Reaction of glycidyl benzoate with acid in the presence of tertiary amines as the catalyst

The reaction of epoxides with carboxylic acids catalysed by tertiary amines has been discussed. The mechanism of the reaction has been deduced and confirmed, using experimental results, on the example of the reaction of glycidyl benzoate with benzoic acid in xylene, catalysed by benzyldimethylamine. The reaction occurs via a combined ionic mechanism as well as via a complex formation, thus explaining the abnormal dependence of the reaction constant on the dielectric constant of the milieu and the found non-integer orders of reaction with respect to the amine and to the acid.