Biochemistry Science Fair Project
Natural Catalyst in the Synthesis of Aspirin


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Project Information
Title: Synthesize aspirin with natural acid catalysts in place of mineral sulfuric acid
Subject: Biochemistry
Grade level: High School - Grades 10-12
Academic Level: Ordinary
Project Type: Experimental
Cost: Medium
Awards: 2nd Place, Canada Wide Virtual Science Fair ($100)
Affiliation: Canada Wide Virtual Science Fair
Year: 2013
Materials, Techniques and Concepts: salicylic acid, acetic anhydride solution, sulfuric acid, infrared spectrophotometer, melting point apparatus, thin layer chromatography
Description: This project is about synthesizing green aspirin by replacing sulfuric acid with a natural acid in the synthesis of aspirin. Citric acid and pineapple juice were used as possible green catalysts but only citric acid worked when used in a high concentration. The infrared spectrophotometer confirmed that when using the natural acids as a catalyst, the product displayed the same functional groups as aspirin.
Link: www.virtualsciencefair.org...
Background

Synthesis of Aspirin

Aspirin also known as acetylsalicylic acid (ASA) is a salicylate drug, often used as an analgesic to relieve minor aches and pains, as an antipyretic to reduce fever, and as an anti-inflammatory medication. Aspirin was first isolated by Felix Hoffmann, a chemist with the German company Bayer in 1897.

Aspirin, an acetyl derivative of salicylic acid, is a white, crystalline, weakly acidic substance, with a melting point of 136 °C (277 °F), and a boiling point of 140 °C (284 °F).

The synthesis of aspirin is classified as an esterification reaction. Salicylic acid is treated with acetic anhydride, an acid derivative, causing a chemical reaction that turns salicylic acid's hydroxyl group into an ester group (R-OH → R-OCOCH3). This process yields aspirin and acetic acid, which is considered a byproduct of this reaction. Small amounts of sulfuric acid (and occasionally phosphoric acid) are almost always used as a catalyst. This method is commonly employed in undergraduate teaching labs.

Formulations containing high concentrations of aspirin often smell like vinegar because aspirin can decompose through hydrolysis in moist conditions, yielding salicylic and acetic acids.

The acid dissociation constant (pKa) for acetylsalicylic acid is 3.5 at 25°.

See also:
Physical Properties of Aspirin
History of Aspirin

Source: Wikipedia (All text is available under the terms of the Creative Commons Attribution-ShareAlike License)

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