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Synthesis of Aspirin and Analysis of Aspirin

Szczeklik asserted that the bark and leaves of willow trees contain the active component of salicylic acid (SA), but its acidity is higher than pH of the human stomach which could cause digestion problems and it is very important to synthesize the acetylsalicylic acid (ASA, aspirin) to avoid this issue.

Edwards explained that the result of the synthesis of acetylsalicylic acid (ASA, aspirin) from salicylic acid (SA), which consists of two acidic functional groups – a carboxylic acid and a phenol, through the process of esterification is formation of an ester that replaces the acidic phenol in ASA. The author furthermore explained that the first step of esterification is creating a suspension of SA (a solid) in acetic anhydride (a liquid reactant and a solvent) with a phosphoric acid catalyst (H3PO4) needed for the reaction. H+ from H3PO4 binds to the reaction complex as a catalyst and once all solid salicylic acid has disappeared and the acetylsalicylic acid dissolves, the reaction is finished. Acetic anhydride is hydrolyzed by adding water, very slowly, to acetic acid. The ASA product is created by placing the flask in an ice bath and then collecting the crude product by filtration and through purification of the product.

Edwards explained fully that the ASA product purity can be analyzed by determining the melting point, finding unreacted salicylic acid complex with Fe3+ and by determining thin layer chromatography. The melting range of the mixture would be the smaller, the purer the sample of the analyzed product. The mixture's colligative property depends on the number of solute particles and solvent molecules present in the solution. If there is any unreacted salicylic acid complex in the sample with Fe3+, a purple complex would be created. Thin layer chromatography helps determining impurities with silica (the stationary phase) and with an organic solvent (mobile phase). Depending on the intermolecular interactions between the polar and less polar silica plate, different compounds in aspirin move towards TLC plate at different rates. Less polar components move higher andmore polar components do not move close to the TLC plate, absorbing to the silica.

According to the New Jersey Department of Health, acetic anhydride and sodium hydroxide can cause burns. Safety goggles and aprons are an important safety precaution during synthesis and analysis of aspirin. The affected areas must be immediately washed with cold water.

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