Synthesis of p-Aminophenol by Catalytic Hydrogenation of Nitrobenzene

Organic Process Research & Development (Impact Factor: 2.53). 11/1999; 3(6). DOI: 10.1021/op990040r


The present work describes the preparation of p-aminophenol via single-step catalytic hydrogenation of nitrobenzene in acid medium. A conventional method of synthesis of p-aminophenol is a two-step reaction involving iron−acid reduction of p-nitrophenol. This method causes serious effluent disposal problems due to the stoichiometric use of iron−acid, which leads to the formation of Fe−FeO sludge (1.2 kg/kg of product) in the process, which cannot be recycled. The single-step hydrogenation of nitrobenzene was carried out using platinum catalyst, and the process conditions were optimized. Complete conversion of nitrobenzene was achieved with selectivity to p-aminophenol as high as 75% under the best set of conditions. Furthermore, the catalyst can be easily recovered and efficiently recycled giving the TON as high as 1.38 × 10.5 This paper presents studies on the effect of various process parameters such as temperature, hydrogen pressure, and substrate and acid concentration on the rate of reaction and selectivity to p-aminophenol.

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