Wednesday, June 25, 2008
Congressional Room (Capital Hilton)
109

Greening up the Synthesis of Aspirin

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

Traditionally aspirin is synthesized by an esterification reaction between the phenolic hydrogen of salicylic acid and acetic anhydride in the presence of a Brønsted–Lowery acid catalyst, sulfuric acid, in the absence of water. If water is present, aspirin is known to undergo a hydrolysis reaction which yields the 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, the reaction does not produce aspirin in high yield or purity. The major impurity that has been identified by Infrared Spectroscopy and melting point determination is salicylic acid. Salicylic acid can be attributed to the small amount of water in the laboratory equipment causing the reverse 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 catalyst. The use of a suitable transition metal catalyst makes the reactions 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.