Benzonitrile, from ammoxidation

Ammoxidation Acrylonitrile from propylene Benzonitrile from toluene and acrylonitrile from propylene... 

Ammoxidation, a vapor-phase reaction of hydrocarbon with ammonia and oxygen (air) (eq. 2). can be used to produce hydrogen cyanide (HCN), acrylonitrile, acetonitrile (as a by-product of acrylonitrile manufacture), methacrylonitrile, benzonitrile, and toluinitriles from methane, propylene, butylene, toluene, and xylenes, respectively. See also Acrylonitrile and Methacrylic Acid and Derivatives,... 

Fig. 4. Mechanism of toluene ammoxidation to benzonitrile. Reprinted from Ref. (71), Copyright (1988), with permission from Elsevier Science.

Moreover, an aerobic oxidative decarboxylative ammoxidation of phenylacetic acids and a-hydroxyphenylacetic acids to primary benzamides was realized with CU2O catalyst [28] (Scheme 3.10). The C(C=0)-N bond was formed with NH3 as nitrogen source and O2 as the sole terminal oxidant. Benzonitrile which is generated from phenylacetic acid through decarboxylation and ammoxidation with ammonia is the key intermediate for this transformation. It could convert into benzamide through ammonolysis and hydrolysis. A variety of primary benzamides could be prepared in 36-85 % yields form the corresponding acid. 

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