US4014910A
Expired / Lapsed
US
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Process for the preparation of an (ar)alkane carboxylic acid
Assignee: Akzo NV
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Filing: 1975-09-15
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Granted: 1977-03-29
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Expires: 1995-09-15
Abstract
Abstract A process is disclosed for making an (ar)alkane carboxylic acid in high yield when reacting an (ar)alkene with a carbonyl compound having at least one hydrogen atom attached to the alpha-carbon atom in the presence of a manganese compound which is at least trivalent by observing the following reaction parameters: (a) having at least 60% by weight of a carboxylic anhydride in the carbonyl compound, (b) having a manganese compound concentration of from 10 - 3 to 10 - 10 moles/l and (c) maintaining the (ar)alkene concentration below 0.1 mole/l.
Inventors
- 👤 Willem J. de Klein
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 11:21
CPC Classifications
C; C07; C07C; C07C51/00; C07C51/347; C07C51/353
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
127 words
In a process for the preparation of a carboxylic acid through hydrolysis of the product, obtained by reaction under inert conditions and in the presence of a trivalent manganese compound, of an ethylenically unsaturated hydrocarbon compound with a carbonyl compound having at least one hydrogen atom attached to an alpha-carbon atom, the improvements comprising: a. using for the carbonyl compound a member selected from the group consisting of a lower carboxylic anhydride and a mixture of a lower carboxylic anhydride and a lower carboxylic acid wherein the acid is present in an amount up to 40% by weight, b. employing the trivalent manganese compound in an amount of 10.sup. -3 to 10.sup. -10 moles/liter, and c. maintaining the concentration of the ethylenically unsaturated hydrocarbon below 0.1 mole/liter.
Claim 2
Dependent Claim
127 words
In a process for the preparation of a carboxylic acid through hydrolysis of the product, obtained by reaction under inert conditions and in the presence of a trivalent manganese compound, of an ethylenically unsaturated hydrocarbon compound with a carbonyl compound having at least one hydrogen atom attached to an alpha-carbon atom, the improvements comprising: a. using for the carbonyl compound a member selected from the group consisting of a lower carboxylic anhydride and a mixture of a lower carboxylic anhydride and a lower carboxylic acid wherein the acid is present in an amount up to 40% by weight, b. employing the trivalent manganese compound in an amount of 10.sup. -3 to 10.sup. -10 moles/liter, and c. maintaining the concentration of the ethylenically unsaturated hydrocarbon below 0.1 mole/liter.
Claim 3
Dependent Claim
19 words
The process of claim 1 wherein said carbonyl compound contains at least 95% by weight of the carboxylic anhydride.
Claim 4
Dependent Claim
21 words
The process of claim 1 wherein the manganese compound is present in an amount of 10.sup. -5 to 10.sup. -7 mole/1.
Claim 5
Dependent Claim
21 words
The process of claim 1 wherein the concentration of said ethylenically unsaturated hydrocarbon compound is 10.sup. -4 to 10.sup. -5 moles/1.
Claim 6
Dependent Claim
23 words
The process of claim 1 wherein said manganese compound is employed as a salt of a carboxylic acid related to said carboxylic anhydride.
Claim 7
Dependent Claim
16 words
The process of claim 1 wherein said manganese compound is gradually added to the reaction mixture.
Claim 8
Dependent Claim
18 words
The process of claim 1 wherein said ethylenically unsaturated hydrocarbon compound is gradually added to the reaction mixture.
Claim 9
Dependent Claim
42 words
The process of claim 1 wherein the reaction is carried out at a temperature above the boiling point of water and above that of the carboxylic acid derived from the anhydride used but below the boiling point of the carboxylic anhydride used.
Claim 10
Dependent Claim
91 words
The process of claim 1 wherein the process is carried out continuously in a reactor in such a way that the ethylenically unsaturated hydrocarbon compound, the manganese compound and the carboxylic anhydride are each separately and gradually added to the properly homogenized reaction mixture obtained, which mixture is heated at such a temperature that the resulting water and lower carboxylic acid can be discharged from the top of the reactor, whereas the heavier boiling products are continuously collected at the bottom of the reactor to be successively cooled, filtered and isolated.
Claim 11
Dependent Claim
11 words
The process of claim 1 wherein the anhydride is acetic anhydride.
Claim 12
Dependent Claim
57 words
A process for making a carboxylic acid which comprises reacting an alpha-olefin having from 2 to 22 carbon atoms with an anhydride of a lower fatty acid in a reaction mixture containing from 10.sup. -3 to 10.sup. -10 moles per liter of trivalent manganese compound and containing said alpha-olefin in a concentration below 0.1 mole per liter.
Claim 13
Dependent Claim
57 words
A process for making a carboxylic acid which comprises reacting an alpha-olefin having from 2 to 22 carbon atoms with an anhydride of a lower fatty acid in a reaction mixture containing from 10.sup. -3 to 10.sup. -10 moles per liter of trivalent manganese compound and containing said alpha-olefin in a concentration below 0.1 mole per liter.
Claim 14
Dependent Claim
27 words
The process of claim 11 wherein said anhydride is mixed with a lower fatty acid and the mixture contains at least 60% by weight of the anhydride.
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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) | 1980-03-28 | 1980-09-27 | 1981-03-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-28 | 1984-09-27 | 1985-03-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-28 | 1988-09-27 | 1989-03-29 | $7700.00 | Window Closed / Lapsed |