Chlorohydration

Chlorohydrination of 2-methyl-2-butene.

Chlorohydration is the addition of hypochlorous acid to an olefinic double bond. This creates chlorine alcohols, so-called chlorohydrins , in which the chlorine and the hydroxyl group are bound to neighboring carbon atoms.

use

General structure of chlorohydrins –X = Cl

Chlorohydrins may be prepared by elimination of hydrogen chloride to epoxides implement.

The production of epichlorohydrin is of technical importance . By chlorohydration of allyl chloride with hypochlorous acid, 1,3-dichloropropan-2-ol and 2,3-dichloropropan-1-ol are obtained:

Reaction with sodium hydroxide produces racemic epichlorohydrin:

Propylene chlorohydrin (PCH) and propylene oxide can be obtained in the same way by chlorohydrination of propene .

literature

• E. Bartholomé (Ed.), E. Biekert (Ed.), H. Hellmann (Ed.): Ullmanns Encyklopädie der technischen Chemie . Wiley-VCH, 1984, ISBN 978-3527200009 .

Individual evidence

1. ↑ E. Buss, A. Rockstuhl, FRD Schnurpfeil: Investigations on the mechanism of the chlorohydrination of olefins. In: Journal for Practical Chemistry. 324, 1982, pp. 197-208, doi : 10.1002 / prac.19823240204 .
2. ↑ Patent DE 19614683 , process for the production of propylene oxide by chlorohydration and alkali lye saponification , filed April 13, 1996.