Pressure at 4:20 PM]{weather-underground-egnt} and laboratory altitude of \SI{55.30}{\metre} above mean sea level~\footcite[Latitude: \SI{54.7683}{\degree}, Longitude: \SI{-1.5711}{\degree}]{os-maps-lab} with equation~\ref{eqn:pressure-diff}. - -\begin{equation}\label{eqn:pressure-diff} - \Delta P = - \rho g \Delta h -\end{equation} - -Using $\rho = \SI{1.29}{\kilo\gram\per\metre\cubed}\text{ (obtained by linearly interpolating between given values to \SI{270}{\kelvin})}$\footcite[Thermophysical Properties of Air, 6-18]{crc-handbook} and $g = \SI{9.81}{\meter\per\second\squared}$. While assuming that the temperature of the air is constant at \SI{270}{\kelvin} and the density of the air remains constant. - -\begin{align*} - \text{Laboratory Air Pressure} &\approx \SI{102.6e3}{\pascal} - \SI{1.29}{\kilo\gram\per\metre\cubed} \times \SI{9.81}{\metre\per\second\squared} \times \SI{55.30}{\metre} = \SI{102}{\kilo\pascal} \\ - \therefore \text{Difference from Published Pressure} &\approx \SI{101.325}{\kilo\pascal} - \SI{102}{\kilo\pascal} = \SI{0.575}{\kilo\pascal} -\end{align*} - -The Clausius-Clapeyron equation (equation~\ref{eqn:clausius-clapeyron}) and can be rearranged to make $T_2$ the subject (equation~\ref{eqn:clausius-clapeyron-rearranged}) and hence can be used to determine the boiling temperature elevation caused by this pressure difference. - -\begin{equation}\label{eqn:clausius-clapeyron} - \log_e\left(\frac{P_1}{P_2}\right) = \frac{\Delta H_{\text{vap}}}{R} \left(\frac{1}{T_2} - \frac{1}{T_1}\right) -\end{equation} - -\begin{equation}\label{eqn:clausius-clapeyron-rearranged} - T_2 = \frac{T_1 \Delta H_{\text{vap}}}{R T_1 \log_e\left(\frac{P_1}{P_2}\right) + \Delta H_{\text{vap}}} -\end{equation} - -With $\Delta H_\text{vap}(\SI{82.9}{\celsius}) = \SI{30.46}{\kilo\joule\per\mole}$ (assuming this remains constant in the temperature range considered).~\footcite[Enthalpy of Vaporization, 6-141]{crc-handbook} - -\begin{align*} - \text{New boiling temperature} &\approx \frac{(82.9 + 273.15)\text{ \si{\kelvin}} \times \SI{30.46e3}{\joule\per\mole}}{\SI{8.31}{\joule\per\mole\per\kelvin} \times (82.9 + 273.15)\text{ \si{\kelvin}} \times \log_e\left(\frac{\SI{101.325}{\kilo\pascal}}{\SI{102}{\kilo\pascal}}\right) + \SI{30.46e3}{\joule\per\mole}} \\ - &\approx \SI{356}{\kelvin} = \SI{83.1}{\celsius} \\ - \therefore \text{Difference in Boiling Temperature} &\approx \SI{83.1}{\celsius} - \SI{81.5}{\celsius} = \SI{1.6}{\celsius} -\end{align*} -% -\subsection{Yield} -The overall percentage yield obtained was very low (\SI{19.4}{\percent}), despite the fairly high percentage of water obtained compared to the theoretical maxima (\SI{69}{\percent}) after the initial distillation. However this water percentage is likely to be a fairly inaccurate measure of the initial yield since the water which formed an emulsion in the organic layer is not represented in this figure and it doesn't account for any water which was originally contained within the reagents (such as the water in the concentrated phosphoric acid solution) which may have also been collected. - -Some of the cyclohexene was lost during transfers both due to some liquid remaining the in previous vessel and due to evaporative losses. To reduce these evaporative losses during transfer the flask containing the product could be cooled in an ice bath at all intermediate stages in the experiment, not just during distillation, hence reducing the temperature of the liquid being transferred. In addition after the distillations some of the cyclohexene remained in the distillation apparatus. To reduce this a 'chaser' solvent with a higher boiling temperature than the cyclohexene -- such as toluene -- could have been added to the reaction vessel at the end of the first distillation to force any remaining cyclohexene into the collection flask.~\footcite{unmass-cyclohexene-synthesis} This solvent would then be removed from the cyclohexene by the second distillation step. - -The yield calculated is likely to also have been low since not all of the product was distilled for a second time (due to the small size of the round-bottomed flask used) and the second distillation itself was stopped prematurely due to time constraints. - -\end{document} diff --git a/16a/Electrophillic-Addition-Mechanism.png b/16a/Electrophillic-Addition-Mechanism.png deleted file mode 100755 index 61ab6d6..0000000 Binary files a/16a/Electrophillic-Addition-Mechanism.png and /dev/null differ diff --git a/16a/Synthesis-Mechanism.png b/16a/Synthesis-Mechanism.png deleted file mode 100755 index b6bb392..0000000 Binary files a/16a/Synthesis-Mechanism.png and /dev/null differ diff --git a/16a/specific.bib b/16a/specific.bib deleted file mode 100644 index 128579b..0000000 --- a/16a/specific.bib +++ /dev/null @@ -1,31 +0,0 @@ -@article{burgot98, - author = {Jean-Lewis Burgot}, - title = {New point of view on the meaning and on the values of $K_{\text{a}}^\circ$(\ce{H3O+}, \ce{H2O}) and $K_{\text{b}}^\circ$(\ce{H2O}, \ce{OH-}) pairs in water}, - year = {1998}, - journal = {Analyst}, - volume = {123}, - % number = {}, - pages = {409--410} -} - -@online{weather-underground-egnt, - title = {Weather History for EGNV - February, 2018}, - author = {TWC Product and Technology, LLC}, - date = {2018-02-27}, - url = {https://www.wunderground.com/history/airport/EGNV/2018/2/27/DailyHistory.html}, - urldate = {2018-02-28} -} - -@online{os-maps-lab, - title = {OS Maps Online}, - author = {Ordnance Survey}, - url = {https://osmaps.ordnancesurvey.co.uk/54.76830,-1.57110,20}, - urldate = {2018-02-28} -} - -@online{unmass-cyclohexene-synthesis, - title = {Synthesis of Cyclohexene, The Dehydration of Cyclohexanol}, - author = {Peter Samal}, - url = {https://people.chem.umass.edu/samal/269/cyclohexene.pdf}, - urldate = {2018-03-03} -} diff --git a/3a/3a.bcf b/3a/3a.bcf deleted file mode 100644 index c3af979..0000000 --- a/3a/3a.bcf +++ /dev/null @@ -1,2147 +0,0 @@ - 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-\numberwithin{equation}{subsection} %Number equations based on their subsection. -\bibliography{../bibliography/coretextbooks} %Use Bibliography of Core textbooks. - -%Document Headings. -\begin{document} -\title{Determination of the $M_{r}$ of an Unknown Solid Acid using Titration (3A/ABT)} -\author{Sam White} -\date{31/10/2017} -%\date{\vhCurrentDate\\\vhCurrentVersion} -\maketitle - -\section{Aim} -To determine the $M_r$ of an unknown solid acid ($A$) using a titrimetric method of analysis. - -\section{Results and Analysis} -\begin{displaymath} - \begin{aligned} - \text{Batch of \ce{HCl} used}&: B \\ - \text{Concentration of \ce{HCl}}&: \SI{0.1029}{\mole\per\deci\metre\cubed} \\ - \text{Batch of \ce{NaOH} Used}&: B - \end{aligned} -\end{displaymath} - -\subsection{Titration between \ce{NaOH} and \ce{HCl}} -\begin{equation} \label{eq:naoh-hcl} - \ce{HCl(aq) + NaOH(aq) -> NaCl(aq) + H2O(l)} -\end{equation} - -Phenolphthalein was used as the indicator (colour change from pink to colourless at the end point). - -\begin{table}[h] - \caption{Results from titrating \SI{25.00}{\centi\metre\cubed} of \ce{NaOH} with \ce{HCl}.} - \centering - \begin{tabular}{|c|c|c|c|} - \hline - {Run} & {Start Volume / \si{\centi\metre\cubed}} & {End Volume / \si{\centi\metre\cubed}} & {Titre / \si{\centi\metre\cubed}} \\ - \hline - 1 & 6.60 & 30.95 & 24.35 \\ - \hline - 2 & 2.00 & 25.85 & 23.85 \\ - \hline - 3 & 4.20 & 28.30 & 24.10 \\ - \hline - 4 & 4.45 & 28.55 & 24.10 \\ - \hline - \end{tabular} -\end{table} - -\begin{displaymath} - \text{Average titre} = \frac{\SI{24.10}{\centi\metre\cubed} + \SI{24.10}{\centi\metre\cubed}}{2} = \SI{24.10}{\centi\metre\cubed} -\end{displaymath} - -\begin{displaymath} - \begin{aligned} - \text{Moles of \ce{HCl} in titre} &= \SI{24.10}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3 \times \SI{0.1029}{\mole\per\deci\metre\cubed} \\ - &= \SI{24.10e-3}{\deci\metre\cubed} \times \SI{0.1029}{\mole\per\deci\metre\cubed} \\ - &= \SI{2.480e-3}{\mole} - \end{aligned} -\end{displaymath} - -From equation~\ref{eq:naoh-hcl} there is a 1:1 molar ratio between \ce{HCl} and \ce{NaOH}. - -\begin{displaymath} - \begin{aligned} - \therefore \text{Moles of \ce{NaOH} in \SI{25.00}{\centi\metre\cubed}} &= \SI{2.480e-3}{\mole} \\ - \text{Concentration of \ce{NaOH}} &= \frac{\SI{2.480e-3}{\mole}}{\SI{25.00}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3} \\ - &= \frac{\SI{2.480e-3}{\mole}}{\SI{25.00e-3}{\deci\metre\cubed}} \\ - &= \SI{0.09920}{\mole\per\deci\metre\cubed} - \end{aligned} -\end{displaymath} - - -\subsection{Titration between \ce{NaOH} and Unknown Acid $A$} -For \ce{HA} being the unknown acid $A$ and assuming \ce{HA} is monobasic: -\begin{equation} \label{eq:naoh-ha} - \ce{HA(aq) + NaOH(aq) -> NaA(aq) + H2O(l)} -\end{equation} - -Phenolphthalein was used as the indicator (colour change from pink to colourless at the end point). - -A mass of \SI{1.8525}{\gram} of \ce{HA} was dissolved with distilled water in a \SI{200.00}{\centi\metre\cubed} volumetric flask. - -\begin{table}[h] - \caption{Results from titrating \SI{20.00}{\centi\metre\cubed} of \ce{NaOH} with \ce{HA}.} - \centering - \begin{tabular}{|c|c|c|c|} - \hline - {Run} & {Start Volume / \si{\centi\metre\cubed}} & {End Volume / \si{\centi\metre\cubed}} & {Titre / \si{\centi\metre\cubed}} \\ - \hline - 1 & 4.00 & 24.90 & 20.90 \\ - \hline - 2 & 4.00 & 24.10 & 20.10 \\ - \hline - 3 & 4.05 & 24.20 & 20.15 \\ - \hline - \end{tabular} -\end{table} - -\begin{displaymath} - \text{Average titre} = \frac{\SI{20.10}{\centi\metre\cubed} + \SI{20.15}{\centi\metre\cubed}}{2} = \SI{20.13}{\centi\metre\cubed} -\end{displaymath} - -\begin{displaymath} - \begin{aligned} - \text{Moles of \ce{NaOH} in \SI{20.00}{\centi\metre\cubed} aliquot} &= \SI{20.00}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3 \times \SI{0.09920}{\mole\per\deci\metre\cubed} \\ - &= \SI{20.00e-3}{\deci\metre\cubed} \times \SI{0.09920}{\mole\per\deci\metre\cubed} \\ - &= \SI{1.984e-3}{\mole} - \end{aligned} -\end{displaymath} - -From equation \ref{eq:naoh-ha} there is a 1:1 molar ratio between \ce{NaOH} and \ce{HA}. - -\begin{displaymath} - \begin{aligned} - \therefore \text{Moles of \ce{HA} in \SI{20.13}{\centi\metre\cubed}} &= \SI{1.984e-3}{\mole} \\ - \text{Concentration of \ce{HA}} &= \frac{\SI{1.984e-3}{\mole}}{\SI{20.13}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3} \\ - &= \frac{\SI{1.984e-3}{\mole}}{\SI{20.13e-3}{\deci\metre\cubed}} \\ - &= \SI{0.09855}{\mole\per\deci\metre\cubed} - \end{aligned} -\end{displaymath} - -Hence for the whole \SI{200.00}{\centi\metre\cubed} volumetric flask: -\begin{displaymath} - \begin{aligned} - \text{Moles of \ce{HA}} &= \SI{0.09855}{\mole\per\deci\metre\cubed} \times \SI{200.00}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3 \\ - &= \SI{0.09855}{\mole\per\deci\metre\cubed} \times \SI{200.00e-3}{\deci\metre\cubed} \\ - &= \SI{0.01971}{\mole} - \end{aligned} -\end{displaymath} - -Since: -\begin{displaymath} - \begin{aligned} - \text{Amount \si{\mole}} &= \frac{\text{Mass \si{\gram}}}{M_r \text{ \si{\gram\per\mole}}} \\ - M_r \text{ \si{\gram\per\mole}} &= \frac{\text{Mass \si{\gram}}}{\text{Amount \si{\mole}}} \\ - \end{aligned} -\end{displaymath} -Hence: -\begin{displaymath} - \begin{aligned} - M_r \text{ of \ce{HA}} = \frac{\SI{1.8525}{\gram}}{\SI{0.01971}{\mole}} = \SI{93.98}{\gram\per\mole} - \end{aligned} -\end{displaymath} - -\end{document} diff --git a/7a/7a.bcf b/7a/7a.bcf deleted file mode 100644 index c4f19f8..0000000 --- a/7a/7a.bcf +++ /dev/null @@ -1,2149 +0,0 @@ - - - - - - output_encoding - ascii - - - input_encoding - ascii - - - debug - 0 - - - mincrossrefs - 2 - - - minxrefs - 2 - - - sortcase - 1 - - - sortupper - 1 - - - - - - - alphaothers - + - - - labelalpha - 0 - - - labelnamespec - shortauthor - author - shorteditor - editor - translator - - - labeltitle - 0 - - - labeltitlespec - shorttitle - title - maintitle - - - labeltitleyear - 0 - - - labeldateparts - 0 - - - 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- - - - - - - - - - - - - - - - - - - - - - - -]> - - - latex - - 7a.bcf - - - 7a.bbl - - - blx-dm.def - blx-compat.def - biblatex.def - verbose.bbx - authortitle.bbx - standard.bbx - verbose.cbx - biblatex.cfg - british.lbx - english.lbx - - - - biber - - biber - 7a - - - 7a.bcf - - - 7a.bbl - - - 7a.bbl - - - 7a.bcf - - - ../bibliographies/additionaltextbooks.bib - - - diff --git a/7a/7a.tex b/7a/7a.tex deleted file mode 100644 index 5e5970a..0000000 --- a/7a/7a.tex +++ /dev/null @@ -1,196 +0,0 @@ -%Document Setup. -\documentclass{article} -\usepackage{graphicx} %Allows import of images. -\usepackage{float} -\usepackage[extreme,mathspacing=normal,leading=normal]{savetrees} %Reduce whitespace. -\usepackage{siunitx} %SI Units formatting. -%\usepackage{vhistory} %Revision History. -\usepackage[version=4]{mhchem} %Chemical Equations. -\usepackage{amsmath} %Mathematical alignments. -\usepackage{amssymb} %Mathematical symbols e.g. therefore. -\usepackage[parfill]{parskip} %Blank lines between paragraphs. -\usepackage[autostyle]{csquotes} -\usepackage{array} %Table centering. -\usepackage[british]{babel} %British localisation. -\usepackage[backend=biber,style=verbose]{biblatex} %Bibliography. - -\numberwithin{equation}{subsection} %Number equations based on their subsection. -\bibliography{../bibliographies/additionaltextbooks} %Use Bibliography of additional textbooks. - -%Document Headings. -\begin{document} -\title{Preparation of Pear Essence (Propyl Acetate) (7A/PPE)} -\author{Sam White} -\date{07/11/2017} -%\date{\vhCurrentDate\\\vhCurrentVersion} -\maketitle - -%\section{Aim} -%To prepare propyl acetate from propan-1-ol and acetic acid and then determine the percentage yield. - -\section{Reaction Mechanism\footcite[Preparation of Esters, p.~1014]{klein-organic} and Overall Equation} -\begin{figure}[H] - \centering - \includegraphics[width=0.75\textwidth]{Mechanism.png} - \caption{Mechanism for reaction \label{fig:mechanism}} -\end{figure} -\begin{figure}[H] - \centering - \includegraphics[width=0.55\textwidth]{Equation.png} - \caption{Overall Equation for Reaction \label{fig:equation}} -\end{figure} - -\section{Results and Analysis} -{\centering Boiling temperature of pure product: \SI{101}{\celsius} - -Mass of pure product: \SI{4.43}{\gram} - -} -%\begin{table}[h] -% \caption{Masses recorded at end of experiment.} -% \centering -% \begin{tabular}{|c|c|} -% \hline -% Item & Mass / \si{\gram} \\ -% \hline -% Empty Sample Bottle and Lid & 11.93 \\ -% \hline -% Filled Sample Bottle and Lid & 16.36 \\ -% \hline -% Mass of Propyl Acetate & 4.43 \\ -% \hline -% \end{tabular} -%\end{table} - -%\begin{equation} \label{eq:ppyl-acte-abbr} -% \ce{CH3CH2CH2OH(l) + CH3COOH(l) <=>[H+] CH3COOCH2CH2CH3(l) + H2O(l)} -%\end{equation} - -\subsection{Yield Calculation} -\begin{displaymath} - \begin{aligned} - \text{Moles of propan-1-ol at start of reaction} &= \frac{\SI{9.6}{\gram}}{(3(12.011) + 8(1.008) + 15.999) \text{ \si{\gram\per\mole}}} \\ - &= \frac{\SI{9.6}{\gram}}{\SI{60.096}{\gram\per\mole}} = \SI{0.16}{\mole} \\ - \text{Moles of acetic acid at start of reaction} &= \frac{\SI{24}{\gram}}{(2(12.011) + 4(1.008) + 2(15.999))\text{ \si{\gram\per\mole}}} \\ - &= \frac{\SI{24}{\gram}}{\SI{60.052}{\gram\per\mole}} = \SI{0.40}{\mole} - \end{aligned} -\end{displaymath} - -From the equation shown in figure~\ref{fig:equation} there is a 1:1 molar ratio between propan-1-ol and acetic acid, hence the acetic acid is in excess. The equation also shows a 1:1 molar ratio between the propan-1-ol and propyl acetate, hence the theoretical amount of propyl acetate produced is \SI{0.16}{\mole}. - -\begin{displaymath} - \begin{aligned} - \therefore \text{Theoretical yield of propyl acetate} &= \SI{0.16}{\mole} \times (5(12.011) + 10(1.008) + 2(15.999)) \text{ \si{\gram\per\mole}} \\ - &= \SI{0.16}{\mole} \times \SI{102.133}{\gram\per\mole} = \SI{16}{\gram} \\ - \therefore \text{Percentage yield} &= \frac{\SI{4.43}{\gram}}{\SI{16}{\gram}} \times \SI{100}{\percent} = \SI{27}{\percent} - \end{aligned} -\end{displaymath} - -This is quite low. This may be due to losses during the purification (e.g. containers were not washed after transfers and some product remained in the filter paper) and a consequence of the reversible nature of the reaction. %The mass of the reactants should have been measured to increase the accuracy and precision of the percentage yield. - -%This could be due to losses during the purification steps performed (such transfer losses since the containers of the product were not washed after transfers and since a fair amount of product remained in the filter paper) as well as due to the reaction not proceeding entirely to completion since it is reversible. In addition the actual masses of the reactants should have been measured at the start of the experiment to allow a more accurate and precise percentage yield to be determined. -\subsection{Spectra} -%\subsubsection{Reactants} -\begin{table}[h] - \caption{IR Spectrum of propan-1-ol.} - \centering - \begin{tabular}{|c|c|c|} - \hline - Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ - \hline - 2976.7 & Weak & \ce{CH3} Absorption \\ - \hline - 2936.0 & Weak & \ce{C-H2} Absorption \\ - \hline - 2962.3 & Weak & \ce{C-H3} Absorption \\ - \hline - 3319.0 & Weak and Broad & \ce{O-H} Absorption in Alcohol \\ - \hline - \end{tabular} -\end{table} -\begin{table}[h] - \caption{$^1$H NMR Spectrum of propan-1-ol.} - \centering - \begin{tabular}{|c|c|>{\centering}m{2.2cm}|m{7.9cm}|} - \hline - Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ - \hline - Approx. 7.3 & Singlet & Not Integrated & Characteristic for \ce{CDCl3} (Solvent) \\ - \hline - 3.66 & Triplet & 0.99 & Two $\alpha$-protons to alcohol group. Coupled to two protons. \\ - \hline - 2.03 & Singlet & 3.00 & \ce{OH} proton. Exchange decoupled. \\ \cline{1-2} \cline{4-4} - 1.57 & Quintet (Unclear) & (Integrated together) & Additional splitting possibly obscured by adjacent peaks. Coupled to four or five protons. \\ \cline{1-2} \cline{4-4} - 1.00 & Triplet (Small right-hand peak) & & Coupled to two protons. \\ - \hline - \end{tabular} -\end{table} -\begin{table}[h] - \caption{IR Spectrum of acetic acid.} - \centering - \begin{tabular}{|c|c|c|} - \hline - Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ - \hline - 1703.9 & Strong & \ce{C=O} Absorption close to acid range (1725-1705 \si{\per\centi\metre}) \\ - \hline - 3032.6 & Weak and Broad & \ce{O-H} Absorption close to carboxylic acid range (3000-2500 \si{\per\centi\metre}) \\ - \hline - \end{tabular} -\end{table} -\begin{table}[h] - \caption{$^1$H NMR Spectrum of acetic acid.} - \centering - \begin{tabular}{|c|c|c|c|} - \hline - Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ - \hline - 10.67 & Singlet & 0.90 & Single proton in \ce{-COOH} group. Exchange decoupled. \\ - \hline - Approx. 7.4 & Singlet & Not Integrated & Characteristic for \ce{CDCl3} (Solvent). \\ - \hline - 2.19 & Singlet & 3.00 & Three $\alpha$-protons to carboxyl group. \\ - \hline - \end{tabular} -\end{table} - -%\subsubsection{Product} -\begin{table}[h] - \caption{IR Spectrum of Product.} - \centering - \begin{tabular}{|c|c|c|} - \hline - Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ - \hline - 1738.0 & Strong & \ce{C=O} Absorption in the ester range (1740-1710 \si{\per\centi\metre}) \\ - \hline - 2882.5 & Weak & \ce{C-H} Absorption \\ - \hline - 2970.5 & Weak & \ce{C-H} Absorption \\ - \hline - \end{tabular} -\end{table} -\begin{table}[h] - \caption{$^1$H NMR Spectrum of Product.} - \centering - \begin{tabular}{|c|c|c|p{7.9cm}|} - \hline - Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ - \hline - Approx. 7.4 & Singlet & 0.030 & Characteristic for \ce{CDCl3} (Solvent) \\ - \hline - 4.14 & Triplet & 1.98 & Two protons (\ce{RCOO-C\underline{H}}). Coupled to two protons. \\ - \hline - 2.17 & Singlet & 3.28 & Three protons in unique environment \\ - \hline - Approx. 1.8 & Quartet (Unclear) & 1.90 & Two protons coupled three or four protons: splitting pattern difficult to interpret. \\ - \hline - 1.06 & Triplet (Small right-hand peak) & 2.75 & Three protons coupled to two protons. \\ - \hline - \end{tabular} -\end{table} -These spectra are consistent with propyl acetate as a product since the starting materials both had a broad peak corresponding to \ce{O-H} absorptions in their IR spectra, however this is absent in the product's IR spectrum. Also the NMR spectrum for the product shows it has four distinct hydrogen environments with the expected chemical shifts and (mostly) the expected splitting pattens for propyl acetate. In the IR spectra the \ce{C=O} absorption has shifted position from being at \SI{1703.9}{\per\centi\metre} in acetic acid to \SI{1738.0}{\per\centi\metre} in the product: this higher wavenumber is expected for the production of an ester. - -%These spectra are consistent with the product made being propyl acetate since the IR spectrum clearly shows the \ce{C=O} bond in the correct range for an ester and appropriate \ce{C-H} bond absorptions while the $^1$H NMR spectrum shows the correct number of environments, appropriate chemical shifts and roughly correct splitting pattens and areas for propyl acetate. The lack of the broad \ce{O-H} peak in the IR spectrum (which is present in both reactants) also indicates the formation of propyl acetate and little/no reactant impurities. The ambiguity in the splitting pattens in the $^1$H NMR spectrum around 1.6 ppm as well as the deviations of the areas of the peaks from the expected values may be due to the presence of impurities in the product mixture and also possibly due to the solvent residual water peak at 1.5 ppm. - -\end{document} diff --git a/7a/Equation.png b/7a/Equation.png deleted file mode 100755 index 71ceb1e..0000000 Binary files a/7a/Equation.png and /dev/null differ diff --git a/7a/Mechanism.png b/7a/Mechanism.png deleted file mode 100755 index 51431e4..0000000 Binary files a/7a/Mechanism.png and /dev/null differ diff --git a/8a/8a.bcf b/8a/8a.bcf deleted file mode 100644 index 6f39cd6..0000000 --- a/8a/8a.bcf +++ /dev/null @@ -1,1964 +0,0 @@ - - - - - - output_encoding - ascii - - - input_encoding - ascii - - - debug - 0 - - - mincrossrefs - 2 - - - minxrefs - 2 - - - sortcase - 1 - - - sortupper - 1 - - - - - - - alphaothers - + - - - labelalpha - 0 - - - labelnamespec - shortauthor - author - shorteditor - 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for ranges and only have a single unit. - -%Document Headings. -\begin{document} -\title{A Redox Titration to Determine the Ethanol Content of Wine (8A/RTE)} -\author{Sam White (Author) and Mihkel Raidal} -\date{05/12/2017} -%\date{\vhCurrentDate\\\vhCurrentVersion} -\maketitle - -{\centering Reported percentage of alcohol by volume (\si{\percent} ABV): \SI{13}{\percent} - -} -% -\section{Titration Results and Calculation of \si{\percent} ABV of Wine} -A mass of \SI{7.7910}{\gram} of \ce{(NH4)2Fe(SO4)2.6H2O} was dissolved in \SI{60}{\centi\metre\cubed} of \ce{H2SO4} and made up to \SI{200.00}{\centi\metre\cubed} with deionised water in a volumetric flask. Each \ce{(NH4)2Fe(SO4)2.6H2O} molecule liberates one \ce{Fe^{2+}} ion in solution, thus their concentrations in the solution are equal. The molar mass of \ce{(NH4)2Fe(SO4)2.6H2O} is \SI{392.139}{\gram\per\mole}.