Abstract
The liquid phase hydrogenation of benzonitrile over a 5 wt % Pd/C catalyst using a stirred autoclave is investigated. The reaction conforms to a consecutive reaction sequence: first benzonitrile is...
Highlights
Primary aromatic amines represent an important class of chemicals with widespread application in many areas of the chemical industry.[1]
Reaction schemes are proposed to describe (i) the deuteration of benzonitrile resulting in the formation of toluene-d3 and (ii) the direct deuterolysis of benzylamine resulting in formation of toluened[1]
McMillan and co-workers previously reported on benzonitrile hydrogenation over the same 5 wt % Pd/C catalyst under consideration here.[7]
Summary
Primary aromatic amines represent an important class of chemicals with widespread application in many areas of the chemical industry.[1]. The presence of a hydrogenolysis pathway to yield toluene was acknowledged.[12] the presence of a hydrogenolysis step as a side reaction when hydrogenating nitriles was reported by Yap and co-workers.[13,14] This heteroatom cleavage has not been a predominant feature of the heterogeneous catalysis literature, with the phenomenon thought to be the dominant process of the reaction only under “harsh” reaction conditions.[14,15] Despite this, selective production of the hydrogenolysis product under mild conditions has been reported; for example, by Maschmeyer et al.,[14] through the study of benzonitrile over a Pd/C catalyst. Reaction schemes are proposed to describe (i) the deuteration of benzonitrile resulting in the formation of toluene-d3 and (ii) the direct deuterolysis of benzylamine resulting in formation of toluened[1]
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