Gulf Research & Development Company

Ching-Yong Wu

Thaddeus P Kobylinski

John E Bozik

Harold E Swift

Wayne R Pretzer

Propylene is converted to propylene glycol at high selectivity in a process in which ethylbenzene hydroperoxide and water are reacted with propylene in the presence of osmium tetroxide catalyst and a base at a pH of about 14.

Preparation of propylene glycol from propylene

Cumene hydroperoxide in a solvent comprising phenol and acetone is decomposed to phenol and acetone using a soluble rhenium compound.

Decomposition of cumene hydroperoxide with a homogeneous catalyst

The hydroperoxides of diisopropylbenzene are prepared by the oxidation of diisopropylbenzene with molecular oxygen in the presence of a minute amount of solid barium oxide.

Preparation of diisopropylebenzene hydroperoxide

A catalyst residue containing osmium catalyst having a substantial component with a valency state less than +5 is regenerated to a valency state greater than +5 by contacting the residue with an organic hydroperoxide at a pH greater than 7 and the regenerated catalyst residue is recycled to a hydroxylation reactor containing ethylene or propylene, a polar organic solvent, an aqueous solution of cesium, rubidium, potassium or tetraalkylammonium hydroxide and an organic hydroperoxide.

Regenerating perosmate catalyst

Ethylene is converted to ethylene glycol at high selectivity in a process in which ethylbenzene hydroperoxide and water are reacted with ethylene in the presence of osmium tetroxide catalyst and a base at a pH of about 14.

Preparation of ethylene glycol from ethylene

Ethylbenzene is converted to styrene at high selectivity in a multistage process in which ethylbenzene is oxidized to ethylbenzene hydroperoxide which is reacted with ethylene or propylene to produce a mixture of 1-phenylethanol and acetophenone which are converted to styrene.

Preparation of styrene from ethylbenzene

Ethylene or propylene is converted to the corresponding glycol at high selectivity in a process in which t.butyl hydroperoxide is reacted with the olefin in a two-phase liquid, organic-aqueous reaction system in the presence of osmium tetroxide and cesium, rubidium or potassium hydroxide.

Converting ethylene and propylene to the glycol using t.butyl

A process for epoxidizing an alpha-olefin by adding an alpha-olefin and an oxygen transfer catalyst to a hydroperoxide stabilized with barium oxide.

Epoxidation of alpha-olefins

Osmium (III) or (IV) in an anionic complex with oxygen and having an alkali metal, ammonium or tetra(lower)alkylammonium cation is oxidized to a valency state higher than 5 by reaction with an organic hydroperoxide, such as ethylbenzene hydroperoxide, at a temperature less than 30.degree. C.

Method of oxidizing osmium (III) and osmium (IV) to a higher valency

1,3-Dicyanocyclopentane is prepared by the hydrocyanation of 2-cyanocyclopentene in the presence of a catalyst system comprising a zero valent nickel complex, free of carbon monoxide, and a promoting amount of a metal compound such as zinc chloride.

Preparation of 1,3-dicyanocyclopentane

Ethylbenzene hydroperoxide and ethylene or propylene are converted to acetophenone, 1-phenylethanol and the corresponding glycol at high selectivity in a process in which ethylbenzene hydroperoxide is reacted with the olefin in a two-phase liquid, organic-aqueous reaction system in the presence of osmium tetroxide and cesium, rubidium or potassium hydroxide.

Hydroxidation of gaseous olefins with ethylbenzene hydroperoxide in a

Cumene hydroperoxide in a solvent is decomposed to phenol and acetone using a non-soluble rhenium compound.

Decomposition of cumene hydroperoxide with a heterogeneous catalyst

Ethylbenzene hydroperoxide is prepared by the oxidation of ethylbenzene with molecular oxygen in the presence of a minute amount of solid barium oxide.

Preparation of ethylbenzene hydroperoxide

Cumene hydroperoxide is prepared by the oxidation of cumene with molecular oxygen in the presence of a minute amount of solid barium oxide.

Preparation of cumene hydroperoxide

A mixture of 3,8- and 4,8-dicyanotricyclo[5.2.1.0]decane is prepared by the hydrocyanation of 8-cyanotricyclo[5.2.1.0]dec-3-ene in the presence of a catalyst system comprising a zero valent nickel complex, free of carbon monoxide, a promoting amount of a metal compound such as zinc chloride and a hydroxy-containing aryl compound such as p-cresol as a solvent.

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O'Hara Township, PA, United States of America

Ching-Yong Wu