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US4237067A
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Process for the manufacture of α,β-unsaturated N-substituted carboxylic acid amides
Assignee: Stockhausen GmbH and Co KG
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Filing: 1979-05-03
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Granted: 1980-12-02
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Expires: 1999-05-03
Abstract
Abstract Process for the manufacture of α,β-unsaturated N-substituted carboxylic acid amides of the general formula ##STR1## in which R 1 represents H or CH 3 R 2 represents H or CH 3 , and Y represents a divalent straight-chain or branched organic radical having 2-30 carbon atoms, and R 3 represents H or the radical of an amine of the formula --N(R 4 )(R 5 ), in which R 4 and R 5 represent alkyl radicals having 1 to 4 carbon atoms, by reacting β-substituted carboxylic acid amides of the formula ##STR2## in which Z represents OH or the radical R 6 O--, in which R 6 is an alkyl radical having 1 to 4 carbon atoms, with amines of the general formula H.sub.2 N--(Y)--R.sub.3 III at temperatures in the range of 100° to 200° C., preferably 120° to 175° C., with the elimination of ammonia, and heating the resulting N-substituted β-hydroxycarboxylic or β-alkoxycarboxylic acid amides in the presence of catalysts, water or alcohol, respectively, being split off. The water is split off at temperatures of 100°-250° C. with acidic catalysts such as phosphoric acid, or basic catalysts such as sodium hydroxide, and alcohol is split off at 70°-150° C. with basic catalysts such as sodium or potassium hydroxide. The reaction product is separated by distillation, optionally in vacuo.
Inventors
- 👤 Erich Kuster
- 👤 Bernhard Goossens
- 👤 Eduard Barthell
- 👤 Kurt Dahmen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 12:39
CPC Classifications
C; C07; C07C; C07C233/00; C07C233/01
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
156 words
A process for the manufacture of an α,β-unsaturated N-substituted carboxylic acid amide of the formula ##STR5## in which R 1 and R 2 are independently is H or CH 3 , Y is a divalent organic radical having 2-30 carbon atoms, R 3 is H or a radical of the formula-N(R 4 )(R 5 ), and R 4 and R 5 each independently is an alkyl radical having 1 to 4 carbon atoms, comprising reacting an α,β-substituted carboxylic acid amid of the formula ##STR6## in which Z is a hydroxy group or an alkoxy radical having 1 to 4 carbon atoms, with an amine of the formula H.sub.2 N--(Y)--R.sub.3 at a temperature of about 100° to 200° C. with the elimination of ammonia thereby to form an N-substituted β-hydroxycarboxylic or β-alkoxycarboxylic acid amide of the formula ##STR7## and heating such amide in the presence of a catalyst thereby to produce the corresponding α,β-unsaturated carboxylic acid amide.
Claim 2
Dependent Claim
156 words
A process for the manufacture of an α,β-unsaturated N-substituted carboxylic acid amide of the formula ##STR5## in which R 1 and R 2 are independently is H or CH 3 , Y is a divalent organic radical having 2-30 carbon atoms, R 3 is H or a radical of the formula-N(R 4 )(R 5 ), and R 4 and R 5 each independently is an alkyl radical having 1 to 4 carbon atoms, comprising reacting an α,β-substituted carboxylic acid amid of the formula ##STR6## in which Z is a hydroxy group or an alkoxy radical having 1 to 4 carbon atoms, with an amine of the formula H.sub.2 N--(Y)--R.sub.3 at a temperature of about 100° to 200° C. with the elimination of ammonia thereby to form an N-substituted β-hydroxycarboxylic or β-alkoxycarboxylic acid amide of the formula ##STR7## and heating such amide in the presence of a catalyst thereby to produce the corresponding α,β-unsaturated carboxylic acid amide.
Claim 3
Dependent Claim
40 words
A process according to claim 1, in which Z is a hydroxy group and heating of the N-substituted β-hydroxycarboxylic acid amide to produce the N-substituted α,β-unsaturated carboxylic acid amide is effected in the presence of an acidic or basic catalyst.
Claim 4
Dependent Claim
26 words
A process according to claim 2, in which phosphorus pentoxide, phosphoric acid, phosphorous acid, polyphosphoric acid, sulphuric acid or sodium hydroxide is used as the catalyst.
Claim 5
Dependent Claim
20 words
A process according to claim 2, in which heating is effected at a temperature of about 100° to 250° C.
Claim 6
Dependent Claim
105 words
A processing according to claim 3, in which Y is a radical of the formula--(Y 1 ) m --(Y 2 ) n --(Y 3 ) t , in which Y 1 , Y 2 and Y 3 each independently is an alkylene radical or the radical of a cyclic organic ring system having 5 or 6 carbon atoms, and the sum of m, n and t is 2 or 3, and heating is effected in the liquid phase at a temperature of about 150° to 200° C., the resulting α,β-unsaturated N-substituted carboxylic acid amide being isolated from the reaction mixture by distillation under reduced pressure.
Claim 7
Dependent Claim
42 words
A process according to claim 1, in which Z is an alkoxy radical and heating of the N-substituted α,β-alkoxycarboxylic acid amide to produce the N-substituted α,β-unsaturated carboxylic acid amide by splitting off alcohol is effected in the presence of a basic catalyst.
Claim 8
Dependent Claim
32 words
A process according to claim 6, in which sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, calcium oxide and/or barium oxide is used as the basic catalyst for splitting off the alcohol.
Claim 9
Dependent Claim
20 words
A process according to claim 7, in which the alcohol is split off at a temperature of about 70°-150° C.
Claim 10
Dependent Claim
107 words
A process according to claim 7, in which Y is a radical of the formula--(Y 1 ) m --(Y 2 ) n --(Y 3 ) t , in which Y 1 , Y 2 and Y 3 each independently is an alkylene radical or the radical of a cyclic organic ring system having 5 or 6 carbon atoms, and the sum of m, n and t is 2 or 3, and the alcohol is split off in the liquid phase at a temperature of about 90° to 110° C., the resulting α,β-unsaturated N-substituted carboxylic acid amide being isolated from the reaction mixture by distillation under reduced pressure.
Claim 11
Dependent Claim
33 words
A process according to claim 1, in which the heating of the α,β-hydroxycarboxylic acid amide or α,β-alkoxycarboxylic acid amide to produce the N-substituted α,β-unsaturated carboxylic acid amide is effected in the liquid phase.
Claim 12
Dependent Claim
28 words
A process according to claim 1, including the further step of isolating the resulting α,β-unsaturated N-substituted carboxylic acid amide from the reaction mixture by distillation under reduced pressure.
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) | 1983-12-02 | 1984-06-02 | 1984-12-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-12-02 | 1988-06-02 | 1988-12-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-12-02 | 1992-06-02 | 1992-12-02 | $7700.00 | Window Closed / Lapsed |