US3944623A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Isomering oxidation of ethylenic alcohols to give ethylenic carbonyl compounds
Assignee: Rhone Poulenc SA
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Filing: 1970-12-18
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Granted: 1976-03-16
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Expires: 1990-12-18
Abstract
Abstract Ethylenic carbonyl compounds are obtained by heating an alpha -ethylenic tertiary alcohol with oxygen and 0.0001 to 5% by weight, based on the alcohol, of a catalyst comprising a compound of a transition metal of Groups V, VI or VII of the Periodic Table.
Inventors
- 👤 Pierre Chabardes
- 👤 Charles Grard
- 👤 Charles Schneider
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 20:26
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/27; C07C45/32; C07C45/37
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
143 words
A process for the preparation of ethylenic carbonyl compounds of the formulae: ##EQU3## and the tautomers thereof, comprising heating in the liquid phase an ethylenic tertiary alcohol of the formulae: ##EQU4## in the presence of oxygen and a catalyst of a compound of the transition metal vanadium, and wherein R 1 , R 2 and R 3 are inert under the conditions of the process and R 1 and R 2 are selected from the group consisting of aliphatic, cycloaliphatic, arylaliphatic and aromatic radicals, and wherein R 1 and R 2 may represent a divalent radical of 2 to 30 carbon atoms which may be saturated or unsaturated, and wherein the aliphatic, cycloaliphatic, arylaliphatic or aromatic radicals may be substituted by halogen, hydroxy, alkoxy, acyl or acyloxy substituents and R 3 may be the same as R 1 and R 2 or hydrogen.
Claim 2
Dependent Claim
143 words
A process for the preparation of ethylenic carbonyl compounds of the formulae: ##EQU3## and the tautomers thereof, comprising heating in the liquid phase an ethylenic tertiary alcohol of the formulae: ##EQU4## in the presence of oxygen and a catalyst of a compound of the transition metal vanadium, and wherein R 1 , R 2 and R 3 are inert under the conditions of the process and R 1 and R 2 are selected from the group consisting of aliphatic, cycloaliphatic, arylaliphatic and aromatic radicals, and wherein R 1 and R 2 may represent a divalent radical of 2 to 30 carbon atoms which may be saturated or unsaturated, and wherein the aliphatic, cycloaliphatic, arylaliphatic or aromatic radicals may be substituted by halogen, hydroxy, alkoxy, acyl or acyloxy substituents and R 3 may be the same as R 1 and R 2 or hydrogen.
Claim 3
Dependent Claim
35 words
Process according to claim 1 wherein the alcohol is one in which R 3 represents hydrogen and R 1 and R 2 each represent an alkyl, alkenyl or alkynyl radical having upto 15 carbon atoms.
Claim 4
Dependent Claim
16 words
Process according to claim 1, wherein the process is carried out at a temperature of 100°-200°C.
Claim 5
Dependent Claim
13 words
Process according to claim 1, wherein the process pressure is below 100 bars.
Claim 6
Dependent Claim
26 words
Process according to claim 1, wherein the catalyst is present in an amount of 0.05 to 2.0% by weight based on the weight of the alcohol.
Claim 7
Dependent Claim
20 words
Process according to claim 1 wherein the catalyst is tetrahydrolinalyl orthovanadate, ammonium metavanadate, vanadyl triethanolamine triethanolamine orthovanadate or cyclohexyl orthovanadate.
Claim 8
Dependent Claim
16 words
Process according to claim 1, wherein the starting alcohol is linalol, and the product is citral.
Claim 9
Dependent Claim
16 words
Process according to claim 1, wherein the starting alcohol is nerolidol, and the product is farnesal.
Claim 10
Dependent Claim
26 words
Process according to claim 1, wherein the catalyst is present in an amount of 0.0001% to 5% by weight based on the weight of the alcohol.
Claim 11
Dependent Claim
17 words
Process according to claim 1, wherein the process is carried out at a temperature of 50°- 250°C.
Claim 12
Dependent Claim
18 words
Process according to claim 1, wherein the catalyst is an ester of an oxyacid derived from said metal.
Claim 13
Dependent Claim
11 words
Process according to claim 1, wherein the catalyst is a vanadate.
Claim 14
Dependent Claim
20 words
Process according to claim 1, wherein the process is carried out in the presence of a solvent and/or a co-catalyst.
Claim 15
Dependent Claim
15 words
Process according to claim 1, wherein the source of oxygen is pure oxygen and/or air.
Claim 16
Dependent Claim
54 words
Process according to claim 1, wherein the compound of the transition metal is selected from the group consisting of the halides, chalcogenides, chelates, coordination complexes, alcoholates, oxygen-containing inorganic acid salts of said metals, aliphatic, cycloaliphatic and aromatic organic acid salts of said metals, and the salts and esters of acids derived from said metals.
References Cited (Backward Citations)
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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) | 1979-03-16 | 1979-09-15 | 1980-03-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-03-16 | 1983-09-15 | 1984-03-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-03-16 | 1987-09-15 | 1988-03-16 | $7700.00 | Window Closed / Lapsed |