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US4292437A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of isobutyric acid and esters

Assignee: ICI Acrylics Inc
•
Filing: 1979-06-27
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Granted: 1981-09-29
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Expires: 1999-06-27
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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.

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

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