Allied Corporation

Jeffrey P Solar

Frank Mares

Steven E Diamond

Deborah A Muccigrosso

A process for the oxidation of olefinically unsaturated substrates of the formula R--CH.dbd.CH-R' wherein R and R' are independently selected from members of the group consisting of H, alkyl, alkenyl, cycloalkyl, aryl and halo-, cyano- and ether-substituted alkyl, alkenyl, cycloalkyl and aryl which comprises reacting in the liquid phase said substrate with a rhodium nitro complex of the formula L.sub.n RhNO.sub.2, wherein n is 4 or 5 and wherein L.sub.n represents any combination of monodentate, bidentate, tridentate and tetradentate ligands such as to provide four or five bonding sites, for a time sufficient to produce an oxidized product of the formula RCH.sub.2 C(O)R' and a reduced product of the formula L.sub.n RhNO is disclosed. A preferred embodiment of the process wherein the rhodium nitro complex contains at least one ligand replaceable by olefin to be oxidized and operates to produce the oxidized product RCH.sub.2 C(O)R' in the absence of other Group VIII metals as co-catalyst is also disclosed.

Oxidation of olefins using rhodium nitro complex

An olefinically unsaturated substrate is reacted with a transition metal nitro complex, having the transition metal bonded to the nitrogen of the nitro radical, in the presence of a thallium(III) compound as cocatalyst to cause the production of oxirane products, rather than aldehydes or ketones. The process is applicable to the production of ethylene oxide, propylene oxide, epichlorohydrin, epoxidized fatty acids and oxiranes from various other internal and terminal olefins.

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Flanders, NJ, United States of America

Jeffrey P Solar