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allyl alcohol : ウィキペディア英語版
allyl alcohol

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Allyl alcohol (IUPAC name: 3-propenol) is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid, but it is more toxic than typical small alcohols. Allyl alcohol is used as a raw material for the production of glycerol, but is also used as a precursor to many specialized compounds such as flame-resistant materials, drying oils, and plasticizers.〔Ludger Krähling, Jürgen Krey, Gerald Jakobson, Johann Grolig, Leopold Miksche “Allyl Compounds” Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. pg. 7-11 〕 Today allyl alcohol can be obtained by many methods. Allyl alcohol is the smallest representative of the allylic alcohols.
==Production==
Allyl alcohol was first prepared in 1856 by Auguste Cahours and August Hofmann by saponification
of allyl iodide.〔 Today allyl alcohol is produced commercially by the Dow and Shell corporations through the hydrolysis of allyl chloride:
:CH2CHCH2Cl + NaOH → CH2CHCH2OH + NaCl
Allyl alcohol can also be made by the rearrangement of propylene oxide, a reaction that is catalyzed by potassium alum at high temperature. The advantage of this method relative to the allyl chloride route is that it does not generate salt. Also avoiding chloride-containing intermediates is the "acetoxylation" of propylene to allyl acetate:
:CH2=CHCH3 + 1/2 O2 + CH3CO2H → CH2CHCH2O2CCH3 + H2O
Hydrolysis of this acetate gives allyl alcohol. In alternative fashion, propylene can be oxidized to acrolein, which upon hydrogenation gives the alcohol.

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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