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US4292437A
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Preparation of isobutyric acid and esters
Assignee: ICI Acrylics Inc
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Filing: 1979-06-27
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Granted: 1981-09-29
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Expires: 1999-06-27
Abstract
Abstract Preparation of isobutyric acid and esters by carbonylation of propylene in the presence of water or an alcohol, a palladium catalyst and ortho-substituted triarylphosphine.
Inventors
- 👤 Edward N. Squire
- 👤 Francis J. Waller
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 09:22
CPC Classifications
C; C07; C07C; C07C51/00; C07C51/10; C07C51/14; B; B01; B01J; B01J31/00; B01J31/16; B01J31/24; B01J31/2404; B01J31/2442; B01J31/2447; C07C67/00; C07C67/36; C07C67/38; B01J2231/00; B01J2231/30; B01J2231/32; B01J2231/321; B01J2531/00; B01J2531/80; B01J2531/82; B01J2531/824
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
215 words
In the process for the carbonylation of propylene by contacting the propylene and carbon monoxide with water or a lower alkanol of 1 to 4 carbon atoms in the presence of solvent and a palladium catalyst in complex with a ligand, the improvement which comprises using as said ligand an ortho-substituted ligand of the formula P Ar 3 wherein each Ar is independently selected from ##STR4## and wherein the Ar moieties bear a total of one or two substituents in positions ortho to one or two carbon-phosphorus bonds, the substituents being selected from the group consisting of lower alkyl of 1-4 carbon atoms, lower alkoxy and phenyl, and wherein the Ar groups each contain up to three substituents in positions meta or para to a carbon-phosphorus bond and selected from the group consisting of lower alkyl, lower alkoxy, chloride, fluoride, hydroxyl and carboxyl and provided that when Ar is ##STR5## one or two of the Ar moieties can each bear one substituent selected from phenoxy and a fused aromatic hydrocarbon ring at an ortho position to form 1-naphthyl, and provided further that when the substituent is a fused aromatic hydrocarbon ring, each such Ar moiety can bear one additional substituent at a second ortho position selected from alkyl of 1-4 carbon atoms, alkoxy and phenyl.
Claim 2
Dependent Claim
215 words
In the process for the carbonylation of propylene by contacting the propylene and carbon monoxide with water or a lower alkanol of 1 to 4 carbon atoms in the presence of solvent and a palladium catalyst in complex with a ligand, the improvement which comprises using as said ligand an ortho-substituted ligand of the formula P Ar 3 wherein each Ar is independently selected from ##STR4## and wherein the Ar moieties bear a total of one or two substituents in positions ortho to one or two carbon-phosphorus bonds, the substituents being selected from the group consisting of lower alkyl of 1-4 carbon atoms, lower alkoxy and phenyl, and wherein the Ar groups each contain up to three substituents in positions meta or para to a carbon-phosphorus bond and selected from the group consisting of lower alkyl, lower alkoxy, chloride, fluoride, hydroxyl and carboxyl and provided that when Ar is ##STR5## one or two of the Ar moieties can each bear one substituent selected from phenoxy and a fused aromatic hydrocarbon ring at an ortho position to form 1-naphthyl, and provided further that when the substituent is a fused aromatic hydrocarbon ring, each such Ar moiety can bear one additional substituent at a second ortho position selected from alkyl of 1-4 carbon atoms, alkoxy and phenyl.
Claim 3
Dependent Claim
65 words
A process of claim 1 wherein the ortho-substituted ligand is selected from the group consisting of: ##STR6## in which n=1 or 2 and wherein Ar is ##STR7## R 1 is selected from the group consisting of alkyl of 1-4 carbon atoms, alkoxy, and phenyl; and R 2 is selected from the group consisting of alkyl of 1-4 carbon atoms, alkoxy, chloride, fluoride, hydroxyl and carboxyl.
Claim 4
Dependent Claim
31 words
A process of claim 1 wherein the catalyst is present in amounts to provide about from 1 to 1×10 -5 moles of palladium per mole of propylene in the reaction mixture.
Claim 5
Dependent Claim
14 words
A process of claim 1 wherein the ortho-substituted ligand consists essentially of ortho-tolyl diphenylphosphine.
Claim 6
Dependent Claim
13 words
A process of claim 1 wherein the ortho-substituted ligand consists essentially of bis(o-tolyl)phenylphosphine.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-09-28 | 1985-03-30 | 1985-09-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-09-28 | 1989-03-30 | 1989-09-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-09-28 | 1993-03-30 | 1993-09-29 | $7700.00 | Window Closed / Lapsed |