Epoxidation of cottonseed oil by aqueous hydrogen peroxide catalysed by liquid inorganic acids

Abstract

The kinetics of epoxidation of cottonseed oil by peroxyacetic acid generated in situ from hydrogen peroxide and glacial acetic acid in the presence of liquid inorganic acid catalysts were studied. It was possible to obtain up to 78% relative conversion to oxirane with very less oxirane cleavage by in situ technique. The rate constants for sulphuric acid catalysed epoxidation of cottonseed oil were in the range 0.39-5.4 × 10-6 L mol-1 s-1 and the activation energy was found to be 11.7 kcal mol-1. Some thermodynamic parameters such as enthalpy, entropy, and free energy of activation were determined to be of 11.0 kcal mol-1, -51.4 cal mol-1 K-1 and 28.1 kcal mol-1, respectively. The order of effectiveness of catalysts was found to be sulphuric acid > phosphoric acid > nitric acid > hydrochloric acid. Acetic acid was found to be superior to formic acid for the in situ cottonseed oil epoxidation. © 2007 Elsevier Ltd. All rights reserved.