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Epichlorohydrin : ウィキペディア英語版
Epichlorohydrin

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Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organic solvents. It is a chiral molecule generally existing as a racemic mixture of right-handed and left-handed enantiomers. Epichlorohydrin is a highly reactive compound and is used in the production of glycerol, plastics, epoxy glues and resins, and elastomers. In contact with water, epichlorohydrin hydrolyzes to 3-MCPD, a carcinogen found in food.
==Production==
Epichlorohydrin was first described in 1848 by Marcellin Berthelot. The compound was isolated during studies on reactions between glycerol and gaseous hydrogen chloride.
Epichlorohydrin is manufactured from allyl chloride in two steps, beginning with the addition of hypochlorous acid, which affords a mixture of two alcohols:〔Géza Braun "Epichlorohydrin and Epibromohydrin" Organic Syntheses,1936, Vol. 16, p.30. 〕
:CH2=CHCH2Cl + HOCl → HOCH2CHClCH2Cl and, or ClCH2CH(OH)CH2Cl
In the second step, this mixture is treated with base to give the epoxide:
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In this way, more than 800,000 tons (1997) of epichlorohydrin are produced annually.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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