CHLORINATION OF PROPYLENE  (Allyl Chloride [CH₂=CHCH₂Cl])

Allyl chloride is a colorless liquid, insoluble in water but soluble in many organic solvents. It has a strong pungent odor and an irritating effect on the skin. As a chemical, allyl chloride is used to make allyl alcohol, glycerol, and epichlorohydrin.

The production of allyl chloride could be effected by direct chlorination of propylene at high temperatures (approximately 500°C and one atmosphere). The reaction substitutes an allylic hydrogen with a chlorine atom. Hydrogen chloride is a by-product from this reaction:

The major by-products are cis- and trans- 1,3-dichloropropene, which are used as soil fumigants. The most important use of allyl chloride is to produce glycerol via an epichlorohydrin intermediate. The epichlorohydrin is hydrolyzed to glycerol:

Glycerol, a trihydric alcohol, is used to produce polyurethane foams and alkyd resins. It is also used in the manufacture of plasticizers.