Process for the preparation of N-vinyl-N-alkyl-carboxylic acid amides

US4322271A · kind A · utility

Assignee

• Hoechst GmbH · DE

Inventors

• Harald Jensen
• Erwin Schmidt · Baltmannsweiler, DE
• Michael Mitzlaff
• Jurgen Cramer · Eppstein, DE
• Rudolf Pistorius
• Hartmut Pietsch · Bad Homburg vor der Höhe, DE
• Klaus Dehmer · Kelkheim, DE

Key dates

• Filing date: May 14, 1980
• Grant date: Mar 30, 1982
• Expiry date: May 14, 2000

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C231/00
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

N-Vinyl-N-alkyl-carboxylic acid amides are prepared, starting from N-ethyl-carboxylic acid amides, in a 3-stage process consisting of the following stages: PA1 (a) anodic alkoxylation of the N-ethyl-carboxylic acid amides to give N-.alpha.-alkoxyethyl-carboxylic acid amides; PA1 (b) alkylation of these N-.alpha.-alkoxyethyl-carboxylic acid amides with an alkyl halide or dialkyl sulfate in an alkaline medium to give N-.alpha.-alkoxyethyl-N-alkyl-carboxylic acid amides; and PA1 (c) splitting off of alcohol from the products of stage (b) by heating to temperatures between about 60.degree. and about 350.degree. C. Instead of stages (b) and (c), it is also possible to carry out the following stages after stage (a): PA1 (b.sub.1) splitting off of alcohol from the N-.alpha.-alkoxyethylcarboxylic acid amides obtained in stage (a) by heating to temperatures of about 60.degree. to about 600.degree. C., to give N-vinyl-carboxylic acid amides; and PA1 (c.sub.1) alkylation of these N-vinyl-carboxylic acid amides by reaction with an alkylating agent of the same type as in stage (b) in an alkaline medium. The N-vinyl-N-alkyl-carboxylic acid amides obtained by the process are valuable intermediate…