Oxidation of p-Dialkylbenzene (III)

Formation of mono-and dihydroperoxide from p-secbutylisopropylbenzene

Abstract

dihydroperoxide of p-sec-butyl-isopropylbenzene were obtained by the liquid phase oxidation at 95°C and the results were quite similar to the case in the oxidation of p-diisopylbeznne. As an initiator, benzoylperoxide, mono-and dihydroperoxide of the said compound were used and the HP0% was maximum up to 62.5% in the case where dihydroperoxide was used.
Monohydroperoxide was oxidized by the use of ferric sulfate and gave p-diacetylbenzene, whereas by the decomposition with diluted sulfuric acid gave hydroquinone.
Na2S2O3 reduced the monohydroperoxide to p-sec-butyl-2, 2-dimethylbenzylalcohol . From the above-mentioned results, the OOH group was confirmed to be attached to isopropyl group.Thus the oxidation of isopropyl group seems to occurr preferably as compared with sec-butyl one.
Mono-hydroperoxide is a liquid boiling at 89-90°C/0 .05mm Hg and identified by the elementary analysis as well as by the infrared spectrum.
Dihydroperoxide is a colorles solid melting at 78-90°C and its structure wes confirmed by the elementary and infrared analysis.
Next, monohydroperoxide was reacted with p-sec-butyl-a-ai-dimethylbenzylalcohol in the stream of nitrogen at 95°C for 48hrs and the product was confirmed to be di-p-secbutyl- cumyl-peroxide which was pale yellov liquid boiling higher than 100°C/0 .002mmHg.