Standard Article

Preparation of Ketenes and Ketene Dimers

  1. W. E. Hanford,
  2. John C. Sauer

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or003.03

Organic Reactions

Organic Reactions

How to Cite

Hanford, W. E. and Sauer, J. C. 2011. Preparation of Ketenes and Ketene Dimers . Organic Reactions. 3:3:108–140.

Author Information

  1. E. I. du Pont de Nemours and Company

Publication History

  1. Published Online: 15 MAR 2011

Abstract

Ketenes contain the functional group [BOND]C[DOUBLE BOND]C[DOUBLE BOND]O. They have been classified as aldoketenes and ketoketenes. The ketenes are prepared by modifications of the general methods for the synthesis of olefins. The ketenes are much more reactive than simple olefins, however, and are more likely to enter into combination with the reagents from wich they are prepared or with solvents used or into self-condensation to yield dimers or polymers, Many of the aldoketenes, which are generally more reactive than ketoketenes, have not been isolated as the pure monomers. The dimers of aldoketenes have some of the properties of ketenes and some are useful.

Keywords:

  • ketenes;
  • Ketene dimers;
  • malonic acid derivatives;
  • ketoketenes;
  • dehalogenation;
  • haloacyl halides;
  • regeneration;
  • experimental procedures