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Information @ a Glance

General

  • 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.

  • Compounds containing the allyl group are often referred to as being allylic. Allylic carbons are sp hybridized, vinylic carbons are sp hybridized.

  • 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.

  • Allylic methylene groups show special reactivity such as demonstrated in allylic oxidations, ene reactions and the Trost asymmetric allylic alkylation.

Production and Process

  • 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.

  • Allyl chloride has conventionally been produced by hot chlorination of propylene.

  • The catalyst used in the production process can work at any pressure from atmospheric up to 40 bar. The active temperature range is between 400C and 540C.

Applications

  • 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.

  • Allylbenzene and Allyl Phenyl Ether are used as a chain-transfer agents in radical polymerization.

  • 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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