\footcite[Physical Constants of Inorganic Compounds, 4-46]{crc-handbook} -% -\begin{displaymath} - \text{Moles of \ce{Fe^{2+}} in \SI{200.00}{\centi\metre\cubed} standard solution} = \frac{\SI{7.7910}{\gram}}{\SI{392.139}{\gram\per\mole}} = \SI{0.019868}{\mole} -\end{displaymath} -Hence: -\begin{align} \label{[fe2+]} - \text{Concentration of \ce{Fe^{2+}} in standard solution} = \frac{\SI{0.019868}{\mole}}{\SI{200.00}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3} = \frac{\SI{0.019869}{\mole}}{\SI{200.00e-3}{\deci\metre\cubed}} = \SI{0.099340}{\mole\per\deci\metre\cubed} -\end{align} -% -%\section{Titration between \ce{K2Cr2O7} and \ce{(NH4)2Fe(SO4)2.6H2O}} -The reaction which occurred in both titrations was: -\begin{equation} \label{eq:cr2o72--fe2+} - \ce{Cr2O7^{2-} + 14H+ + 6Fe^{2+} -> 6Fe^{3+} + 2Cr^{3+} + 7H2O} -\end{equation} -With sodium diphenylamine-4-sulphonate used as the indicator (colour change from green (due to \ce{Cr^{3+}}) to purple at the end point). -% -\begin{table}[h] - \caption{Results of titration between \ce{K2Cr2O7} and standard solution of \ce{(NH4)2Fe(SO4)2.6H2O}} - \centering - \begin{tabular}{|c|c|c|c|} - \hline - Run & Start Volume / \si{\centi\metre\cubed} & End Volume / \si{\centi\metre\cubed} & Titre / \si{\centi\metre\cubed} \\ - \hline - 1 & 2.40 & 18.30 & 15.90 \\ - \hline - 2 & 2.20 & 18.80 & 16.60 \\ - \hline - 3 & 2.25 & 18.85 & 16.60 \\ - \hline - \end{tabular} -\end{table} -% -\begin{gather*} - \text{Average titre} = \frac{\SI{16.60}{\centi\metre\cubed} + \SI{16.60}{\centi\metre\cubed}}{2} = \SI{16.60}{\centi\metre\cubed} \\ - \text{Using~\ref{[fe2+]}, moles of \ce{Fe^{2+}} in \SI{20.00}{\centi\metre\cubed} aliquot} = \SI{0.099340}{\mole\per\deci\metre\cubed} \times \SI{20.00}{\centi\metre\cubed} \times \frac{\SI{1}{\deci\metre\cubed}}{\SI{1000}{\centi\metre\cubed}} = \SI{1.987e-3}{\mole} -\end{gather*} -% -From chemical equation~\ref{eq:cr2o72--fe2+} there is a 6:1 molar ratio between the \ce{Fe^{2+}} and \ce{Cr2O7^{2-}}. -\begin{equation} \label{[cr2o72-]} - \text{Concentration of \ce{Cr2O7^{2-}}} = \frac{\frac{1}{6} \times \SI{1.987e-3}{\mole}}{\SI{16.60}{\centi\metre\cubed} \times \frac{\SI{1}{\deci\metre\cubed}}{\SI{1000}{\centi\metre\cubed}}} = \frac{\SI{3.311e-4}{\mole}}{\SI{16.60e-3}{\deci\metre\cubed}} = \SI{0.01995}{\mole\per\deci\metre\cubed} -\end{equation} -% -%\section{Titration between Product Mixture and \ce{(NH4)2Fe(SO4)2.6H2O}} -During the reflux the ethanol from the sample of wine was oxidised by the \ce{Cr2O7^{2-}} ions to acetic acid as shown in this equation: -\begin{equation} \label{eq:ethanol-cr2o72-} - \ce{3CH3CH2OH + 2Cr2O7^{2-} + 16H+ -> 3CH3COOH + 4Cr^{3+} + 11H2O} -\end{equation} -During this the solution changed colour from orange (due to the \ce{Cr2O7^{2-}}) to dark green (due to the liberation of \ce{Cr^{3+}}). A back titration was then performed with the standard solution of \ce{Fe^{2+}} ions. The volumes used for this were half of those stated in the method since when the stated volumes were used the titre was very large and a maximum of two more titrations would have possible before the reaction mixture was exhausted. This would have been problematic if these titres were not concordant since the completion of additional titrations would have been impossible. -% -\begin{table}[h] - \centering - \caption{Results of titration between \ce{K2Cr2O7} in product mixture and standard solution of \ce{(NH4)2Fe(SO4)2.6H2O}} - \begin{tabular}{|c|c|c|c|} - \hline - Run & Start Volume / \si{\centi\metre\cubed} & End Volume / \si{\centi\metre\cubed} & Titre / \si{\centi\metre\cubed} \\ - \hline - 1 & 2.20 & 18.40 & 16.20 \\ - \hline - 2 & 18.90 & 35.25 & 16.35 \\ - \hline - 3 & 3.10 & 19.50 & 16.40 \\ - \hline - \end{tabular} -\end{table} -% -\begin{gather*} - \text{Average titre} = \frac{\SI{16.35}{\centi\metre\cubed}+\SI{16.40}{\centi\metre\cubed}}{2} = \SI{16.38}{\centi\metre\cubed} \\ - \text{Using~\ref{[fe2+]}, moles of \ce{Fe^{2+}} in \SI{5.00}{\centi\metre\cubed} aliquot} = \SI{0.099340}{\mole\per\deci\metre\cubed} \times \SI{5.00}{\centi\metre\cubed} \times \frac{\SI{1}{\deci\metre\cubed}}{\SI{1000}{\centi\metre\cubed}} = \SI{4.97e-4}{\mole} -\end{gather*} -% -From chemical equation~\ref{eq:cr2o72--fe2+} there is a 6:1 molar ratio between \ce{Fe^{2+}} and \ce{Cr2O7^{2-}}. -\begin{align*} - \text{Concentration of \ce{Cr2O7^{2-}} in product mixture} &= \frac{\frac{1}{6} \times \SI{4.97e-4}{\mole}}{\SI{16.38}{\centi\metre\cubed}} = \SI{5.05e-6}{\mole\per\centi\metre\cubed} \\ - \therefore\text{Moles of \ce{Cr2O7^{2-}} in \SI{126}{\centi\metre\cubed} product mixture} &= \SI{5.05e-6}{\mole\per\centi\metre\cubed} \times \SI{126}{\centi\metre\cubed} = \SI{6.37e-4}{\mole} -\end{align*} -% -%\section{Calculation of \si{\percent} ABV of the Wine} -Initially \SI{100.00}{\centi\metre\cubed} of \ce{Cr2O7^{2-}} of concentration \SI{0.01995}{\mole\per\deci\metre\cubed} (from~\ref{[cr2o72-]}) was in the reactant mixture. -\begin{align*} - \text{Initial moles of \ce{Cr2O7^{2-}}} &= \SI{100.00}{\centi\metre\cubed} \times \frac{\SI{1}{\deci\metre\cubed}}{\SI{1000}{\centi\metre\cubed}} \times \SI{0.01995}{\mole\per\deci\metre\cubed} = \SI{1.995e-3}{\mole} \\ - \therefore\text{Moles of \ce{Cr2O7^{2-}} which reacted} &= \SI{1.995e-3}{\mole} - \SI{6.37e-4}{\mole} = \SI{1.36e-3}{\mole} -\end{align*} -% -From chemical equation~\ref{eq:ethanol-cr2o72-} molar ratio between \ce{Cr2O7^{2-}} and ethanol is 2:3. The molar mass of ethanol is \SI{46.068}{\gram\per\mole}.\footcite[Physical Constants of Organic Compounds, 3-246]{crc-handbook} -\begin{align*} - \text{Moles of ethanol in \SI{1.00}{\centi\metre\cubed} sample} &= \frac{\SI{1.36e-3}{\mole}}{2} \times 3 = \SI{2.04e-3}{\mole} \\ - \therefore\text{Mass of ethanol in \SI{1.00}{\centi\metre\cubed}} &= \SI{2.04e-3}{\mole} \times \SI{46.068}{\gram\per\mole} = \SI{0.0938}{\gram} -\end{align*} -The density of ethanol is \SI{0.7893}{\gram\per\centi\metre\cubed}.$^2$ %Quick and dirty way to make footer smaller. -%\footcite[Physical Constants of Organic Compounds, 3-246]{crc-handbook} -\begin{displaymath} - \text{\si{\percent} ABV of wine} = \frac{\SI{0.0938}{\gram}}{\SI{0.7893}{\gram\per\centi\metre\cubed}}\times \frac{\SI{100}{\percent}}{\SI{1.00}{\centi\metre\cubed}} = \SI{11.9}{\percent} -% \text{Volume of ethanol in \SI{1.00}{\centi\metre\cubed}} &= \frac{\SI{0.0938}{\gram}}{\SI{0.7893}{\gram\per\centi\metre\cubed}} = \SI{0.119}{\centi\metre\cubed} \\ -% \text{Hence, \si{\percent} ABV of wine} &= \frac{\SI{0.119}{\centi\metre\cubed}}{\SI{1.00}{\centi\metre\cubed}} \times \SI{100}{\percent} = \SI{11.9}{\percent} -\end{displaymath} -% -\section{Error Propagation} -\begin{align*} - \delta\ce{[Fe^{2+}]} &= \pm\SI{0.099340}{\mole\per\deci\metre\cubed} \sqrt{\left(\frac{\pm\SI{0.00005}{\gram}\times2}{\SI{7.7910}{\gram}}\right)^2 + \left(\frac{\pm\SI{0.001}{\gram\per\mole}}{\SI{392.139}{\gram\per\mole}}\right)^2 + \left(\frac{\pm\SI{0.15}{\centi\metre\cubed}}{\SI{200.00}{\centi\metre\cubed}}\right)^2} = \pm\SI{0.00007}{\mol\per\deci\metre\cubed} \\ -% - \delta\ce{[Cr2O7^{2-}]} &= \pm\SI{0.01995}{\mole\per\deci\metre\cubed} \sqrt{\left(\frac{\pm\SI{0.00007}{\mole\per\deci\metre\cubed}}{\SI{0.099340}{\mole\per\deci\metre\cubed}}\right)^2 + \left(\frac{\pm\SI{0.06}{\centi\metre\cubed}}{\SI{20.00}{\centi\metre\cubed}}\right)^2 + \left(\frac{\pm\SI{0.1}{\centi\metre\cubed}\times 2}{\SI{16.60}{\centi\metre\cubed}}\right)^2} = \pm\SI{0.0002}{\mole\per\deci\metre\cubed} \\ - % - \delta V_{reaction \text{ } mixture} &= \pm\sqrt{\left(\pm\SI{0.015}{\centi\metre\cubed}\right)^2 + \left(\pm\SI{0.15}{\centi\metre\cubed}\right)^2 + \left(\pm\SI{0.06}{\centi\metre\cubed}\right)^2} = \pm\SI{0.2}{\centi\metre\cubed} \\ -% - \delta n_{initial \text{ } \ce{Cr2O7^{2-}}} &= \pm\SI{1.995e-3}{\mole} \sqrt{\left(\frac{\pm\SI{0.15}{\centi\metre\cubed}}{\SI{100.00}{\centi\metre\cubed}}\right)^2 + \left(\frac{\pm\SI{0.0002}{\mole\per\deci\metre\cubed}}{\SI{0.01995}{\mole\per\deci\metre\cubed}}\right)^2} = \pm\SI{0.02e-3}{\mole} \\ -% - \delta n_{final \text{ } \ce{Cr2O7^{2-}}} &= \pm\SI{6.37e-4}{\mole} \sqrt{\left(\frac{\pm\SI{0.00007}{\mole\per\deci\metre\cubed}}{\SI{0.099340}{\mole\per\deci\metre\cubed}}\right)^2 + \left(\frac{\pm\SI{0.03}{\centi\metre\cubed}}{\SI{5.00}{\centi\metre\cubed}}\right)^2 + \left(\frac{\pm\SI{0.1}{\centi\metre\cubed}\times2}{\SI{16.38}{\centi\metre\cubed}}\right)^2 + \left(\frac{\pm\SI{0.2}{\centi\metre\cubed}}{\SI{126}{\centi\metre\cubed}}\right)^2} \\ - &= \pm\SI{0.09e-4}{\mole} \\ -% - \delta n_{ethanol} &= \sqrt{\left(\pm\SI{0.02e-3}{\mole}\right)^2 + \left(\pm\SI{0.09e-4}{\mole}\right)^2} = \pm\SI{0.03e-3}{\mole} \\ -% - \delta \si{\percent} \text{ } ABV &= \pm\SI{11.9}{\percent} \sqrt{\left(\frac{\pm\SI{0.03e-3}{\mole}}{\SI{2.04e-3}{\mole}}\right)^2 + \left(\frac{\pm\SI{0.0001}{\gram\per\centi\metre\cubed}}{\SI{0.7893}{\gram\per\centi\metre\cubed}}\right)^2 + \left(\frac{\pm\SI{0.001}{\gram\per\mole}}{\SI{46.068}{\gram\per\mole}}\right)^2} = \pm\SI{0.2}{\percent} -\end{align*} -Hence the \si{\percent} ABV of ethanol of the wine was found to be $11.9 \pm 0.2 \si{\percent}$. -% -\section{Analysis of Results} -The reported \si{\percent} ABV value of the wine is greater than that determined by experiment, however the reported \si{\percent} ABV value of wine is only required to be accurate within $\pm\SI{1}{\percent}$\footcite[Annex XII]{eur-32011R1169-en}, hence there is a slight overlap between the possible error in the reported value and that of the determined value from \SIrange{12.0}{12.1}{\percent}. Despite this systematic errors are likely to have influenced the \si{\percent} ABV determined since this is at the extreme end of the uncertainty in the reported value, hence it is unlikely that the true \si{\percent} ABV value lies within this range. - -A possible error is that the ethanol might not have been fully oxidised to acetic acid hence reducing the amount of \ce{Cr2O7^{2-}} which reacted and thus the \si{\percent} ABV value determined. To minimise this error the reaction mixture could be refluxed for longer (e.g. 2 hours). There may have also been a loss of ethanol and ethanal vapour while the reactants were being transferred into the round bottomed flask. To minimise this the flask could have been cooled in an ice bath until the condenser was added, hence reducing losses due to evaporation. There was also uncertainty about the end point for the second titration since the indicator colour change was not very distinct. To minimise this an alternative indicator such as 1,10-phenanthroline ferrous sulphate solution could be used which would have more distinct colour change from blue-green to brown at the end point.\footcite[pp.~3]{senior-chem} -\end{document} diff --git a/8a/specific.bib b/8a/specific.bib deleted file mode 100644 index 5c30bb6..0000000 --- a/8a/specific.bib +++ /dev/null @@ -1,14 +0,0 @@ -@online{eur-32011R1169-en, - title = {Regulation (EU) No 1169/2011 of the European Parliament and of the Council of 25 October 2011}, - author = {Official Journal of the European Union}, - date = {2011-11-22}, - url = {http://eur-lex.europa.eu/legal-content/EN/TXT/HTML/?uri=CELEX:30211R1169}, - urldate = {2017-12-08} -} - -@online{senior-chem, - title = {Estimation of Alcohol Content in Wine by Dichromate Oxidation followed by Redox Titration}, - author = {Sirromet Wines Pty Ltd}, - url = {http://seniorchem.com/4. Alcohol-Content-bu-Dichromate-Oxidation-and-Redox-Titration.pdf}, - urldate = {2017-12-09} -} diff --git a/project/ZSM-5-Chain.png b/project/ZSM-5-Chain.png deleted file mode 100755 index d9f57ee..0000000 Binary files a/project/ZSM-5-Chain.png and /dev/null differ diff --git a/project/ZSM-5-Layer.png b/project/ZSM-5-Layer.png deleted file mode 100755 index 0e8bdb9..0000000 Binary files a/project/ZSM-5-Layer.png and /dev/null differ diff --git a/project/ZSM-5-SBU.png b/project/ZSM-5-SBU.png deleted file mode 100755 index ffbc3e9..0000000 Binary files a/project/ZSM-5-SBU.png and /dev/null differ diff --git a/project/project.bcf b/project/project.bcf deleted file mode 100644 index 232388c..0000000 --- a/project/project.bcf +++ /dev/null @@ -1,2028 +0,0 @@ - - - - - - output_encoding - ascii - - - input_encoding - ascii - - - debug - 0 - - - mincrossrefs - 2 - - - minxrefs - 2 - - - sortcase - 1 - - - sortupper - 1 - - - - - - - alphaothers - + - - - labelalpha - 0 - - - labelnamespec - shortauthor - 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- - project.bbl - - - project.bcf - - - ../bibliographies/reference.bib - ../bibliographies/coretextbooks.bib - specific.bib - - - diff --git a/project/project.tex b/project/project.tex deleted file mode 100644 index f50c9bc..0000000 --- a/project/project.tex +++ /dev/null @@ -1,716 +0,0 @@ -%Document Setup. -\documentclass[a4paper,11pt]{article} -\usepackage[a4paper]{geometry} %Set page size to A4. -\usepackage{graphicx} %Allows import of images. -%\usepackage{float} -\usepackage{floatrow} %Align tables and figures side-by-side. -%\usepackage[moderate, mathspacing=normal,leading=normal]{savetrees} %Reduce whitespace. -\usepackage{siunitx} %SI Units formatting. -%\usepackage{vhistory} %Revision History. -\usepackage[version=4]{mhchem} %Chemical Equations. -\usepackage{amsmath} %Mathematical alignments. -\usepackage{amssymb} %Mathematical symbols e.g. therefore. -\usepackage[parfill]{parskip} %Blank lines between paragraphs. -\usepackage[autostyle]{csquotes} -\usepackage{array} %Table centering. -\usepackage[british]{babel} %British localisation. -%\usepackage[backend=biber,citestyle=verbose-note,autocite=footnote]{biblatex} %Bibliography. -\usepackage[backend=biber,style=chem-rsc]{biblatex} %Bibliography. - -\numberwithin{equation}{subsection} %Number equations based on their section. -\bibliography{../bibliographies/reference,../bibliographies/coretextbooks,specific} %Use Bibliography of reference books. -\floatsetup[table]{style = plaintop} %Put captions on top of tables. -\floatsetup[figure]{style = plain} %Ensure figure captions are below figures. -\sisetup{range-phrase = --,range-units = single} %Use - for ranges and only have a single unit shown after. -\sisetup{separate-uncertainty = true,multi-part-units=single} %Use \pm for uncertainties. -\setcounter{secnumdepth}{4} %Label paragraphs as subsubsubsections. -\setcounter{tocdepth}{4} %Treat paragraphs as sections in table of contents. - -%Allow manual adding of very large brackets. -\makeatletter -\newcommand{\vast}{\bBigg@{3}} -\newcommand{\vastt}{\bBigg@{4}} -\newcommand{\Vast}{\bBigg@{5}} -\newcommand{\Vastt}{\bBigg@{6}} -\makeatother - -%Document Headings. -\begin{document} -\title{Effect of the Copper and Zinc Cations on the Ion Exchange Level Obtained for the Aqueous Phase Ion Exchange Process with the ZSM-5 Zeolite} -\author{Sam White} -\date{06/03/2018} -%\date{\vhCurrentDate\\\vhCurrentVersion} -\maketitle - -\begin{abstract} - An investigation into how the ion exchange level for ZSM-5 differs when using copper and zinc cations in an aqueous phase ion exchange process was attempted. The spectrophotometric method utilised for the measurement of the exchange level for the copper cations was found to be ineffective at producing meaningful results within the timescale of the investigation, hence precluding the comparison of the exchange levels for the different metal cations. -\end{abstract} - -\section{Aim} -This project aimed to compare how the ion exchange level for a HZSM-5 zeolite differs for the aqueous phase ion exchange process with copper and zinc cations. - -\section{Introduction} -Zeolites are crystalline, microporous solids used for a large number of uses such as for catalytic cracking, air purification, water softening and as desiccants.~\autocite{hardsoftwater,petrov12} This project was completed using the ZSM-5 (Zeolite Socony Mobil-5)\autocite{zhang15} zeolite which is used within the petrochemical industry for the conversion of methanol to gasoline, dewaxing of distillates, separation of organic products (such as separating para-xylene from its isomers) and the interconversion of hydrocarbons.\autocite{olson81,rasouli12,sarkany99} - -\subsection{Structure} -Zeolites are comprised of a finite or infinite number of unique unit cells each of which is made from a constant, integral number of the same type of secondary building unit (SBU) with each vertex in the SBU being a tetrahedron of either \ce{[SiO4]} or \ce{[AlO4]^{-}} (which are themselves known as the primary building units and are henceforth generically referred to as \ce{XO4} tetrahedra).\autocite{zeolite-atlas,petrov12,ic-zeolite-structure,han09,danaher17} Each aluminium tetrahedron in the SBU introduces a negative charge -- since aluminium has a 3+ oxidation state whereas silicon has a 4+ oxidation state -- which is balanced by the presence of cationic counterions.\autocite{gomez16,petrov12,han09,danaher17} - -The ZSM-5 zeolite used is a pentasil\autocite{danaher17,olson81} zeolite (constructed of eight five-membered rings) with an SBU containing twelve \ce{XO4} tetrahedra which form a pair of five-one units\autocite{zeolite-atlas,olson81,wu79} as shown in figure \ref{fig:zsm-5-sbu} where the vertices represent the \ce{X} atoms and the X-O-X bridges are shown as straight lines for clarity which is a reasonable approximation since the X-O-X bond angle is around $\text{\SIrange{140}{150}{\degree}} \approx \SI{180}{\degree}$ for silicas and aluminosilicates.\autocite{zeolite-atlas} - -\begin{figure}[H] - \centering - \includegraphics[width=0.25\textwidth]{ZSM-5-SBU.png} - \caption{Secondary building unit for ZSM-5 zeolite.\autocite{olson81}}\label{fig:zsm-5-sbu} -\end{figure} - -These SBUs then form long chains (depicted in figure \ref{fig:zsm-5-chain}) which themselves interconnect to form layers hence giving a unit cell containing eight SBUs shown at the centre of figure \ref{fig:zsm-5-layer}.\autocite{olson81} In figure \ref{fig:zsm-5-layer} one of the chains (shown in figure \ref{fig:zsm-5-chain}) is highlighted to demonstrate how the chains interconnect to form layers. - -\begin{figure}[H] -\begin{floatrow} - \centering - \ffigbox - {\includegraphics[width=0.2\textwidth]{ZSM-5-Chain.png}} - {\caption{Chain building unit for ZSM-5 zeolite.\autocite{olson81}}\label{fig:zsm-5-chain}} - \ffigbox - {\includegraphics[width=0.4\textwidth]{ZSM-5-Layer.png}} - {\caption{Layer of ZSM-5 zeolite.\autocite{olson81}}\label{fig:zsm-5-layer}} -\end{floatrow} -\end{figure} - -As there are eight SBUs of twelve tetrahedra per unit cell in ZSM-5 there are $8 \times 12 = 96$ \ce{X} atoms per cell hence there are $2 \times 96 = 192$ oxygen atoms per cell\autocite{zeolite-atlas} since there are two oxygen atoms per individual \ce{X} atom.\autocite{patent3702886A} This gives the unit cell formula given in \ref{eq:unit-cell} where \ce{M} is a cation with a charge of $q$, so $\frac{1}{q}$ of these cations are required per negative charge and hence aluminium atom.\autocite{ismagilov00} - -\begin{equation}\label{eq:unit-cell} - \ce{M_{\frac{n}{q}} Al_n Si_{96-n}O_{192}.x H2O} -\end{equation} - -\subsection{Ion Exchange} -These \ce{M^{$q$+}} cations can be exchanged with other ions in a process called ion exchange. Changing the counterion of the ZSM-5 zeolite can alter the acidity, hydrophobicity, reaction selectivity and other properties of the zeolite.~\autocite{rasouli12,chaudhari02,han09} - -The copper exchanged form of ZSM-5 is known to be one of the best forms of ZSM-5 for the selective catalytic reduction of \ce{NO} by \ce{C2-C4} hydrocarbons.~\autocite{sato91,yashnik05,ismagilov00} This is an important use case since large amounts of \ce{NO} are produced in vehicle and industrial boiler emissions and \ce{NO} is known to cause air pollution and acid rain.~\autocite{iwamoto91} - -Similarly the zinc exchanged form of ZSM-5 is currently subject to much research since it has been found to be effective at selectively converting methanol to use aromatic species such as benzene, toluene and xylene (important for the manufacture of polyester fibers, dyes, pesticides and medicines) as an alternative method to petroleum processing.~\autocite{niu14,wang16} Specifically ZnZSM-5 has -- so far -- been the best choice of cation for this purpose since it is cheap, non-toxic and highly effective at the aforementioned aromatization process.~\autocite{sun18} - -A ZSM-5 zeolite with a low \ce{SiO2}/\ce{AlO3} ratio of 23 was used in this investigation since this maximised the number of sites which were available for ion exchange due to the higher aluminium content. In addition zeolites with a high \ce{SiO2}/\ce{AlO3} ratio are hydrophobic\autocite{chen76,han09,olson99} hence in aqueous phase ion exchange the cation solution does not spontaneously enter the zeolite nanopores so ion exchange happens only at sites close to the pore entrance.\autocite{han09,olson99} This maximisation of the ion exchange is important since it should accentuate any differences between the ion exchange level with the different cations and make them easier to detect. - -\section{Experimental}\label{sec:experimental} -Standard solutions of \ce{Cu^{2+}} and \ce{Zn^{2+}} (\SI{50.00}{\centi\metre\cubed}) were made using \ce{CuSO4.5H2O} and \ce{ZnSO4.7H2O} with concentrations of \SI{2.008e-3}{\mole\per\deci\metre\cubed} and \SI{2.02e-3}{\mole\per\deci\metre\cubed} respectively. The absorbance of the standard copper sulphate solution was taken at \SI{806}{\nano\metre} (\num{0.484}) then \SI{20.00}{\centi\metre\cubed} of the solutions was added to \SI{0.4810}{\gram} (for the copper solution) and \SI{0.5274}{\gram} (for the zinc solution) of HZSM-5 zeolite with an \ce{SiO2}/\ce{AlO3} ratio of 23 (forming an opaque white suspension) prior to heating both solutions with stirring at \SI{70}{\celsius} for one hour. Centrifugation was completed on part of the resultant copper mixture, however time constraints prevented the completion of this process. The two mixtures were then stored in a fridge for one week until the following laboratory session. - -After one week the zeolite had sedimented so clear solution was collected and the remainder was centrifuged for 30 minutes before the supernatant was reintroduced to rest of the solution producing a slightly cloudy copper and a moderately cloudy zinc solution. The solutions were made up to \SI{100.00}{\centi\metre\cubed} before the absorbance of the copper solution at \SI{806}{\nano\metre} was determined (\num{0.110}) and \SI{20.00}{\centi\metre\cubed} aliquots of the zinc solution in a pH 10 buffer solution (\SI{2}{\centi\metre\cubed}) were titrated against a standard ethylenediaminetetraacetate (EDTA) solution (batch A: \SI{0.4993}{\mole\per\deci\metre\cubed}) with an eriochrome black T indicator (colour change from red to light blue). - -\section{Results} - -\subsection{Copper-Exchanged Zeolite} -\begin{table}[h] - \caption{Masses used for the preparation of CuZSM-5.}\label{tbl:cu-masses} - \centering - \begin{tabular}{|c|c|} - \hline - Substance & Mass / \si{\gram} \\ - \hline - \ce{CuSO4.5H2O} & 0.5014 \\ - \hline - HZSM-5 & 0.4810 \\ - \hline - \end{tabular} -\end{table} - -\begin{table}[h] - \caption{Spectrophotometric results for the copper sulphate solutions.}\label{tbl:cu-absorbance} - \centering - \begin{tabular}{|c|c|} - \hline - Substance & Absorbance \\ - \hline - Standard Solution & 0.484 \\ - \hline - Post-Reaction Solution & 0.110 \\ - \hline - \end{tabular} -\end{table} - -The uncertainty in these absorbance values can be modelled using the following equation:~\autocite{galban07} - -\begin{equation}\label{eq:spectrophotometer-uncertainty} - \delta Abs = Abs \sqrt{ \left( \frac{0.434}{Abs} k_2 \sqrt{1 + 10^{Abs}} \right)^2 - + \left( \frac{0.434}{Abs} k_3 \right)^2 } -\end{equation} - -Where $k_2$ is a measure of the expected precision of the instrument itself for a specific solution and $k_3$ is a measure of the uncertainty introduced by replacing the cuvette. - -Values of $k_2=\num{4.5e-4}$ and $k_3=\num{27e-4}$ were used (recorded by Galb\'{a}n et al.\@ for the PerkinElmer Lambda 5 spectrophotometer with ferroin solution)~\autocite{galban07} since they produce the largest overall uncertainty of values recorded by Galb\'{a}n et al.\@, hence giving the most generous estimate in the uncertainty of the absorbances recorded. Letting $A_{\ce{Cu}_\text{std.}}$ be the absorbance of the standard \ce{CuSO4} solution and $A_{\ce{Cu}_\text{prod.}}$ be the absorbance of the post-reaction solution thus gives: - -\begin{align} - \delta A_{\ce{Cu}_\text{std.}} &= 0.484 \sqrt{ \left( \frac{0.434}{0.484} \times \num{4.5e-4} \sqrt{1 + 10^{0.484}} \right)^2 - + \left( \frac{0.434}{0.484} \times \num{27e-4} \right)^2 } \nonumber \\ - \label{eq:cu-std-abs-uncertainty} - &= 0.001 \\ - \delta A_{\ce{Cu}_\text{prod.}} &= 0.110 \sqrt{ \left( \frac{0.434}{0.110} \times \num{4.5e-4} \sqrt{1 + 10^{0.110}} \right)^2 - + \left( \frac{0.434}{0.110} \times \num{27e-4} \right)^2 } \nonumber \\ - \label{eq:cu-prod-abs-uncertainty} - &= 0.001 -\end{align} - -\subsection{Zinc-Exchanged Zeolite} -\begin{table}[h] - \caption{Mass used in preparation of the \ce{ZnSO4} standard solution utilised in the standardisation of the \ce{EDTA} solution.}\label{tbl:zn-std-masses} - \centering - \begin{tabular}{|c|c|} - \hline - Substance & Mass / \si{\gram} \\ - \hline - \ce{ZnSO4.7H2O} & 0.4587 \\ - \hline - \end{tabular} -\end{table} - -\begin{table}[h] - \caption{Masses used for the preparation of ZnZSM-5.}\label{tbl:zn-zsm-5-masses} - \centering - \begin{tabular}{|c|c|} - \hline - Substance & Mass / \si{\gram} \\ - \hline - \ce{ZnSO4.7H2O} & 0.6331 \\ - \hline - HZSM-5 & 0.5274 \\ - \hline - \end{tabular} -\end{table} - -The reaction which occurred during the titrations between the \ce{EDTA^4-} and \ce{Zn^2+} ions in given in equation \ref{eq:edta-zn-reaction}: - -\begin{equation}\label{eq:edta-zn-reaction} - \ce{Zn^2+ (aq) + EDTA^4- (aq) -> ZnEDTA^2-(aq)} -\end{equation} - -%TODO: Reference. Include? -%The pH 10 buffer was used to ensure the EDTA existed in the deprotonated form which is able to complex to metal cations and also to ensure the eriochrome black T indicator exhibits the desired colour change. - -\begin{table} - \caption{Titration results from standardisation of the batch A \ce{EDTA} solution with the standard zinc sulphate solution.