Allyl alcohol

Allyl alcohol is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols, it is a water-soluble, colourless liquid. However, 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. Allyl alcohol is the smallest representative of the allylic alcohols.

Production

Allyl alcohol can be obtained by many methods. The major industrial method to produce allyl alcohol involves the hydrolysis of allyl chloride:

CH2=CHCH2Cl + H2O → CH2=CHCH2OH + HCl

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 is that propylene oxide is a relatively inexpensive raw material.

Uses

Allyl alcohol is converted mainly to glycerol, a reaction that proceeds via allyl chloride and allyl dichloride. It is also a precursor to synthetic glycerol, epichlorohydrin, allyl esters, and allylamine. Because the alcohol and the chloride are easily interchangeable, a wide variety of derivatives can be prepared.

Safety

Allyl alcohol is highly toxic both from acute (short-term) and chronic (long-term) exposure. The LD50 for rats is 64 mg/kg. Allyl alcohol is classified as an extremely hazardous substance in the United States and is subject to strict reporting requirements.

See also

• Allyl
• Alcohol
• Organic compound
• Glycerol