US3940429A
Expired / Lapsed
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Oxidation of unsaturated amines
Assignee: Monsanto Co
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Filing: 1974-12-09
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Granted: 1976-02-24
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Expires: 1994-12-09
Abstract
Abstract Oxidation of an unsaturated amine to an unsaturated nitrile is carried out in presence of cuprous chloride, a nitrogen base and a halide salt soluble in the nitrogen base.
Inventors
- 👤 John S. McConaghy, Jr.
- 👤 Dennis C. Owsley
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 11:05
CPC Classifications
C; C07; C07C; C07C255/00; C07C255/01; C07C255/06; C07C255/07; C07C255/08
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
120 words
A process for the production of an unsaturated nitrile which comprises reacting an unsaturated amine having the formula ##EQU5## or phenyl--CH 2 NH 2 wherein R 1 , R 2 and R 3 represent hydrogen or a C 1 to C 4 alkyl group with molecular oxygen in the presence of cuprous chloride, a nitrogen base that is not oxidized under the reaction conditions and a halide salt which is soluble in the nitrogen base and is selected from alkali metal halides, alkaline earth metal halides, quaternary ammonium halides, and phosphonium halides, the relative proportions of cuprous chloride and halide salt being from 1:10 to 10:1, at a temperature of from 0° to 200°C. and at atmospheric pressure or above.
Claim 2
Dependent Claim
120 words
A process for the production of an unsaturated nitrile which comprises reacting an unsaturated amine having the formula ##EQU5## or phenyl--CH 2 NH 2 wherein R 1 , R 2 and R 3 represent hydrogen or a C 1 to C 4 alkyl group with molecular oxygen in the presence of cuprous chloride, a nitrogen base that is not oxidized under the reaction conditions and a halide salt which is soluble in the nitrogen base and is selected from alkali metal halides, alkaline earth metal halides, quaternary ammonium halides, and phosphonium halides, the relative proportions of cuprous chloride and halide salt being from 1:10 to 10:1, at a temperature of from 0° to 200°C. and at atmospheric pressure or above.
Claim 3
Dependent Claim
24 words
A process according to claim 1 in which the unsaturated amine is allylamine or methallylamine and the unsaturated nitrile produced is acrylonitrile or methacrylonitrile.
Claim 4
Dependent Claim
22 words
A process according to claim 2 in which the halide salt soluble in the nitrogen base is lithium chloride or lithium bromide.
Claim 5
Dependent Claim
15 words
A process according to claim 2 in which the nitrogen base is pyridine or dimethylacetamide.
Claim 6
Dependent Claim
67 words
A process for the production of acrylonitrile or methacrylonitrile which comprises reacting allylamine or methallylamine with molecular oxygen in the presence of a solution in pyridine of cuprous chloride and a lithium halide selected from lithium chloride and lithium bromide, in a cuprous chloride to lithium halide ratio of from 10:1 to 1:10, at a temperature of from 0° to 200°C and at atmospheric pressure or above.
Claim 7
Dependent Claim
67 words
A process for the production of acrylonitrile or methacrylonitrile which comprises reacting allylamine or methallylamine with molecular oxygen in the presence of a solution in pyridine of cuprous chloride and a lithium halide selected from lithium chloride and lithium bromide, in a cuprous chloride to lithium halide ratio of from 10:1 to 1:10, at a temperature of from 0° to 200°C and at atmospheric pressure or above.
Claim 8
Dependent Claim
20 words
A process according to claim 5 in which the reaction is performed at a pressure of up to 500 p.s.i.
Claim 9
Dependent Claim
20 words
A process according to claim 5 in which the reaction is performed at a temperature of from 25° to 75°C.
Claim 10
Dependent Claim
57 words
A process according to claim 5 in which the oxidation reaction is carried out at a pressure of from 100 to 400 p.s.i. and a temperature of 25° to 75°C. in the presence of a solution in pyridine of a major weight proportion of cuprous chloride and a minor weight proportion of lithium chloride or lithium bromide.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-02-23 | 1979-08-25 | 1980-02-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-02-23 | 1983-08-25 | 1984-02-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-02-23 | 1987-08-25 | 1988-02-24 | $7700.00 | Window Closed / Lapsed |