Kinetics of addition of acetic acid to epichlorohydrin in the presence of alkali metal acetates

Abstract

The kinetics of the reaction between acetic acid and epichlorohydrin in the presence of lithium, sodium and potassium acetates have been studied. The composition of the reaction mixture was followed chromatographically. Beside the two isomeric products of addition of epichlorohydrin to acetic acid, the presence was found of glycidyl acetate, glycerine dichlorohydrin and other products of parallel and subsequent reactions between the substrates and chlorohydroxyesters. A mechanism of the reaction, which takes into account the formation of the identified compounds has been proposed and a set of appropriate differential and balance equations developed. The rate constants for individual reactions as well as the catalysts used have been determined.

The solvent effects in the reactions of carboxylic acids with oxiranes. 1. Kinetics of the reaction of acetic acid with epichlorohydrin in butan-1-ol

“…The values of rate constant k 1 depend on the molar ratio of reagents, as shown in Table IV. Analogous dependence was observed before for the reaction of acetic acid with epichlorohydrin without a solvent and catalyzed with chromium(III) [17] or sodium [20] acetate.…”

“…The addition was found to be a relatively highly selective and regioselective reaction. Both selectivity and regioselectivity were much better than for the same reactions carried out in the presence basic catalysts, such as alkali metal acetates [20].…”

Kinetics of addition of acetic acid to epichlorohydrin in the presence of DMF or DMSO

“…Reactions (1) and (2) proceed according to the mechanism identical to that of the addition of carboxylic acids to epichlorohydrin in the presence of alkali metal carboxylates described in Ref. 10. The role of nucleophiles is played in nitrogen or sulphur atoms for DMF and DMSO, respectively.…”

Kinetic studies for the esterification of acetic acid with epichlorohydrin over an anion exchange resin catalyst

“…As any non-symmetric compound epichlorohydrin leads to two isomeric esters (Scheme 1) [4,5]. Of the two possible isomeric products the normal ester is formed as the main product in neutral or basic medium, whereas an acidic medium favors the formation of the abnormal product.…”