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Cyanoethylation

  1. Herman Alexander Bruson

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or005.02

Organic Reactions

Organic Reactions

How to Cite

Bruson, H. A. 2011. Cyanoethylation . Organic Reactions. 5:2:79–135.

Author Information

  1. Resinous Products and Chemicals Company Rohm and Haas Company, Inc.

Publication History

  1. Published Online: 15 MAR 2011

Chemistry Terms

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Abstract

A variety of organic and inorganic compounds possessing labile hydrogen atoms add readily to acrylonitrile with the formation of molecules containing a cyanoethyl grouping. This reaction is commonly know as cyanoethylation and resembles closely a Michael type of reaction. The cyanoethylation except with certain amines usually require the presence of an alkaline catalysts, e.g., hydroxides, alkoxides, hydrides, etc. The strongly basic quarternary ammonium hydroxides are particularly effective. The cyanoethylation of certain amines require and acidic catalyst. Many of the reactions are exothermic and require cooling to prevent excessive polymerization of the acrylonitrile. Inert solvents are helpful. Typical compounds involved in this reaction are discussed.

Keywords:

  • cyanoethylation;
  • ammonia;
  • amines;
  • amides;
  • water;
  • alcohols;
  • formaldehdye;
  • phenols;
  • oximes;
  • hydrogen sulfide;
  • acids;
  • haloforms Sulfones;
  • ketones;
  • aldehydes;
  • nitriles dienes;
  • acrylonitrile;
  • homologs;
  • experimental procedures