Atlantic Richfield Company

Ashland Oil, Inc.

Lee R Zehner

James C Vartuli

Haven S Kesling, Jr

John G Zajacek

Richard V Norton

Dace Grote

Ralph F Pascoe

R Warren Lenton

John E Corn, Jr

Richard W Sauer, Deceased

John J Heffron, Executor

A process for the production of isobutyric acid anhydride in which propylene is initially carbonylated in the presence of a substantial molar excess of liquid anhydrous hydrogen fluoride to provide a reaction mixture of isobutyroyl fluoride and unreacted hydrogen fluoride. Following distillation of the reaction mixture to recover a recycle stream of hydrogen fluoride, the isobutyroyl fluoride residue is partially hydrolyzed in the presence of a hydrogen fluoride acceptor resulting in a hydrolysis product consisting essentially of isobutyroyl fluoride, isobutyric acid anhydride and a hydrogen fluoride complex of said acceptor. Following removal of the solid complex, the hydrolysis product is fractionally distilled to yield an overhead fraction of isobutyroyl fluoride for reuse in the hydrolysis reaction.

Process for the production of isobutyric acid anhydride

A method for the preparation of a chromium, molybdenum or tungsten (Group VIB metal) promoted single phase vanadium(IV)bis(metaphosphate) catalyst useful for the vapor phase oxidation of hydrocarbons and particularly the oxidation of linear C.sub.4 unsaturated olefins to prepare maleic anhydride.

Preparation of a vanadium(IV)bis(metaphosphate) hydrocarbon oxidation

A method for the preparation of a cerium or thorium (lanthanide or actinide metal) promoted single phase vanadium(IV)bis(metaphosphate) catalyst useful for the vapor phase oxidation of hydrocarbons and particularly the oxidation of linear C.sub.4 unsaturated olefins to prepare maleic anhydride.

Preparation of vanadium(IV)bis(metaphosphate) hydrocarbon oxidation

A method for the preparation of a titanium promoted single phase vanadium(IV)bis(metaphosphate) catalyst useful for the vapor phase oxidation of a linear C.sub.4 unsaturated olefins to prepare maleic anhydride.

Preparation of a titanium promoted VO(PO.sub.3).sub.2 oxidation catalyst

A method for the preparation of a thallium promoted single phase vanadium(IV)bis(metaphosphate) catalyst useful for the vapor phase oxidation of linear C.sub.4 unsaturated olefins to prepare maleic anhydride.

Preparation of thallium promoted VO(PO.sub.3).sub.2 oxidation catalyst

A method for the preparation of a single phase crystalline vanadium(IV)bis(metaphosphate), VO(PO.sub.3).sub.2, catalyst having an improved intrinsic surface area of from about 5 to 15 m.sup.2 /g. and useful for the vapor phase oxidation of linear C.sub.4 unsaturated olefins, such as n-butenes, to prepare maleic anhydride.

Single phase vanadium(IV)bis(metaphosphate) oxidation catalyst with

A process for the preparation of an unsaturated monoester having the formula ##STR1## wherein R is an alkyl group of from 1 to 4 carbon atoms and R' is hydrogen, a halogen or a methyl group, by reacting carbon monoxide, oxygen, and at least a stoichiometric amount of an enol ether, or a 1-alkoxycycloalkene dehydrating agent with a diolefin having the formula ##STR2## wherein R' is as hereinabove described, in the presence of a catalytic amount of a platinum group metal compound and a copper or iron oxidant salt compound. Alternatively, a ligand or coordination complex compound of the metal salt compound and catalytic quantitites of an alcohol may be employed.

Preparation of unsaturated monoesters by the catalytic oxidative

A process for the preparation of an unsaturated monoester having the formula ##STR1## wherein R is an alkyl group of from 1 to 4 carbon atoms and R' is hydrogen or a methyl group which comprises reacting carbon monoxide and oxygen with a diolefin having the formula ##STR2## wherein R' is as hereinabove described, in the presence of a catalytic amount of a platinum group metal compound, a copper or iron oxidant salt compound and a stoichiometric amount of a dehydrating agent. Alternatively, a ligand or coordination complex compound of the metal salt compound, and catalytic quantities of an alcohol may be employed.

