GB1111945A - Production of epoxy compounds - Google Patents

Abstract

Epoxy compounds are produced by contacting a hydrocarbon having a secondary or tertiary saturated carbon atom with molecular oxygen to produce an organic hydroperoxide, reacting the hydroperoxide in the liquid phase with an olefinically unsaturated hydrocarbon having the same carbon skeletal structure in the presence of a metal epoxidation catalyst to produce an epoxy compound and the alcohol corresponding to the hydroperoxide, dehydrating at least part of the alcohol to the corresponding olefinically unsaturated hydrocarbon and epoxidizing this unsaturated hydrocarbon in the epoxidizing reaction with additional amounts of the organic hydroperoxide. The preferred hydrocarbons used as starting materials are aralkanes having at least one carbon atom on the alkyl carbon adjacent to the aromatic ring, e.g. ethyl benzene, cumene, ethyl toluene, p-cumene, tetrahydronaphthalene, p-diisopropyl benzene, ethyl naphthalene, isopropyl naphthalene, p-diethyl benzene, p-tertiary-butyl ethyl benzene and phenyl cyclo-hexane. Other suitable starting materials are, e.g., isobutane, isopentane, cyclohexane, methyl cyclohexane, dimethyl cyclohexanes and 2,5-dimethyl benzene. Suitable epoxidation catalysts are Ti, V, Cr, Se, Zr, Nb, Mo, Te, Ta, W, Re or U. In the Examples: (a) cumene is oxidized to cumene hydroperoxide which is reacted with a -methyl styrene to give a -methyl styrene oxide and cumyl alcohol; part of the cumyl alcohol is dehydrated to a -methyl styrene which is recycled with the rest of the cumyl alcohol to the epoxidation step; (b) ethyl benzene is oxidized to ethyl benzene hydroperoxide which is used to epoxidize styrene and phenylethanol which is dehydrated to styrene and recycled to the epoxidation step.