Preparation of carboxylic acids from hydroxy compounds by oxidation with ozone

Abstract

Abstract Various mono‐ and dicarboxylic acids were obtained with appreciable yields from saturated hydroxy compounds by oxidation in aqueous acetic acid with a mixture of ozone and oxygen followed with oxygen. The starting materials and the mono‐ and dicarboxylic acids obtained were as follows: Primary alcohols RCH 2 OH → RCOOH; α,ω‐glycols HOCH 2 (CH 2 ) n CH 2 OH → HOOC(CH 2 ) n COOH; secondary alcohols and 12‐hydroxyoctadecanoic acid R 1 CH 2 CH(OH)CH 2 R 2 → R 1 COOH + R 2 CH 2 COOH + R 1 CH 2 COOH + R 2 COOH; alicyclic alcohols CH 2 (CH 2 ) n CHOH → HOOC(CH 2 ) n COOH; 9,10‐dihydroxyoctadecanoic acid CH 3 (CH 2 ) 7 CH(OH)CH(OH) (CH 2 ) 7 COOH → CH 3 (CH 2 ) 7 COOH + HOOC(CH 2 ) 7 COOH. Small amounts of aldehydes, ketones, and carboxylic acids having fewer carbon atoms than those of the carboxylic acids formed as main products were also detected from some of the oxidation products.