Gold-catalyzed synthesis of dicarboxylic and monocarboxylic acids

Abstract

Vicinal dihydroxy derivatives of oleic acid, methyl oleate, and erucic acid were converted by oxidative cleavage to the respective di- and monocarboxylic acids according to an environmentally benign process carried out in the presence of supported gold catalysts and molecular oxygen as oxidant in an aqueous-basic medium. Au(0) nanoparticles with particle sizes between 0.5 and 4.1 nm were deposited as catalytically active species on different oxidic supports. The influence of the catalyst composition and morphology as well as of the reaction conditions on conversion of dihydroxy fatty acids and yields of products were investigated. Thus, the reaction of 9,10-dihydroxystearic acid catalyzed by Au/Al₂O₃ leads to azelaic acid (86% yield) and pelargonic acid (99% yield).