(I) Synthesis of Hydroquinone from p-Diisopropylbenze by the Liquid phase Oxidation.
p-Diisopropylbenzene is produced as a by-product in the synthesis of cumene from benzene and propylene. This compouhd was oxidized at 85°C in the presence of sodium carbonate and sodium stearate, the former being used as a pH conrtoller and the latter as an emusifier. As the catalysts, benzoyl peroxide, cobalt naphthenate as well as mono-and di-hydroperoxide of p-diisopropylbenzene were used.
The-OOH% was largest, reaching up to 57.5%, when the dihydroperoxide was used as an oxidation initiator. The main oxidation products were mono-and di-hydroperoxide and di-compound seems to be unknown, the melting point of which is 142-144°C 42-144°C.
Mono-hydroperoxide was decomposed with 13% H2SO4 and converted to australol with 54% yield. Di-hydroperoxide was, converted to hydroquinone with 60.5% yield in the decomposition with 20% H2SO4. Na2SO3 reduced di-hydroperoxide to the corresponding dialcohol quantitatively.
(II) Synthesis of'Hydroperoxide of p-Di-sec-Butylbenzene by the Low Tempoerature Oxidation.
Mono-and di-hydroperoxide of p-di-sec-butylbenzene were obtained by the atmos-pheric oxidation at 95°C and in the presence of water, sodium carbonate, sodium stearate and catalysts. The catalysts used were benzoylperoxide, mono-and di-hydroperoxides of the said compound. The maximum yield of -OOH was obtained when the di-hydroperoxide was used as an oxidation initiator, reaching up to 39.5%.
The di-hyroperoxide was plate white crystal, melting at 82-83°C and the structure of which was confirmed by the infrared spectrum and elementary analysis. The mono-hydroperoxide was light yellow color liquid.
The di-hydroperoxide was reduced quantitatively to the corresponding dialcohol by the use of sodium bisulfite which melted at 79-80°C. The sulfuric acid catalysed decomposition of di-hydroperoxide produced hydroquinone, whereas mono-compound p-sec-butylphenol and methyl-ethyl-ke ton.
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