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Synthesis of Aspirin

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Introduction

Aim In the first part of the experiment was to synthesize quality of aspirin (Acetylsalicylic acid) and in the second part of the lab, the TCL plate was performed to confirm the identity of the aspirin and to detect any impurities. Introduction Acetylsalicylic acid normally known as aspirin and often used to relieve pain, reduce inflammation, and lower fever. The first aspirin was synthesized in 1893 by Felix Hoffman and Arthur Eichengr´┐Żn. There were about 325 milligrams of acetylsalicylic acid in average tablet. [i] The chemical name of aspirin was 2-acetoxybenzoic acid and the structural formula was: [iii] In this experiment aspirin (3) could be prepared by a slow reaction between salicylic acid (2) and ethanoic anhydride (also known as acetic anhydride) (1) with a small amount of catalyst, which in this experiment used sulphuric acid as the catalyst. [ii] The chemical equation was: (CH3CO)2O (l) + C6H4(OH)COOH (l) H+ CH3COOH (l) + C6H4(OCOCH3)COOH (l) [ii] Reagents needed during experiment: Salicylic acid Ethanoic anhydride (acetic anhydride) Concentrated sulphuric acid Distilled water Mixture of methanol: dichloromethane in the ratio of 1:8 by volume Ethanol Container of ice Equipment needed during experiment: 1) ...read more.

Middle

* The spot was less 2mm in diameter and after spotting. * Solutions S and P were separately performed the same procedure as the solution A by using other clean pipettes. 2.4. Performing the Thin Layer Chromatography: * Sufficient eluent was added into a developing jar. * The plate was place into the jar with a lid on. * Waited about 3-4 minutes and taken out, which till the solvent front is approximately 5mm from the top of the plate. * A line was drawn to indicate the final position of the eluent front. 2.5. Assessment of the chromatogram * The plate was placed under a ultra-violet light. * The positions of the compounds were marked by pencil. * The distances from the bottom line to the marked point were recorded 2.6. at the end of the lab * Used glasses dropping pipettes were washed and placed into the broken glass container. * Product from the 1st part of the lab was put into a bag with the name on and so as the TLC chromatogram. * Solutions A, S and P were disposed of in the organic solvents waste bottle * Sample tubes and the lids were rinsed and placed into the tray provided. ...read more.

Conclusion

Secondly, the solvent was dried directly due to the ions were already presented in an aqueous solution. After that, the ions were drawn into the mass spec by the electric field. The next step was to separate the ions by mass, this was where the ion trap occurred. [vi] The graph of the mass spectrum of aspirin was attached in Appendix A. The big peak in the spectrum in the Appendix A was a fragment. The lower peak was expected 180 due to the molecular mass of pure aspirin was 180g/mol but it appeared 178.9, which was a negative ion chromatography. So there had a loss of H+. In this experiment the purity of the product may due to some errors, such as product was not transferred completely from the boiling tube to the conical flask when salicylic acid reacted with ethanoic anhydride. Reference [i] http://chemistry.about.com/od/demonstrationsexperiments/ss/aspirin.htm (Feb.2008) [ii] Synthesis of Aspirin handout from Michele Raychaudhuri. (Feb.2008) [iii] http://www.chemsoc.org/PDF/LearnNet/rsc/Aspirin_full.pdf. (Feb.2008) [iv]Hand out of Lesson3-Atoms, Molecules and Stoichiometry from Michele Raychaudhuri [v] Rob Lewis and Wynne Evans. Chemistry. Page 362. 3rd edition. 2006 [vi] http://www.jic.ac.uk/Services/Metabolomics/index.htm (Feb.2008) ?? ?? ?? ?? 1 Lab Report: Synthesis of Aspirin. By Min. ...read more.

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