Английская Википедия:Dichloroacetaldehyde

Материал из Онлайн справочника
Перейти к навигацииПерейти к поиску

Шаблон:Chembox Dichloroacetaldehyde is a chlorinated aldehyde with the chemical formula Шаблон:Chem2. 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]

Hydration of the aldehyde

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]

Formation of hexachloroparaldehyde

Reduction with lithium aluminium hydride gives dichloroethanol.[2]

Uses

Dichloroacetaldehyde is used to produce other chemical compounds such as mitotane.Шаблон:Cn Condensation with chlorobenzene yields p,p′-dichloro-1,1-diphenyl-2,2-dichloroethane, which was previously used as an insecticide:[1]

Файл: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][3]

References

Шаблон:Reflist

  1. 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, Шаблон:Doi.
  2. Шаблон:Cite journal
  3. Шаблон:HSDB