Allyl chloride
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Through Organic compound, Chemical formula and Carbon
Production
Laboratory scale
Allyl chloride was first produced in 1857 by Auguste Cahours and August Hofmann by reacting allyl alcohol with phosphorus trichloride. Modern preparation protocols economize this approach, replacing relatively expensive phosphorus trichloride with hydrochloric acid and a catalyst such as copper(I) chloride.
Industrial scale
Allyl chloride is produced by the chlorination of propylene. At lower temperatures, the main product is 1,2-dichloropropane, but at 500 °C, allyl chloride predominates, being formed via a free radical reaction:
- CH3CH=CH2 + Cl2 → ClCH2CH=CH2 + HCl
An estimated 800,000 tonnes were produced this way in 1997.
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Reactions and uses
The great majority of allyl chloride is converted to epichlorohydrin. Other commercially significant derivatives include allyl alcohol, allylamine, allyl isothiocyanate (synthetic mustard oil), and 1-bromo-3-chloropropane.
As an alkylating agent, it is useful in the manufacture of pharmaceuticals and pesticides, such as mustard oil.
Illustrative reactions
Illustrative of its reactivity is its cyanation to allyl cyanide (CH2=CHCH2CN). Being a reactive alkyl halide, it undergoes reductive coupling to give diallyl:
- 2 ClCH2CH=CH2 + Mg → (CH2)2(CH=CH2)2 + MgCl2
It undergoes oxidative addition to palladium(0) to give allylpalladium chloride dimer, (C3H5)2Pd2Cl2. Dehydrohalogenation gives cyclopropene.
Safety
Allyl chloride is highly toxic and flammable. Eye effects may be delayed and may lead to possible impairment of vision.