Chemical Changes of Organic Compounds in Chlorinated Water. XVIII. Kinetics and Mechanisms for Chlorohydrin Formation during Reactions of Aqueous Chlorine with Lipid Components.

Abstract

A series of fatty acids and their triglycerides were subjected to chlorination under similar conditions to those for water chlorination. Unsaturated fatty acids were more reactive towards chlorine than their corresponding ester derivatives, as shown by the reaction rate and the extent of chlorine incorporation. However, saturated fatty acids did not react with chlorine. A number of chlorinated and oxygenated products of these reactions were tentatively identified using electron impact and chemical ionization mass spectrometry. Chlorohydrin, as a major product, resulting from the reaction of oleic acid with chlorine was stable in water. However, chlorohydrins and dichlorohydrins formed by the reactions of linoleic or linolenic acid with chlorine further reacted with chlorine to give organic chlorinated compounds which were stable in water.