}\label{tbl:zn-standardisation} - \centering - \begin{tabular}{|c|c|c|c|} - \hline - Run & Start Volume / \si{\centi\metre\cubed} & End Volume / \si{\centi\metre\cubed} & Titre Volume / \si{\centi\metre\cubed} \\ - \hline - 1 & 1.45 & 33.70 & 32.25 \\ - \hline - 2 & 2.25 & 34.20 & 31.95 \\ - \hline - \end{tabular} -\end{table} - -Due to time constraints the standardisation of the \ce{EDTA} solution was not fully completed, hence the accurate titre volume ($V_{\ce{EDTA}_\text{std.}}$) has been assumed to be the titre volume from the second run (see table \ref{tbl:zn-standardisation}): - -\begin{equation}\label{eq:edta-v-standardisation} - V_{\ce{EDTA}_{std.}} = \SI{31.95}{\centi\metre\cubed} -\end{equation} - -\begin{table} - \caption{Titration results between zinc solution after ion-exchange process and standardised \ce{EDTA} solution.}\label{tbl:zn-analytical-titration} - \centering - \begin{tabular}{|c|c|c|c|} - \hline - Run & Start Volume / \si{\centi\metre\cubed} & End Volume / \si{\centi\metre\cubed} & Titre Volume / \si{\centi\metre\cubed} \\ - \hline - 1 & 2.40 & 29.10 & 26.70 \\ - \hline - 2 & 2.90 & 29.55 & 26.65 \\ - \hline - 3 & 1.40 & 28.00 & 26.60 \\ - \hline - 4 & 11.35 & 37.70 & 26.35 \\ - \hline - \end{tabular} -\end{table} - -The average titre volume for the titration with the post ion exchange solution ($V_{\ce{EDTA}_\text{prod.}}$) was determined from the second and third runs (see table \ref{tbl:zn-analytical-titration}) since the first run was a rough titration and the fourth run can be clearly seen be be anomalous. - -\begin{equation}\label{eq:edta-v-analytical} - V_{\ce{EDTA}_\text{prod.}} = \frac{\SI{26.65}{\centi\metre\cubed} + \SI{26.60}{\centi\metre\cubed}}{2} = \SI{20.63}{\centi\metre\cubed} -\end{equation} - -\section{Calculations} - -\subsection{Calculation of Maximum Theoretical Number of Ion Exchanges} -The \ce{SiO2}/\ce{Al2O3} ratio in the zeolite used was $23$. There are two \ce{Al} atoms in \ce{Al2O3} compared to one \ce{Si} atom in \ce{SiO2}, hence $\ce{Si}/\ce{Al} = \frac{23}{2} = 11.5$. - -Using the unit cell general formula (equation \ref{eq:unit-cell}) and letting the \ce{Si}/\ce{Al} ratio be $r$ and $n$ be the number of aluminium atoms per unit cell: - -\begin{align*} - r &= \frac{\text{Number of \ce{Si} per unit cell}}{\text{Number of \ce{Al} per unit cell}} \\ - \therefore r &= \frac{96 - n}{n} \\ - n r + n &= 96 \\ - \therefore n &= \frac{96}{r + 1} -\end{align*} - -Hence for $r = 11.5$ there are $n = \frac{96}{11.5 + 1} = 7.68$ \ce{Al} per unit cell. Letting $q$ be the cation charge and $x$ be the number of water molecules for unit cell thus gives: - -\begin{align*} - Mr_{\text{unit cell}} = \frac{7.68}{q} Mr_{\text{cation}} &+ (11.5(26.982)+ (96-7.68)(28.085) + 192(15.999) \\ - &+ x(2(1.008) + 15.999)) \si{\gram\per\mole} \\ - = \frac{7.68}{q} Mr_{\text{cation}} &+ \SI{5759.469}{\gram\per\mole} + x(\SI{450.375}{\gram\per\mole}) -\end{align*} - -Thus for HZSM-5 where the cation is \ce{H+} and $x \approx 25$~\autocite{donder06}. -\begin{equation}\label{eq:hzsm-5-mr} -\begin{split} - Mr_{\text{HZSM-5 unit cell}} &= \frac{7.68}{1} \times \SI{1.008}{\gram\per\mole} + (5759.469 + 25(450.375)) \text{ \si{\gram\per\mole}} \\ - &= \SI{6217.613}{\gram\per\mole} -\end{split} -\end{equation} - -Let: $q$ be the cation charge; $n_{\text{max. cation}}$ be the theoretical maximum amount of cation which can be exchanged and $n_{\text{cation}}$, $m_{\text{cation}}$ and $Mr_{\text{cation}}$ respectively be the actual amount, mass and $Mr$ of the cation exchanged. - -\begin{align} - n_{\text{HZSM-5 unit cell}} &= \frac{m_{\text{HZSM-5}}}{Mr_{\text{HZSM-5 unit cell}}} \nonumber \\ - n_{\text{max. cation}} &= \frac{7.68}{q} n_{\text{HZSM-5 unit cell}} \nonumber \\ - &= \frac{7.68}{q} \frac{m_{\text{HZSM-5}}}{Mr_{\text{HZSM-5 unit cell}}} \nonumber \\ -% - \si{\percent} \text{ Exchange Level} &= \frac{n_{\text{cation}}}{n_{\text{max. cation}}} \times \SI{100}{\percent} \nonumber \\ - \label{eq:cation-percent-exchanged} - &= \frac{q Mr_{\text{HZSM-5 unit cell}} n_{\text{cation}}}{7.68 m_{\text{HZSM-5}}} \times \SI{100}{\percent} -\end{align} - -\subsection{Calculations for Copper Solution} -\subsubsection{Determination of Molar Extinction Coefficient}\label{sec:cu-percent-exchanged} -Let $V_{\ce{Cu}_\text{std.}}$ be the volume and $[\ce{CuSO4}]_\text{std.}$ be the concentration of the standard \ce{Cu^{2+}} solution. -\begin{align} - n_{\ce{CuSO4}} &= \frac{m_{\ce{CuSO4.5H2O}}}{Mr_{\ce{CuSO4.5H2O}}} \nonumber \\ - [\ce{CuSO4}]_\text{std.} &= \frac{n_{\ce{CuSO4}}}{V_{\ce{Cu}_\text{std.}}} \nonumber\\ - \label{eq:[cuso4]-std} - &= \frac{m_{\ce{CuSO4.5H2O}}}{V_{\ce{Cu}_\text{std.}} Mr_{\ce{CuSO4.5H2O}}} -\end{align} - -Rearranging the Beer-Lambert law (equation \ref{eq:beer-lambert}) for the molar extinction coefficient: - -\begin{align} - \label{eq:beer-lambert} - A = \epsilon c l \\ - \label{eq:beer-lambert-epsilon} - \epsilon = \frac{A}{c l} -\end{align} - -Hence using equations \ref{eq:[cuso4]-std} and \ref{eq:beer-lambert-epsilon}: - -\begin{equation} -\begin{split} \label{eq:molar-extinction} - \epsilon_{\ce{CuSO4}} &= \frac{A_{\ce{Cu}_\text{std.}}}{[\ce{CuSO4}]_\text{std.} l} \\ - &= \frac{A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{std.}} Mr_{\ce{CuSO4.5H2O}}}{l m_{\ce{CuSO4.5H2O}}} -\end{split} -\end{equation} - -%This hence gives: -%\begin{align} -% \epsilon_{\text{\ce{CuSO4}}} &= \frac{0.484 \times \SI{50.00e-3}{\deci\metre\cubed} \times (63.546 + 32.066 + 4(15.999) + 5(2(1.008) + 15.999)) \text{ \si{\gram\per\mole}}}{\SI{1.0}{\centi\metre} \times \SI{0.5014}{\gram}} \nonumber\\ -% \label{eq:molar-extinction-calc} -% &= \frac{0.484 \times \SI{50.00e-3}{\deci\metre\cubed} \times \SI{249.677}{\gram\per\mole}}{\SI{1.0}{\centi\metre} \times \SI{0.5014}{\gram}} = \SI{12.05}{\deci\metre\cubed\per\mole\per\centi\metre} -%\end{align} - -\subsubsection{Determination of \ce{Cu^2+} Ion Exchange Level} -By rearranging the Beer-Lambert Law (equation \ref{eq:beer-lambert}) for concentration: - -\begin{equation} \label{eq:beer-lambert-c} - c = \frac{A}{\epsilon l} -\end{equation} - -Letting $[\ce{CuSO4}]_\text{prod.}$ be the concentration, $n_{\ce{Cu}_\text{prod.}}$ be the amount of \ce{Cu^{2+}} ions and $V_{\ce{Cu}_\text{prod.}}$ be the volume of the solution after the ion exchange process while using equation \ref{eq:beer-lambert-c}: - -\begin{align} - [\ce{CuSO4}]_\text{prod.} &= \frac{A_{\ce{Cu}_\text{prod.}}}{\epsilon_{\text{\ce{CuSO4}}} l} \nonumber \\ - \text{So: } n_{\ce{Cu}_\text{prod.}} &= [\ce{CuSO4}]_\text{prod.} V_{\ce{Cu}_\text{prod.}} \nonumber \\ - \label{eq:n_cu-prod} - &= \frac{A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}}}{\epsilon_{\text{\ce{CuSO4}}} l} -\end{align} - -Substituting equation \ref{eq:molar-extinction} into \ref{eq:n_cu-prod}: - -\begin{equation} \label{eq:n_cu-prod-final} - n_{\ce{Cu}_\text{prod.}} = \frac{A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} m_{\ce{CuSO4.5H2O}}}{A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{std.}} Mr_{\ce{CuSO4.5H2O}}} -\end{equation} - -The amount of \ce{Cu^2+} exchanged ($n_{\ce{Cu}_\text{ex.}}$) can hence be determined using equations \ref{eq:[cuso4]-std} and \ref{eq:n_cu-prod-final} where $V_{\ce{Cu}_\text{react.}}$ is the volume of the standard copper solution added to the HZSM-5. - -\begin{align} - n_{\ce{Cu}_\text{ex.}} &= [\ce{CuSO4}]V_{\ce{Cu}_\text{react.}} - n_{\ce{Cu}_\text{prod.}} \nonumber\\ - % \label{ - &= \frac{m_{\ce{CuSO4.5H2O}} V_{\ce{Cu}_\text{react.}}}{V_{\ce{Cu}_\text{std.}} Mr_{\ce{CuSO4.5H2O}}} - \frac{A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} m_{\ce{CuSO4.5H2O}}}{A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{std.}} Mr_{\ce{CuSO4.5H2O}}} \nonumber \\ - \label{eq:cu-exchanged} - &= \frac{m_{\ce{CuSO4.5H2O}} \left(A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{react.}} - A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} \right)}{A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{std.}} Mr_{\ce{CuSO4.5H2O}}} -\end{align} - -Substituting equation \ref{eq:cu-exchanged} into equation \ref{eq:cation-percent-exchanged} as $n_\text{cation}$ and setting $q = 2$ hence gives: - -\begin{equation} \label{eq:cu-percent-exchanged} -\begin{split} - \si{\percent} \text{ \ce{Cu^{2+}} Exchanged} &= \frac{2 Mr_{\text{HZSM-5 unit cell}} m_{\ce{CuSO4.5H2O}} \left(A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{react.}} - A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} \right)}{7.68 m_{\text{HZSM-5}} A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{std.}} Mr_{\ce{CuSO4.5H2O}}} \\ - &\phantom{=} \times \SI{100}{\percent} -\end{split} -\end{equation} - -Using \ref{eq:cu-percent-exchanged} with: - -\begin{align*} - Mr_{\text{HZSM-5 unit cell}} &= \SI{6217.613}{\gram\per\mole} \text{ from equation \ref{eq:hzsm-5-mr}} \\ - m_{\ce{CuSO4.5H2O}} &= \SI{0.5014 \pm 0.00005}{\gram} \text{ from table \ref{tbl:cu-masses}} \\ - A_{\ce{Cu}_\text{std.}} &= \num{0.484 \pm 0.001} \text{ from table \ref{tbl:cu-absorbance} and equation \ref{eq:cu-std-abs-uncertainty}} \\ - V_{\ce{Cu}_\text{react.}} &= \SI{20.00 \pm 0.06 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})} \\ - A_{\ce{Cu}_\text{prod.}} &= \num{0.110 \pm 0.001} \text{ from table \ref{tbl:cu-absorbance} and equation \ref{eq:cu-prod-abs-uncertainty}} \\ - V_{\ce{Cu}_\text{prod.}} &= \SI{100.00 \pm 0.20 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})}\\ - m_{\text{HZSM-5}} &= \SI{0.4810 \pm 0.00005}{\gram} \text{ from table \ref{tbl:cu-masses}} \\ - V_{\ce{Cu}_\text{std.}} &= \SI{50.00 \pm 0.06 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})} \\ - Mr_{\ce{CuSO4.5H2O}} &= \SI{249.685}{\gram\per\mole} \text{ \autocite[Physical Constants of Inorganic Compounds, 4-60]{crc-handbook}} -\end{align*} - -\begin{align*} - \begin{split} - \si{\percent} \text{ \ce{Cu^{2+}} Exchanged} &= \frac{2 \times \SI{6217.613}{\gram\per\mole} \times \SI{0.50140}{\gram}\left(0.484 \times 20.00 - 0.110 \times 100.00\right)\num{e-3} \text{ \si{\deci\metre\cubed}}}{7.68 \times \SI{0.4810}{\gram} \times 0.484 \times \SI{50.00e-3}{\deci\metre\cubed} \times \SI{249.577}{\gram\per\mole}} \\ - &\phantom{=} \times \SI{100}{\percent} - \end{split} \\ - &= \SI{-37}{\percent} -\end{align*} - -\subsubsection{Error Propagation} \label{sec:cu-error-propagation} -Let the percentage exchange level of \ce{Cu^2+} be $v_{\ce{Cu}}$ in the error propagation below: - -\begin{equation} -\label{eq:cu-error-propagation-initial} -\begin{split} - \delta v_{\ce{Cu}} = &v_{\ce{Cu}} - \vast( %Manually putting in large brackets for square root. - \left( \frac{\delta Mr_{\text{HZSM-5 unit cell}}}{Mr_{\text{HZSM-5 unit cell}}}\right)^2 - + \left( \frac{\delta m_{\ce{CuSO4.5H2O}}}{m_{\ce{CuSO4.5H2O}}}\right)^2 - + \left( - \frac{ - \delta \left( A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{react.}} - A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} \right) - } - { - A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{react.}} - A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} - } - \right)^2 \\ - %New Line - %New Line. - &+ \left( \frac{\delta m_{\text{HZSM-5}}}{m_{\text{HZSM-5}}} \right)^2 - + \left( \frac{\delta A_{\ce{Cu}_\text{std.}}}{A_{\ce{Cu}_\text{std.}}} \right)^2 - + \left( \frac{\delta V_{\ce{Cu}_\text{std.}}}{V_{\ce{Cu}_\text{std.}}} \right)^2 - + \left( \frac{\delta Mr_{\ce{CuSO4.5H2O}}}{Mr_{\ce{CuSO4.5H2O}}} \right)^2 - \vast)^{1/2} -\end{split} -\end{equation} - -Let $S = A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{react.}} - A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}}$, thus: - -\begin{align} - \delta S = - &\left( - \left( \delta \left( A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{react.}} \right) \right)^2 - + \left( \delta \left( A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} \right) \right)^2 - \right)^{1/2} \nonumber \\ - %Next Line. - \begin{split} - = &\vastt( - \left( - A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{react.}} - \left( - \left( \frac{\delta A_{\ce{Cu}_\text{std.}}}{A_{\ce{Cu}_\text{std.}}} \right)^2 - + \left( \frac{ \delta V_{\ce{Cu}_\text{react.}}}{V_{\ce{Cu}_\text{react.}}} \right)^2 - \right)^{1/2} - \right)^2 \\ - %Split Equation. - &+ - \left( - A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} - \left( - \left( \frac{\delta A_{\ce{Cu}_\text{prod.}}}{A_{\ce{Cu}_\text{prod.}}} \right)^2 - + \left( \frac{ \delta V_{\ce{Cu}_\text{prod.}}}{V_{\ce{Cu}_\text{prod.}}} \right)^2 - \right)^{1/2} - \right)^2 - \vastt)^{1/2} - \end{split} \nonumber \\ - %Next Line. - \begin{split} \label{eq:delta-s} - = &\vast( - A_{\ce{Cu}_\text{std.}}^2 V_{\ce{Cu}_\text{react.}}^2 - \left( - \left( \frac{\delta A_{\ce{Cu}_\text{std.}}}{A_{\ce{Cu}_\text{std.}}} \right)^2 - + \left( \frac{ \delta V_{\ce{Cu}_\text{react.}}}{V_{\ce{Cu}_\text{react.}}} \right)^2 - \right) \\ - %Split Equation. - &+ - A_{\ce{Cu}_\text{prod.}}^2 V_{\ce{Cu}_\text{prod.}}^2 - \left( - \left( \frac{\delta A_{\ce{Cu}_\text{prod.}}}{A_{\ce{Cu}_\text{prod.}}} \right)^2 - + \left( \frac{ \delta V_{\ce{Cu}_\text{prod.}}}{V_{\ce{Cu}_\text{prod.}}} \right)^2 - \right) - \vast)^{1/2} - \end{split} -\end{align} - -Hence substituting equation \ref{eq:delta-s} into \ref{eq:cu-error-propagation-initial} gives: - -\begin{equation} -\label{eq:cu-error-propagation} -\begin{split} - \delta v_{\ce{Cu}} = &v_{\ce{Cu}} - \Vast( %Manually putting in large brackets for square root. - \left(\frac{\delta Mr_{\text{HZSM-5 unit cell}}}{Mr_{\text{HZSM-5 unit cell}}}\right)^2 - + \left(\frac{\delta m_{\ce{CuSO4.5H2O}}}{m_{\ce{CuSO4.5H2O}}}\right)^2 \\ - %New Line - &+ \frac{ - A_{\ce{Cu}_\text{std.}}^2 V_{\ce{Cu}_\text{react.}}^2 - \left( - \left(\frac{\delta A_{\ce{Cu}_\text{std.}}}{A_{\ce{Cu}_\text{std.}}}\right)^2 - + \left(\frac{\delta V_{\ce{Cu}_\text{react.}}}{V_{\ce{Cu}_\text{react.}}}\right)^2 - \right) - + A_{\ce{Cu}_\text{prod.}}^2 V_{\ce{Cu}_\text{prod.}}^2 - \left( - \left(\frac{\delta A_{\ce{Cu}_\text{prod.}}}{A_{\ce{Cu}_\text{prod.}}}\right)^2 - + \left(\frac{\delta V_{\ce{Cu}_\text{prod.}}}{V_{\ce{Cu}_\text{prod.}}}\right)^2 - \right) - } - { - \left( - A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{react.}} - A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} - \right)^2 - } \\ - %New Line. - &+ \left(\frac{\delta m_{\text{HZSM-5}}}{m_{\text{HZSM-5}}}\right)^2 - + \left(\frac{\delta A_{\ce{Cu}_\text{std.}}}{A_{\ce{Cu}_\text{std.}}}\right)^2 - + \left(\frac{\delta V_{\ce{Cu}_\text{std.}}}{V_{\ce{Cu}_\text{std.}}}\right)^2 - + \left(\frac{\delta Mr_{\ce{CuSO4.5H2O}}}{Mr_{\ce{CuSO4.5H2O}}}\right)^2 - \Vast)^{1/2} -\end{split} -\end{equation} - -Substituting values into equation \ref{eq:cu-error-propagation} yields: - -\begin{displaymath} - \delta v_{\ce{Cu}} = \pm \SI{3}{\percent} -\end{displaymath} - -So the percentage exchange level of \ce{Cu^2+} is \SI{-37 \pm 3}{\percent}. - -\subsection{Calculations for Zinc Solution} -\subsubsection{Determination of EDTA Solution (Batch A) Concentration} -Let: $V_{\ce{Zn}_\text{std.}}$ be the volume, $[\ce{ZnSO4}]_\text{std.}$ be the concentration and $m_{\ce{ZnSO4.7H2O}_\text{std}.}$ be the mass of \ce{ZnSO4.7H2O} used for the preparation of the \ce{ZnSO4} standard solution used to standardise the \ce{EDTA} solution. Thus: - -\begin{equation}\label{eq:[znso4]-std} - [\ce{ZnSO4}]_\text{std.} = \frac{m_{\ce{ZnSO4.7H2O}_\text{std}.}}{Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std.}}} -\end{equation} - -From equation \ref{eq:edta-zn-reaction} there is a 1:1 stoichiometric ratio between the \ce{Zn^2+} and \ce{EDTA^4-} ions. Letting $[\ce{EDTA^4-}]$ be the concentration of the \ce{EDTA} solution, $n_{\ce{Zn}_\text{std. analyte}}$ be the amount and $V_{\ce{Zn}_\text{std. aliquot}}$ be the volume of \ce{Zn^2+} ions in the analyte hence gives: - -\begin{equation}\label{eq:[edta]-1} - [\ce{EDTA^4-}] = \frac{n_{\ce{Zn}_\text{std. analyte}}}{V_{\ce{EDTA}_\text{std.}}} = \frac{[\ce{ZnSO4}]_\text{std.} V_{\ce{Zn}_\text{std. aliquot}}}{V_{\ce{EDTA}_\text{std.}}} -\end{equation} - -Substituting equation \ref{eq:[znso4]-std} into equation \ref{eq:[edta]-1} gives: - -\begin{equation}\label{eq:[edta]-final} - [\ce{EDTA^4-}] = \frac{m_{\ce{ZnSO4.7H2O}_\text{std}.} V_{\ce{Zn}_\text{std. aliquot}}}{Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}}} -\end{equation} - -\subsubsection{Determination of \ce{Zn^2+} Ion Exchange Level}\label{sec:zn-percent-exchanged} -For the standard \ce{ZnSO4} solution added to the HZSM-5 let $m_{\ce{ZnSO4.7H2O}_\text{orig.}}$ be the mass of \ce{ZnSO4.7H2O} used and let $V_{\ce{Zn}_\text{std. orig.}}$ and $[\ce{ZnSO4}]_\text{std. orig.}$ be the volume and concentration of the solution respectively. - -\begin{equation} - \label{eq:[znso4]-std-orig} - [\ce{ZnSO4}]_\text{std. orig.} = \frac{m_{\ce{ZnSO4.7H2O}_\text{orig.}}}{Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std. orig.}}} -\end{equation} - -Using equation \ref{eq:[znso4]-std-orig} with $V_{\ce{Zn}_\text{orig.}}$ as the volume of the standard solution used in the ion-exchange process: - -\begin{align} - n_{\ce{Zn}_\text{orig.}} &= [\ce{ZnSO4}]_\text{std. orig.} V_{\ce{Zn}_\text{orig.}} \nonumber \\ - \label{eq:zn-amount-orig} - &= \frac{m_{\ce{ZnSO4.7H2O}_\text{orig.}} V_{\ce{Zn}_\text{orig.}}}{Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std. orig.}}} -\end{align} - -The amount of zinc remaining in solution after the ion exchange ($n_{\ce{Zn}_\text{prod.}}$) can be calculated using equation \ref{eq:[edta]-final} with $V_{\ce{Zn}_\text{prod.}}$ being the volume the solution after the reaction and $V_{\ce{Zn}_\text{prod. aliquot}}$ being the volume of the aliquot titrated. By equation \ref{eq:edta-zn-reaction} the stoichiometric ratio for the reaction between the \ce{Zn^2+} and \ce{EDTA^4-} in the titration is 1:1, so: - -\begin{align} - n_{\ce{Zn}_\text{prod.}} &= \frac{V_{\ce{EDTA}_\text{prod.}} [\ce{EDTA^4-}]}{V_{\ce{Zn}_\text{prod. aliquot}}} \times V_{\ce{Zn}_\text{prod.}} \nonumber \\ - \label{eq:zn-amount-product} - &= \frac{V_{\ce{EDTA}_\text{prod.}} m_{\ce{ZnSO4.7H2O}_\text{std.}} V_{\ce{Zn}_\text{std. aliquot}} V_{\ce{Zn}_\text{prod.}}}{V_{\ce{Zn}_\text{prod. aliquot}} Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}}} -\end{align} - -Using equations \ref{eq:zn-amount-orig} and \ref{eq:zn-amount-product} to calculate the amount of \ce{Zn^2+} ions exchanged with the HZSM-5 ($n_{\ce{Zn}_\text{ex.}}$) gives: - -\begin{align} - n_{\ce{Zn}_\text{ex.}} &= n_{\ce{Zn}_\text{orig.}} - n_{\ce{Zn}_\text{prod.}} \nonumber \\ - &= \frac{m_{\ce{ZnSO4.7H2O}_\text{orig.}} V_{\ce{Zn}_\text{orig.}}}{Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std. orig.}}} - \frac{V_{\ce{EDTA}_\text{prod.}} m_{\ce{ZnSO4.7H2O}_\text{std.}} V_{\ce{Zn}_\text{std. aliquot}} V_{\ce{Zn}_\text{prod.}}}{V_{\ce{Zn}_\text{prod. aliquot}} Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}}} \nonumber \\ - \begin{split} - \label{eq:zn-amount-exchanged} - &= \frac{V_{\ce{Zn}_\text{prod. aliquot}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}} m_{\ce{ZnSO4.7H2O}_\text{orig.}} V_{\ce{Zn}_\text{orig.}}}{V_{\ce{Zn}_\text{std. orig.}} V_{\ce{Zn}_\text{prod. aliquot}} Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}}} \\ - &\phantom{=} - \frac{V_{\ce{Zn}_\text{std. orig.}} V_{\ce{EDTA}_\text{prod.}} m_{\ce{ZnSO4.7H2O}_\text{std.}} V_{\ce{Zn}_\text{std. aliquot}} V_{\ce{Zn}_\text{prod.}}}{V_{\ce{Zn}_\text{std. orig.}} V_{\ce{Zn}_\text{prod. aliquot}} Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}}} - \end{split} -\end{align} - -Hence substituting equation \ref{eq:zn-amount-exchanged} into \ref{eq:cation-percent-exchanged} for $n_\text{cation}$ and setting $q=2$ gives: - -\begin{equation}\label{eq:zn-percent-exchanged} -\begin{split} - \text{\si{\percent} \ce{Zn} Exchanged} &= \frac{2 Mr_{\text{HZSM-5 unit cell}}}{7.68 m_{\text{HZSM-5}} V_{\ce{Zn}_\text{std. orig.}} V_{\ce{Zn}_\text{prod. aliquot}} Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}}} \\ - &\phantom{=} \times (V_{\ce{Zn}_\text{prod. aliquot}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}} m_{\ce{ZnSO4.7H2O}_\text{orig.}} V_{\ce{Zn}_\text{orig.}} \\ - &\phantom{= \times (} - V_{\ce{Zn}_\text{std. orig.}} V_{\ce{EDTA}_\text{prod.}} m_{\ce{ZnSO4.7H2O}_\text{std.}} V_{\ce{Zn}_\text{std. aliquot}} V_{\ce{Zn}_\text{prod.}}) \times \SI{100}{\percent} -\end{split} -\end{equation} - -Using equation \ref{eq:zn-percent-exchanged} with: - -\begin{align*} - Mr_\text{HZSM-5 unit cell} &= \SI{6217.613}{\gram\per\mole} \text{ from equation \ref{eq:hzsm-5-mr}} \\ - V_{\ce{Zn}_\text{prod. aliquot}} &= \SI{20.00 \pm 0.06 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})} \\ - V_{\ce{Zn}_\text{std.}} &= \SI{100.00 \pm 0.20 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})} \\ - V_{\ce{EDTA}_\text{std.}} &= \SI{31.95 \pm 0.2 e-3}{\deci\metre\cubed} \text{ from equation \ref{eq:edta-v-standardisation}} \\ - m_{\ce{ZnSO4.7H2O}_\text{orig.}} &= \SI{0.6331 \pm 0.00005 e-3}{\gram} \text{ from table \ref{tbl:zn-zsm-5-masses}} \\ - V_{\ce{Zn}_\text{orig.}} &= \SI{20.00 \pm 0.06 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})} \\ - V_{\ce{Zn}_\text{std. orig.}} &= \SI{50.00 \pm 0.06 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})} \\ - V_{\ce{EDTA}_\text{prod.}} &= \SI{26.63 \pm 0.2 e-3}{\deci\metre\cubed} \text{ from equation \ref{eq:edta-v-analytical}} \\ - m_{\ce{ZnSO4.7H2O}_\text{std.}} &= \SI{0.4587 \pm 0.00005}{\gram} \text{ from table \ref{tbl:zn-std-masses}} \\ - V_{\ce{Zn}_\text{std. aliquot}} &= \SI{10.00 \pm 0.04 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})} \\ - V_{\ce{Zn}_\text{prod.}} &= \SI{100.00 \pm 0.20 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})} \\ - m_{\text{HZSM-5}} &= \SI{0.5274 \pm 0.00005}{\gram} \text{ from table \ref{tbl:zn-zsm-5-masses}} \\ - Mr_{\ce{ZnSO4.7H2O}} &= \SI{287.578}{\gram\per\mole} \text{ \autocite[Phyical Constants of Inorganic Compounds, 4-96]{crc-handbook}} -\end{align*} - -Gives: - -\begin{displaymath} - \text{\si{\percent} \ce{Zn} Exchanged} = \SI{66}{\percent} -\end{displaymath} - -\subsubsection{Error Propagation} -Let the percentage of \ce{Zn^2+} exchanged be $v_{\ce{Zn}}$ in the following error propagation: - -\begin{equation} -\label{eq:zn-error-propagation-1} -\begin{split} - \delta v_{\ce{Zn}} = &v_{\ce{Zn}} - \vast( - \left( \frac{\delta Mr_\text{HZSM-5 unit cell}}{Mr_\text{HZSM-5 unit cell}} \right)^2 + - \left( \frac{\delta m_{\text{HZSM-5}}}{m_{\text{HZSM-5}}} \right)^2 + - \left( \frac{\delta V_{\ce{Zn}_\text{std. orig.}}}{V_{\ce{Zn}_\text{std. orig.}}} \right)^2 + - \left( \frac{\delta V_{\ce{Zn}_\text{prod. aliquot}}}{V_{\ce{Zn}_\text{prod. aliquot}}} \right)^2 \\ - %New Line - &+ \left( \frac{\delta Mr_{\ce{ZnSO4.7H2O}}}{Mr_{\ce{ZnSO4.7H2O}}} \right)^2 + - \left( \frac{\delta V_{\ce{Zn}_\text{std.}}}{V_{\ce{Zn}_\text{std.}}} \right)^2 + - \left( \frac{\delta V_{\ce{EDTA}_\text{std.}}}{V_{\ce{EDTA}_\text{std.}}} \right)^2 \\ - %New Line - &+ \Bigg( - \frac{ - \delta \big( V_{\ce{Zn}_\text{prod. aliquot}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}} m_{\ce{ZnSO4.7H2O}_\text{orig.}} V_{\ce{Zn}_\text{orig.}} - V_{\ce{Zn}_\text{std. orig.}} V_{\ce{EDTA}_\text{prod.}} - } - { - V_{\ce{Zn}_\text{prod. aliquot}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}} m_{\ce{ZnSO4.7H2O}_\text{orig.}} V_{\ce{Zn}_\text{orig.}} - V_{\ce{Zn}_\text{std. orig.}} V_{\ce{EDTA}_\text{prod.}} - } \\ - %New Line - &\frac{ - m_{\ce{ZnSO4.7H2O}_\text{std.}} V_{\ce{Zn}_\text{std. aliquot}} V_{\ce{Zn}_\text{prod.}} \big) - } - { - m_{\ce{ZnSO4.7H2O}_\text{std.}} V_{\ce{Zn}_\text{std. aliquot}} V_{\ce{Zn}_\text{prod.}} - } - \Bigg)^2 - \vast)^{1/2} -\end{split} -\end{equation} - -Using the same process demonstrated in section \ref{sec:cu-error-propagation} used for equation \ref{eq:delta-s} to expand the subtraction within equation \ref{eq:zn-error-propagation-1} hence gives equation \ref{eq:zn-error-propagation} below: - -\begin{equation} -\label{eq:zn-error-propagation} -\begin{split} - \delta v_{\ce{Zn}} = &v_{\ce{Zn}} - \Vastt( - \left( \frac{\delta Mr_\text{HZSM-5 unit cell}}{Mr_\text{HZSM-5 unit cell}} \right)^2 + - \left( \frac{\delta m_{\text{HZSM-5}}}{m_{\text{HZSM-5}}} \right)^2 + - \left( \frac{\delta V_{\ce{Zn}_\text{std. orig.}}}{V_{\ce{Zn}_\text{std. orig.}}} \right)^2 + - \left( \frac{\delta V_{\ce{Zn}_\text{prod. aliquot}}}{V_{\ce{Zn}_\text{prod. aliquot}}} \right)^2 \\ - %New Line - &+ \left( \frac{\delta Mr_{\ce{ZnSO4.7H2O}}}{Mr_{\ce{ZnSO4.7H2O}}} \right)^2 + - \left( \frac{\delta V_{\ce{Zn}_\text{std.}}}{V_{\ce{Zn}_\text{std.}}} \right)^2 + - \left( \frac{\delta V_{\ce{EDTA}_\text{std.}}}{V_{\ce{EDTA}_\text{std.}}} \right)^2 \\ - %New Line - &+ \frac{ - V_{\ce{Zn}_\text{prod. aliquot}}^2 V_{\ce{Zn}_\text{std.}}^2 V_{\ce{EDTA}_\text{std.}}^2 m_{\ce{ZnSO4.7H2O}_\text{orig.