Thursday, 17 May 2007
3rd Floor Hall (Pfahler Hall)
399

Synthesis of Aspirin - A “Greener“ Approach

Kathleen D. Field and Dr. Carolyn Supplee. Monmouth University, West Long Branch, NJ

Traditionally aspirin is synthesized by an esterification reaction between the phenolic hydrogens of salicylic acid and acetic anhydride with a Bronsted –Lowery such as sulfuric acid as the catalyst in the absence of water. In the presence of water, aspirin is known to undergo a hydrolysis reaction to yield back starting materials. The synthesis of aspirin is often used as an experiment in General Chemistry to demonstrate the concepts of chemical kinetics and equilibrium and to teach students synthetic chemistry skills. Since the reagents used in the synthesis of aspirin and the aspirin product, itself, are colorless, the General Chemistry experiment for the synthesis of aspirin is not visually interesting to students. And often times, General Chemistry students do not produce any aspirin or impure aspirin in low yields. The major impurity has been identified by Infrared Spectroscopy and melting point determination as salicylic acid. The presence of salicylic has been attributed to the presence of water in laboratory equipment and the hydrolysis reaction. In order to make the experiment visually more interesting, increase the quality and quantity of aspirin produced and reduce the students' exposure to concentrated sulfuric acid, an alternative procedure for the synthesis of aspirin was developed using a transition metal as the acid catalyst. The use of a suitable transition metal catalyst makes the reaction solutions highly colored, produces a high quality of aspirin and allows for the synthesis of aspirin without the use of concentrated sulfuric acid. This study examines the affect of changing the catalyst on the synthesis of aspirin.

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