Selective epoxidation of natural triglycerides using acidic ion exchange resin as catalyst

Epoxidation is a very useful reaction in organic synthesis. Due to the high reactivity of the epoxide group it can be used as an active intermediate for the synthesis of many high-value products. Epoxides are commercial products and they have many industrial uses. Understanding the kinetics of epoxidation reactions can lead to production of value-added products from locally available renewable natural resources. This research investigated the kinetics of epoxidation of cottonseed oil by peroxyacetic acid (PAA) generated in situ from hydrogen peroxide and glacial acetic acid (AA) in the presence of acidic ion exchange resin (AIER) catalysts, namely Amberlite IR-120. The effect of several variables including temperature, stirring speed, catalyst loading, and particle size, concentration of hydrogen peroxide and AA on oxirane conversion was studied. A satisfactory level of oxirane conversion (greater than 65%) with high selectivity (greater than 90%) could be obtained if the epoxidation was carried out at optimum conditions, using in situ generated PAA. The LangmuirHinshelwoodHougenWatson (LHHW) kinetic model approach has been adopted for the development of overall reaction rate equations, and the proposed kinetic model includes the major side reactions for the estimation of kinetic parameters. Kinetic parameters were estimated by fitting experimental data using a nonlinear regression method. From the estimated kinetic constants, the activation energy for the AIER catalysed epoxidation of cottonseed oil was found to be 10.1 kcal mol-1. Copyright (c) 2010 Curtin University of Technology and John Wiley & Sons, Ltd.