}}^2 V_{\ce{Zn}_\text{orig.}}^2 - \vast( - \left( \frac{\delta V_{\ce{Zn}_\text{prod. aliquot}}}{V_{\ce{Zn}_\text{prod. aliquot}}} \right)^2 - } - { - \big( V_{\ce{Zn}_\text{prod. aliquot}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}} m_{\ce{ZnSO4.7H2O}_\text{orig.}} V_{\ce{Zn}_\text{orig.}} - V_{\ce{Zn}_\text{std. orig.}} V_{\ce{EDTA}_\text{prod.}} - } \\ - %New Line. - &\frac{ - + \left( \frac{\delta V_{\ce{Zn}_\text{std.}}}{V_{\ce{Zn}_\text{std.}}} \right)^2 - + \left( \frac{\delta V_{\ce{EDTA}_\text{std.}}}{V_{\ce{EDTA}_\text{std.}}} \right)^2 - + \left( \frac{\delta m_{\ce{ZnSO4.7H2O}_\text{orig.}}}{m_{\ce{ZnSO4.7H2O}_\text{orig.}}} \right)^2 - + \left( \frac{\delta V_{\ce{Zn}_\text{orig.}}}{V_{\ce{Zn}_\text{orig.}}} \right)^2 - \vast) - + V_{\ce{Zn}_\text{std. orig.}}^2 - } - { - m_{\ce{ZnSO4.7H2O}_\text{std.}} V_{\ce{Zn}_\text{std. aliquot}} V_{\ce{Zn}_\text{prod.}} \big)^2 \hfill - } \\ - %New Line. - &\frac{ - V_{\ce{EDTA}_\text{prod.}}^2 m_{\ce{ZnSO4.7H2O}_\text{std.}}^2 V_{\ce{Zn}_\text{std. aliquot}}^2 V_{\ce{Zn}_\text{prod.}}^2 - \vast( - \left( \frac{\delta V_{\ce{Zn}_\text{std. orig.}}}{V_{\ce{Zn}_\text{std. orig.}}} \right)^2 - + \left( \frac{\delta V_{\ce{EDTA}_\text{prod.}}}{V_{\ce{EDTA}_\text{prod.}}} \right)^2 - } - {} \\ - %New Line - &\frac{ - + \left( \frac{\delta m_{\ce{ZnSO4.7H2O}_\text{std.}}}{m_{\ce{ZnSO4.7H2O}_\text{std.}}} \right)^2 - + \left( \frac{\delta V_{\ce{Zn}_\text{std. aliquot}}}{V_{\ce{Zn}_\text{std. aliquot}}} \right)^2 - + \left( \frac{\delta V_{\ce{Zn}_\text{prod.}}}{V_{\ce{Zn}_\text{prod.}}} \right)^2 - \vast) - } - {} - \Vastt)^{1/2} -\end{split} -\end{equation} - -Substituting values into equation \ref{eq:zn-error-propagation} gives: - -\begin{displaymath} - \delta v_{\ce{Zn}} = \pm \SI{3}{\percent} -\end{displaymath} - -Hence the percentage ion exchange level of \ce{Zn^2+} is \SI{66 \pm 3}{\percent}. - -\section{Discussion} -%TODO: Compared molar extinction coefficient value to literature value. -%TODO: Note the acidity of some metal ions formed other substances in solution. -%TODO: add note explaining when separate ZnSO4 solution prepared for standardisation of EDTA solution - not a primary analytical standard. - -\subsection{General} -Between laboratory sessions the solutions were stored in a fridge in an attempt to reduce the rate of ion exchange since some of the ZSM-5 had already been separated out of the copper solution. This is not likely to have been very effective since the temperature of the fridge is still fairly high and the samples were left for a long period of time (one week), hence both samples are likely to have reached new equilibriums during this time thus effecting the results collected. It would have been better if the initial centrifugation of the copper solution was not completed since then both mixtures would have been exposed to the same conditions, hence still allowing direct comparison of the ion exchange results. - -Losses of the non-exchanged ions occurred for both solutions during the centrifugation process since some metal ions will have remained within the precipitate and in the centrifuge tube when the supernatant fluid was collected. To reduce this loss distilled water could be added to the centrifuge tube and additional centrifugation performed, hence washing the tube. This was not completed due to time limitations. - -Both the copper and zinc solutions were cloudy following the centrifugation indicating that some ZSM-5 remained suspended in the solutions. Further centrifugation would have reduced the amount of suspended zeolite from the solutions and hence the errors resultant from this (see sections \ref{sec:cu-discussion} and \ref{sec:zn-discussion}). Centrifugation was chosen instead of filtration to separate the zeolite since the nano-size particles of ZSM-5 can block the filter paper during filtrations hence resulting in very long filtration times.~\autocite{russell} - -While monomeric species such as \ce{Cu^2+} and \ce{Zn^2+} are likely to be the predominant species present in the ZSM-5 zeolite after the ion exchange process other species such as (\ce{[ZnOH]+} which subsequently form \ce{[ZnOZn]^2+} dimeric bridges upon drying) and \ce{[Cu2(OH)2]^2+} may alternatively be formed.\autocite{almutairi11,schreier05,mhamdi09} The formation of these species allows a 1:1 exchange between the hydrogen and the metal cations thus allowing the possibility of an ion exchange level greater than the maximum calculated,~\autocite{almutairi11,schreier05} however the exchange of the monomeric species is thermodynamically preferred and the alternative species only form at isolated \ce{Al} centres when using aqueous phase ion exchange as the preparation technique.~\autocite{aleksandrov10,penzien04} It is thus unlikely that a large amount of the dimeric species was present in the products created, thus they can be assumed to have no effect on the ion exchange level obtained. - -\subsection{Copper Exchanged ZSM-5}\label{sec:cu-discussion} -As seen in section \ref{sec:cu-percent-exchanged} the calculated exchange level for the \ce{Cu^2+} ions with the HZSM-5 was negative. This can be explained by the presence of the suspended ZSM-5 in solution which increased the absorbance value of the sample thus resulting in the negative yield calculated. To reduce the effect of this suspended zeolite a titrimetric method for calculating the copper ion concentration could have been used for example using \ce{EDTA} solution as the titrant and Fast Sulphon F as the indicator.~\autocite{denby-copper-conc} This would also allow a better comparison between the copper and zinc ion exchange processes since the similar methods could compensate for common systematic errors. - -\subsection{Zinc Exchanged ZSM-5}\label{sec:zn-discussion} -From section \ref{sec:zn-percent-exchanged} the percentage of zinc calculated to have been exchanged with the ZSM-5 zeolite was \SI{66 \pm 3}{\percent}. Tamiyakul et al.\@ completed an ion exchange between HZSM-5 with an \ce{SiO2}/\ce{AlO3} ratio of 30 and \ce{Zn(NO3)2} at \SI{70}{\celsius} for 12 hours and obtained an ion exchange level of $\frac{\SI{0.64}{\percent}}{\SI{1.5}{\percent}} \times \SI{100}{\percent} = \SI{43}{\percent}$.\autocite{tamiyakul15} The \ce{SiO2}/\ce{AlO3} ratio of the HZSM-5 used by Tamiyakul et al.\@ is larger than that used in this project, hence a higher ion exchange level is expected, however Yashnik et al.\@ only obtained a \SI{22}{\percent} higher ion exchange level with \ce{CuSO4} while using HZSM-5 with an \ce{SiO2}/\ce{AlO3} ratio of 17 compared to when HZSM-5 with a ratio of 30 was used.~\autocite{yashnik05} The difference in the \ce{SiO2}/\ce{AlO3} ratio of the HZSM-5 between this project and the HZSM-5 used by Tamiyakul et al.\@ is almost half of the difference between the samples compared by Yashnik et al.\@ while the difference in ion exchange level is slightly greater (\SI{23}{\percent}), thus suggesting that the ion exchange level obtained is too high. - -This can be explained by the losses in the centrifugation described earlier and also since the post-ion exchange solution contained suspended zeolite hence the aliquot volume in the titration was too small since the suspended zeolite displaced some of the solution when the volume was being measured. This thus reduced the titre volume recorded which can be seen to have inflated the ion exchange level calculated (by inspection of equation \ref{eq:zn-percent-exchanged}). - -This may also partially explain the anomalous final titre volume obtained in the titration (see run 4 in table \ref{tbl:zn-analytical-titration}) since some of the solid zeolite may have settled in the bottom of the volumetric flask, hence for this final titration the pipette contained a greater number of suspended zeolite particles thus further reducing the analyte volume and resulting in the anomalously small titre volume. - -\subsection{Uncertainties} -The percentage uncertainty in both of the obtained results is quite high at \SI{3}{\percent}, although the actual error is greater than this due to the systematic errors discussed. This could be reduced by instead using Diffuse Reflectance Fourier Transform Infrared Spectroscopy (DRIFT-IR)\autocite{pollanen05} on the ZSM-5 samples and obtaining the ion exchange level through comparing the integration of the \SIrange{3570}{3630}{\per\centi\metre} peak between the ion exchanged ZSM-5 samples and the original HZSM-5 sample.~\autocite{yu12} This would result in a smaller error compared to the titrimetric method since the number of measurements required for the calculation is much less hence reducing the number of errors introduced. - -%Bibliography. -\printbibliography - -\section{Supplementary Information} -%TODO: Attach risk assessments. - -\end{document} diff --git a/project/risk-assessment/combined.pdf b/project/risk-assessment/combined.pdf deleted file mode 100644 index e101082..0000000 Binary files a/project/risk-assessment/combined.pdf and /dev/null differ diff --git a/project/risk-assessment/project.pdf b/project/risk-assessment/project.pdf deleted file mode 100644 index 684d35d..0000000 Binary files a/project/risk-assessment/project.pdf and /dev/null differ diff --git a/project/risk-assessment/risk-assessment.odt b/project/risk-assessment/risk-assessment.odt deleted file mode 100644 index 9c25742..0000000 Binary files a/project/risk-assessment/risk-assessment.odt and /dev/null differ diff --git a/project/risk-assessment/risk-assessment.pdf b/project/risk-assessment/risk-assessment.pdf deleted file mode 100644 index de03f44..0000000 Binary files a/project/risk-assessment/risk-assessment.pdf and /dev/null differ diff --git a/project/specific.bib b/project/specific.bib deleted file mode 100644 index 7ef9bba..0000000 --- a/project/specific.bib +++ /dev/null @@ -1,332 +0,0 @@ -@article{donder06, - author = {Vera Dondur and Vesna Raki\'{c} and Ljiljana Damjanovi\'{c} and Radmila Hercigonja and Aline Auroux}, - title = {Temperature-Programmed Desorption of n-hexane from Hydrated HZSM-5 and \ce{NH4}ZSM-5 Zeolites}, - year = {2006}, - journal = {Journal of Thermal Analysis and Calorimetry}, - volume = {84}, - number = {1}, - pages = {233--238} -} - -@online{ic-zeolite-structure, - title = {Zeolite Structure}, - author = {Wyn Locke}, - date = {1999}, - url = {http://www.ch.ic.ac.uk/vchemlib/course/zeolite/structure.html}, - urldate = {2018-03-02} -} - -@article{han09, - title = {High-pressure cation-exchange treatment of a ZSM-5 zeolite}, - author = {Aijie Han and Yu Qiao}, - month = {7}, - year = {2009}, - journal = {Journal of Materials Research}, - volume = {24}, - number = {7}, - pages = {2416--2419} -} - -@article{olson99, - title = {Use of water as a probe of zeolitic properties: interaction of water with HZSM-5}, - author = {D. 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Vayssilov}, - year = {2010}, - volume = {152}, - issue = {1--4}, - pages = {78--87} -} - -@article{mhamdi09, - title = {Influence of the cobalt salt precursors on the cobalt speciation and catalytic properties of H-ZSM-5 modified with cobalt by solid-state ion exchange reaction}, - author = {Mourad Mhamdi and Sihem Khaddar-Zine and Abdelhamid Ghorbel}, - year = {2009}, - journal = {Applied Catalysis A: General}, - volume = {357}, - pages = {42--50} -} diff --git a/year1/10a/10a.bcf b/year1/10a/10a.bcf new file mode 100644 index 0000000..1402288 --- /dev/null +++ b/year1/10a/10a.bcf @@ -0,0 +1,1961 @@ + + + + + + output_encoding + ascii + + + input_encoding + ascii + + + debug + 0 + + + mincrossrefs + 2 + + + minxrefs + 2 + + + sortcase + 1 + + + sortupper + 1 + + + + + + + alphaothers + + + + + labelalpha + 0 + + + labelnamespec + shortauthor + author + shorteditor + editor + translator + + + labeltitle + 0 + + + labeltitlespec + shorttitle + title + maintitle + + + labeltitleyear + 0 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+ + + + biber + + biber + 10a + + + 10a.bcf + + + 10a.bbl + + + 10a.bbl + + + 10a.bcf + + + ../bibliographies/reference.bib + + + diff --git a/year1/10a/10a.tex b/year1/10a/10a.tex new file mode 100644 index 0000000..6c9aa5a --- /dev/null +++ b/year1/10a/10a.tex @@ -0,0 +1,228 @@ +%Document Setup. +\documentclass{article} +\usepackage{graphicx} %Allows import of images. +%\usepackage{float} +\usepackage{floatrow} %Align tables and figures side-by-side. +\usepackage[extreme,mathspacing=normal,leading=normal]{savetrees} %Reduce whitespace. +\usepackage{siunitx} %SI Units formatting. +%\usepackage{vhistory} %Revision History. +\usepackage[version=4]{mhchem} %Chemical Equations. +\usepackage{amsmath} %Mathematical alignments. +\usepackage{amssymb} %Mathematical symbols e.g. therefore. +\usepackage[parfill]{parskip} %Blank lines between paragraphs. +\usepackage[autostyle]{csquotes} +\usepackage{array} %Table centering. +\usepackage[british]{babel} %British localisation. +\usepackage[backend=biber,style=verbose]{biblatex} %Bibliography. + +\numberwithin{equation}{subsection} %Number equations based on their subsection. +\bibliography{../bibliographies/reference} %Use Bibliography of reference books. +\floatsetup[table]{style=plaintop} %Put captions on top of tables. +\floatsetup[figure]{style=plain} %Ensure figure captions are below figures. + +%Document Headings. +\begin{document} +\title{Preparation of Aspirin (10A/PA)} +\author{Sam White} +\date{28/11/2017} +%\date{\vhCurrentDate\\\vhCurrentVersion} +\maketitle + +\section{Reaction Mechanism and Overall Equation} +\begin{figure}[H] + \centering + \includegraphics[width=0.85\textwidth]{Mechanism.png} + \caption{Mechanism for the reaction where ROH is salicylic acid.\label{fig:mechanism}} +\end{figure} +\begin{figure}[H] + \centering + \includegraphics[width=0.55\textwidth]{Equation.png} + \caption{Equation for the reaction.\label{fig:equation}} +\end{figure} + +\section{Summary of Method} +Salicylic acid (\SI{3.50}{\gram}), glacial acetic acid (\SI{5}{\centi\metre\cubed}) and acetic anhydride (\SI{3}{\centi\metre\cubed}) were boiled under reflux for 10 minutes. The product was precipitated by pouring into ice-cold water (\SI{75}{\centi\metre\cubed}) and then recrystallised in a water and glacial acetic acid mixture (1:1 by volume) using ice to cool the mixture. The crude product, recrystallised product, salicylic acid and a sample of pure aspirin (each in \SI{0.5}{\centi\metre\cubed} dichloromethane) were then analysed using thin-layer chromatography (TLC) with light petroleum ether and ethyl acetate (70:30 by volume) as the TLC solvent. The melting point of the purified product was then determined. + +\section{Results and Analysis} + +{\centering Mass of purified product: \SI{3.99}{\gram} + +} + +\subsection{Thin-Layer Chromatography (TLC) Results} \label{tlc-results} +\begin{table}[H] + \centering + \begin{tabular}{|c|c|c|} + \hline + Substance & $R_{f}$ Value of First Spot & $R_{f}$ Value of Second Spot \\ + \hline + Salicylic acid & 0.64 & N/A \\ + \hline + Pure aspirin & 0.32 (Diffuse) & N/A \\ + \hline + Crude product & 0.42 & 0.58 \\ + \hline + Purified product & 0.43 & N/A \\ + \hline + \end{tabular} +\end{table} +The crude product gave two distinct spots on the TLC plate indicating the presence of two substances in the sample. The $R_{f}$ value for the first spot (at 0.42) is different to that for the aspirin, however the aspirin produced a diffuse mark on the plate (possibly since too much solution was added to the plate) with the $R_{f}$ values for the bottom and top of the mark being 0.18 and 0.45 respectively. The $R_{f}$ value for the first spot from the crude product is within this range, hence suggesting that the crude product contains aspirin. The $R_{f}$ value of 0.58 for the second spot of the crude product is close to the $R_{f}$ value of the salicylic acid which suggests the presence of salicylic acid as an impurity in the product. This indicates that the reaction did not proceed to completion since the salicylic acid was the limiting reagent (see the percentage yield calculation in section~\ref{yield-calculation}). This is expected since the reaction is reversible (see figure~\ref{fig:mechanism}), hence an equilibrium between the reactants and products will be established. + +The TLC result for the purified product only shows a single spot at almost the same position as that for the spot assigned to aspirin in the crude product. This suggests that the recrystallisation was effective at removing the salicylic acid impurity since the spot due to this impurity is no longer present. + +\subsection{Melting Point Determination} \label{melting-point} +\begin{table}[H] + \caption{Melting Point Determination Results.} + \centering + \begin{tabular}{|c|c|c|} + \hline + Run & Melting Started / \si{\celsius} & Melting Finished / \si{\celsius} \\ + \hline + 1 & 95.1 & 101.9 \\ + \hline + 2 & 88.7 & 112.0 \\ + \hline + 3 & 91.1 & 100.4 \\ + \hline + \end{tabular} +\end{table} +The expected melting point for aspirin is \SI{136}{\celsius}.\footcite[Physical Constants of Organic Compounds, 3-8]{crc-handbook} The melting temperature results show a wide temperature range of over \SI{10}{\celsius} for the melting of the product and the temperature at which the product melted is much lower than the expected value. This is likely to have occurred since the product was not completely dry (the product consisted of clumps and upon grinding with a pestle and mortar some of the product formed a thin paste instead of forming a fine powder). + +To reduce the amount of solvent contaminating the product it could have been left in the B\"{u}chner funnel for a longer period of time after the final filtration, however it is unlikely that this would result in a fully dried product since the solvent used was not particularly volatile (the boiling temperature of water is \SI{100}{\celsius} and that of acetic acid is \SI{117.9}{\celsius}\footcite[Physical Constants of Organic Compounds, 3-4]{crc-handbook}). A more effective way to dry the product would have been to leave it in a vacuum desiccator overnight, since then the ambient pressure would be reduced below the vapour pressure of the solvent, hence causing it to evaporate much faster and leave a drier product. + +\subsection{Yield Calculation} \label{yield-calculation} +The density of acetic anhydride is \SI{1.082}{\gram\per\centi\metre\cubed}.\footcite[Physical Constants of Organic Compounds, 3-4]{crc-handbook} +\begin{displaymath} + \begin{aligned} + \text{Moles of salicylic acid at start of reaction} &= \frac{\SI{3.50}{\gram}}{(7(12.011) + 6(1.008) + 3(15.999)) \text{ \si{\gram\per\mole}}} \\ + &= \frac{\SI{3.50}{\gram}}{\SI{138.122}{\gram\per\mole}} = \SI{0.0253}{\mole} \\ + \text{Moles of acetic anhydride at start of reaction} &= \frac{\SI{3.00}{\centi\metre\cubed} \times \SI{1.082}{\gram\per\centi\metre\cubed}}{(4(12.011) + 6(1.008) + 3(15.999))\text{ \si{\gram\per\mole}}} \\ + &= \frac{\SI{3.246}{\gram}}{\SI{102.089}{\gram\per\mole}} = \SI{0.0318}{\mole} + \end{aligned} +\end{displaymath} + +From the equation (see figure~\ref{fig:equation}) there is a 1:1 molar ratio between salicylic acid and acetic anhydride, hence the acetic anhydride is in excess. The equation also shows a 1:1 molar ratio between the salicylic acid and aspirin, hence the theoretical amount of aspirin produced is \SI{0.0253}{\mole}. + +\begin{displaymath} + \begin{aligned} + \therefore \text{Theoretical yield of aspirin} &= \SI{0.0253}{\mole} \times (9(12.011) + 8(1.008) + 4(15.999)) \text{ \si{\gram\per\mole}} \\ + &= \SI{0.0253}{\mole} \times \SI{180.159}{\gram\per\mole} = \SI{4.57}{\gram} \\ + \therefore \text{Percentage yield} &= \frac{\SI{3.99}{\gram}}{\SI{4.57}{\gram}} \times \SI{100}{\percent} = \SI{87.4}{\percent} + \end{aligned} +\end{displaymath} + +This is very high: this is because the aspirin was not fully dry before the mass was determined (see section~\ref{melting-point}). This yield value is much higher than expected since the reaction is reversible and hence will not proceed to completion (as shown in section~\ref{tlc-results} with the TLC results of the crude product). + +In addition there were significant transfer losses at all transfers since the product was difficult to completely remove the sides of the vessels and while washing with ice-cold water aided in the transfer of product this would have also reduced the yield since some of the product would have dissolved in the water. + +\subsection{Spectra} +\begin{table}[H] +\begin{floatrow} + \CenterFloatBoxes + \ttabbox + {\caption{IR Spectrum of Salicylic Acid.}} + {\begin{tabular}{|c|c|c|} + \hline + Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ + \hline + 1609.7 & Moderate & \ce{C=C} Absorption. \\ + \hline + 1651.5 & Moderate & \ce{C=O} Absorption. \\ + \hline + 2850.8 & Weak and Broad & \ce{O-H} Absorption in hydroxyl group. \\ + \hline + \end{tabular} + } + \killfloatstyle + \ffigbox + {\includegraphics[height=2cm]{Salicylic-acid-NMR.png}\label{fig:salicylic-acid-nmr}} + {\caption{Salicylic acid.}} +\end{floatrow} +\end{table} + +\begin{table}[H] + \caption{$^1$H NMR Spectrum of Salicylic Acid in DMSO.} + \centering + \begin{tabular}{|c|>{\centering}m{3.3cm}|>{\centering}m{2.2cm}|m{7.9cm}|} + \hline + Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ + \hline + 9.6 & Broad Singlet & Not Integrated & Proton in (6) (carboxyl group). \\ + \hline + 7.6 & Doublet of Doublets & 4.00 & Proton in (5), coupling with (4) and (3). \\ \cline{1-2} \cline{4-4} + 7.2 & Doublet of Doublets & & Proton in (2), coupling with (3) and (4). \\ \cline{1-2} \cline{4-4} + 6.6 & Triplet of Doublets (Considerable Roofing) & (Integrated together) & One proton in (3) and one in (4), coupling with (2) and (5) (and with each other). \\ + \hline + 2.4 & Singlet & 0.17 & Characteristic of \ce{DMSO} (solvent). \\ + \hline + \end{tabular} +\end{table} +\begin{table}[H] + \caption{IR Spectrum of Acetic Anhydride.} + \centering + \begin{tabular}{|c|c|c|} + \hline + Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ + \hline + 1751.0 & Strong & \ce{C=O} Absorption. \\ + \hline + 1821.9 & Strong & \ce{C=O} Absorption. \\ + \hline + \end{tabular} +\end{table} +\begin{table}[H] + \caption{$^1$H NMR Spectrum of Acetic Anhydride.} + \centering + \begin{tabular}{|c|c|c|c|} + \hline + Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ + \hline + 2.3 & Singlet & 1.00 & Six protons in equivalent environment (from the two methyl groups). \\ + \hline + \end{tabular} +\end{table} + +\begin{table}[H] +\begin{floatrow} + \CenterFloatBoxes + \ttabbox + {\caption{IR Spectrum of Product.}} + {\begin{tabular}{|c|c|c|} + \hline + Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ + \hline + 1602.5 & Moderate & \ce{C=C} Absorption. \\ + \hline + 1681.7 & Strong & \ce{C=O} Absorption. \\ + \hline + 1750.4 & Moderate & \ce{C=O} Absorption. \\ + \hline + 2835.7 & Weak and Broad & \ce{O-H} in hydroxyl group. \\ + \hline + \end{tabular} + } + \killfloatstyle + \ffigbox + {\includegraphics[height=2cm]{Aspirin-NMR.png}\label{fig:aspirin-nmr}} + {\caption{Aspirin.}} +\end{floatrow} +\end{table} + +\begin{table}[H] + \caption{$^1$H NMR Spectrum of Product.