Kinetic Modeling of the Synthesis Path for the Production of a Sustainable Epoxy Resin Based on Allyl Sorbate

The homogeneous catalytic reaction steps for the production of 1,2-epoxy-6-methyl-triglycidyl-3,4,5-cyclohexantricarboxylate (EGCHC) starting from allyl sorbate were studied. The promising largely bio-based bisphenol A and epichlorohydrine-free epoxy compound was synthesized with a three-step reaction network consisting of a Diels-Alder reaction with maleic anhydride, an esterification with allyl alcohol, and an epoxidation with 3-chloroperbenzoic acid. All reactions were performed batchwise in defined temperature ranges between 2 and 103 °C depending on the respective reaction. Reaction progress was monitored with ¹H NMR spectroscopy. For all studied reactions, kinetic models were established and regressed with acquired experimental data to gather information about pre-exponential factors and activation energies. A model comparison for the esterification using both maximum likelihood and parsimony showed that the reaction is second order and proceeds through two intermediates toward the product. Moreover, the reactivity of the different double-bond types in the epoxidation is compared and discussed. The postulated models fitted well with the experimental measurements and thus were found to accurately describe the underlying reaction mechanisms.