PHASE TRANSFER CATALYSIS OF HETEROGENEOUS REACTIONS BY QUATERNARY SALTS

摘要

1324763 Heterogeneous oxidation of olefins CONTINENTAL OIL CO 19 March 1971 7280/71 Addition to 1227144 Heading C2C A heterogeneous ionic oxidation is carried out between an olefin in a liquid phase and an oxidizing agent in a contiguous immiscible liquid phase in the presence of an organic quaternary salt having the formula where M is a pentavalent ion of an element consisting of nitrogen, phosphorus, arsenic, antimony or bismuth, R 1 , R 2 , R 3 and R 4 are hydrocarbon radicals wherein one of the hydrocarbon radicals may be substituted by a further quaternary group the total number of carbon atoms being from 18 to 70, and X- is an anion which will dissociate from the cation in an aqueous environment, said organic quaternary salt being substantially more soluble in the less polar of said reactant-containing phases than in the other of said reactantcontaining phases and a compound consisting of osmium, ruthenium, molybdenum, tungsten, selenium, vanadium, chromium, titanium, cerium, nickel, manganese, cobalt, platinum, iron, lead or palladium. In examples, 1-octene is oxidized to heptanol and heptenoic acid, cyclohexene is oxidized to cyclohexane-1,2-diol, cyclohexene oxide, cyclohexene-2-one and cyclohexen-2-ol, 1,5-hexadiene is oxidized to the corresponding epoxides, diols and tetraols, 3,3- dimethyl-1-butene is oxidized to the epoxide and diol, cis- and trans-2-hexenes and 2-octenes were oxidized to the cis- and trans-epoxides and the erythro- and threo-diols and styrene is oxidized to styrene oxide and 2-phenyl-1,2- ethanediol.