} + \centering + \begin{tabular}{|c|c|c|p{7.9cm}|} + \hline + Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ + \hline + 8.4-6.8 & Complex Multiplet & 16.21 & Protons (2), (3), (4) and (5) from aspirin and salicylic acid impurity. \\ + \hline + 2.4 & Singlet & 7.40 & Six protons from acetic anhydride impurity. \\ + \hline + 2.2 & Singlet & 3.00 & Three protons in (1) from aspirin. \\ + \hline + \end{tabular} +\end{table} + +The product used for the $^1$H NMR spectra was not pure since the spectrum contains a singlet peak from the two methyl groups in acetic anhydride and the relative area for the aromatic peaks is greater than four with a poorly defined splitting patten, hence indicating the presence of salicylic acid. Some aspirin can be seen to have been produced by the presence of the additional peak at 2.2 ppm due to the three protons in (1). The composition of the product can be determined by comparing the areas of the peaks sue to each substance and is 1.00:1.23:3.05 (aspirin:acetic anhydride:salicylic acid). This indicates that the purification steps were not very successful since the sample mostly consisted of impurities. The IR spectrum shows that aspirin was produced since the number of peaks due to carbonyl bonds increased from the one in salicylic acid to two in the product: is expected for an acylation. +\end{document} diff --git a/year1/10a/Aspirin-NMR.png b/year1/10a/Aspirin-NMR.png new file mode 100755 index 0000000..b9cf6f8 Binary files /dev/null and b/year1/10a/Aspirin-NMR.png differ diff --git a/year1/10a/Equation.png b/year1/10a/Equation.png new file mode 100755 index 0000000..c18da07 Binary files /dev/null and b/year1/10a/Equation.png differ diff --git a/year1/10a/Mechanism.png b/year1/10a/Mechanism.png new file mode 100755 index 0000000..5534a79 Binary files /dev/null and b/year1/10a/Mechanism.png differ diff --git a/year1/10a/Salicylic-acid-NMR.png b/year1/10a/Salicylic-acid-NMR.png new file mode 100755 index 0000000..15376e2 Binary files /dev/null and b/year1/10a/Salicylic-acid-NMR.png differ diff --git a/year1/16a/16a.bcf b/year1/16a/16a.bcf new file mode 100644 index 0000000..43cd3dc 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b/year1/16a/16a.tex @@ -0,0 +1,130 @@ +%Document Setup. +\documentclass{article} +\usepackage{graphicx} %Allows import of images. +%\usepackage{float} +\usepackage{floatrow} %Align tables and figures side-by-side. +\usepackage[extreme,mathspacing=normal,leading=normal]{savetrees} %Reduce whitespace. +\usepackage{siunitx} %SI Units formatting. +%\usepackage{vhistory} %Revision History. +\usepackage[version=4]{mhchem} %Chemical Equations. +\usepackage{amsmath} %Mathematical alignments. +\usepackage{amssymb} %Mathematical symbols e.g. therefore. +\usepackage[parfill]{parskip} %Blank lines between paragraphs. +\usepackage[autostyle]{csquotes} +\usepackage{array} %Table centering. +\usepackage[british]{babel} %British localisation. +\usepackage[backend=biber,citestyle=verbose-note]{biblatex} %Bibliography. + +\numberwithin{equation}{subsection} %Number equations based on their section. +\bibliography{../bibliographies/reference,../bibliographies/coretextbooks,specific} %Use Bibliography of reference books. +\floatsetup[table]{style = plaintop} %Put captions on top of tables. +\floatsetup[figure]{style = plain} %Ensure figure captions are below figures. +\sisetup{range-phrase = --,range-units = single} %Use - for ranges and only have a single unit shown after. +\sisetup{separate-uncertainty = true,multi-part-units=single} %Use \pm for uncertainties. + +%Document Headings. +\begin{document} +\title{Preparation of Cyclohexene (16A/PC)} +\author{Sam White (Author) and Mihkel Raidal} +\date{27/02/2018} +%\date{\vhCurrentDate\\\vhCurrentVersion} +\maketitle + +\section{Introduction} +The aim of this experiment was to synthesise cyclohexene through the dehydration of cyclohexanol. Phosphoric acid was used as a catalyst and can be seen to behave catalytically in the reaction mechanism (figure~\ref{fig:syn-mechanism}) since it is regenerated by the proton donation from the more acidic hydronium ion (p$K_{\text{a}}$(\ce{H3O+}) = -0.7~\footcite{burgot98}, p$K_{\text{a}}$(\ce{H3PO4}) = 2.16~\footcite[Dissociation Constants of Inorganic Acids and Bases, 5-87]{crc-handbook}) in the final step. +% +\begin{figure}[H] + \centering + \includegraphics[width=0.85\textwidth]{Synthesis-Mechanism.png} + \caption{Mechanism for the dehydration reaction.\label{fig:syn-mechanism}} +\end{figure} +% +The overall chemical equation for this reaction is given by equation~\ref{eqn:overall-reaction}. + +\begin{equation}\label{eqn:overall-reaction} + \ce{C6H11OH(l) ->[H3PO4] C6H10(l) + H2O(l)} +\end{equation} + +An azeotropic distillation was completed in this experiment with an azeotrope (a mixture of two liquids that boils at constant composition)~\footcite[pp.~53]{oxford-chemistry-dictionary} formed between the water and cyclohexene, hence depressing the boiling temperature of the mixture due to positive excess Gibbs free energy associated with the unfavourable mixing of this liquids relative to an ideal mixture.~\footcite[Azeotropes, pp.~207]{atkins-physical} This distillation removed the products of the reaction from the reaction vessel hence driving the reaction to completion. +% +\section{Experimental Method} +A mixture of concentrated (\SI{85}{\percent}) phosphoric acid (\SI{10.0}{\centi\metre\cubed}) and cyclohexanol (\SI{24.00}{\gram}) was distilled at \SIrange{85}{95}{\celsius} (with collection in a ice-cold flask) until white fumes were evolved from the mixture residue. This produced a colourless, but cloudy distillate containing \SI{3.0}{\centi\metre\cubed} of water (\SI{69}{\percent} of the theoretical maximum volume). The distillate was washed with \SI{15}{\centi\metre\cubed} of concentrated sodium chloride solution and then the organic product was dried using anhydrous calcium chloride. After drying the organic product was very slightly cloudy. A further distillation of the dry organic product was completed (boiling temperature \SI{81.5}{\celsius} compared to the literature value of \SI{82.9(2)}{\celsius})~\footcite[Physical Constants of Organic Compounds, 3-134]{crc-handbook} and \SI{3.81}{\gram} of perfectly clear cyclohexene (\SI{19.4}{\percent} yield) was collected in a ice-cold flask. +% +\subsection{Calculations} +\subsubsection{Percentage Yield} +From equation~\ref{eqn:overall-reaction}, there is a 1:1 molar ratio between the cyclohexanol and the cyclohexene. + +\begin{align*} + \text{Amount of Product Synthesised} &= \frac{\SI{3.81}{\gram}}{(6(12.011) + 10(1.008)) \text{ \si{\gram\per\mole}}} = \frac{\SI{3.81}{\gram}}{\SI{82.15}{\gram\per\mole}} = \SI{46.4e-3}{\mole} \\ + \text{Theoretical Product Yield} &= \frac{\SI{24.00}{\gram}}{(6(12.011) + 12(1.008) + 15.999) \text{ \si{\gram\per\mole}}} = \frac{\SI{24.00}{\gram}}{\SI{100.2}{\gram\per\mole}} = \SI{0.2396}{\mole} \\ + \therefore \text{Percentage Yield} &= \frac{\SI{46.4e-3}{\mole}}{\SI{0.2396}{\mole}} \times \SI{100}{\percent} = \SI{19.4}{\percent} +\end{align*} + +\subsubsection{Percentage of Water Obtained Compared to the Theoretical Maximum} +Also from equation~\ref{eqn:overall-reaction}, there is a 1:1 molar ratio between the cyclohexanol and the water. The density of water at \SI{20.0}{\celsius} is \SI{0.998}{\gram\per\centi\metre\cubed}.\footcite[Standard Density of Water, 6-7]{crc-handbook} + +\begin{align*} + \text{Theoretical Yield of Water} &= \SI{0.2396}{\mole} \times (2(1.008) + 15.999)\text{ \si{\gram\per\mole}} = \SI{4.317}{\gram} \\ + \text{Mass of Obtained Water} &= \SI{0.998}{\gram\per\centi\metre\cubed} \times \SI{3.0}{\centi\metre\cubed} = \SI{3.0}{\gram} \\ + \therefore \text{Percentage} &= \frac{\SI{3.0}{\gram}}{\SI{4.317}{\gram}} \times \SI{100}{\percent} = \SI{69}{\percent} +\end{align*} +% +\section{Analysis} +During the experiment both cyclohexanol and water impurities were removed from the product. After the first distillation the product was heavily contaminated with water and hence appeared cloudy due to the emulsion formed. Washing with concentrated sodium chloride solution removed most of this water due to the negative Gibbs free energy change associated with the further solvation of the sodium and chloride ions in the saturated solution. In addition this washing removed any cyclohexanol from the crude product since it is soluble in water,\footcite[Physical Constants of Organic Compounds, 3-134]{crc-handbook} although it is likely that little cyclohexanol was present as an impurity since it has a high boiling temperature of \SI{160.9(2)}{\celsius}.~\footcite[Physical Constants of Organic Compounds, 3-134]{crc-handbook} The subsequent drying with anhydrous calcium chloride was intended to remove any remaining water and the final distillation removed byproducts formed from side reactions (e.g. nucleophilic substitution). +% +\subsection{Tests Performed} +Three drops of a solution of bromine in dichloromethane (since cyclohexene is insoluble in water,\footcite[Physical Constants of Organic Compounds, 3-134]{crc-handbook} also a different product of (1S,2S)-2-bromocyclohexan-1-ol would result from using an aqueous bromine solution although this is inconsequential since this is also colourless) were added to approximately \SI{1}{\centi\metre\cubed} of the collected cyclohexene. This caused the bromine solution to change colour from red-orange to colourless as the reaction shown in figure~\ref{fig:electro-add-mechanism} occurred. This demonstrated the presence of the nucleophilic double bond in the cyclohexene product, hence suggesting the intended product was successfully synthesised. +% +\begin{figure}[H] + \centering + \includegraphics[width=0.5\textwidth]{Electrophillic-Addition-Mechanism.png} + \caption{Mechanism for the electrophilic addition reaction between the cyclohexene and bromine.\label{fig:electro-add-mechanism}} +\end{figure} +% +\subsection{Boiling Temperature} +The boiling temperature of the distillate collected appears to be close to the published value (\SI{1.4}{\celsius} lower) and there was no noticeable range of boiling temperatures which suggests that the cyclohexene produced was fairly pure. However the true difference in boiling temperature is slightly greater than this since the air pressure in the laboratory was greater (by approximately \SI{0.575}{\kilo\pascal}) than the air pressure for which the literature value is reported at (\SI{101.325}{\kilo\pascal}). This would have slightly elevated the boiling temperature of the product (since the vapour pressure of the liquid would have to be greater for boiling to occur) thus the true difference in boiling temperatures between pure cyclohexene and the product was instead approximately \SI{1.6}{\celsius}. The calculations used to determine these numbers are included in section \ref{sec:boiling-calculations}. + +This lower boiling temperature could be due to a combination of factors such as a slight cooling of the vapour as it travelled up the still head and the presence of impurities in the vapour. The product could have been analysed using NMR spectroscopy to definitively identify any impurities in the product, and the thermometer could have been temporarily moved to a position just above the boiling liquid during the distillation in order to obtain a more accurate value for its boiling temperature. An electronic thermometer could also have been used hence giving a more precise temperature reading and allowing the easier establishment of the range of boiling temperatures for the solution. + +However it is likely that there was still a little water impurity in the product after the drying since it was very slightly cloudy when compared to the distilled product. This may have been since the solution was not left to dry for 10 minutes as recommended in the laboratory manual due to time constraints, however a possible improvement to the method could be be grind the drying agent into a fine powder to increase its surface area and thus reduce the time required to dry the product. +% +\subsubsection{Boiling Temperature Calculations}\label{sec:boiling-calculations} +The approximate laboratory air pressure was calculated using an adjusted sea-level air pressure of approximately \SI{102.6}{\kilo\pascal}~\footcite[Pressure at 4:20 PM]{weather-underground-egnt} and laboratory altitude of \SI{55.30}{\metre} above mean sea level~\footcite[Latitude: \SI{54.7683}{\degree}, Longitude: \SI{-1.5711}{\degree}]{os-maps-lab} with equation~\ref{eqn:pressure-diff}. + +\begin{equation}\label{eqn:pressure-diff} + \Delta P = - \rho g \Delta h +\end{equation} + +Using $\rho = \SI{1.29}{\kilo\gram\per\metre\cubed}\text{ (obtained by linearly interpolating between given values to \SI{270}{\kelvin})}$\footcite[Thermophysical Properties of Air, 6-18]{crc-handbook} and $g = \SI{9.81}{\meter\per\second\squared}$. While assuming that the temperature of the air is constant at \SI{270}{\kelvin} and the density of the air remains constant. + +\begin{align*} + \text{Laboratory Air Pressure} &\approx \SI{102.6e3}{\pascal} - \SI{1.29}{\kilo\gram\per\metre\cubed} \times \SI{9.81}{\metre\per\second\squared} \times \SI{55.30}{\metre} = \SI{102}{\kilo\pascal} \\ + \therefore \text{Difference from Published Pressure} &\approx \SI{101.325}{\kilo\pascal} - \SI{102}{\kilo\pascal} = \SI{0.575}{\kilo\pascal} +\end{align*} + +The Clausius-Clapeyron equation (equation~\ref{eqn:clausius-clapeyron}) and can be rearranged to make $T_2$ the subject (equation~\ref{eqn:clausius-clapeyron-rearranged}) and hence can be used to determine the boiling temperature elevation caused by this pressure difference. + +\begin{equation}\label{eqn:clausius-clapeyron} + \log_e\left(\frac{P_1}{P_2}\right) = \frac{\Delta H_{\text{vap}}}{R} \left(\frac{1}{T_2} - \frac{1}{T_1}\right) +\end{equation} + +\begin{equation}\label{eqn:clausius-clapeyron-rearranged} + T_2 = \frac{T_1 \Delta H_{\text{vap}}}{R T_1 \log_e\left(\frac{P_1}{P_2}\right) + \Delta H_{\text{vap}}} +\end{equation} + +With $\Delta H_\text{vap}(\SI{82.9}{\celsius}) = \SI{30.46}{\kilo\joule\per\mole}$ (assuming this remains constant in the temperature range considered).~\footcite[Enthalpy of Vaporization, 6-141]{crc-handbook} + +\begin{align*} + \text{New boiling temperature} &\approx \frac{(82.9 + 273.15)\text{ \si{\kelvin}} \times \SI{30.46e3}{\joule\per\mole}}{\SI{8.31}{\joule\per\mole\per\kelvin} \times (82.9 + 273.15)\text{ \si{\kelvin}} \times \log_e\left(\frac{\SI{101.325}{\kilo\pascal}}{\SI{102}{\kilo\pascal}}\right) + \SI{30.46e3}{\joule\per\mole}} \\ + &\approx \SI{356}{\kelvin} = \SI{83.1}{\celsius} \\ + \therefore \text{Difference in Boiling Temperature} &\approx \SI{83.1}{\celsius} - \SI{81.5}{\celsius} = \SI{1.6}{\celsius} +\end{align*} +% +\subsection{Yield} +The overall percentage yield obtained was very low (\SI{19.4}{\percent}), despite the fairly high percentage of water obtained compared to the theoretical maxima (\SI{69}{\percent}) after the initial distillation. However this water percentage is likely to be a fairly inaccurate measure of the initial yield since the water which formed an emulsion in the organic layer is not represented in this figure and it doesn't account for any water which was originally contained within the reagents (such as the water in the concentrated phosphoric acid solution) which may have also been collected. + +Some of the cyclohexene was lost during transfers both due to some liquid remaining the in previous vessel and due to evaporative losses. To reduce these evaporative losses during transfer the flask containing the product could be cooled in an ice bath at all intermediate stages in the experiment, not just during distillation, hence reducing the temperature of the liquid being transferred. In addition after the distillations some of the cyclohexene remained in the distillation apparatus. To reduce this a 'chaser' solvent with a higher boiling temperature than the cyclohexene -- such as toluene -- could have been added to the reaction vessel at the end of the first distillation to force any remaining cyclohexene into the collection flask.~\footcite{unmass-cyclohexene-synthesis} This solvent would then be removed from the cyclohexene by the second distillation step. + +The yield calculated is likely to also have been low since not all of the product was distilled for a second time (due to the small size of the round-bottomed flask used) and the second distillation itself was stopped prematurely due to time constraints. + +\end{document} diff --git a/year1/16a/Electrophillic-Addition-Mechanism.png b/year1/16a/Electrophillic-Addition-Mechanism.png new file mode 100755 index 0000000..61ab6d6 Binary files /dev/null and b/year1/16a/Electrophillic-Addition-Mechanism.png differ diff --git a/year1/16a/Synthesis-Mechanism.png b/year1/16a/Synthesis-Mechanism.png new file mode 100755 index 0000000..b6bb392 Binary files /dev/null and b/year1/16a/Synthesis-Mechanism.png differ diff --git a/year1/16a/specific.bib b/year1/16a/specific.bib new file mode 100644 index 0000000..128579b --- /dev/null +++ b/year1/16a/specific.bib @@ -0,0 +1,31 @@ +@article{burgot98, + author = {Jean-Lewis Burgot}, + title = {New point of view on the meaning and on the values of $K_{\text{a}}^\circ$(\ce{H3O+}, \ce{H2O}) and $K_{\text{b}}^\circ$(\ce{H2O}, \ce{OH-}) pairs in water}, + year = {1998}, + journal = {Analyst}, + volume = {123}, + % number = {}, + pages = {409--410} +} + +@online{weather-underground-egnt, + title = {Weather History for EGNV - February, 2018}, + author = {TWC Product and Technology, LLC}, + date = {2018-02-27}, + url = {https://www.wunderground.com/history/airport/EGNV/2018/2/27/DailyHistory.html}, + urldate = {2018-02-28} +} + +@online{os-maps-lab, + title = {OS Maps Online}, + author = {Ordnance Survey}, + url = {https://osmaps.ordnancesurvey.co.uk/54.76830,-1.57110,20}, + urldate = {2018-02-28} +} + +@online{unmass-cyclohexene-synthesis, + title = {Synthesis of Cyclohexene, The Dehydration of Cyclohexanol}, + author = {Peter Samal}, + url = {https://people.chem.umass.edu/samal/269/cyclohexene.pdf}, + urldate = {2018-03-03} +} diff --git a/year1/3a/3a.bcf b/year1/3a/3a.bcf new file mode 100644 index 0000000..c3af979 --- /dev/null +++ b/year1/3a/3a.bcf @@ -0,0 +1,2147 @@ + + + + + + output_encoding + ascii + + + input_encoding + ascii + + + debug + 0 + + + mincrossrefs + 2 + + + minxrefs + 2 + + + sortcase + 1 + + + sortupper + 1 + + + + + + + alphaothers + + + + + labelalpha + 0 + + + labelnamespec + shortauthor + author + shorteditor + editor + translator + + + labeltitle + 0 + + + labeltitlespec + shorttitle + title + maintitle + + + labeltitleyear + 0 + + + labeldateparts + 0 + + + labeldatespec + date + year + eventdate + origdate + urldate + nodate + + + julian + 0 + + + gregorianstart + 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0000000..0ef044d Binary files /dev/null and b/year1/3a/3a.pdf differ diff --git a/year1/3a/3a.run.xml b/year1/3a/3a.run.xml new file mode 100644 index 0000000..1488d13 --- /dev/null +++ b/year1/3a/3a.run.xml @@ -0,0 +1,86 @@ + + + + + + + + + + + + + + + + + + + + + + + + +]> + + + latex + + 3a.bcf + + + 3a.bbl + + + blx-dm.def + blx-compat.def + biblatex.def + numeric.bbx + standard.bbx + numeric.cbx + biblatex.cfg + british.lbx + english.lbx + + + + biber + + biber + 3a + + + 3a.bcf + + + 3a.bbl + + + 3a.bbl + + + 3a.bcf + + + ../bibliography/coretextbooks.bib + + + diff --git a/year1/3a/3a.tex b/year1/3a/3a.tex new file mode 100644 index 0000000..1ad6fda --- /dev/null +++ b/year1/3a/3a.tex @@ -0,0 +1,160 @@ +%Document Setup. +\documentclass{article} +\usepackage{graphicx} %Allows import of images. +\usepackage{float} +\usepackage[extreme,mathspacing=normal,leading=normal]{savetrees} %Reduce whitespace. +\usepackage{siunitx} %SI Units formatting. +%\usepackage{vhistory} %Revision History. +\usepackage[version=4]{mhchem} %Chemical Equations. +\usepackage{amsmath} %Mathematical alignments. +\usepackage{amssymb} %Mathematical symbols e.g. therefore. +\usepackage[parfill]{parskip} %Blank lines between paragraphs. +\usepackage[autostyle]{csquotes} +\usepackage[british]{babel} %British localisation. +\usepackage[backend=biber]{biblatex} %Bibliography. + +\numberwithin{equation}{subsection} %Number equations based on their subsection. +\bibliography{../bibliography/coretextbooks} %Use Bibliography of Core textbooks. + +%Document Headings. +\begin{document} +\title{Determination of the $M_{r}$ of an Unknown Solid Acid using Titration (3A/ABT)} +\author{Sam White} +\date{31/10/2017} +%\date{\vhCurrentDate\\\vhCurrentVersion} +\maketitle + +\section{Aim} +To determine the $M_r$ of an unknown solid acid ($A$) using a titrimetric method of analysis. + +\section{Results and Analysis} +\begin{displaymath} + \begin{aligned} + \text{Batch of \ce{HCl} used}&: B \\ + \text{Concentration of \ce{HCl}}&: \SI{0.1029}{\mole\per\deci\metre\cubed} \\ + \text{Batch of \ce{NaOH} Used}&: B + \end{aligned} +\end{displaymath} + +\subsection{Titration between \ce{NaOH} and \ce{HCl}} +\begin{equation} \label{eq:naoh-hcl} + \ce{HCl(aq) + NaOH(aq) -> NaCl(aq) + H2O(l)} +\end{equation} + +Phenolphthalein was used as the indicator (colour change from pink to colourless at the end point). + +\begin{table}[h] + \caption{Results from titrating \SI{25.00}{\centi\metre\cubed} of \ce{NaOH} with \ce{HCl}.} + \centering + \begin{tabular}{|c|c|c|c|} + \hline + {Run} & {Start Volume / \si{\centi\metre\cubed}} & {End Volume / \si{\centi\metre\cubed}} & {Titre / \si{\centi\metre\cubed}} \\ + \hline + 1 & 6.60 & 30.95 & 24.35 \\ + \hline + 2 & 2.00 & 25.85 & 23.85 \\ + \hline + 3 & 4.20 & 28.30 & 24.10 \\ + \hline + 4 & 4.45 & 28.55 & 24.10 \\ + \hline + \end{tabular} +\end{table} + +\begin{displaymath} + \text{Average titre} = \frac{\SI{24.10}{\centi\metre\cubed} + \SI{24.10}{\centi\metre\cubed}}{2} = \SI{24.10}{\centi\metre\cubed} +\end{displaymath} + +\begin{displaymath} + \begin{aligned} + \text{Moles of \ce{HCl} in titre} &= \SI{24.10}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3 \times \SI{0.1029}{\mole\per\deci\metre\cubed} \\ + &= \SI{24.10e-3}{\deci\metre\cubed} \times \SI{0.1029}{\mole\per\deci\metre\cubed} \\ + &= \SI{2.480e-3}{\mole} + \end{aligned} +\end{displaymath} + +From equation~\ref{eq:naoh-hcl} there is a 1:1 molar ratio between \ce{HCl} and \ce{NaOH}. + +\begin{displaymath} + \begin{aligned} + \therefore \text{Moles of \ce{NaOH} in \SI{25.00}{\centi\metre\cubed}} &= \SI{2.480e-3}{\mole} \\ + \text{Concentration of \ce{NaOH}} &= \frac{\SI{2.480e-3}{\mole}}{\SI{25.00}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3} \\ + &= \frac{\SI{2.480e-3}{\mole}}{\SI{25.00e-3}{\deci\metre\cubed}} \\ + &= \SI{0.09920}{\mole\per\deci\metre\cubed} + \end{aligned} +\end{displaymath} + + +\subsection{Titration between \ce{NaOH} and Unknown Acid $A$} +For \ce{HA} being the unknown acid $A$ and assuming \ce{HA} is monobasic: +\begin{equation} \label{eq:naoh-ha} + \ce{HA(aq) + NaOH(aq) -> NaA(aq) + H2O(l)} +\end{equation} + +Phenolphthalein was used as the indicator (colour change from pink to colourless at the end point). + +A mass of \SI{1.8525}{\gram} of \ce{HA} was dissolved with distilled water in a \SI{200.00}{\centi\metre\cubed} volumetric flask. + +\begin{table}[h] + \caption{Results from titrating \SI{20.00}{\centi\metre\cubed} of \ce{NaOH} with \ce{HA}.} + \centering + \begin{tabular}{|c|c|c|c|} + \hline + {Run} & {Start Volume / \si{\centi\metre\cubed}} & {End Volume / \si{\centi\metre\cubed}} & {Titre / \si{\centi\metre\cubed}} \\ + \hline + 1 & 4.00 & 24.90 & 20.90 \\ + \hline + 2 & 4.00 & 24.10 & 20.10 \\ + \hline + 3 & 4.05 & 24.20 & 20.15 \\ + \hline + \end{tabular} +\end{table} + +\begin{displaymath} + \text{Average titre} = \frac{\SI{20.10}{\centi\metre\cubed} + \SI{20.15}{\centi\metre\cubed}}{2} = \SI{20.13}{\centi\metre\cubed} +\end{displaymath} + +\begin{displaymath} + \begin{aligned} + \text{Moles of \ce{NaOH} in \SI{20.00}{\centi\metre\cubed} aliquot} &= \SI{20.00}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3 \times \SI{0.09920}{\mole\per\deci\metre\cubed} \\ + &= \SI{20.00e-3}{\deci\metre\cubed} \times \SI{0.09920}{\mole\per\deci\metre\cubed} \\ + &= \SI{1.984e-3}{\mole} + \end{aligned} +\end{displaymath} + +From equation \ref{eq:naoh-ha} there is a 1:1 molar ratio between \ce{NaOH} and \ce{HA}. + +\begin{displaymath} + \begin{aligned} + \therefore \text{Moles of \ce{HA} in \SI{20.13}{\centi\metre\cubed}} &= \SI{1.984e-3}{\mole} \\ + \text{Concentration of \ce{HA}} &= \frac{\SI{1.984e-3}{\mole}}{\SI{20.13}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3} \\ + &= \frac{\SI{1.984e-3}{\mole}}{\SI{20.13e-3}{\deci\metre\cubed}} \\ + &= \SI{0.09855}{\mole\per\deci\metre\cubed} + \end{aligned} +\end{displaymath} + +Hence for the whole \SI{200.00}{\centi\metre\cubed} volumetric flask: +\begin{displaymath} + \begin{aligned} + \text{Moles of \ce{HA}} &= \SI{0.09855}{\mole\per\deci\metre\cubed} \times \SI{200.00}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3 \\ + &= \SI{0.09855}{\mole\per\deci\metre\cubed} \times \SI{200.00e-3}{\deci\metre\cubed} \\ + &= \SI{0.01971}{\mole} + \end{aligned} +\end{displaymath} + +Since: +\begin{displaymath} + \begin{aligned} + \text{Amount \si{\mole}} &= \frac{\text{Mass \si{\gram}}}{M_r \text{ \si{\gram\per\mole}}} \\ + M_r \text{ \si{\gram\per\mole}} &= \frac{\text{Mass \si{\gram}}}{\text{Amount \si{\mole}}} \\ + \end{aligned} +\end{displaymath} +Hence: +\begin{displaymath} + \begin{aligned} + M_r \text{ of \ce{HA}} = \frac{\SI{1.8525}{\gram}}{\SI{0.01971}{\mole}} = \SI{93.98}{\gram\per\mole} + \end{aligned} +\end{displaymath} + +\end{document} diff --git 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7a.bcf + + + 7a.bbl + + + blx-dm.def + blx-compat.def + biblatex.def + verbose.bbx + authortitle.bbx + standard.bbx + verbose.cbx + biblatex.cfg + british.lbx + english.lbx + + + + biber + + biber + 7a + + + 7a.bcf + + + 7a.bbl + + + 7a.bbl + + + 7a.bcf + + + ../bibliographies/additionaltextbooks.bib + + + diff --git a/year1/7a/7a.tex b/year1/7a/7a.tex new file mode 100644 index 0000000..5e5970a --- /dev/null +++ b/year1/7a/7a.tex @@ -0,0 +1,196 @@ +%Document Setup. +\documentclass{article} +\usepackage{graphicx} %Allows import of images. +\usepackage{float} +\usepackage[extreme,mathspacing=normal,leading=normal]{savetrees} %Reduce whitespace. +\usepackage{siunitx} %SI Units formatting. +%\usepackage{vhistory} %Revision History. +\usepackage[version=4]{mhchem} %Chemical Equations. +\usepackage{amsmath} %Mathematical alignments. +\usepackage{amssymb} %Mathematical symbols e.g. therefore. +\usepackage[parfill]{parskip} %Blank lines between paragraphs. +\usepackage[autostyle]{csquotes} +\usepackage{array} %Table centering. +\usepackage[british]{babel} %British localisation. +\usepackage[backend=biber,style=verbose]{biblatex} %Bibliography. + +\numberwithin{equation}{subsection} %Number equations based on their subsection. +\bibliography{../bibliographies/additionaltextbooks} %Use Bibliography of additional textbooks. + +%Document Headings. +\begin{document} +\title{Preparation of Pear Essence (Propyl Acetate) (7A/PPE)} +\author{Sam White} +\date{07/11/2017} +%\date{\vhCurrentDate\\\vhCurrentVersion} +\maketitle + +%\section{Aim} +%To prepare propyl acetate from propan-1-ol and acetic acid and then determine the percentage yield. + +\section{Reaction Mechanism\footcite[Preparation of Esters, p.