Preparation of unsaturated monoesters by catalytic oxidative

A process for the preparation of dimethyl adipate by the hydrogenation of dimethyl hex-3-endioate, having the formula CH.sub.3 O.sub.2 CCH.sub.2 CH.dbd.CHCH.sub.2 CO.sub.2 CH.sub.3, derived from the oxidative carbonylation of 1,3-butadiene with a mixture of carbon monoxide and oxygen at a temperature of from 60.degree. C. to 200.degree. C. and pressures of from 15 psig to 5000 psig in the presence of a catalytic mixture of a platinum group metal compound and a copper or iron oxidant salt compound with at least a stoichiometric amount of a dehydrating agent, which comprises subjecting the dimethyl hex-3-endioate to a liquid phase hydrogenation at temperatures of from about ambient to about 150.degree. C. under hydrogen pressures of from about 10 psig to 1000 psig in the presence of an effective amount of a hydrogenation catalyst to produce dimethyl adipate, and recovering the dimethyl adipate.

Preparation of dimethyl adipate by the hydrogenation of dimethyl

A process for the preparation of an unsaturated diester having the formula ##STR1## wherein R is an alkyl group of from 1 to 8 carbon atoms or an aralkyl group containing 6 carbon atoms in the ring and from 1 to 4 carbon atoms in the alkyl substituent, and R.sub.1 to R.sub.4 is hydrogen, a halogen, an alkyl group of from 1 to 4 carbon atoms or an aryl group containing 6 carbon atoms in the ring, by reacting carbon monoxide and oxygen with a diolefin having the formula ##STR2## wherein R.sub.1 to R.sub.4 which may be the same or different is as hereinabove described, in the presence of a catalytic amount of a platinum group metal compound, a copper for iron oxidant salt compound and a stoichiometric amount of a dehydrating agent. Alternatively, a ligand or coordination complex compound of the metal salt compound, and catalytic quantities of an alcohol may be employed.

Preparation of unsaturated diesters by catalytic oxidative carbonylation

A process for the preparation of an unsaturated diester having the formula ##STR1## wherein R is an alkyl group of from 1 to 8 carbon atoms or an aralkyl group containing 6 carbon atoms in the ring and from 1 to 4 carbon atoms in the alkyl substituent and R.sub.1 to R.sub.4 is hydrogen, a halogen, an alkyl group of from 1 to 4 carbon atoms or an aryl group containing 6 carbon atoms in the ring, by reacting carbon monoxide, oxygen, at least a stoichiometric amount of an enol ether or alkoxycycloalkene and at least an equal molar quantity of an alcohol based on the enol ether or alkoxycycloalkene, with a diolefin having the formula ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different is as hereinabove described, in the presence of a catalytic amount of a platinum group metal compound and a copper or iron oxidant salt compound. Alternatively, a ligand or coordination complex compound of the metal salt compound may be employed as a co-catalyst.

Preparation of unsaturated diesters by the catalytic oxidative

A process for the preparation of ethylene glycol by the vapor phase hydrogenation of oxalate esters, such as a dibutyl oxalate, at elevated temperatures and at relatively low hydrogen pressures in the presence of a suitable hydrogenation catalyst, such as a copper chromite catalyst, while minimizing the hydrogenolysis of the glycol and other side reactions and maximizing the hydrogenation catalyst activity.

Process for the preparation of ethylene glycol

A process for the preparation of oxalate esters by reacting an alcohol with a mixture of carbon monoxide and oxygen in the presence of a catalytic mixture of:

Process for the preparation of oxalate esters

A process for the preparation of oxalate esters by the catalytic oxidative carbonylation of an alkoxycycloalkene with carbon monoxide, an alcohol and oxygen or an oxygen-containing gas in the presence of a metal salt catalyst and an amine base. In addition, a catalytic amount of particular metal oxidizing salts is employed along with a catalytic amount of an acid or an amine salt compound. Alternatively various counterions and ligands of the metal salt catalysts may be employed.

Preparation of oxalate esters from carbon monoxide and an

A process for the preparation of oxalate esters by the catalytic oxidative carbonylation of an enol ether with carbon monoxide, an alcohol and oxygen-containing gas in the presence of a metal salt catalyst and an amine base. In addition, a catalytic amount of particular metal oxidizing salts is employed along with a catalytic amount of an acid or an amine salt compound. Alternatively various counterions and ligands of the metal salt catalysts may be employed.

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Media, PA, United States of America

Lee R Zehner