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General
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An allyl group is
an alkene hydrocarbon group with the formula H2C=CH-CH2-. It is
made up of a vinyl group, CH2=CH-, attached to a methylene -CH2.
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Compounds
containing the allyl group are often referred to as being
allylic. Allylic carbons are sp³ hybridized, vinylic carbons are
sp² hybridized.
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The site of the
saturated carbon atom, where the vinyl group attaches (e.g. next
to the OH in allyl alcohol) is called the allylic position or
allylic site. A group, such as -OH, attached at an allylic site
is sometimes described as allylic. Two examples of simple allyl
compounds are allyl chloride and allyl alcohol.
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Allylic methylene
groups show special reactivity such as demonstrated in allylic
oxidations, ene reactions and the Trost asymmetric allylic
alkylation.
Production
and Process
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In a process for
production of allyl chloride whereby allyl alcohol and hydrogen
chloride are reacted in the presence of a catalyst and the
resulting allyl chloride is distilled off from the reaction
system, the by-production of diallyl ether is suppressed by
lowering the molar concentration ratio of hydrogen chloride with
respect to allyl alcohol in the reaction solution.
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Allyl chloride
has conventionally been produced by hot chlorination of
propylene.
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The catalyst used
in the production process can work at any pressure from
atmospheric up to 40 bar. The active temperature range is
between 400°C and 540°C.
Applications
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The most
important derivative of allyl chloride is epichlorohydrin, which
is produced captively and is mainly used for epoxy resin
production. The largest allyl chloride market is the manufacture
of quaternary ammonium flocculants for raw and potab water
clarification.
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Allylbenzene and
Allyl Phenyl Ether are used as a chain-transfer agents in
radical polymerization.
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Monoallyl ester
of glycerol (MAEG) and mixture of di- and triallyl esters of
glycerol (DAEG) are useful for the production of polyesters
finding their application in paint and varnish industry and
laminated plastics manufacture.
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