Catalysis of the epichlorohydrin acidolysis by tetraalkylammonium salts: effect of temperature and nature of anion of salt.

Abstract

The kinetic regularities of epichlorohydrin acidolysis by benzoic acid in the presence of tetraethylammonium salts (nitrate, bromide, iodide) in the temperature range of 30 ÷ 70 ° C have been investigated. The reaction was carried out under conditions of significant excess of epichlorohydrin, which is both a solvent and a substrate. The zero reaction order for the acid reagent and the first reaction order for the catalyst were established. It is shown that the catalytic reaction is a pseudofirst order reaction. The relationship between the catalytic activity of tetraethylammonium salts and the nucleophilicity of the salt anion was established. The activation parameters of the reaction corresponding to the reactions of the bimolecular nucleophilic substitution are determined. Activation entropy has been found to be the most sensitive to the nature of the tetraethylalkylammonium anion anion.