Process for the manufacture of .alpha.,.beta.-unsaturated N-substituted carboxylic acid amides

US4237067A · kind A · utility

Assignee

• Chemische Fabrik Stockhausen & Cie · DE

Inventors

• Erich Kuster · Krefeld, DE
• Bernhard Goossens · Velbert, DE
• Eduard Barthell · Krefeld, DE
• Kurt Dahmen · Rheydt, DE

Key dates

• Filing date: May 3, 1979
• Grant date: Dec 2, 1980
• Expiry date: May 3, 1999

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C233/01
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Process for the manufacture of .alpha.,.beta.-unsaturated N-substituted carboxylic acid amides of the general formula ##STR1## in which R.sup.1 represents H or CH.sub.3 PA1 R.sup.2 represents H or CH.sub.3, and PA1 Y represents a divalent straight-chain or branched organic radical having 2-30 carbon atoms, and PA1 R.sup.3 represents H or the radical of an amine of the formula --N(R.sup.4)(R.sup.5), in which R.sup.4 and R.sup.5 represent alkyl radicals having 1 to 4 carbon atoms, by reacting .beta.-substituted carboxylic acid amides of the formula ##STR2## in which Z represents OH or the radical R.sup.6 O--, in which R.sup.6 is an alkyl radical having 1 to 4 carbon atoms, with amines of the general formula EQU H.sub.2 N--(Y)--R.sub.3 III at temperatures in the range of 100.degree. to 200.degree. C., preferably 120.degree. to 175.degree. C., with the elimination of ammonia, and heating the resulting N-substituted .beta.-hydroxycarboxylic or .beta.-alkoxycarboxylic acid amides in the presence of catalysts, water or alcohol, respectively, being split off. The water is split off at temperatures of 100.degree.-250.degree. C. with acidic catalysts such as phosphoric acid, or basic catalys…