Chemistry:Dichloroacetaldehyde
Dichloroacetaldehyde is a chlorinated aldehyde with the chemical formula HCCl
2CHO. Along with monochloroacetaldehyde and trichloroacetaldehyde, it is one of the three possible chlorinated acetaldehydes.
Properties and reactions
Dichloroacetaldehyde is a highly volatile liquid that is easily soluble in water to form Hydrates. A geminal diol, also known as monohydrate, 2,2-dichloro-1,1-ethanediol, is formed in water.[1]
The compound decomposes when heated. In the presence of Lewis acids such as antimony trichloride, iron(III) chloride, aluminum trichloride, tin(IV) chloride or boron trifluoride, the trimer hexachloroparaldehyde (2,4,6-tris(dichloromethyl)-1,3,5-trioxane) can be obtained.[1] The trimer forms colourless crystals that melt at 131–132 °C. At the boiling point of 210–220 °C, dichloroacetaldehyde decomposes.[1]
Reduction with lithium aluminium hydride gives dichloroethanol.[2]
Uses
Dichloroacetaldehyde is used to produce other chemical compounds such as mitotane.[3] Condensation with chlorobenzene yields p,p′-dichloro-1,1-diphenyl-2,2-dichloroethane, which was previously used as an insecticide:[1]
- File:Synthesis Dichlorodiphenyldichloroethane.svg
Synthesis
Dichloroacetaldehyde can be obtained by chlorinating acetaldehyde or paraldehyde. Hypochlorination of 1,2-dichloroethylene using chlorine and water produces pure dichloroacetaldehyde.[1][4]
References
- ↑ 1.0 1.1 1.2 1.3 1.4 Jira, R.; Kopp, E.; McKusick, B.C.; Röderer, G.; Bosch, A.; Fleischmann, G.: Chloroacetaldehydes in Ullmann’s Encyclopedia of Industrial Chemistry, 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, doi:10.1002/14356007.a06_527.pub2.
- ↑ Sroog, C. E.; Woodburn, H. M. (1952). "2,2-Dichloroethanol". Organic Syntheses 32: 46. doi:10.15227/orgsyn.032.0046.
- ↑ Ullmann, Fritz (2000). Ullmann's Encyclopedia of Industrial Chemistry. 1 (6th ed.). Germany: Wiley. ISBN 9783527306732.
- ↑ Template:HSDB
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