A study of the volatile compounds produced by the autoxidation of methyl oleate, oleic acid, and cis‐9‐octadecene

Summary Methyl oleate, oleic acid, and cis‐9‐octadecene were oxidized at 80° with a stream of air, and the volatile decomposition products were collected in dry ice traps. The volatile material consisted of an aqueous fraction and water‐soluble substances, an oil fraction, and a crystalline product. The substances in the aqueous fractions were characterized as formic and acetic acid, and their formation was studied during the autoxidation of the various substrates up to 21 days. The crystalline material was purified, and its properties were examined. The purified crystals showed chemical and infrared properties very similar to a sample of synthesized bis‐(hydroxyheptyl) peroxide. Formic and acetic acid were also shown to be produced during the decomposition of hydroxyalkyl peroxides.