~1014]{klein-organic} and Overall Equation} +\begin{figure}[H] + \centering + \includegraphics[width=0.75\textwidth]{Mechanism.png} + \caption{Mechanism for reaction \label{fig:mechanism}} +\end{figure} +\begin{figure}[H] + \centering + \includegraphics[width=0.55\textwidth]{Equation.png} + \caption{Overall Equation for Reaction \label{fig:equation}} +\end{figure} + +\section{Results and Analysis} +{\centering Boiling temperature of pure product: \SI{101}{\celsius} + +Mass of pure product: \SI{4.43}{\gram} + +} +%\begin{table}[h] +% \caption{Masses recorded at end of experiment.} +% \centering +% \begin{tabular}{|c|c|} +% \hline +% Item & Mass / \si{\gram} \\ +% \hline +% Empty Sample Bottle and Lid & 11.93 \\ +% \hline +% Filled Sample Bottle and Lid & 16.36 \\ +% \hline +% Mass of Propyl Acetate & 4.43 \\ +% \hline +% \end{tabular} +%\end{table} + +%\begin{equation} \label{eq:ppyl-acte-abbr} +% \ce{CH3CH2CH2OH(l) + CH3COOH(l) <=>[H+] CH3COOCH2CH2CH3(l) + H2O(l)} +%\end{equation} + +\subsection{Yield Calculation} +\begin{displaymath} + \begin{aligned} + \text{Moles of propan-1-ol at start of reaction} &= \frac{\SI{9.6}{\gram}}{(3(12.011) + 8(1.008) + 15.999) \text{ \si{\gram\per\mole}}} \\ + &= \frac{\SI{9.6}{\gram}}{\SI{60.096}{\gram\per\mole}} = \SI{0.16}{\mole} \\ + \text{Moles of acetic acid at start of reaction} &= \frac{\SI{24}{\gram}}{(2(12.011) + 4(1.008) + 2(15.999))\text{ \si{\gram\per\mole}}} \\ + &= \frac{\SI{24}{\gram}}{\SI{60.052}{\gram\per\mole}} = \SI{0.40}{\mole} + \end{aligned} +\end{displaymath} + +From the equation shown in figure~\ref{fig:equation} there is a 1:1 molar ratio between propan-1-ol and acetic acid, hence the acetic acid is in excess. The equation also shows a 1:1 molar ratio between the propan-1-ol and propyl acetate, hence the theoretical amount of propyl acetate produced is \SI{0.16}{\mole}. + +\begin{displaymath} + \begin{aligned} + \therefore \text{Theoretical yield of propyl acetate} &= \SI{0.16}{\mole} \times (5(12.011) + 10(1.008) + 2(15.999)) \text{ \si{\gram\per\mole}} \\ + &= \SI{0.16}{\mole} \times \SI{102.133}{\gram\per\mole} = \SI{16}{\gram} \\ + \therefore \text{Percentage yield} &= \frac{\SI{4.43}{\gram}}{\SI{16}{\gram}} \times \SI{100}{\percent} = \SI{27}{\percent} + \end{aligned} +\end{displaymath} + +This is quite low. This may be due to losses during the purification (e.g. containers were not washed after transfers and some product remained in the filter paper) and a consequence of the reversible nature of the reaction. %The mass of the reactants should have been measured to increase the accuracy and precision of the percentage yield. + +%This could be due to losses during the purification steps performed (such transfer losses since the containers of the product were not washed after transfers and since a fair amount of product remained in the filter paper) as well as due to the reaction not proceeding entirely to completion since it is reversible. In addition the actual masses of the reactants should have been measured at the start of the experiment to allow a more accurate and precise percentage yield to be determined. +\subsection{Spectra} +%\subsubsection{Reactants} +\begin{table}[h] + \caption{IR Spectrum of propan-1-ol.} + \centering + \begin{tabular}{|c|c|c|} + \hline + Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ + \hline + 2976.7 & Weak & \ce{CH3} Absorption \\ + \hline + 2936.0 & Weak & \ce{C-H2} Absorption \\ + \hline + 2962.3 & Weak & \ce{C-H3} Absorption \\ + \hline + 3319.0 & Weak and Broad & \ce{O-H} Absorption in Alcohol \\ + \hline + \end{tabular} +\end{table} +\begin{table}[h] + \caption{$^1$H NMR Spectrum of propan-1-ol.} + \centering + \begin{tabular}{|c|c|>{\centering}m{2.2cm}|m{7.9cm}|} + \hline + Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ + \hline + Approx. 7.3 & Singlet & Not Integrated & Characteristic for \ce{CDCl3} (Solvent) \\ + \hline + 3.66 & Triplet & 0.99 & Two $\alpha$-protons to alcohol group. Coupled to two protons. \\ + \hline + 2.03 & Singlet & 3.00 & \ce{OH} proton. Exchange decoupled. \\ \cline{1-2} \cline{4-4} + 1.57 & Quintet (Unclear) & (Integrated together) & Additional splitting possibly obscured by adjacent peaks. Coupled to four or five protons. \\ \cline{1-2} \cline{4-4} + 1.00 & Triplet (Small right-hand peak) & & Coupled to two protons. \\ + \hline + \end{tabular} +\end{table} +\begin{table}[h] + \caption{IR Spectrum of acetic acid.} + \centering + \begin{tabular}{|c|c|c|} + \hline + Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ + \hline + 1703.9 & Strong & \ce{C=O} Absorption close to acid range (1725-1705 \si{\per\centi\metre}) \\ + \hline + 3032.6 & Weak and Broad & \ce{O-H} Absorption close to carboxylic acid range (3000-2500 \si{\per\centi\metre}) \\ + \hline + \end{tabular} +\end{table} +\begin{table}[h] + \caption{$^1$H NMR Spectrum of acetic acid.} + \centering + \begin{tabular}{|c|c|c|c|} + \hline + Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ + \hline + 10.67 & Singlet & 0.90 & Single proton in \ce{-COOH} group. Exchange decoupled. \\ + \hline + Approx. 7.4 & Singlet & Not Integrated & Characteristic for \ce{CDCl3} (Solvent). \\ + \hline + 2.19 & Singlet & 3.00 & Three $\alpha$-protons to carboxyl group. \\ + \hline + \end{tabular} +\end{table} + +%\subsubsection{Product} +\begin{table}[h] + \caption{IR Spectrum of Product.} + \centering + \begin{tabular}{|c|c|c|} + \hline + Wavenumber / \si{\per\centi\metre} & Strength & Assignment \\ + \hline + 1738.0 & Strong & \ce{C=O} Absorption in the ester range (1740-1710 \si{\per\centi\metre}) \\ + \hline + 2882.5 & Weak & \ce{C-H} Absorption \\ + \hline + 2970.5 & Weak & \ce{C-H} Absorption \\ + \hline + \end{tabular} +\end{table} +\begin{table}[h] + \caption{$^1$H NMR Spectrum of Product.} + \centering + \begin{tabular}{|c|c|c|p{7.9cm}|} + \hline + Chemical Shift / ppm & $J$-Coupling & Integral Area & Summary \\ + \hline + Approx. 7.4 & Singlet & 0.030 & Characteristic for \ce{CDCl3} (Solvent) \\ + \hline + 4.14 & Triplet & 1.98 & Two protons (\ce{RCOO-C\underline{H}}). Coupled to two protons. \\ + \hline + 2.17 & Singlet & 3.28 & Three protons in unique environment \\ + \hline + Approx. 1.8 & Quartet (Unclear) & 1.90 & Two protons coupled three or four protons: splitting pattern difficult to interpret. \\ + \hline + 1.06 & Triplet (Small right-hand peak) & 2.75 & Three protons coupled to two protons. \\ + \hline + \end{tabular} +\end{table} +These spectra are consistent with propyl acetate as a product since the starting materials both had a broad peak corresponding to \ce{O-H} absorptions in their IR spectra, however this is absent in the product's IR spectrum. Also the NMR spectrum for the product shows it has four distinct hydrogen environments with the expected chemical shifts and (mostly) the expected splitting pattens for propyl acetate. In the IR spectra the \ce{C=O} absorption has shifted position from being at \SI{1703.9}{\per\centi\metre} in acetic acid to \SI{1738.0}{\per\centi\metre} in the product: this higher wavenumber is expected for the production of an ester. + +%These spectra are consistent with the product made being propyl acetate since the IR spectrum clearly shows the \ce{C=O} bond in the correct range for an ester and appropriate \ce{C-H} bond absorptions while the $^1$H NMR spectrum shows the correct number of environments, appropriate chemical shifts and roughly correct splitting pattens and areas for propyl acetate. The lack of the broad \ce{O-H} peak in the IR spectrum (which is present in both reactants) also indicates the formation of propyl acetate and little/no reactant impurities. The ambiguity in the splitting pattens in the $^1$H NMR spectrum around 1.6 ppm as well as the deviations of the areas of the peaks from the expected values may be due to the presence of impurities in the product mixture and also possibly due to the solvent residual water peak at 1.5 ppm. + +\end{document} diff --git a/year1/7a/Equation.png b/year1/7a/Equation.png new file mode 100755 index 0000000..71ceb1e Binary files /dev/null and b/year1/7a/Equation.png differ diff --git a/year1/7a/Mechanism.png b/year1/7a/Mechanism.png new file mode 100755 index 0000000..51431e4 Binary files /dev/null and b/year1/7a/Mechanism.png differ diff --git a/year1/8a/8a.bcf b/year1/8a/8a.bcf new file mode 100644 index 0000000..6f39cd6 --- /dev/null +++ b/year1/8a/8a.bcf @@ -0,0 +1,1964 @@ + + + + + + output_encoding + ascii + + + input_encoding + ascii + + + debug + 0 + + + mincrossrefs + 2 + + + minxrefs + 2 + + + sortcase + 1 + + + sortupper + 1 + + + + + + + alphaothers + + + + + labelalpha + 0 + + + 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+ + + + + + + + + + + + + +]> + + + latex + + 8a.bcf + + + 8a.bbl + + + blx-dm.def + blx-compat.def + biblatex.def + numeric.bbx + standard.bbx + verbose-note.cbx + biblatex.cfg + british.lbx + english.lbx + + + + biber + + biber + 8a + + + 8a.bcf + + + 8a.bbl + + + 8a.bbl + + + 8a.bcf + + + ../bibliographies/reference.bib + specific.bib + + + diff --git a/year1/8a/8a.tex b/year1/8a/8a.tex new file mode 100644 index 0000000..a3179b9 --- /dev/null +++ b/year1/8a/8a.tex @@ -0,0 +1,157 @@ +%Document Setup. +\documentclass{article} +\usepackage{graphicx} %Allows import of images. +%\usepackage{float} +\usepackage{floatrow} %Align tables and figures side-by-side. +\usepackage[extreme,mathspacing=normal,leading=normal]{savetrees} %Reduce whitespace. +\usepackage{siunitx} %SI Units formatting. +%\usepackage{vhistory} %Revision History. +\usepackage[version=4]{mhchem} %Chemical Equations. +\usepackage{amsmath} %Mathematical alignments. +\usepackage{amssymb} %Mathematical symbols e.g. therefore. +\usepackage[parfill]{parskip} %Blank lines between paragraphs. +\usepackage[autostyle]{csquotes} +\usepackage{array} %Table centering. +\usepackage[british]{babel} %British localisation. +\usepackage[backend=biber,citestyle=verbose-note]{biblatex} %Bibliography. + +\numberwithin{equation}{section} %Number equations based on their section. +\bibliography{../bibliographies/reference,specific} %Use Bibliography of reference books. +\floatsetup[table]{style=plaintop} %Put captions on top of tables. +\floatsetup[figure]{style=plain} %Ensure figure captions are below figures. +\sisetup{range-phrase=--,range-units=single} %Use - for ranges and only have a single unit. + +%Document Headings. +\begin{document} +\title{A Redox Titration to Determine the Ethanol Content of Wine (8A/RTE)} +\author{Sam White (Author) and Mihkel Raidal} +\date{05/12/2017} +%\date{\vhCurrentDate\\\vhCurrentVersion} +\maketitle + +{\centering Reported percentage of alcohol by volume (\si{\percent} ABV): \SI{13}{\percent} + +} +% +\section{Titration Results and Calculation of \si{\percent} ABV of Wine} +A mass of \SI{7.7910}{\gram} of \ce{(NH4)2Fe(SO4)2.6H2O} was dissolved in \SI{60}{\centi\metre\cubed} of \ce{H2SO4} and made up to \SI{200.00}{\centi\metre\cubed} with deionised water in a volumetric flask. Each \ce{(NH4)2Fe(SO4)2.6H2O} molecule liberates one \ce{Fe^{2+}} ion in solution, thus their concentrations in the solution are equal. The molar mass of \ce{(NH4)2Fe(SO4)2.6H2O} is \SI{392.139}{\gram\per\mole}.\footcite[Physical Constants of Inorganic Compounds, 4-46]{crc-handbook} +% +\begin{displaymath} + \text{Moles of \ce{Fe^{2+}} in \SI{200.00}{\centi\metre\cubed} standard solution} = \frac{\SI{7.7910}{\gram}}{\SI{392.139}{\gram\per\mole}} = \SI{0.019868}{\mole} +\end{displaymath} +Hence: +\begin{align} \label{[fe2+]} + \text{Concentration of \ce{Fe^{2+}} in standard solution} = \frac{\SI{0.019868}{\mole}}{\SI{200.00}{\centi\metre\cubed} \times (\frac{\SI{1}{\deci\metre}}{\SI{10}{\centi\metre}})^3} = \frac{\SI{0.019869}{\mole}}{\SI{200.00e-3}{\deci\metre\cubed}} = \SI{0.099340}{\mole\per\deci\metre\cubed} +\end{align} +% +%\section{Titration between \ce{K2Cr2O7} and \ce{(NH4)2Fe(SO4)2.6H2O}} +The reaction which occurred in both titrations was: +\begin{equation} \label{eq:cr2o72--fe2+} + \ce{Cr2O7^{2-} + 14H+ + 6Fe^{2+} -> 6Fe^{3+} + 2Cr^{3+} + 7H2O} +\end{equation} +With sodium diphenylamine-4-sulphonate used as the indicator (colour change from green (due to \ce{Cr^{3+}}) to purple at the end point). +% +\begin{table}[h] + \caption{Results of titration between \ce{K2Cr2O7} and standard solution of \ce{(NH4)2Fe(SO4)2.6H2O}} + \centering + \begin{tabular}{|c|c|c|c|} + \hline + Run & Start Volume / \si{\centi\metre\cubed} & End Volume / \si{\centi\metre\cubed} & Titre / \si{\centi\metre\cubed} \\ + \hline + 1 & 2.40 & 18.30 & 15.90 \\ + \hline + 2 & 2.20 & 18.80 & 16.60 \\ + \hline + 3 & 2.25 & 18.85 & 16.60 \\ + \hline + \end{tabular} +\end{table} +% +\begin{gather*} + \text{Average titre} = \frac{\SI{16.60}{\centi\metre\cubed} + \SI{16.60}{\centi\metre\cubed}}{2} = \SI{16.60}{\centi\metre\cubed} \\ + \text{Using~\ref{[fe2+]}, moles of \ce{Fe^{2+}} in \SI{20.00}{\centi\metre\cubed} aliquot} = \SI{0.099340}{\mole\per\deci\metre\cubed} \times \SI{20.00}{\centi\metre\cubed} \times \frac{\SI{1}{\deci\metre\cubed}}{\SI{1000}{\centi\metre\cubed}} = \SI{1.987e-3}{\mole} +\end{gather*} +% +From chemical equation~\ref{eq:cr2o72--fe2+} there is a 6:1 molar ratio between the \ce{Fe^{2+}} and \ce{Cr2O7^{2-}}. +\begin{equation} \label{[cr2o72-]} + \text{Concentration of \ce{Cr2O7^{2-}}} = \frac{\frac{1}{6} \times \SI{1.987e-3}{\mole}}{\SI{16.60}{\centi\metre\cubed} \times \frac{\SI{1}{\deci\metre\cubed}}{\SI{1000}{\centi\metre\cubed}}} = \frac{\SI{3.311e-4}{\mole}}{\SI{16.60e-3}{\deci\metre\cubed}} = \SI{0.01995}{\mole\per\deci\metre\cubed} +\end{equation} +% +%\section{Titration between Product Mixture and \ce{(NH4)2Fe(SO4)2.6H2O}} +During the reflux the ethanol from the sample of wine was oxidised by the \ce{Cr2O7^{2-}} ions to acetic acid as shown in this equation: +\begin{equation} \label{eq:ethanol-cr2o72-} + \ce{3CH3CH2OH + 2Cr2O7^{2-} + 16H+ -> 3CH3COOH + 4Cr^{3+} + 11H2O} +\end{equation} +During this the solution changed colour from orange (due to the \ce{Cr2O7^{2-}}) to dark green (due to the liberation of \ce{Cr^{3+}}). A back titration was then performed with the standard solution of \ce{Fe^{2+}} ions. The volumes used for this were half of those stated in the method since when the stated volumes were used the titre was very large and a maximum of two more titrations would have possible before the reaction mixture was exhausted. This would have been problematic if these titres were not concordant since the completion of additional titrations would have been impossible. +% +\begin{table}[h] + \centering + \caption{Results of titration between \ce{K2Cr2O7} in product mixture and standard solution of \ce{(NH4)2Fe(SO4)2.6H2O}} + \begin{tabular}{|c|c|c|c|} + \hline + Run & Start Volume / \si{\centi\metre\cubed} & End Volume / \si{\centi\metre\cubed} & Titre / \si{\centi\metre\cubed} \\ + \hline + 1 & 2.20 & 18.40 & 16.20 \\ + \hline + 2 & 18.90 & 35.25 & 16.35 \\ + \hline + 3 & 3.10 & 19.50 & 16.40 \\ + \hline + \end{tabular} +\end{table} +% +\begin{gather*} + \text{Average titre} = \frac{\SI{16.35}{\centi\metre\cubed}+\SI{16.40}{\centi\metre\cubed}}{2} = \SI{16.38}{\centi\metre\cubed} \\ + \text{Using~\ref{[fe2+]}, moles of \ce{Fe^{2+}} in \SI{5.00}{\centi\metre\cubed} aliquot} = \SI{0.099340}{\mole\per\deci\metre\cubed} \times \SI{5.00}{\centi\metre\cubed} \times \frac{\SI{1}{\deci\metre\cubed}}{\SI{1000}{\centi\metre\cubed}} = \SI{4.97e-4}{\mole} +\end{gather*} +% +From chemical equation~\ref{eq:cr2o72--fe2+} there is a 6:1 molar ratio between \ce{Fe^{2+}} and \ce{Cr2O7^{2-}}. +\begin{align*} + \text{Concentration of \ce{Cr2O7^{2-}} in product mixture} &= \frac{\frac{1}{6} \times \SI{4.97e-4}{\mole}}{\SI{16.38}{\centi\metre\cubed}} = \SI{5.05e-6}{\mole\per\centi\metre\cubed} \\ + \therefore\text{Moles of \ce{Cr2O7^{2-}} in \SI{126}{\centi\metre\cubed} product mixture} &= \SI{5.05e-6}{\mole\per\centi\metre\cubed} \times \SI{126}{\centi\metre\cubed} = \SI{6.37e-4}{\mole} +\end{align*} +% +%\section{Calculation of \si{\percent} ABV of the Wine} +Initially \SI{100.00}{\centi\metre\cubed} of \ce{Cr2O7^{2-}} of concentration \SI{0.01995}{\mole\per\deci\metre\cubed} (from~\ref{[cr2o72-]}) was in the reactant mixture. +\begin{align*} + \text{Initial moles of \ce{Cr2O7^{2-}}} &= \SI{100.00}{\centi\metre\cubed} \times \frac{\SI{1}{\deci\metre\cubed}}{\SI{1000}{\centi\metre\cubed}} \times \SI{0.01995}{\mole\per\deci\metre\cubed} = \SI{1.995e-3}{\mole} \\ + \therefore\text{Moles of \ce{Cr2O7^{2-}} which reacted} &= \SI{1.995e-3}{\mole} - \SI{6.37e-4}{\mole} = \SI{1.36e-3}{\mole} +\end{align*} +% +From chemical equation~\ref{eq:ethanol-cr2o72-} molar ratio between \ce{Cr2O7^{2-}} and ethanol is 2:3. The molar mass of ethanol is \SI{46.068}{\gram\per\mole}.\footcite[Physical Constants of Organic Compounds, 3-246]{crc-handbook} +\begin{align*} + \text{Moles of ethanol in \SI{1.00}{\centi\metre\cubed} sample} &= \frac{\SI{1.36e-3}{\mole}}{2} \times 3 = \SI{2.04e-3}{\mole} \\ + \therefore\text{Mass of ethanol in \SI{1.00}{\centi\metre\cubed}} &= \SI{2.04e-3}{\mole} \times \SI{46.068}{\gram\per\mole} = \SI{0.0938}{\gram} +\end{align*} +The density of ethanol is \SI{0.7893}{\gram\per\centi\metre\cubed}.$^2$ %Quick and dirty way to make footer smaller. +%\footcite[Physical Constants of Organic Compounds, 3-246]{crc-handbook} +\begin{displaymath} + \text{\si{\percent} ABV of wine} = \frac{\SI{0.0938}{\gram}}{\SI{0.7893}{\gram\per\centi\metre\cubed}}\times \frac{\SI{100}{\percent}}{\SI{1.00}{\centi\metre\cubed}} = \SI{11.9}{\percent} +% \text{Volume of ethanol in \SI{1.00}{\centi\metre\cubed}} &= \frac{\SI{0.0938}{\gram}}{\SI{0.7893}{\gram\per\centi\metre\cubed}} = \SI{0.119}{\centi\metre\cubed} \\ +% \text{Hence, \si{\percent} ABV of wine} &= \frac{\SI{0.119}{\centi\metre\cubed}}{\SI{1.00}{\centi\metre\cubed}} \times \SI{100}{\percent} = \SI{11.9}{\percent} +\end{displaymath} +% +\section{Error Propagation} +\begin{align*} + \delta\ce{[Fe^{2+}]} &= \pm\SI{0.099340}{\mole\per\deci\metre\cubed} \sqrt{\left(\frac{\pm\SI{0.00005}{\gram}\times2}{\SI{7.7910}{\gram}}\right)^2 + \left(\frac{\pm\SI{0.001}{\gram\per\mole}}{\SI{392.139}{\gram\per\mole}}\right)^2 + \left(\frac{\pm\SI{0.15}{\centi\metre\cubed}}{\SI{200.00}{\centi\metre\cubed}}\right)^2} = \pm\SI{0.00007}{\mol\per\deci\metre\cubed} \\ +% + \delta\ce{[Cr2O7^{2-}]} &= \pm\SI{0.01995}{\mole\per\deci\metre\cubed} \sqrt{\left(\frac{\pm\SI{0.00007}{\mole\per\deci\metre\cubed}}{\SI{0.099340}{\mole\per\deci\metre\cubed}}\right)^2 + \left(\frac{\pm\SI{0.06}{\centi\metre\cubed}}{\SI{20.00}{\centi\metre\cubed}}\right)^2 + \left(\frac{\pm\SI{0.1}{\centi\metre\cubed}\times 2}{\SI{16.60}{\centi\metre\cubed}}\right)^2} = \pm\SI{0.0002}{\mole\per\deci\metre\cubed} \\ + % + \delta V_{reaction \text{ } mixture} &= \pm\sqrt{\left(\pm\SI{0.015}{\centi\metre\cubed}\right)^2 + \left(\pm\SI{0.15}{\centi\metre\cubed}\right)^2 + \left(\pm\SI{0.06}{\centi\metre\cubed}\right)^2} = \pm\SI{0.2}{\centi\metre\cubed} \\ +% + \delta n_{initial \text{ } \ce{Cr2O7^{2-}}} &= \pm\SI{1.995e-3}{\mole} \sqrt{\left(\frac{\pm\SI{0.15}{\centi\metre\cubed}}{\SI{100.00}{\centi\metre\cubed}}\right)^2 + \left(\frac{\pm\SI{0.0002}{\mole\per\deci\metre\cubed}}{\SI{0.01995}{\mole\per\deci\metre\cubed}}\right)^2} = \pm\SI{0.02e-3}{\mole} \\ +% + \delta n_{final \text{ } \ce{Cr2O7^{2-}}} &= \pm\SI{6.37e-4}{\mole} \sqrt{\left(\frac{\pm\SI{0.00007}{\mole\per\deci\metre\cubed}}{\SI{0.099340}{\mole\per\deci\metre\cubed}}\right)^2 + \left(\frac{\pm\SI{0.03}{\centi\metre\cubed}}{\SI{5.00}{\centi\metre\cubed}}\right)^2 + \left(\frac{\pm\SI{0.1}{\centi\metre\cubed}\times2}{\SI{16.38}{\centi\metre\cubed}}\right)^2 + \left(\frac{\pm\SI{0.2}{\centi\metre\cubed}}{\SI{126}{\centi\metre\cubed}}\right)^2} \\ + &= \pm\SI{0.09e-4}{\mole} \\ +% + \delta n_{ethanol} &= \sqrt{\left(\pm\SI{0.02e-3}{\mole}\right)^2 + \left(\pm\SI{0.09e-4}{\mole}\right)^2} = \pm\SI{0.03e-3}{\mole} \\ +% + \delta \si{\percent} \text{ } ABV &= \pm\SI{11.9}{\percent} \sqrt{\left(\frac{\pm\SI{0.03e-3}{\mole}}{\SI{2.04e-3}{\mole}}\right)^2 + \left(\frac{\pm\SI{0.0001}{\gram\per\centi\metre\cubed}}{\SI{0.7893}{\gram\per\centi\metre\cubed}}\right)^2 + \left(\frac{\pm\SI{0.001}{\gram\per\mole}}{\SI{46.068}{\gram\per\mole}}\right)^2} = \pm\SI{0.2}{\percent} +\end{align*} +Hence the \si{\percent} ABV of ethanol of the wine was found to be $11.9 \pm 0.2 \si{\percent}$. +% +\section{Analysis of Results} +The reported \si{\percent} ABV value of the wine is greater than that determined by experiment, however the reported \si{\percent} ABV value of wine is only required to be accurate within $\pm\SI{1}{\percent}$\footcite[Annex XII]{eur-32011R1169-en}, hence there is a slight overlap between the possible error in the reported value and that of the determined value from \SIrange{12.0}{12.1}{\percent}. Despite this systematic errors are likely to have influenced the \si{\percent} ABV determined since this is at the extreme end of the uncertainty in the reported value, hence it is unlikely that the true \si{\percent} ABV value lies within this range. + +A possible error is that the ethanol might not have been fully oxidised to acetic acid hence reducing the amount of \ce{Cr2O7^{2-}} which reacted and thus the \si{\percent} ABV value determined. To minimise this error the reaction mixture could be refluxed for longer (e.g. 2 hours). There may have also been a loss of ethanol and ethanal vapour while the reactants were being transferred into the round bottomed flask. To minimise this the flask could have been cooled in an ice bath until the condenser was added, hence reducing losses due to evaporation. There was also uncertainty about the end point for the second titration since the indicator colour change was not very distinct. To minimise this an alternative indicator such as 1,10-phenanthroline ferrous sulphate solution could be used which would have more distinct colour change from blue-green to brown at the end point.\footcite[pp.