US4026947A
Expired / Lapsed
US
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Process for the oxidation of β-isophorone
Assignee: Rhone Poulenc Industries SA
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Filing: 1976-02-23
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Granted: 1977-05-31
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Expires: 1996-02-23
Abstract
Abstract A process for the oxidation of β-ethylenically unsaturated ketones, especially β-isophorone, is provided whereby the ketone is oxidized with a source of molecular oxygen in an organic liquid solvent in the presence of a base and certain chelate catalysts of cobalt or manganese as defined.
Inventors
- 👤 Michel Costantini
- 👤 Adrien Dromard
- 👤 Michel Jouffret
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 17:53
CPC Classifications
B; B01; B01J; B01J31/00; B01J31/16; B01J31/22; B01J31/2204; B01J31/2208; B01J31/2226; B01J31/2243; C; C07; C07C; C07C45/00; C07C45/27; C07C45/32; C07C45/33; C07C45/34; B01J2531/00; B01J2531/02; B01J2531/0238; B01J2531/0241; B01J2531/0252; B01J2531/70; B01J2531/72; B01J2531/80; B01J2531/84; B01J2531/845
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
162 words
A process for the preparation of 3,5,5-trimethylcyclohex-2-ene-1,4-dione by oxidation of β-isophorone, which comprises oxidizing the β-isophorone with molecular oxygen or a gas containing molecular oxygen, in a liquid organic solvent medium in the presence of an alkylamine and a chelate of the general formula: ##STR2## in which: M represents cobalt or manganese, R 1 , r 2 and R 3 , which may be identical or different, each represents a hydrogen atom or an alkyl radical containing 1 to 4 carbon atoms; or R 2 and R 3 , together with the 2 carbon atoms of the double bond, form a benzene ring carrying one or more hydrogen or halogen atoms, nitro groups, alkyl radicals containing 1 to 4 carbon atoms or alkoxy radicals containing 1 to 4 carbon atoms, and R 4 represents a divalent hydrocarbon radical containing 2 to 15 carbon atoms or an alkyl chain interrupted by one or more heteroatoms and containing from 4 to 10 carbon atoms.
Claim 2
Dependent Claim
162 words
A process for the preparation of 3,5,5-trimethylcyclohex-2-ene-1,4-dione by oxidation of β-isophorone, which comprises oxidizing the β-isophorone with molecular oxygen or a gas containing molecular oxygen, in a liquid organic solvent medium in the presence of an alkylamine and a chelate of the general formula: ##STR2## in which: M represents cobalt or manganese, R 1 , r 2 and R 3 , which may be identical or different, each represents a hydrogen atom or an alkyl radical containing 1 to 4 carbon atoms; or R 2 and R 3 , together with the 2 carbon atoms of the double bond, form a benzene ring carrying one or more hydrogen or halogen atoms, nitro groups, alkyl radicals containing 1 to 4 carbon atoms or alkoxy radicals containing 1 to 4 carbon atoms, and R 4 represents a divalent hydrocarbon radical containing 2 to 15 carbon atoms or an alkyl chain interrupted by one or more heteroatoms and containing from 4 to 10 carbon atoms.
Claim 3
Dependent Claim
39 words
A process according to claim 1, wherein the chelate is one in which R 2 and R 3 , together with the 2 carbon atoms of the double bond, form a benzene ring optionally substituted by a nitro group.
Claim 4
Dependent Claim
19 words
A process according to claim 1, wherein the chelate is one in which R 1 is a hydrogen atom.
Claim 5
Dependent Claim
21 words
A process according to claim 1, wherein the chelate is one in which R 4 is an ethylene or propylene radical.
Claim 6
Dependent Claim
16 words
A process according to claim 1, wherein the heteroatom in R 4 is oxygen or nitrogen.
Claim 7
Dependent Claim
22 words
A process according to claim 1, wherein the chelate is a condensation product of ethylenediamine and 2-hydroxybenzaldehyde, or of ethylenediamine and 2-hydroxy-3-nitrobenzaldehyde.
Claim 8
Dependent Claim
32 words
A process according to claim 1, wherein the chelate is present in an amount to provide 10.sup. -6 to 0.2 gram atom of cobalt or manganese per mol of β-ethylenically unsaturated ketone.
Claim 9
Dependent Claim
16 words
A process according to claim 7, wherein the amount of 10.sup. -5 to 0.05 gram atoms.
Claim 10
Dependent Claim
22 words
A process according to claim 1, wherein the alkylamine is a member selected from the class of secondary and tertiary alkyl amines.
Claim 11
Dependent Claim
25 words
A process according to claim 9, wherein the base is a member selected from the class consisting of dimethylamine, diethylamine, diisobutylamine, trimethylamine, triethylamine and triisobutylamine.
Claim 12
Dependent Claim
18 words
A process according to claim 1, wherein the molar ratio of alkylamine to β-isophorone is 0.01:1 to 10:1.
Claim 13
Dependent Claim
13 words
A process according to claim 11, wherein the ratio is 0.1:1 to 4:1.
Claim 14
Dependent Claim
50 words
A process according to claim 1, wherein the reaction solvent is a member selected from the class consisting of an aromatic hydrocarbon, chlorinated aliphatic hydrocarbon, lower aliphatic alcohol, saturated and unsaturated aliphatic and cycloaliphatic ketones, linear and cyclic carboxamides, aliphatic and aromatic nitriles, secondary and tertiary amines and an ether.
Claim 15
Dependent Claim
36 words
A process according to claim 13, wherein the reaction solvent is a member selected from the class consisting of acetonitrile, chloroform, ethyl ether, dimethoxyethane, triethylamine, a mixture of dimethoxyethane and water, α-isophorone and methyl isobutyl ketone.
Claim 16
Dependent Claim
26 words
A process according to claim 1, wherein the oxidation is carried out at a temperature of -30° to +60° C., at atmospheric pressure or under pressure.
Claim 17
Dependent Claim
14 words
A process according to claim 15, wherein the temperature is -10° to +45° 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) | 1980-05-30 | 1980-11-29 | 1981-05-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-30 | 1984-11-29 | 1985-05-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-30 | 1988-11-29 | 1989-05-31 | $7700.00 | Window Closed / Lapsed |