Abstract
Publisher Summary This chapter discusses homogeneous nickel-catalyzed olefin hydrocyanation. It describes the chemistry behind the du Pont adiponitrile process from a mechanistic viewpoint. The hydrocyanation process can be broken down into two major steps. In the first step, hydrogen cyanide (HCN) is added to butadiene in the presence of NiL4 catalyst to give 3-pentenenitrile (3PN) and 2-methyl-3-butenenitrile (2M3BN). In the second step, a Lewis acid promoter is added to the NiL4 (L = a phosphorus ligand) catalyst to effect the double bond isomerization of 3PN to 4-pentenenitrile (4PN) concurrently with the selective addition of HCN to 4PN. By-products in the second step include 2-methylglutaronitrile (MGN), ethylsuccinonitrile (ESN), and 2-pentenenitrile (2PN) arising, respectively, from Markovnikov addition to 4PN, direct addition of HCN to 3PN, and isomerization of 3PN to its conjugated isomer that is not hydrocyanated. The three different types of reactor system include (1) semibatch, (2) pulse, and (3) continuous. The semibatch reactor is the simplest. All reagents except the HCN are placed in a thermostated vessel (usually glass).
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