~3]{senior-chem} +\end{document} diff --git a/year1/8a/specific.bib b/year1/8a/specific.bib new file mode 100644 index 0000000..5c30bb6 --- /dev/null +++ b/year1/8a/specific.bib @@ -0,0 +1,14 @@ +@online{eur-32011R1169-en, + title = {Regulation (EU) No 1169/2011 of the European Parliament and of the Council of 25 October 2011}, + author = {Official Journal of the European Union}, + date = {2011-11-22}, + url = {http://eur-lex.europa.eu/legal-content/EN/TXT/HTML/?uri=CELEX:30211R1169}, + urldate = {2017-12-08} +} + +@online{senior-chem, + title = {Estimation of Alcohol Content in Wine by Dichromate Oxidation followed by Redox Titration}, + author = {Sirromet Wines Pty Ltd}, + url = {http://seniorchem.com/4. Alcohol-Content-bu-Dichromate-Oxidation-and-Redox-Titration.pdf}, + urldate = {2017-12-09} +} diff --git a/year1/project/ZSM-5-Chain.png b/year1/project/ZSM-5-Chain.png new file mode 100755 index 0000000..d9f57ee Binary files /dev/null and b/year1/project/ZSM-5-Chain.png differ diff --git a/year1/project/ZSM-5-Layer.png b/year1/project/ZSM-5-Layer.png new file mode 100755 index 0000000..0e8bdb9 Binary files /dev/null and b/year1/project/ZSM-5-Layer.png differ diff --git a/year1/project/ZSM-5-SBU.png b/year1/project/ZSM-5-SBU.png new file mode 100755 index 0000000..ffbc3e9 Binary files /dev/null and b/year1/project/ZSM-5-SBU.png differ diff --git a/year1/project/project.bcf b/year1/project/project.bcf new file mode 100644 index 0000000..232388c --- /dev/null +++ b/year1/project/project.bcf @@ -0,0 +1,2028 @@ + + + + + + output_encoding + ascii + + + input_encoding + ascii + + + debug + 0 + + + mincrossrefs + 2 + + + minxrefs + 2 + + + sortcase + 1 + + + sortupper + 1 + + + + + + + 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+ + blx-dm.def + blx-compat.def + biblatex.def + chem-rsc.bbx + numeric-comp.bbx + numeric.bbx + standard.bbx + chem-rsc.cbx + numeric-comp.cbx + biblatex.cfg + british.lbx + english.lbx + + + + biber + + biber + project + + + project.bcf + + + project.bbl + + + project.bbl + + + project.bcf + + + ../bibliographies/reference.bib + ../bibliographies/coretextbooks.bib + specific.bib + + + diff --git a/year1/project/project.tex b/year1/project/project.tex new file mode 100644 index 0000000..f50c9bc --- /dev/null +++ b/year1/project/project.tex @@ -0,0 +1,716 @@ +%Document Setup. +\documentclass[a4paper,11pt]{article} +\usepackage[a4paper]{geometry} %Set page size to A4. +\usepackage{graphicx} %Allows import of images. +%\usepackage{float} +\usepackage{floatrow} %Align tables and figures side-by-side. +%\usepackage[moderate, mathspacing=normal,leading=normal]{savetrees} %Reduce whitespace. +\usepackage{siunitx} %SI Units formatting. +%\usepackage{vhistory} %Revision History. +\usepackage[version=4]{mhchem} %Chemical Equations. +\usepackage{amsmath} %Mathematical alignments. +\usepackage{amssymb} %Mathematical symbols e.g. therefore. +\usepackage[parfill]{parskip} %Blank lines between paragraphs. +\usepackage[autostyle]{csquotes} +\usepackage{array} %Table centering. +\usepackage[british]{babel} %British localisation. +%\usepackage[backend=biber,citestyle=verbose-note,autocite=footnote]{biblatex} %Bibliography. +\usepackage[backend=biber,style=chem-rsc]{biblatex} %Bibliography. + +\numberwithin{equation}{subsection} %Number equations based on their section. +\bibliography{../bibliographies/reference,../bibliographies/coretextbooks,specific} %Use Bibliography of reference books. +\floatsetup[table]{style = plaintop} %Put captions on top of tables. +\floatsetup[figure]{style = plain} %Ensure figure captions are below figures. +\sisetup{range-phrase = --,range-units = single} %Use - for ranges and only have a single unit shown after. +\sisetup{separate-uncertainty = true,multi-part-units=single} %Use \pm for uncertainties. +\setcounter{secnumdepth}{4} %Label paragraphs as subsubsubsections. +\setcounter{tocdepth}{4} %Treat paragraphs as sections in table of contents. + +%Allow manual adding of very large brackets. +\makeatletter +\newcommand{\vast}{\bBigg@{3}} +\newcommand{\vastt}{\bBigg@{4}} +\newcommand{\Vast}{\bBigg@{5}} +\newcommand{\Vastt}{\bBigg@{6}} +\makeatother + +%Document Headings. +\begin{document} +\title{Effect of the Copper and Zinc Cations on the Ion Exchange Level Obtained for the Aqueous Phase Ion Exchange Process with the ZSM-5 Zeolite} +\author{Sam White} +\date{06/03/2018} +%\date{\vhCurrentDate\\\vhCurrentVersion} +\maketitle + +\begin{abstract} + An investigation into how the ion exchange level for ZSM-5 differs when using copper and zinc cations in an aqueous phase ion exchange process was attempted. The spectrophotometric method utilised for the measurement of the exchange level for the copper cations was found to be ineffective at producing meaningful results within the timescale of the investigation, hence precluding the comparison of the exchange levels for the different metal cations. +\end{abstract} + +\section{Aim} +This project aimed to compare how the ion exchange level for a HZSM-5 zeolite differs for the aqueous phase ion exchange process with copper and zinc cations. + +\section{Introduction} +Zeolites are crystalline, microporous solids used for a large number of uses such as for catalytic cracking, air purification, water softening and as desiccants.~\autocite{hardsoftwater,petrov12} This project was completed using the ZSM-5 (Zeolite Socony Mobil-5)\autocite{zhang15} zeolite which is used within the petrochemical industry for the conversion of methanol to gasoline, dewaxing of distillates, separation of organic products (such as separating para-xylene from its isomers) and the interconversion of hydrocarbons.\autocite{olson81,rasouli12,sarkany99} + +\subsection{Structure} +Zeolites are comprised of a finite or infinite number of unique unit cells each of which is made from a constant, integral number of the same type of secondary building unit (SBU) with each vertex in the SBU being a tetrahedron of either \ce{[SiO4]} or \ce{[AlO4]^{-}} (which are themselves known as the primary building units and are henceforth generically referred to as \ce{XO4} tetrahedra).\autocite{zeolite-atlas,petrov12,ic-zeolite-structure,han09,danaher17} Each aluminium tetrahedron in the SBU introduces a negative charge -- since aluminium has a 3+ oxidation state whereas silicon has a 4+ oxidation state -- which is balanced by the presence of cationic counterions.\autocite{gomez16,petrov12,han09,danaher17} + +The ZSM-5 zeolite used is a pentasil\autocite{danaher17,olson81} zeolite (constructed of eight five-membered rings) with an SBU containing twelve \ce{XO4} tetrahedra which form a pair of five-one units\autocite{zeolite-atlas,olson81,wu79} as shown in figure \ref{fig:zsm-5-sbu} where the vertices represent the \ce{X} atoms and the X-O-X bridges are shown as straight lines for clarity which is a reasonable approximation since the X-O-X bond angle is around $\text{\SIrange{140}{150}{\degree}} \approx \SI{180}{\degree}$ for silicas and aluminosilicates.\autocite{zeolite-atlas} + +\begin{figure}[H] + \centering + \includegraphics[width=0.25\textwidth]{ZSM-5-SBU.png} + \caption{Secondary building unit for ZSM-5 zeolite.\autocite{olson81}}\label{fig:zsm-5-sbu} +\end{figure} + +These SBUs then form long chains (depicted in figure \ref{fig:zsm-5-chain}) which themselves interconnect to form layers hence giving a unit cell containing eight SBUs shown at the centre of figure \ref{fig:zsm-5-layer}.\autocite{olson81} In figure \ref{fig:zsm-5-layer} one of the chains (shown in figure \ref{fig:zsm-5-chain}) is highlighted to demonstrate how the chains interconnect to form layers. + +\begin{figure}[H] +\begin{floatrow} + \centering + \ffigbox + {\includegraphics[width=0.2\textwidth]{ZSM-5-Chain.png}} + {\caption{Chain building unit for ZSM-5 zeolite.\autocite{olson81}}\label{fig:zsm-5-chain}} + \ffigbox + {\includegraphics[width=0.4\textwidth]{ZSM-5-Layer.png}} + {\caption{Layer of ZSM-5 zeolite.\autocite{olson81}}\label{fig:zsm-5-layer}} +\end{floatrow} +\end{figure} + +As there are eight SBUs of twelve tetrahedra per unit cell in ZSM-5 there are $8 \times 12 = 96$ \ce{X} atoms per cell hence there are $2 \times 96 = 192$ oxygen atoms per cell\autocite{zeolite-atlas} since there are two oxygen atoms per individual \ce{X} atom.\autocite{patent3702886A} This gives the unit cell formula given in \ref{eq:unit-cell} where \ce{M} is a cation with a charge of $q$, so $\frac{1}{q}$ of these cations are required per negative charge and hence aluminium atom.\autocite{ismagilov00} + +\begin{equation}\label{eq:unit-cell} + \ce{M_{\frac{n}{q}} Al_n Si_{96-n}O_{192}.x H2O} +\end{equation} + +\subsection{Ion Exchange} +These \ce{M^{$q$+}} cations can be exchanged with other ions in a process called ion exchange. Changing the counterion of the ZSM-5 zeolite can alter the acidity, hydrophobicity, reaction selectivity and other properties of the zeolite.~\autocite{rasouli12,chaudhari02,han09} + +The copper exchanged form of ZSM-5 is known to be one of the best forms of ZSM-5 for the selective catalytic reduction of \ce{NO} by \ce{C2-C4} hydrocarbons.~\autocite{sato91,yashnik05,ismagilov00} This is an important use case since large amounts of \ce{NO} are produced in vehicle and industrial boiler emissions and \ce{NO} is known to cause air pollution and acid rain.~\autocite{iwamoto91} + +Similarly the zinc exchanged form of ZSM-5 is currently subject to much research since it has been found to be effective at selectively converting methanol to use aromatic species such as benzene, toluene and xylene (important for the manufacture of polyester fibers, dyes, pesticides and medicines) as an alternative method to petroleum processing.~\autocite{niu14,wang16} Specifically ZnZSM-5 has -- so far -- been the best choice of cation for this purpose since it is cheap, non-toxic and highly effective at the aforementioned aromatization process.~\autocite{sun18} + +A ZSM-5 zeolite with a low \ce{SiO2}/\ce{AlO3} ratio of 23 was used in this investigation since this maximised the number of sites which were available for ion exchange due to the higher aluminium content. In addition zeolites with a high \ce{SiO2}/\ce{AlO3} ratio are hydrophobic\autocite{chen76,han09,olson99} hence in aqueous phase ion exchange the cation solution does not spontaneously enter the zeolite nanopores so ion exchange happens only at sites close to the pore entrance.\autocite{han09,olson99} This maximisation of the ion exchange is important since it should accentuate any differences between the ion exchange level with the different cations and make them easier to detect. + +\section{Experimental}\label{sec:experimental} +Standard solutions of \ce{Cu^{2+}} and \ce{Zn^{2+}} (\SI{50.00}{\centi\metre\cubed}) were made using \ce{CuSO4.5H2O} and \ce{ZnSO4.7H2O} with concentrations of \SI{2.008e-3}{\mole\per\deci\metre\cubed} and \SI{2.02e-3}{\mole\per\deci\metre\cubed} respectively. The absorbance of the standard copper sulphate solution was taken at \SI{806}{\nano\metre} (\num{0.484}) then \SI{20.00}{\centi\metre\cubed} of the solutions was added to \SI{0.4810}{\gram} (for the copper solution) and \SI{0.5274}{\gram} (for the zinc solution) of HZSM-5 zeolite with an \ce{SiO2}/\ce{AlO3} ratio of 23 (forming an opaque white suspension) prior to heating both solutions with stirring at \SI{70}{\celsius} for one hour. Centrifugation was completed on part of the resultant copper mixture, however time constraints prevented the completion of this process. The two mixtures were then stored in a fridge for one week until the following laboratory session. + +After one week the zeolite had sedimented so clear solution was collected and the remainder was centrifuged for 30 minutes before the supernatant was reintroduced to rest of the solution producing a slightly cloudy copper and a moderately cloudy zinc solution. The solutions were made up to \SI{100.00}{\centi\metre\cubed} before the absorbance of the copper solution at \SI{806}{\nano\metre} was determined (\num{0.110}) and \SI{20.00}{\centi\metre\cubed} aliquots of the zinc solution in a pH 10 buffer solution (\SI{2}{\centi\metre\cubed}) were titrated against a standard ethylenediaminetetraacetate (EDTA) solution (batch A: \SI{0.4993}{\mole\per\deci\metre\cubed}) with an eriochrome black T indicator (colour change from red to light blue). + +\section{Results} + +\subsection{Copper-Exchanged Zeolite} +\begin{table}[h] + \caption{Masses used for the preparation of CuZSM-5.}\label{tbl:cu-masses} + \centering + \begin{tabular}{|c|c|} + \hline + Substance & Mass / \si{\gram} \\ + \hline + \ce{CuSO4.5H2O} & 0.5014 \\ + \hline + HZSM-5 & 0.4810 \\ + \hline + \end{tabular} +\end{table} + +\begin{table}[h] + \caption{Spectrophotometric results for the copper sulphate solutions.}\label{tbl:cu-absorbance} + \centering + \begin{tabular}{|c|c|} + \hline + Substance & Absorbance \\ + \hline + Standard Solution & 0.484 \\ + \hline + Post-Reaction Solution & 0.110 \\ + \hline + \end{tabular} +\end{table} + +The uncertainty in these absorbance values can be modelled using the following equation:~\autocite{galban07} + +\begin{equation}\label{eq:spectrophotometer-uncertainty} + \delta Abs = Abs \sqrt{ \left( \frac{0.434}{Abs} k_2 \sqrt{1 + 10^{Abs}} \right)^2 + + \left( \frac{0.434}{Abs} k_3 \right)^2 } +\end{equation} + +Where $k_2$ is a measure of the expected precision of the instrument itself for a specific solution and $k_3$ is a measure of the uncertainty introduced by replacing the cuvette. + +Values of $k_2=\num{4.5e-4}$ and $k_3=\num{27e-4}$ were used (recorded by Galb\'{a}n et al.\@ for the PerkinElmer Lambda 5 spectrophotometer with ferroin solution)~\autocite{galban07} since they produce the largest overall uncertainty of values recorded by Galb\'{a}n et al.\@, hence giving the most generous estimate in the uncertainty of the absorbances recorded. Letting $A_{\ce{Cu}_\text{std.}}$ be the absorbance of the standard \ce{CuSO4} solution and $A_{\ce{Cu}_\text{prod.}}$ be the absorbance of the post-reaction solution thus gives: + +\begin{align} + \delta A_{\ce{Cu}_\text{std.}} &= 0.484 \sqrt{ \left( \frac{0.434}{0.484} \times \num{4.5e-4} \sqrt{1 + 10^{0.484}} \right)^2 + + \left( \frac{0.434}{0.484} \times \num{27e-4} \right)^2 } \nonumber \\ + \label{eq:cu-std-abs-uncertainty} + &= 0.001 \\ + \delta A_{\ce{Cu}_\text{prod.}} &= 0.110 \sqrt{ \left( \frac{0.434}{0.110} \times \num{4.5e-4} \sqrt{1 + 10^{0.110}} \right)^2 + + \left( \frac{0.434}{0.110} \times \num{27e-4} \right)^2 } \nonumber \\ + \label{eq:cu-prod-abs-uncertainty} + &= 0.001 +\end{align} + +\subsection{Zinc-Exchanged Zeolite} +\begin{table}[h] + \caption{Mass used in preparation of the \ce{ZnSO4} standard solution utilised in the standardisation of the \ce{EDTA} solution.}\label{tbl:zn-std-masses} + \centering + \begin{tabular}{|c|c|} + \hline + Substance & Mass / \si{\gram} \\ + \hline + \ce{ZnSO4.7H2O} & 0.4587 \\ + \hline + \end{tabular} +\end{table} + +\begin{table}[h] + \caption{Masses used for the preparation of ZnZSM-5.}\label{tbl:zn-zsm-5-masses} + \centering + \begin{tabular}{|c|c|} + \hline + Substance & Mass / \si{\gram} \\ + \hline + \ce{ZnSO4.7H2O} & 0.6331 \\ + \hline + HZSM-5 & 0.5274 \\ + \hline + \end{tabular} +\end{table} + +The reaction which occurred during the titrations between the \ce{EDTA^4-} and \ce{Zn^2+} ions in given in equation \ref{eq:edta-zn-reaction}: + +\begin{equation}\label{eq:edta-zn-reaction} + \ce{Zn^2+ (aq) + EDTA^4- (aq) -> ZnEDTA^2-(aq)} +\end{equation} + +%TODO: Reference. Include? +%The pH 10 buffer was used to ensure the EDTA existed in the deprotonated form which is able to complex to metal cations and also to ensure the eriochrome black T indicator exhibits the desired colour change. + +\begin{table} + \caption{Titration results from standardisation of the batch A \ce{EDTA} solution with the standard zinc sulphate solution.}\label{tbl:zn-standardisation} + \centering + \begin{tabular}{|c|c|c|c|} + \hline + Run & Start Volume / \si{\centi\metre\cubed} & End Volume / \si{\centi\metre\cubed} & Titre Volume / \si{\centi\metre\cubed} \\ + \hline + 1 & 1.45 & 33.70 & 32.25 \\ + \hline + 2 & 2.25 & 34.20 & 31.95 \\ + \hline + \end{tabular} +\end{table} + +Due to time constraints the standardisation of the \ce{EDTA} solution was not fully completed, hence the accurate titre volume ($V_{\ce{EDTA}_\text{std.}}$) has been assumed to be the titre volume from the second run (see table \ref{tbl:zn-standardisation}): + +\begin{equation}\label{eq:edta-v-standardisation} + V_{\ce{EDTA}_{std.}} = \SI{31.95}{\centi\metre\cubed} +\end{equation} + +\begin{table} + \caption{Titration results between zinc solution after ion-exchange process and standardised \ce{EDTA} solution.}\label{tbl:zn-analytical-titration} + \centering + \begin{tabular}{|c|c|c|c|} + \hline + Run & Start Volume / \si{\centi\metre\cubed} & End Volume / \si{\centi\metre\cubed} & Titre Volume / \si{\centi\metre\cubed} \\ + \hline + 1 & 2.40 & 29.10 & 26.70 \\ + \hline + 2 & 2.90 & 29.55 & 26.65 \\ + \hline + 3 & 1.40 & 28.00 & 26.60 \\ + \hline + 4 & 11.35 & 37.70 & 26.35 \\ + \hline + \end{tabular} +\end{table} + +The average titre volume for the titration with the post ion exchange solution ($V_{\ce{EDTA}_\text{prod.}}$) was determined from the second and third runs (see table \ref{tbl:zn-analytical-titration}) since the first run was a rough titration and the fourth run can be clearly seen be be anomalous. + +\begin{equation}\label{eq:edta-v-analytical} + V_{\ce{EDTA}_\text{prod.}} = \frac{\SI{26.65}{\centi\metre\cubed} + \SI{26.60}{\centi\metre\cubed}}{2} = \SI{20.63}{\centi\metre\cubed} +\end{equation} + +\section{Calculations} + +\subsection{Calculation of Maximum Theoretical Number of Ion Exchanges} +The \ce{SiO2}/\ce{Al2O3} ratio in the zeolite used was $23$. There are two \ce{Al} atoms in \ce{Al2O3} compared to one \ce{Si} atom in \ce{SiO2}, hence $\ce{Si}/\ce{Al} = \frac{23}{2} = 11.5$. + +Using the unit cell general formula (equation \ref{eq:unit-cell}) and letting the \ce{Si}/\ce{Al} ratio be $r$ and $n$ be the number of aluminium atoms per unit cell: + +\begin{align*} + r &= \frac{\text{Number of \ce{Si} per unit cell}}{\text{Number of \ce{Al} per unit cell}} \\ + \therefore r &= \frac{96 - n}{n} \\ + n r + n &= 96 \\ + \therefore n &= \frac{96}{r + 1} +\end{align*} + +Hence for $r = 11.5$ there are $n = \frac{96}{11.5 + 1} = 7.68$ \ce{Al} per unit cell. Letting $q$ be the cation charge and $x$ be the number of water molecules for unit cell thus gives: + +\begin{align*} + Mr_{\text{unit cell}} = \frac{7.68}{q} Mr_{\text{cation}} &+ (11.5(26.982)+ (96-7.68)(28.085) + 192(15.999) \\ + &+ x(2(1.008) + 15.999)) \si{\gram\per\mole} \\ + = \frac{7.68}{q} Mr_{\text{cation}} &+ \SI{5759.469}{\gram\per\mole} + x(\SI{450.375}{\gram\per\mole}) +\end{align*} + +Thus for HZSM-5 where the cation is \ce{H+} and $x \approx 25$~\autocite{donder06}. +\begin{equation}\label{eq:hzsm-5-mr} +\begin{split} + Mr_{\text{HZSM-5 unit cell}} &= \frac{7.68}{1} \times \SI{1.008}{\gram\per\mole} + (5759.469 + 25(450.375)) \text{ \si{\gram\per\mole}} \\ + &= \SI{6217.613}{\gram\per\mole} +\end{split} +\end{equation} + +Let: $q$ be the cation charge; $n_{\text{max. cation}}$ be the theoretical maximum amount of cation which can be exchanged and $n_{\text{cation}}$, $m_{\text{cation}}$ and $Mr_{\text{cation}}$ respectively be the actual amount, mass and $Mr$ of the cation exchanged. + +\begin{align} + n_{\text{HZSM-5 unit cell}} &= \frac{m_{\text{HZSM-5}}}{Mr_{\text{HZSM-5 unit cell}}} \nonumber \\ + n_{\text{max. cation}} &= \frac{7.68}{q} n_{\text{HZSM-5 unit cell}} \nonumber \\ + &= \frac{7.68}{q} \frac{m_{\text{HZSM-5}}}{Mr_{\text{HZSM-5 unit cell}}} \nonumber \\ +% + \si{\percent} \text{ Exchange Level} &= \frac{n_{\text{cation}}}{n_{\text{max. cation}}} \times \SI{100}{\percent} \nonumber \\ + \label{eq:cation-percent-exchanged} + &= \frac{q Mr_{\text{HZSM-5 unit cell}} n_{\text{cation}}}{7.68 m_{\text{HZSM-5}}} \times \SI{100}{\percent} +\end{align} + +\subsection{Calculations for Copper Solution} +\subsubsection{Determination of Molar Extinction Coefficient}\label{sec:cu-percent-exchanged} +Let $V_{\ce{Cu}_\text{std.}}$ be the volume and $[\ce{CuSO4}]_\text{std.}$ be the concentration of the standard \ce{Cu^{2+}} solution. +\begin{align} + n_{\ce{CuSO4}} &= \frac{m_{\ce{CuSO4.5H2O}}}{Mr_{\ce{CuSO4.5H2O}}} \nonumber \\ + [\ce{CuSO4}]_\text{std.} &= \frac{n_{\ce{CuSO4}}}{V_{\ce{Cu}_\text{std.}}} \nonumber\\ + \label{eq:[cuso4]-std} + &= \frac{m_{\ce{CuSO4.5H2O}}}{V_{\ce{Cu}_\text{std.}} Mr_{\ce{CuSO4.5H2O}}} +\end{align} + +Rearranging the Beer-Lambert law (equation \ref{eq:beer-lambert}) for the molar extinction coefficient: + +\begin{align} + \label{eq:beer-lambert} + A = \epsilon c l \\ + \label{eq:beer-lambert-epsilon} + \epsilon = \frac{A}{c l} +\end{align} + +Hence using equations \ref{eq:[cuso4]-std} and \ref{eq:beer-lambert-epsilon}: + +\begin{equation} +\begin{split} \label{eq:molar-extinction} + \epsilon_{\ce{CuSO4}} &= \frac{A_{\ce{Cu}_\text{std.}}}{[\ce{CuSO4}]_\text{std.} l} \\ + &= \frac{A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{std.}} Mr_{\ce{CuSO4.5H2O}}}{l m_{\ce{CuSO4.5H2O}}} +\end{split} +\end{equation} + +%This hence gives: +%\begin{align} +% \epsilon_{\text{\ce{CuSO4}}} &= \frac{0.484 \times \SI{50.00e-3}{\deci\metre\cubed} \times (63.546 + 32.066 + 4(15.999) + 5(2(1.008) + 15.999)) \text{ \si{\gram\per\mole}}}{\SI{1.0}{\centi\metre} \times \SI{0.5014}{\gram}} \nonumber\\ +% \label{eq:molar-extinction-calc} +% &= \frac{0.484 \times \SI{50.00e-3}{\deci\metre\cubed} \times \SI{249.677}{\gram\per\mole}}{\SI{1.0}{\centi\metre} \times \SI{0.5014}{\gram}} = \SI{12.05}{\deci\metre\cubed\per\mole\per\centi\metre} +%\end{align} + +\subsubsection{Determination of \ce{Cu^2+} Ion Exchange Level} +By rearranging the Beer-Lambert Law (equation \ref{eq:beer-lambert}) for concentration: + +\begin{equation} \label{eq:beer-lambert-c} + c = \frac{A}{\epsilon l} +\end{equation} + +Letting $[\ce{CuSO4}]_\text{prod.}$ be the concentration, $n_{\ce{Cu}_\text{prod.}}$ be the amount of \ce{Cu^{2+}} ions and $V_{\ce{Cu}_\text{prod.}}$ be the volume of the solution after the ion exchange process while using equation \ref{eq:beer-lambert-c}: + +\begin{align} + [\ce{CuSO4}]_\text{prod.} &= \frac{A_{\ce{Cu}_\text{prod.}}}{\epsilon_{\text{\ce{CuSO4}}} l} \nonumber \\ + \text{So: } n_{\ce{Cu}_\text{prod.}} &= [\ce{CuSO4}]_\text{prod.} V_{\ce{Cu}_\text{prod.}} \nonumber \\ + \label{eq:n_cu-prod} + &= \frac{A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}}}{\epsilon_{\text{\ce{CuSO4}}} l} +\end{align} + +Substituting equation \ref{eq:molar-extinction} into \ref{eq:n_cu-prod}: + +\begin{equation} \label{eq:n_cu-prod-final} + n_{\ce{Cu}_\text{prod.}} = \frac{A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} m_{\ce{CuSO4.5H2O}}}{A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{std.}} Mr_{\ce{CuSO4.5H2O}}} +\end{equation} + +The amount of \ce{Cu^2+} exchanged ($n_{\ce{Cu}_\text{ex.}}$) can hence be determined using equations \ref{eq:[cuso4]-std} and \ref{eq:n_cu-prod-final} where $V_{\ce{Cu}_\text{react.}}$ is the volume of the standard copper solution added to the HZSM-5. + +\begin{align} + n_{\ce{Cu}_\text{ex.}} &= [\ce{CuSO4}]V_{\ce{Cu}_\text{react.}} - n_{\ce{Cu}_\text{prod.}} \nonumber\\ + % \label{ + &= \frac{m_{\ce{CuSO4.5H2O}} V_{\ce{Cu}_\text{react.}}}{V_{\ce{Cu}_\text{std.}} Mr_{\ce{CuSO4.5H2O}}} - \frac{A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} m_{\ce{CuSO4.5H2O}}}{A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{std.}} Mr_{\ce{CuSO4.5H2O}}} \nonumber \\ + \label{eq:cu-exchanged} + &= \frac{m_{\ce{CuSO4.5H2O}} \left(A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{react.}} - A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} \right)}{A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{std.}} Mr_{\ce{CuSO4.5H2O}}} +\end{align} + +Substituting equation \ref{eq:cu-exchanged} into equation \ref{eq:cation-percent-exchanged} as $n_\text{cation}$ and setting $q = 2$ hence gives: + +\begin{equation} \label{eq:cu-percent-exchanged} +\begin{split} + \si{\percent} \text{ \ce{Cu^{2+}} Exchanged} &= \frac{2 Mr_{\text{HZSM-5 unit cell}} m_{\ce{CuSO4.5H2O}} \left(A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{react.}} - A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} \right)}{7.68 m_{\text{HZSM-5}} A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{std.}} Mr_{\ce{CuSO4.5H2O}}} \\ + &\phantom{=} \times \SI{100}{\percent} +\end{split} +\end{equation} + +Using \ref{eq:cu-percent-exchanged} with: + +\begin{align*} + Mr_{\text{HZSM-5 unit cell}} &= \SI{6217.613}{\gram\per\mole} \text{ from equation \ref{eq:hzsm-5-mr}} \\ + m_{\ce{CuSO4.5H2O}} &= \SI{0.5014 \pm 0.00005}{\gram} \text{ from table \ref{tbl:cu-masses}} \\ + A_{\ce{Cu}_\text{std.}} &= \num{0.484 \pm 0.001} \text{ from table \ref{tbl:cu-absorbance} and equation \ref{eq:cu-std-abs-uncertainty}} \\ + V_{\ce{Cu}_\text{react.}} &= \SI{20.00 \pm 0.06 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})} \\ + A_{\ce{Cu}_\text{prod.}} &= \num{0.110 \pm 0.001} \text{ from table \ref{tbl:cu-absorbance} and equation \ref{eq:cu-prod-abs-uncertainty}} \\ + V_{\ce{Cu}_\text{prod.}} &= \SI{100.00 \pm 0.20 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})}\\ + m_{\text{HZSM-5}} &= \SI{0.4810 \pm 0.00005}{\gram} \text{ from table \ref{tbl:cu-masses}} \\ + V_{\ce{Cu}_\text{std.}} &= \SI{50.00 \pm 0.06 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})} \\ + Mr_{\ce{CuSO4.5H2O}} &= \SI{249.685}{\gram\per\mole} \text{ \autocite[Physical Constants of Inorganic Compounds, 4-60]{crc-handbook}} +\end{align*} + +\begin{align*} + \begin{split} + \si{\percent} \text{ \ce{Cu^{2+}} Exchanged} &= \frac{2 \times \SI{6217.613}{\gram\per\mole} \times \SI{0.50140}{\gram}\left(0.484 \times 20.00 - 0.110 \times 100.00\right)\num{e-3} \text{ \si{\deci\metre\cubed}}}{7.68 \times \SI{0.4810}{\gram} \times 0.484 \times \SI{50.00e-3}{\deci\metre\cubed} \times \SI{249.577}{\gram\per\mole}} \\ + &\phantom{=} \times \SI{100}{\percent} + \end{split} \\ + &= \SI{-37}{\percent} +\end{align*} + +\subsubsection{Error Propagation} \label{sec:cu-error-propagation} +Let the percentage exchange level of \ce{Cu^2+} be $v_{\ce{Cu}}$ in the error propagation below: + +\begin{equation} +\label{eq:cu-error-propagation-initial} +\begin{split} + \delta v_{\ce{Cu}} = &v_{\ce{Cu}} + \vast( %Manually putting in large brackets for square root. + \left( \frac{\delta Mr_{\text{HZSM-5 unit cell}}}{Mr_{\text{HZSM-5 unit cell}}}\right)^2 + + \left( \frac{\delta m_{\ce{CuSO4.5H2O}}}{m_{\ce{CuSO4.5H2O}}}\right)^2 + + \left( + \frac{ + \delta \left( A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{react.