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 productionof1,2-epoxy-6-methyl-triglycidyl-3,4,5-cyclohexantricarboxylate (EGCHC)starting from allyl sorbate were studied. The promising largely bio-basedbisphenol A and epichlorohydrine-free epoxy compound was synthesizedwith a three-step reaction network consisting of a Diels-Alderreaction with maleic anhydride, an esterification with allyl alcohol,and an epoxidation with 3-chloroperbenzoic acid. All reactions wereperformed batchwise in defined temperature ranges between 2 and 103 & DEG;C depending on the respective reaction. Reaction progress wasmonitored with H-1 NMR spectroscopy. For all studied reactions,kinetic models were established and regressed with acquired experimentaldata to gather information about pre-exponential factors and activationenergies. A model comparison for the esterification using both maximumlikelihood and parsimony showed that the reaction is second orderand proceeds through two intermediates toward the product. Moreover,the reactivity of the different double-bond types in the epoxidationis compared and discussed. The postulated models fitted well withthe experimental measurements and thus were found to accurately describethe underlying reaction mechanisms.