Allyl Alcohol and Monoallyl Derivatives

Abstract

The technology of introducing a new functional group to the double bond of allyl alcohol was developed in the mid‐1980s. Allyl alcohol is accordingly used as an intermediate compound for synthesizing raw materials such as epichlorohydrin and 1,4‐butanediol, and this development is bringing about expansion of the range of uses of allyl alcohol. Allyl alcohol is a colorless liquid having a pungent odor; its vapor may cause severe irritation and injury to eyes, nose, throat, and lungs. It is also corrosive. Allyl alcohol is freely miscible with water and miscible with many polar organic solvents and aromatic hydrocarbons. It forms an azeotropic mixture with water and a ternary azeotropic mixture with water and organic solvents. Hydroformylation of allyl alcohol is a synthetic route for producing 1,4‐butanediol, a raw material for poly(butylene terephthalate), an engineering plastic. The CC double bond of allyl alcohol undergoes epoxidation by peroxide, yielding glycidol, applied in manufacturing glycidol as an intermediate for industrial production of glycerol. There are two processes for industrial production of allyl alcohol being used industrially at present: isomerization of propylene oxide, and a new process developed by Showa Denko K. K. The monoallyl derivative allyl chloride (AC) is a transparent, mobile, and irritative liquid produced by chlorination of propylene at high temperature. It is used mostly as an intermediate compound for producing epichlorohydrin. Allyl acetate is produced mostly for manufacturing allyl alcohol. Allyl methacrylate (AMA) is used mostly as a raw material for silane coupling agents. Allyl glycidyl ether is used mainly as a raw material for silane coupling agents and epichlorohydrin rubber. Dimethylallylamine is used in the production of insecticides and pesticides. Most allyl compounds are toxic and many are irritants. Precautions should be taken at all times to ensure safe handling.

A perspective on catalytic production of olefinic compounds from biomass

“…Isomerization of propylene oxide has been used in industrial plants built recently. 86 The industrial production amount of allyl alcohol is about 1 million tons per year, which means that total substitution of propylene is possible with glycerol as the raw material of allyl alcohol. There are four methods for production of allyl alcohol from glycerol (Scheme 10): acrolein hydrogenation, 1,2-propanediol dehydration, thermal decomposition of glycerol and deoxydehydration of glycerol.…”