US4562284A
Expired / Lapsed
US
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Process for the preparation of carboxylic acids
Assignee: Shell USA Inc
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Filing: 1984-02-24
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Granted: 1985-12-31
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Expires: 2004-02-24
Abstract
Abstract A process is disclosed for preparation of a carboxylic acid RCOOH wherein R represents certain alkyl, cycloalkyl or aralkyl groups, by heating a formic acid ester HCOOR in the presence of carbon monoxide, a soluble rhodium catalyst and an iodide or bromide source, promoted by certain oxygen-containing compounds of phosphorus, arsenic or antimony.
Inventors
- 👤 Eit Drent
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 14:27
CPC Classifications
C; C07; C07C; C07C51/00; C07C51/347; C07C51/353
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
156 words
A process for the preparation of a carboxylic acid RCOOH wherein R represents an alkyl group having 1-20 carbon atoms, a cycloalkyl group having 5-10 carbon atoms or an aralkyl aralkyl group having 7-13 carbon atoms by heating at a temperature from about 110° to about 225° C. an ester of formic acid HCOOR in the presence of carbon monoxide, and a catalyst system consisting essentially of a soluble rhodium catalyst and an iodide and/or bromide source, and as promoter a compound of the formula ##STR3## wherein a and b are both 0, X is phosphorus and Y is oxygen or sulphur and R 1 , R 2 and R 3 each represent alkyl groups having 1-12 carbon atoms or cycloalkyl, aryl, aralkyl or aralkyl groups having 5-12 carbon atoms, or a complex of a compound of formula I with a hydrocarbon iodide or bromide, an acyl iodide or bromide or a hydrogen iodide or bromide.
Claim 2
Dependent Claim
156 words
A process for the preparation of a carboxylic acid RCOOH wherein R represents an alkyl group having 1-20 carbon atoms, a cycloalkyl group having 5-10 carbon atoms or an aralkyl aralkyl group having 7-13 carbon atoms by heating at a temperature from about 110° to about 225° C. an ester of formic acid HCOOR in the presence of carbon monoxide, and a catalyst system consisting essentially of a soluble rhodium catalyst and an iodide and/or bromide source, and as promoter a compound of the formula ##STR3## wherein a and b are both 0, X is phosphorus and Y is oxygen or sulphur and R 1 , R 2 and R 3 each represent alkyl groups having 1-12 carbon atoms or cycloalkyl, aryl, aralkyl or aralkyl groups having 5-12 carbon atoms, or a complex of a compound of formula I with a hydrocarbon iodide or bromide, an acyl iodide or bromide or a hydrogen iodide or bromide.
Claim 3
Dependent Claim
29 words
A process as in claim 1, wherein R is an alkyl group having 1-6, a cycloalkyl group having 5 or 6, or an aralkyl group having 7-10 carbon atoms.
Claim 4
Dependent Claim
64 words
A process as in claim 1, wherein the iodide and/or bromide source is at least one of elemental iodine or bromine, hydrogen iodide, hydrogen bromide or a compound R 4 I, R 4 Br, R 4 COI or R 4 COBr, wherein R 4 represents alkyl group optionally substituted with bromine or iodine, or an aralkyl group having not more than 12 carbon atoms.
Claim 5
Dependent Claim
42 words
A process as in claim 1, wherein the total number of gram atoms I and/or Br present in the reaction mixture is in the range from about 3 to about 500, gram atoms of I and/or Br per gram atom of rhodium.
Claim 6
Dependent Claim
47 words
A process as in claim 1, wherein Y is oxygen and R 1 , R 2 and R 3 each represent a group selected from alkyl groups having 1-12 carbon atoms and/or phenyl groups which may optionally be substituted with one or more methyl or ethyl groups.
Claim 7
Dependent Claim
20 words
A process as in claim 1, wherein the reaction is carried out at a temperature between 125° and 200° C.
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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) | 1988-12-30 | 1989-07-01 | 1989-12-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-12-30 | 1993-07-01 | 1993-12-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-12-30 | 1997-07-01 | 1997-12-31 | $7700.00 | Window Closed / Lapsed |