Unique shortening of carbon chain during reduction of aliphatic nitro compounds to amines in the presence of supercritical isopropanol on alumina

• Dominant process was to produce amines with shortening of carbon chain.
• Transformations of lower nitroalkanes in sc isopropanol were studied.
• Reactions were performed in a flow reactor in the presence of granular Al2O3.
• Formation of 2-phenylacetonitrile with 2-phenylnitroethane was observed first.

Transformations of lower aliphatic nitrocompounds in supercritical isopropanol in a flow reactor in the presence of alumina were studied. In experiments with 1-nitropropane, the dominant process was the never-before-observed formation of an amine with a shorter by one carbon atom chain as compared to the initial nitroalkane. The reaction mechanism was suggested which adequately explained the formation of all detected products. The reactions of nitroethane and nitromethane partly proceeded by a new transformation route yielding isopropylamine.

Figure optionsDownload as PowerPoint slide