Acrylonitrile, electrochemical hydrodimerization

Reactions of this type are called electrochemical hydrodimerization. They are of great value for the synthesis of various bifunctional compounds. A reaction that has found wide commercial nse is the hydrodimerization of acrylonitrile to adiponitrile (the dinitrile of adipic acid) ... 

A very impressive illustration of the relative costs of the electrolysis step compared to workup and purification procedures is given in Ref. 14. The electrochemical hydrodimerization of acrylonitrile to adiponitrile is reported here. The electrolytic part makes up less than 20% of the whole process sheet, and the costs for the electrolytic part are less than 30%. The process is later discussed in more detail. 

Greatest attention has been paid to the development of an effective method for electrochemical hydrodimerization of acrylonitrile into adiponitrile [14-18], which is a valuable intermediate in... 

An oxidation using a nickel hydroxide electrode is shown in 15.8.433 Electrochemistry is also a way to produce radicals and anions. The hydrodimerization of acrylonitrile to adiponitrile just mentioned may involve the coupling of free radicals. The coupling of carbonyl compounds, such as p lolualdehyde, to form pinacols with up to 100% selectivity, by way of free radicals, can be done electrically.434 Anions can also be formed electrochemically and used in situ, as in example (15.9).435... 

The electrochemical process for adiponitrile involves the cathodic hydrodimerization of acrylonitrile... 

Production of Adiponitrile. The production of adiponitrile by hydrodimerization of acrylonitrile is the only organic electrochemical process used commercially to produce a large volume of organic chemical. Throughout the world, a total of more than 100,000 metric tons per year of adiponitrile is produced by this process. Adiponitrile is hydrogenated to hexamethylenediamine which is one of the components of nylon 66. The success in this process gave a significant impact to nylon industry. 

Hydrodimerization. The reductive dimerization of acrylonitrile can be done either chemically or electrochemically to form adiponitrile. Hydrodimerization with its derivatives also takes place. 

Watson, M., Pletcher, D. and Sopher, D.W. (2000) A microelectrode study of competing electrode reactions in the commercial process for the hydrodimerization of acrylonitrile to adiponitrile. Journal of the Electrochemical Society, 147, 3751-3758. 

The electrochemical route for the conversion of acrylonitrile to adiponitrile is a cathodic hydrodimerization ... 

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