Comparison of the reaction products of oleic acid ozonized in BCl 3-, HCl- and BF 3-MeOH media

Abstract

In BF 3-MeOH medium, the principal ozonolysis reaction products of oleic acid were methyl nonanoate (MMC 9) and dimethyl azelate (DMC 9) in yields of 98% with formation of minor secondary reaction products (methyl octanoate, nonaldehyde with nonaldehyde dimethyl acetal and dimethyl suberate, plus the C 9 half-ester-aldehyde, with its corresponding acetal). The gas-liquid chromatographic analysis of the ozonolysis reaction products in BCl 3- and HCl-MeOH revealed the existence of 4 major components with low yields of methyl nonanoate and dimethyl azelate (45–50%). The two other major reaction products, isolated by a combination of thin-layer chromatography (TLC) and high-pressure liquid chromatography (HPLC), were identified as the chlorinated acetals, 1,1-dimethoxy-2-chloro-nonane and the 8-chloro-9,9-dimethoxy methyl nonanoate.