Ethylene cyanhydrin

CHjiCH-CN. Volatile liquid b.p. 78"C. Manufactured by the catalytic dehydration of ethylene cyanhydrin, by the addition of hydrogen cyanide to ethyne in the presence of CuCI or the reaction of propene, ammonia and air in the presence of a molybdenum-based catalyst. 

CHj=CH—C=N) was commenced by Du Pont in 1940, and by 1942 small quantities of textile fibres were made available for commercial trials. Ethylene, from petroleum cracking, is converted to ethylene oxide which reacts with hydrogen cyanide in the presence of water containing diethylamine and caustic soda at 50°C, to form ethylene cyanhydrin ... 

Glycol Ethers, Ethylene Cyanhydrin and Acrylonitrile, Phenyl Ethyl Alcohol and Related Derivatives of Ethylene Oxide in Germany, FIAT Final Rept. 1131, U. S. Dept. of Commerce, Office of Technical Services, PB-85159. 

Acrylic acid, CH2=CHCOOH, can be produced by a series of processes direct oxidation of acrolein oxidation of ethylene to ethylene oxide, with further reaction with hydrogen cyanide to ethylene cyanhydrin, which is then saponified and dehydrated addition of carbon monoxide and water to acetylene and from acetone by pyrolysis to ketene and addition of formaldehyde to the ketene to produce jS-propiolactone. jS-Propiolactone polymerizes to the corresponding polyester, which depolymerizes at 150 C to acrylic acid ... 

Ammonoxidation of propylene with ammonia and oxygen produces acrylonitrile, CH2=CHCN. Other acrylonitrile syntheses proceed from acetaldehyde and hydrogen cyanide via a-hydroxypropionitrile, or from ethylene oxide via ethylene cyanhydrin. 

From ethylene by oxidation to ethylene oxide, which is converted to ethylene cyanhydrin, HO—CH2—CH2—CN, with HCN (50-60°C, pH > 1). Steam is then blown through a column containing a mixture of ethylene cyanhydrin and 75% sulfuric acid. The aqueous acrylic acid is distilled over and condensed, yielding a solution of about 50 % in water. 

The ethylene cyanhydrine route was the first used to manufacture acrylic acid. Ethylene cyanhydrine is formed by addition of hydrogen cyanide to ethylene... 

Acrylonitrile (AN) was first synthesized in 1893 by Moureu [593], who was also the first (one year later) to report on an acrylonitrile polymer (PAN). The first synthesis of AN was based on the dehydration of ethylene cyanhydrine (1-cyanoethanol) or acrylamide. Early industrial processes for AN production also used ethylene cyanhydrine as starting material, but since 1960 practically the entire AN production has been based on catalytic ammonoxidation of propene. More detailed information on the industrial production processes for AN is given in Ref. [594]. A number of recently published review papers from Japan deals with the ammonoxidation of propane rather than propene to produce acrylonitrile [595 599]. Information on toxicity, mutagenicity, teratogenicity and carcinogenicity of acrylonitrile can be found in Refs. [600-604]. 

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