CHLOROFORM AND CHLOROPHENOL PRODUCTION BY DECARBOXYLATION OF NATURAL ACIDS DURING AQUEOUS CHLORINATION

Naturally occurring carboxylic acids of several structural types reacted in dilute solution with aqueous hypochlorite to afford decarboxylation products. Incorporation of chlorine into the residual organic molecule occurred. Citric acid was efficiently converted to chloroform at pH 7 by a pathway probably involving 3-ketoglutaric acid as an intermediate; in acidic or alkaline solution, yields of CHCl3 were lower. Several other enolizable keto acids (including all three isomers of resorcylic acid) were likewise precursors of CHCl3 or of substances which could thermally be converted to CHCl3; yields varied widely. Two substituted benzoic acids common to natural waters, p-hydroxybenzoic acid and vanillic acid, were decarboxylated by hypochlorite with the production of chlo-rophenols. © 1979, American Chemical Society. All rights reserved.