Styrene oxide (yield 18-25%) and benzaldehyde (yield 40-45%) are the m
ain products of te oxidation of styrene with molecular oxygen at 90 de
grees C in toluene as the solvent. The yield of styrene oxide increase
s, that of benzaldehyde decreases with increasing conversion. Addition
of benzaldehyde at the beginning of the oxidation increases the react
ion rate and the yield of both styrene oxide and ester compounds. Gasc
hromatographic examination of the crude oxidation mixture showed the p
resence of 15 oxygen containing by-products which were quantitatively
and qualitatively analysed. Pathways of by-product formation by cooxid
ation of styrene with benzaldehyde and toluene with participation of b
enzoyl, benzoyloxy, benzoylperoxy or benzyl radicals are proposed.