Esterification of Chloroacetic Acid with Alcohols Catalyzed by Zinc Methanesulfonate

Abstract

Zinc methanesulfonate is prepared and used as a catalyst in many esterification reactions of chloroacetic acid with nearly equimolar amounts of alcohols. The catalytic activity, reusability, and handling of the catalyst are found to be good. Some factors that affect the esterification reaction of chloroacetic acid with isopropanol are investigated. Under the conditions of 1.1:1 molar ratio of isopropanol to chloroacetic acid, 0.5 mol% of the catalyst (molar percent of chloroacetic acid), 2.5 h of reaction time, ca. 14 mol% of cyclohexane (molar percent of chloroacetic acid) as water-carrying agent, and the temperature 85-90°C, the yield of isopropyl chloroacetate is 96.2%. In most cases, the catalyst is reused six times without obvious loss of catalytic activity.