}} - A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} \right) + } + { + A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{react.}} - A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} + } + \right)^2 \\ + %New Line + %New Line. + &+ \left( \frac{\delta m_{\text{HZSM-5}}}{m_{\text{HZSM-5}}} \right)^2 + + \left( \frac{\delta A_{\ce{Cu}_\text{std.}}}{A_{\ce{Cu}_\text{std.}}} \right)^2 + + \left( \frac{\delta V_{\ce{Cu}_\text{std.}}}{V_{\ce{Cu}_\text{std.}}} \right)^2 + + \left( \frac{\delta Mr_{\ce{CuSO4.5H2O}}}{Mr_{\ce{CuSO4.5H2O}}} \right)^2 + \vast)^{1/2} +\end{split} +\end{equation} + +Let $S = A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{react.}} - A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}}$, thus: + +\begin{align} + \delta S = + &\left( + \left( \delta \left( A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{react.}} \right) \right)^2 + + \left( \delta \left( A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} \right) \right)^2 + \right)^{1/2} \nonumber \\ + %Next Line. + \begin{split} + = &\vastt( + \left( + A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{react.}} + \left( + \left( \frac{\delta A_{\ce{Cu}_\text{std.}}}{A_{\ce{Cu}_\text{std.}}} \right)^2 + + \left( \frac{ \delta V_{\ce{Cu}_\text{react.}}}{V_{\ce{Cu}_\text{react.}}} \right)^2 + \right)^{1/2} + \right)^2 \\ + %Split Equation. + &+ + \left( + A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} + \left( + \left( \frac{\delta A_{\ce{Cu}_\text{prod.}}}{A_{\ce{Cu}_\text{prod.}}} \right)^2 + + \left( \frac{ \delta V_{\ce{Cu}_\text{prod.}}}{V_{\ce{Cu}_\text{prod.}}} \right)^2 + \right)^{1/2} + \right)^2 + \vastt)^{1/2} + \end{split} \nonumber \\ + %Next Line. + \begin{split} \label{eq:delta-s} + = &\vast( + A_{\ce{Cu}_\text{std.}}^2 V_{\ce{Cu}_\text{react.}}^2 + \left( + \left( \frac{\delta A_{\ce{Cu}_\text{std.}}}{A_{\ce{Cu}_\text{std.}}} \right)^2 + + \left( \frac{ \delta V_{\ce{Cu}_\text{react.}}}{V_{\ce{Cu}_\text{react.}}} \right)^2 + \right) \\ + %Split Equation. + &+ + A_{\ce{Cu}_\text{prod.}}^2 V_{\ce{Cu}_\text{prod.}}^2 + \left( + \left( \frac{\delta A_{\ce{Cu}_\text{prod.}}}{A_{\ce{Cu}_\text{prod.}}} \right)^2 + + \left( \frac{ \delta V_{\ce{Cu}_\text{prod.}}}{V_{\ce{Cu}_\text{prod.}}} \right)^2 + \right) + \vast)^{1/2} + \end{split} +\end{align} + +Hence substituting equation \ref{eq:delta-s} into \ref{eq:cu-error-propagation-initial} gives: + +\begin{equation} +\label{eq:cu-error-propagation} +\begin{split} + \delta v_{\ce{Cu}} = &v_{\ce{Cu}} + \Vast( %Manually putting in large brackets for square root. + \left(\frac{\delta Mr_{\text{HZSM-5 unit cell}}}{Mr_{\text{HZSM-5 unit cell}}}\right)^2 + + \left(\frac{\delta m_{\ce{CuSO4.5H2O}}}{m_{\ce{CuSO4.5H2O}}}\right)^2 \\ + %New Line + &+ \frac{ + A_{\ce{Cu}_\text{std.}}^2 V_{\ce{Cu}_\text{react.}}^2 + \left( + \left(\frac{\delta A_{\ce{Cu}_\text{std.}}}{A_{\ce{Cu}_\text{std.}}}\right)^2 + + \left(\frac{\delta V_{\ce{Cu}_\text{react.}}}{V_{\ce{Cu}_\text{react.}}}\right)^2 + \right) + + A_{\ce{Cu}_\text{prod.}}^2 V_{\ce{Cu}_\text{prod.}}^2 + \left( + \left(\frac{\delta A_{\ce{Cu}_\text{prod.}}}{A_{\ce{Cu}_\text{prod.}}}\right)^2 + + \left(\frac{\delta V_{\ce{Cu}_\text{prod.}}}{V_{\ce{Cu}_\text{prod.}}}\right)^2 + \right) + } + { + \left( + A_{\ce{Cu}_\text{std.}} V_{\ce{Cu}_\text{react.}} - A_{\ce{Cu}_\text{prod.}} V_{\ce{Cu}_\text{prod.}} + \right)^2 + } \\ + %New Line. + &+ \left(\frac{\delta m_{\text{HZSM-5}}}{m_{\text{HZSM-5}}}\right)^2 + + \left(\frac{\delta A_{\ce{Cu}_\text{std.}}}{A_{\ce{Cu}_\text{std.}}}\right)^2 + + \left(\frac{\delta V_{\ce{Cu}_\text{std.}}}{V_{\ce{Cu}_\text{std.}}}\right)^2 + + \left(\frac{\delta Mr_{\ce{CuSO4.5H2O}}}{Mr_{\ce{CuSO4.5H2O}}}\right)^2 + \Vast)^{1/2} +\end{split} +\end{equation} + +Substituting values into equation \ref{eq:cu-error-propagation} yields: + +\begin{displaymath} + \delta v_{\ce{Cu}} = \pm \SI{3}{\percent} +\end{displaymath} + +So the percentage exchange level of \ce{Cu^2+} is \SI{-37 \pm 3}{\percent}. + +\subsection{Calculations for Zinc Solution} +\subsubsection{Determination of EDTA Solution (Batch A) Concentration} +Let: $V_{\ce{Zn}_\text{std.}}$ be the volume, $[\ce{ZnSO4}]_\text{std.}$ be the concentration and $m_{\ce{ZnSO4.7H2O}_\text{std}.}$ be the mass of \ce{ZnSO4.7H2O} used for the preparation of the \ce{ZnSO4} standard solution used to standardise the \ce{EDTA} solution. Thus: + +\begin{equation}\label{eq:[znso4]-std} + [\ce{ZnSO4}]_\text{std.} = \frac{m_{\ce{ZnSO4.7H2O}_\text{std}.}}{Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std.}}} +\end{equation} + +From equation \ref{eq:edta-zn-reaction} there is a 1:1 stoichiometric ratio between the \ce{Zn^2+} and \ce{EDTA^4-} ions. Letting $[\ce{EDTA^4-}]$ be the concentration of the \ce{EDTA} solution, $n_{\ce{Zn}_\text{std. analyte}}$ be the amount and $V_{\ce{Zn}_\text{std. aliquot}}$ be the volume of \ce{Zn^2+} ions in the analyte hence gives: + +\begin{equation}\label{eq:[edta]-1} + [\ce{EDTA^4-}] = \frac{n_{\ce{Zn}_\text{std. analyte}}}{V_{\ce{EDTA}_\text{std.}}} = \frac{[\ce{ZnSO4}]_\text{std.} V_{\ce{Zn}_\text{std. aliquot}}}{V_{\ce{EDTA}_\text{std.}}} +\end{equation} + +Substituting equation \ref{eq:[znso4]-std} into equation \ref{eq:[edta]-1} gives: + +\begin{equation}\label{eq:[edta]-final} + [\ce{EDTA^4-}] = \frac{m_{\ce{ZnSO4.7H2O}_\text{std}.} V_{\ce{Zn}_\text{std. aliquot}}}{Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}}} +\end{equation} + +\subsubsection{Determination of \ce{Zn^2+} Ion Exchange Level}\label{sec:zn-percent-exchanged} +For the standard \ce{ZnSO4} solution added to the HZSM-5 let $m_{\ce{ZnSO4.7H2O}_\text{orig.}}$ be the mass of \ce{ZnSO4.7H2O} used and let $V_{\ce{Zn}_\text{std. orig.}}$ and $[\ce{ZnSO4}]_\text{std. orig.}$ be the volume and concentration of the solution respectively. + +\begin{equation} + \label{eq:[znso4]-std-orig} + [\ce{ZnSO4}]_\text{std. orig.} = \frac{m_{\ce{ZnSO4.7H2O}_\text{orig.}}}{Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std. orig.}}} +\end{equation} + +Using equation \ref{eq:[znso4]-std-orig} with $V_{\ce{Zn}_\text{orig.}}$ as the volume of the standard solution used in the ion-exchange process: + +\begin{align} + n_{\ce{Zn}_\text{orig.}} &= [\ce{ZnSO4}]_\text{std. orig.} V_{\ce{Zn}_\text{orig.}} \nonumber \\ + \label{eq:zn-amount-orig} + &= \frac{m_{\ce{ZnSO4.7H2O}_\text{orig.}} V_{\ce{Zn}_\text{orig.}}}{Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std. orig.}}} +\end{align} + +The amount of zinc remaining in solution after the ion exchange ($n_{\ce{Zn}_\text{prod.}}$) can be calculated using equation \ref{eq:[edta]-final} with $V_{\ce{Zn}_\text{prod.}}$ being the volume the solution after the reaction and $V_{\ce{Zn}_\text{prod. aliquot}}$ being the volume of the aliquot titrated. By equation \ref{eq:edta-zn-reaction} the stoichiometric ratio for the reaction between the \ce{Zn^2+} and \ce{EDTA^4-} in the titration is 1:1, so: + +\begin{align} + n_{\ce{Zn}_\text{prod.}} &= \frac{V_{\ce{EDTA}_\text{prod.}} [\ce{EDTA^4-}]}{V_{\ce{Zn}_\text{prod. aliquot}}} \times V_{\ce{Zn}_\text{prod.}} \nonumber \\ + \label{eq:zn-amount-product} + &= \frac{V_{\ce{EDTA}_\text{prod.}} m_{\ce{ZnSO4.7H2O}_\text{std.}} V_{\ce{Zn}_\text{std. aliquot}} V_{\ce{Zn}_\text{prod.}}}{V_{\ce{Zn}_\text{prod. aliquot}} Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}}} +\end{align} + +Using equations \ref{eq:zn-amount-orig} and \ref{eq:zn-amount-product} to calculate the amount of \ce{Zn^2+} ions exchanged with the HZSM-5 ($n_{\ce{Zn}_\text{ex.}}$) gives: + +\begin{align} + n_{\ce{Zn}_\text{ex.}} &= n_{\ce{Zn}_\text{orig.}} - n_{\ce{Zn}_\text{prod.}} \nonumber \\ + &= \frac{m_{\ce{ZnSO4.7H2O}_\text{orig.}} V_{\ce{Zn}_\text{orig.}}}{Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std. orig.}}} - \frac{V_{\ce{EDTA}_\text{prod.}} m_{\ce{ZnSO4.7H2O}_\text{std.}} V_{\ce{Zn}_\text{std. aliquot}} V_{\ce{Zn}_\text{prod.}}}{V_{\ce{Zn}_\text{prod. aliquot}} Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}}} \nonumber \\ + \begin{split} + \label{eq:zn-amount-exchanged} + &= \frac{V_{\ce{Zn}_\text{prod. aliquot}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}} m_{\ce{ZnSO4.7H2O}_\text{orig.}} V_{\ce{Zn}_\text{orig.}}}{V_{\ce{Zn}_\text{std. orig.}} V_{\ce{Zn}_\text{prod. aliquot}} Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}}} \\ + &\phantom{=} - \frac{V_{\ce{Zn}_\text{std. orig.}} V_{\ce{EDTA}_\text{prod.}} m_{\ce{ZnSO4.7H2O}_\text{std.}} V_{\ce{Zn}_\text{std. aliquot}} V_{\ce{Zn}_\text{prod.}}}{V_{\ce{Zn}_\text{std. orig.}} V_{\ce{Zn}_\text{prod. aliquot}} Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}}} + \end{split} +\end{align} + +Hence substituting equation \ref{eq:zn-amount-exchanged} into \ref{eq:cation-percent-exchanged} for $n_\text{cation}$ and setting $q=2$ gives: + +\begin{equation}\label{eq:zn-percent-exchanged} +\begin{split} + \text{\si{\percent} \ce{Zn} Exchanged} &= \frac{2 Mr_{\text{HZSM-5 unit cell}}}{7.68 m_{\text{HZSM-5}} V_{\ce{Zn}_\text{std. orig.}} V_{\ce{Zn}_\text{prod. aliquot}} Mr_{\ce{ZnSO4.7H2O}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}}} \\ + &\phantom{=} \times (V_{\ce{Zn}_\text{prod. aliquot}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}} m_{\ce{ZnSO4.7H2O}_\text{orig.}} V_{\ce{Zn}_\text{orig.}} \\ + &\phantom{= \times (} - V_{\ce{Zn}_\text{std. orig.}} V_{\ce{EDTA}_\text{prod.}} m_{\ce{ZnSO4.7H2O}_\text{std.}} V_{\ce{Zn}_\text{std. aliquot}} V_{\ce{Zn}_\text{prod.}}) \times \SI{100}{\percent} +\end{split} +\end{equation} + +Using equation \ref{eq:zn-percent-exchanged} with: + +\begin{align*} + Mr_\text{HZSM-5 unit cell} &= \SI{6217.613}{\gram\per\mole} \text{ from equation \ref{eq:hzsm-5-mr}} \\ + V_{\ce{Zn}_\text{prod. aliquot}} &= \SI{20.00 \pm 0.06 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})} \\ + V_{\ce{Zn}_\text{std.}} &= \SI{100.00 \pm 0.20 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})} \\ + V_{\ce{EDTA}_\text{std.}} &= \SI{31.95 \pm 0.2 e-3}{\deci\metre\cubed} \text{ from equation \ref{eq:edta-v-standardisation}} \\ + m_{\ce{ZnSO4.7H2O}_\text{orig.}} &= \SI{0.6331 \pm 0.00005 e-3}{\gram} \text{ from table \ref{tbl:zn-zsm-5-masses}} \\ + V_{\ce{Zn}_\text{orig.}} &= \SI{20.00 \pm 0.06 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})} \\ + V_{\ce{Zn}_\text{std. orig.}} &= \SI{50.00 \pm 0.06 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})} \\ + V_{\ce{EDTA}_\text{prod.}} &= \SI{26.63 \pm 0.2 e-3}{\deci\metre\cubed} \text{ from equation \ref{eq:edta-v-analytical}} \\ + m_{\ce{ZnSO4.7H2O}_\text{std.}} &= \SI{0.4587 \pm 0.00005}{\gram} \text{ from table \ref{tbl:zn-std-masses}} \\ + V_{\ce{Zn}_\text{std. aliquot}} &= \SI{10.00 \pm 0.04 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})} \\ + V_{\ce{Zn}_\text{prod.}} &= \SI{100.00 \pm 0.20 e-3}{\deci\metre\cubed} \text{ from method (section \ref{sec:experimental})} \\ + m_{\text{HZSM-5}} &= \SI{0.5274 \pm 0.00005}{\gram} \text{ from table \ref{tbl:zn-zsm-5-masses}} \\ + Mr_{\ce{ZnSO4.7H2O}} &= \SI{287.578}{\gram\per\mole} \text{ \autocite[Phyical Constants of Inorganic Compounds, 4-96]{crc-handbook}} +\end{align*} + +Gives: + +\begin{displaymath} + \text{\si{\percent} \ce{Zn} Exchanged} = \SI{66}{\percent} +\end{displaymath} + +\subsubsection{Error Propagation} +Let the percentage of \ce{Zn^2+} exchanged be $v_{\ce{Zn}}$ in the following error propagation: + +\begin{equation} +\label{eq:zn-error-propagation-1} +\begin{split} + \delta v_{\ce{Zn}} = &v_{\ce{Zn}} + \vast( + \left( \frac{\delta Mr_\text{HZSM-5 unit cell}}{Mr_\text{HZSM-5 unit cell}} \right)^2 + + \left( \frac{\delta m_{\text{HZSM-5}}}{m_{\text{HZSM-5}}} \right)^2 + + \left( \frac{\delta V_{\ce{Zn}_\text{std. orig.}}}{V_{\ce{Zn}_\text{std. orig.}}} \right)^2 + + \left( \frac{\delta V_{\ce{Zn}_\text{prod. aliquot}}}{V_{\ce{Zn}_\text{prod. aliquot}}} \right)^2 \\ + %New Line + &+ \left( \frac{\delta Mr_{\ce{ZnSO4.7H2O}}}{Mr_{\ce{ZnSO4.7H2O}}} \right)^2 + + \left( \frac{\delta V_{\ce{Zn}_\text{std.}}}{V_{\ce{Zn}_\text{std.}}} \right)^2 + + \left( \frac{\delta V_{\ce{EDTA}_\text{std.}}}{V_{\ce{EDTA}_\text{std.}}} \right)^2 \\ + %New Line + &+ \Bigg( + \frac{ + \delta \big( V_{\ce{Zn}_\text{prod. aliquot}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}} m_{\ce{ZnSO4.7H2O}_\text{orig.}} V_{\ce{Zn}_\text{orig.}} - V_{\ce{Zn}_\text{std. orig.}} V_{\ce{EDTA}_\text{prod.}} + } + { + V_{\ce{Zn}_\text{prod. aliquot}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}} m_{\ce{ZnSO4.7H2O}_\text{orig.}} V_{\ce{Zn}_\text{orig.}} - V_{\ce{Zn}_\text{std. orig.}} V_{\ce{EDTA}_\text{prod.}} + } \\ + %New Line + &\frac{ + m_{\ce{ZnSO4.7H2O}_\text{std.}} V_{\ce{Zn}_\text{std. aliquot}} V_{\ce{Zn}_\text{prod.}} \big) + } + { + m_{\ce{ZnSO4.7H2O}_\text{std.}} V_{\ce{Zn}_\text{std. aliquot}} V_{\ce{Zn}_\text{prod.}} + } + \Bigg)^2 + \vast)^{1/2} +\end{split} +\end{equation} + +Using the same process demonstrated in section \ref{sec:cu-error-propagation} used for equation \ref{eq:delta-s} to expand the subtraction within equation \ref{eq:zn-error-propagation-1} hence gives equation \ref{eq:zn-error-propagation} below: + +\begin{equation} +\label{eq:zn-error-propagation} +\begin{split} + \delta v_{\ce{Zn}} = &v_{\ce{Zn}} + \Vastt( + \left( \frac{\delta Mr_\text{HZSM-5 unit cell}}{Mr_\text{HZSM-5 unit cell}} \right)^2 + + \left( \frac{\delta m_{\text{HZSM-5}}}{m_{\text{HZSM-5}}} \right)^2 + + \left( \frac{\delta V_{\ce{Zn}_\text{std. orig.}}}{V_{\ce{Zn}_\text{std. orig.}}} \right)^2 + + \left( \frac{\delta V_{\ce{Zn}_\text{prod. aliquot}}}{V_{\ce{Zn}_\text{prod. aliquot}}} \right)^2 \\ + %New Line + &+ \left( \frac{\delta Mr_{\ce{ZnSO4.7H2O}}}{Mr_{\ce{ZnSO4.7H2O}}} \right)^2 + + \left( \frac{\delta V_{\ce{Zn}_\text{std.}}}{V_{\ce{Zn}_\text{std.}}} \right)^2 + + \left( \frac{\delta V_{\ce{EDTA}_\text{std.}}}{V_{\ce{EDTA}_\text{std.}}} \right)^2 \\ + %New Line + &+ \frac{ + V_{\ce{Zn}_\text{prod. aliquot}}^2 V_{\ce{Zn}_\text{std.}}^2 V_{\ce{EDTA}_\text{std.}}^2 m_{\ce{ZnSO4.7H2O}_\text{orig.}}^2 V_{\ce{Zn}_\text{orig.}}^2 + \vast( + \left( \frac{\delta V_{\ce{Zn}_\text{prod. aliquot}}}{V_{\ce{Zn}_\text{prod. aliquot}}} \right)^2 + } + { + \big( V_{\ce{Zn}_\text{prod. aliquot}} V_{\ce{Zn}_\text{std.}} V_{\ce{EDTA}_\text{std.}} m_{\ce{ZnSO4.7H2O}_\text{orig.}} V_{\ce{Zn}_\text{orig.}} - V_{\ce{Zn}_\text{std. orig.}} V_{\ce{EDTA}_\text{prod.}} + } \\ + %New Line. + &\frac{ + + \left( \frac{\delta V_{\ce{Zn}_\text{std.}}}{V_{\ce{Zn}_\text{std.}}} \right)^2 + + \left( \frac{\delta V_{\ce{EDTA}_\text{std.}}}{V_{\ce{EDTA}_\text{std.}}} \right)^2 + + \left( \frac{\delta m_{\ce{ZnSO4.7H2O}_\text{orig.}}}{m_{\ce{ZnSO4.7H2O}_\text{orig.}}} \right)^2 + + \left( \frac{\delta V_{\ce{Zn}_\text{orig.}}}{V_{\ce{Zn}_\text{orig.}}} \right)^2 + \vast) + + V_{\ce{Zn}_\text{std. orig.}}^2 + } + { + m_{\ce{ZnSO4.7H2O}_\text{std.}} V_{\ce{Zn}_\text{std. aliquot}} V_{\ce{Zn}_\text{prod.}} \big)^2 \hfill + } \\ + %New Line. + &\frac{ + V_{\ce{EDTA}_\text{prod.}}^2 m_{\ce{ZnSO4.7H2O}_\text{std.}}^2 V_{\ce{Zn}_\text{std. aliquot}}^2 V_{\ce{Zn}_\text{prod.}}^2 + \vast( + \left( \frac{\delta V_{\ce{Zn}_\text{std. orig.}}}{V_{\ce{Zn}_\text{std. orig.}}} \right)^2 + + \left( \frac{\delta V_{\ce{EDTA}_\text{prod.}}}{V_{\ce{EDTA}_\text{prod.}}} \right)^2 + } + {} \\ + %New Line + &\frac{ + + \left( \frac{\delta m_{\ce{ZnSO4.7H2O}_\text{std.}}}{m_{\ce{ZnSO4.7H2O}_\text{std.}}} \right)^2 + + \left( \frac{\delta V_{\ce{Zn}_\text{std. aliquot}}}{V_{\ce{Zn}_\text{std. aliquot}}} \right)^2 + + \left( \frac{\delta V_{\ce{Zn}_\text{prod.}}}{V_{\ce{Zn}_\text{prod.}}} \right)^2 + \vast) + } + {} + \Vastt)^{1/2} +\end{split} +\end{equation} + +Substituting values into equation \ref{eq:zn-error-propagation} gives: + +\begin{displaymath} + \delta v_{\ce{Zn}} = \pm \SI{3}{\percent} +\end{displaymath} + +Hence the percentage ion exchange level of \ce{Zn^2+} is \SI{66 \pm 3}{\percent}. + +\section{Discussion} +%TODO: Compared molar extinction coefficient value to literature value. +%TODO: Note the acidity of some metal ions formed other substances in solution. +%TODO: add note explaining when separate ZnSO4 solution prepared for standardisation of EDTA solution - not a primary analytical standard. + +\subsection{General} +Between laboratory sessions the solutions were stored in a fridge in an attempt to reduce the rate of ion exchange since some of the ZSM-5 had already been separated out of the copper solution. This is not likely to have been very effective since the temperature of the fridge is still fairly high and the samples were left for a long period of time (one week), hence both samples are likely to have reached new equilibriums during this time thus effecting the results collected. It would have been better if the initial centrifugation of the copper solution was not completed since then both mixtures would have been exposed to the same conditions, hence still allowing direct comparison of the ion exchange results. + +Losses of the non-exchanged ions occurred for both solutions during the centrifugation process since some metal ions will have remained within the precipitate and in the centrifuge tube when the supernatant fluid was collected. To reduce this loss distilled water could be added to the centrifuge tube and additional centrifugation performed, hence washing the tube. This was not completed due to time limitations. + +Both the copper and zinc solutions were cloudy following the centrifugation indicating that some ZSM-5 remained suspended in the solutions. Further centrifugation would have reduced the amount of suspended zeolite from the solutions and hence the errors resultant from this (see sections \ref{sec:cu-discussion} and \ref{sec:zn-discussion}). Centrifugation was chosen instead of filtration to separate the zeolite since the nano-size particles of ZSM-5 can block the filter paper during filtrations hence resulting in very long filtration times.~\autocite{russell} + +While monomeric species such as \ce{Cu^2+} and \ce{Zn^2+} are likely to be the predominant species present in the ZSM-5 zeolite after the ion exchange process other species such as (\ce{[ZnOH]+} which subsequently form \ce{[ZnOZn]^2+} dimeric bridges upon drying) and \ce{[Cu2(OH)2]^2+} may alternatively be formed.\autocite{almutairi11,schreier05,mhamdi09} The formation of these species allows a 1:1 exchange between the hydrogen and the metal cations thus allowing the possibility of an ion exchange level greater than the maximum calculated,~\autocite{almutairi11,schreier05} however the exchange of the monomeric species is thermodynamically preferred and the alternative species only form at isolated \ce{Al} centres when using aqueous phase ion exchange as the preparation technique.~\autocite{aleksandrov10,penzien04} It is thus unlikely that a large amount of the dimeric species was present in the products created, thus they can be assumed to have no effect on the ion exchange level obtained. + +\subsection{Copper Exchanged ZSM-5}\label{sec:cu-discussion} +As seen in section \ref{sec:cu-percent-exchanged} the calculated exchange level for the \ce{Cu^2+} ions with the HZSM-5 was negative. This can be explained by the presence of the suspended ZSM-5 in solution which increased the absorbance value of the sample thus resulting in the negative yield calculated. To reduce the effect of this suspended zeolite a titrimetric method for calculating the copper ion concentration could have been used for example using \ce{EDTA} solution as the titrant and Fast Sulphon F as the indicator.~\autocite{denby-copper-conc} This would also allow a better comparison between the copper and zinc ion exchange processes since the similar methods could compensate for common systematic errors. + +\subsection{Zinc Exchanged ZSM-5}\label{sec:zn-discussion} +From section \ref{sec:zn-percent-exchanged} the percentage of zinc calculated to have been exchanged with the ZSM-5 zeolite was \SI{66 \pm 3}{\percent}. Tamiyakul et al.\@ completed an ion exchange between HZSM-5 with an \ce{SiO2}/\ce{AlO3} ratio of 30 and \ce{Zn(NO3)2} at \SI{70}{\celsius} for 12 hours and obtained an ion exchange level of $\frac{\SI{0.64}{\percent}}{\SI{1.5}{\percent}} \times \SI{100}{\percent} = \SI{43}{\percent}$.\autocite{tamiyakul15} The \ce{SiO2}/\ce{AlO3} ratio of the HZSM-5 used by Tamiyakul et al.\@ is larger than that used in this project, hence a higher ion exchange level is expected, however Yashnik et al.\@ only obtained a \SI{22}{\percent} higher ion exchange level with \ce{CuSO4} while using HZSM-5 with an \ce{SiO2}/\ce{AlO3} ratio of 17 compared to when HZSM-5 with a ratio of 30 was used.~\autocite{yashnik05} The difference in the \ce{SiO2}/\ce{AlO3} ratio of the HZSM-5 between this project and the HZSM-5 used by Tamiyakul et al.\@ is almost half of the difference between the samples compared by Yashnik et al.\@ while the difference in ion exchange level is slightly greater (\SI{23}{\percent}), thus suggesting that the ion exchange level obtained is too high. + +This can be explained by the losses in the centrifugation described earlier and also since the post-ion exchange solution contained suspended zeolite hence the aliquot volume in the titration was too small since the suspended zeolite displaced some of the solution when the volume was being measured. This thus reduced the titre volume recorded which can be seen to have inflated the ion exchange level calculated (by inspection of equation \ref{eq:zn-percent-exchanged}). + +This may also partially explain the anomalous final titre volume obtained in the titration (see run 4 in table \ref{tbl:zn-analytical-titration}) since some of the solid zeolite may have settled in the bottom of the volumetric flask, hence for this final titration the pipette contained a greater number of suspended zeolite particles thus further reducing the analyte volume and resulting in the anomalously small titre volume. + +\subsection{Uncertainties} +The percentage uncertainty in both of the obtained results is quite high at \SI{3}{\percent}, although the actual error is greater than this due to the systematic errors discussed. This could be reduced by instead using Diffuse Reflectance Fourier Transform Infrared Spectroscopy (DRIFT-IR)\autocite{pollanen05} on the ZSM-5 samples and obtaining the ion exchange level through comparing the integration of the \SIrange{3570}{3630}{\per\centi\metre} peak between the ion exchanged ZSM-5 samples and the original HZSM-5 sample.~\autocite{yu12} This would result in a smaller error compared to the titrimetric method since the number of measurements required for the calculation is much less hence reducing the number of errors introduced. + +%Bibliography. +\printbibliography + +\section{Supplementary Information} +%TODO: Attach risk assessments. + +\end{document} diff --git a/year1/project/risk-assessment/combined.pdf b/year1/project/risk-assessment/combined.pdf new file mode 100644 index 0000000..e101082 Binary files /dev/null and b/year1/project/risk-assessment/combined.pdf differ diff --git a/year1/project/risk-assessment/project.pdf b/year1/project/risk-assessment/project.pdf new file mode 100644 index 0000000..684d35d Binary files /dev/null and b/year1/project/risk-assessment/project.pdf differ diff --git a/year1/project/risk-assessment/risk-assessment.odt b/year1/project/risk-assessment/risk-assessment.odt new file mode 100644 index 0000000..9c25742 Binary files /dev/null and b/year1/project/risk-assessment/risk-assessment.odt differ diff --git a/year1/project/risk-assessment/risk-assessment.pdf b/year1/project/risk-assessment/risk-assessment.pdf new file mode 100644 index 0000000..de03f44 Binary files /dev/null and b/year1/project/risk-assessment/risk-assessment.pdf differ diff --git a/year1/project/specific.bib b/year1/project/specific.bib new file mode 100644 index 0000000..7ef9bba --- /dev/null +++ b/year1/project/specific.bib @@ -0,0 +1,332 @@ +@article{donder06, + author = {Vera Dondur and Vesna Raki\'{c} and Ljiljana Damjanovi\'{c} and Radmila Hercigonja and Aline Auroux}, + title = {Temperature-Programmed Desorption of n-hexane from Hydrated HZSM-5 and \ce{NH4}ZSM-5 Zeolites}, + year = {2006}, + journal = {Journal of Thermal Analysis and Calorimetry}, + volume = {84}, + number = {1}, + pages = {233--238} +} + +@online{ic-zeolite-structure, + title = {Zeolite Structure}, + author = {Wyn Locke}, + date = {1999}, + url = {http://www.ch.ic.ac.uk/vchemlib/course/zeolite/structure.html}, + urldate = {2018-03-02} +} + +@article{han09, + title = {High-pressure cation-exchange treatment of a ZSM-5 zeolite}, + author = {Aijie Han and Yu Qiao}, + month = {7}, + year = {2009}, + journal = {Journal of Materials Research}, + volume = {24}, + number = {7}, + pages = {2416--2419} +} + +@article{olson99, + title = {Use of water as a probe of zeolitic properties: interaction of water with HZSM-5}, + author = {D. 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