US4681707A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the production of carboxylic acid esters and/or carboxylic acids
Assignee: BP PLC
•
Filing: 1983-09-28
•
Granted: 1987-07-21
•
Expires: 2003-09-28
Abstract
Abstract Carboxylic acid esters are produced by reacting an unsaturated hydrocarbon, for example an olefin or an alkyne, with carbon monoxide and an alcohol in the presence of a protonic acid and as catalyst (a) at least one of the metals palladium, rhodium, ruthenium, iridium and cobalt, and (b) copper. In a modification of the invention carboxylic acids are produced by omitting the alcohol reactant and replacing it with water in an amount up to 8 mole equivalents based on the unsaturated hydrocarbon and a solvent other than an alochol, for example tetrahydrofuran.
Inventors
- 👤 Howard Alper
- 👤 Bertrand Despeyroux
- 👤 David J. H. Smith
- 👤 James B. Woell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 05:24
CPC Classifications
C; C07; C07C; C07C51/00; C07C51/10; C07C51/14
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
121 words
A process for the production from an olefinically unsaturated hydrocarbon of a branched-chain saturated carboxylic acid ester and/or the corresponding carboxylic acid wherein the number of ester or carboxylic acid groups is equal to the number of olefinic double bonds in the olefinically unsaturated hydrocarbon which process comprises reacting the olefinically unsaturated hydrocarbon with carbon monoxide and either alcohol or water respectively in the presence of oxygen, of an added protonic acid selected from the group consisting of hydrochloric acid, sulphuric acid and an organic acid, and as catalyst (a) palladium, and (b) copper, the component (a) being in the form of an elemental metal or a compound thereof, and the component (b) being in the form of a compound thereof.
Claim 2
Dependent Claim
121 words
A process for the production from an olefinically unsaturated hydrocarbon of a branched-chain saturated carboxylic acid ester and/or the corresponding carboxylic acid wherein the number of ester or carboxylic acid groups is equal to the number of olefinic double bonds in the olefinically unsaturated hydrocarbon which process comprises reacting the olefinically unsaturated hydrocarbon with carbon monoxide and either alcohol or water respectively in the presence of oxygen, of an added protonic acid selected from the group consisting of hydrochloric acid, sulphuric acid and an organic acid, and as catalyst (a) palladium, and (b) copper, the component (a) being in the form of an elemental metal or a compound thereof, and the component (b) being in the form of a compound thereof.
Claim 3
Dependent Claim
33 words
A process according to claim 1 wherein the alcohol has the formula R 2 CHOH wherein R is independently hydrogen, alkyl, aryl or hydroxalkyl, or the two groups R together form a ring.
Claim 4
Dependent Claim
55 words
A process according to claim 1 wherein the olefinically unsaturated hydrocarbon is reacted with carbon monoxide and water, provided that the amount of water is less than 8 mole equivalents based on the olefinically unsaturated hydrocarbon, in the presence of a solvent other than an alcohol and the product produced thereby is the carboxylic acid.
Claim 5
Dependent Claim
12 words
A process according to claim 3 wherein the solvent is an ether.
Claim 6
Dependent Claim
22 words
A process according to claim 1 wherein the reaction is carried out at a temperature in the range 20° to 150° C.
Claim 7
Dependent Claim
89 words
A process for the production of an unsaturated carboxylic acid di-ester and/or the corresponding dicarboxylic acid which process comprises reacting an acetylenically unsaturated hydrocarbon with carbon monoxide and either alcohol or water respectively in the presence of oxygen, a protonic acid selected from the group consisting of hydrochloric acid, sulphuric acid, and an organic acid, and as catalyst (a) palladium, and (b) copper, the component (a) being in the form of elemental metal or a compound thereof, and the component (b) being in the form of a compound thereof.
Claim 8
Dependent Claim
89 words
A process for the production of an unsaturated carboxylic acid di-ester and/or the corresponding dicarboxylic acid which process comprises reacting an acetylenically unsaturated hydrocarbon with carbon monoxide and either alcohol or water respectively in the presence of oxygen, a protonic acid selected from the group consisting of hydrochloric acid, sulphuric acid, and an organic acid, and as catalyst (a) palladium, and (b) copper, the component (a) being in the form of elemental metal or a compound thereof, and the component (b) being in the form of a compound thereof.
Claim 9
Dependent Claim
33 words
A process according to claim 6 wherein the alcohol has the formula R 2 CHOH wherein R is independently hydrogen, alkyl, aryl or hydroxalkyl, or the two groups R together form a ring.
Claim 10
Dependent Claim
55 words
A process according to claim 6 wherein the acetylenically unsaturated hydrocarbon is reacted with carbon monoxide and water, provided that the amount of water is less than 8 mole equivalents based on the acetylenically unsaturated hydrocarbon, in the presence of a solvent other than an alcohol and the product produced thereby is the carboxylic acid.
Claim 11
Dependent Claim
12 words
A process according to claim 8 wherein the solvent is an ether.
Claim 12
Dependent Claim
22 words
A process according to claim 6 wherein the reaction is carried out at a temperature in the range 20° to 150° C.
Claim 13
Dependent Claim
129 words
A process for the production, from an acyclic olefinically unsaturated hydrocarbon of 2 carbon atoms, of a saturated carboxylic acid ester and/or the corresponding carboxylic acid wherein the number of ester or carboxylic acid groups is equal to the number of olefinic double bonds in the olefinically unsaturated hydrocarbon which process comprises reacting the acyclic olefinically unsaturated hydrocarbon of 2 carbon atoms with carbon monoxide and either alcohol or water respectively in the presence of oxygen, of an added protonic acid selected from the group consisting of hydrochloric acid, sulphuric acid and an organic acid, as catalyst (a) palladium, and (b) copper, the component (a) being in the form of an elemental metal or a compound thereof, and the component (b) being in the form of a compound thereof.
Claim 14
Dependent Claim
129 words
A process for the production, from an acyclic olefinically unsaturated hydrocarbon of 2 carbon atoms, of a saturated carboxylic acid ester and/or the corresponding carboxylic acid wherein the number of ester or carboxylic acid groups is equal to the number of olefinic double bonds in the olefinically unsaturated hydrocarbon which process comprises reacting the acyclic olefinically unsaturated hydrocarbon of 2 carbon atoms with carbon monoxide and either alcohol or water respectively in the presence of oxygen, of an added protonic acid selected from the group consisting of hydrochloric acid, sulphuric acid and an organic acid, as catalyst (a) palladium, and (b) copper, the component (a) being in the form of an elemental metal or a compound thereof, and the component (b) being in the form of a compound thereof.
References Cited (Backward Citations)
US3023237A
Cited
US3065242A
Cited
US3397226A
Cited
US3397225A
Cited
US3501518A
Cited
US3579568A
Cited
US3530168A
Cited
US3755421A
Cited
US3717670A
Cited
US3952034A
Cited
US4257973A
Cited
DE2630268A1
Cited
FR2328689A1
Cited
GB2009733A
Cited
US4234740A
Cited
US4354978A
Cited
US4414409A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-07-20 | 1991-01-19 | 1991-07-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-07-20 | 1995-01-19 | 1995-07-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-07-20 | 1999-01-19 | 1999-07-21 | $7700.00 | Window Closed / Lapsed |