The effect of catalyst nature on the kinetics and regioselectivity of the reaction of epichlolohydrin with benzoic acid.

Abstract

The kinetic regularities and the regioselectivity of the catalytic acidolysis of epichlorohydrin by benzoic acids were studied. Synthesized products of catalytic acidolysis of epichlorohydrin by benzoic and 3-nitrobenzoic acids are isomeric chlorhydrin esters: "normal" and "abnormal". The content of isomers is determined. The dependence of the output of the "abnormal" product on pKa acid is shown. It was found that tertiary amines provide higher regioselectivity of the reaction. The kinetic regularities of epichlorohydrin acidolysis by benzoic acids in the temperature range of 30 ÷ 60 ° C have been established. The activation parameters of the reaction are calculated. It is shown that the reaction of opening the oxirane cycle of epichlorohydrin with benzoic acids in the presence of catalysts of the basic nature takes place mainly by the SN2 mechanism.