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US3887595A Expired / Lapsed US ⏱️ 0.0 years remaining

Carbonylation process

Assignee: Shell USA Inc
•
Filing: 1973-03-05
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Granted: 1975-06-03
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Expires: 1993-03-05
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Abstract

Abstract An improved catalyst composition for carbonylating olefinically unsaturated hydrocarbons with carbon monoxide and a hydroxylic compound comprises a zero-valent palladium or platinum complex incorporating stabilizing phosphine ligands, and excess ligand. Use of these catalyst compositions results in a high ratio of straight-chain to branch-chain product when employed in the carbonylation of alpha olefins to produce carboxylic acids, esters or acid anhydrides.

Inventors

  • 👤 Kenzie Nozaki

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 02:11
CPC Classifications
B; B01; B01J; B01J31/00; B01J31/16; B01J31/24; B01J31/2404; C; C07; C07C; C07C51/00; C07C51/10; C07C51/14; B01J2231/00; B01J2231/30; B01J2231/32; B01J2231/321; B01J2531/00; B01J2531/80; B01J2531/82; B01J2531/824; B01J2531/828; B01J31/1616

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 216 words
In the process of carbonylating olefinically unsaturated hydrocarbons of from 2 to 30 carbon atoms free from acetylenic unsaturation and conjugated olefinic unsaturation with carbon monoxide and with at least one hydroxylic compound selected from the group consisting of water, alkanol of from 1 to 20 carbon atoms, carboxylic acid of from 2-20 carbon atoms and mixtures thereof in the presence of a catalyst, the improvement which comprises producing predominately straight chain products by employing as said catalyst a composition consisting essentially of a. a zerovalent noble metal phosphine complex of the general formula (R3P)nM wherein M is palladium or platinum, n is a whole number from 1 to 4 inclusive and R independently is a monovalent hydrocarbyl or substituted hydrocarbyl moiety of from 1 to 20 carbon atoms inclusive of substituents, is free from aliphatic carbon-carbon unsaturation and is selected from the group consisting of unsubstituted alkyl, unsubstituted phenyl, monosubstituted alkyl and monosubstituted phenyl wherein said substitutent is selected from the group consisting of alkoxy, carbalkoxy, trihalomethyl, halo, dialkylamino, alkanoyloxy and phenyl, in an amount of from about 0.0001 to about 0.1 mole percent of noble metal phosphine complex per mole of olefinic double bond present, and b. from about 10 moles to about 150 moles of R3P per mole of said noble metal-phosphine complex.
Claim 2
Dependent Claim 216 words
In the process of carbonylating olefinically unsaturated hydrocarbons of from 2 to 30 carbon atoms free from acetylenic unsaturation and conjugated olefinic unsaturation with carbon monoxide and with at least one hydroxylic compound selected from the group consisting of water, alkanol of from 1 to 20 carbon atoms, carboxylic acid of from 2-20 carbon atoms and mixtures thereof in the presence of a catalyst, the improvement which comprises producing predominately straight chain products by employing as said catalyst a composition consisting essentially of a. a zerovalent noble metal phosphine complex of the general formula (R3P)nM wherein M is palladium or platinum, n is a whole number from 1 to 4 inclusive and R independently is a monovalent hydrocarbyl or substituted hydrocarbyl moiety of from 1 to 20 carbon atoms inclusive of substituents, is free from aliphatic carbon-carbon unsaturation and is selected from the group consisting of unsubstituted alkyl, unsubstituted phenyl, monosubstituted alkyl and monosubstituted phenyl wherein said substitutent is selected from the group consisting of alkoxy, carbalkoxy, trihalomethyl, halo, dialkylamino, alkanoyloxy and phenyl, in an amount of from about 0.0001 to about 0.1 mole percent of noble metal phosphine complex per mole of olefinic double bond present, and b. from about 10 moles to about 150 moles of R3P per mole of said noble metal-phosphine complex.
Claim 3
Dependent Claim 94 words
IN THE PROCESS OF CARBONYLATING OLEFINICALLY UNSATURATED HYDROCARBON OF FROM 2 TO 30 CARBON ATOMS FREE FROM ACETYLENIC UNSATURATION AND CONJUGATED OLEFINIC UNSATURATION WITH CARBON MONOXIDE AND WITH AT LEAST ONE HYDROXYLIC COMPOUND SELECTED FROM THE GROUP CONSISTING OF WATER, ALKANOL OF FROM 1 TO 20 CARBON ATOMS, CARBOXYLIC ACID OF FROM 2-20 CARBON ATOMS AND MIXTURES THEREOF IN THE PRESENCE OF A CATALYST, THE IMPROVEMENT WHICH COMPRISES PRODUCING PREDOMINATELY STRAIGHT CHAIN PRODUCTS BY EMPLOYING AS SAID CATALYST A COMPOSITION CONSISTING ESSENTIALLY OF A. A ZEROVALENT NOBLE METAL PHOSPHINE COMPLEX OF THE GENERAL FORMULA
Claim 4
Dependent Claim 94 words
IN THE PROCESS OF CARBONYLATING OLEFINICALLY UNSATURATED HYDROCARBON OF FROM 2 TO 30 CARBON ATOMS FREE FROM ACETYLENIC UNSATURATION AND CONJUGATED OLEFINIC UNSATURATION WITH CARBON MONOXIDE AND WITH AT LEAST ONE HYDROXYLIC COMPOUND SELECTED FROM THE GROUP CONSISTING OF WATER, ALKANOL OF FROM 1 TO 20 CARBON ATOMS, CARBOXYLIC ACID OF FROM 2-20 CARBON ATOMS AND MIXTURES THEREOF IN THE PRESENCE OF A CATALYST, THE IMPROVEMENT WHICH COMPRISES PRODUCING PREDOMINATELY STRAIGHT CHAIN PRODUCTS BY EMPLOYING AS SAID CATALYST A COMPOSITION CONSISTING ESSENTIALLY OF A. A ZEROVALENT NOBLE METAL PHOSPHINE COMPLEX OF THE GENERAL FORMULA
Claim 5
Dependent Claim 24 words
The process of claim 1 wherein the olefinically unsaturated compound is selected from the group consisting of aliphatic alpha monoolefins and aliphatic terminal diolefins.
Claim 6
Dependent Claim 11 words
The process of claim 2 wherein the hydroxylic compound is water.
Claim 7
Dependent Claim 18 words
The process of claim 2 wherein the hydroxylic compound is alkanol of from 1 to 10 carbon atoms.
Claim 8
Dependent Claim 20 words
The process of claim 2 wherein the hydroxylic compound is a terminal alkanediol of from 2 to 10 carbon atoms.
Claim 9
Dependent Claim 22 words
The process of claim 2 wherein the hydroxylic compound is a monobasic aliphatic carboxylic acid of from 2 to 20 carbon atoms.
Claim 10
Dependent Claim 22 words
The process of claim 2 wherein the hydroxylic compound is a dibasic aliphatic carboxylic acid of from 4 to 10 carbon atoms.

References Cited (Backward Citations)

US3780074A Cited
US3668249A Cited
US3793369A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-06-02 1978-12-02 1979-06-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-06-02 1982-12-02 1983-06-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-06-02 1986-12-02 1987-06-03 $7700.00 Window Closed / Lapsed

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