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An unusual reduction route of 2,4,6-trinitrobenzoic acid under conditions of aqueous-phase hydrogenation over Pd/Sibunit catalyst

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Abstract

For the first time it was established that the catalytic hydrogenation of 2,4,6-trinitrobenzoic acid to 1,3,5-triaminobenzene can proceed via the formation of aromatic hydroxyamines and cyclohexane-1,3,5-trione trioxime. As a result of aqueous-phase hydrogenation of sodium salt of 2,4,6-trinitrobenzoic acid in the presence of 5%Pd/Sibunit catalyst at a temperature of 323 K and pressure of 0.5 MPa, a trioxime in high yield (about 70 %) was obtained. Due to high selectivity to cyclohexane-1,3,5-trione trioxime the catalytic hydrogenation of sodium salt of 2,4,6-trinitrobenzoic acid can be considered as a new method for its synthesis.

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Authors and Affiliations

  1. Institute of Hydrocarbons Processing, Siberian Branch of the Russian Academy of Sciences, 54 ul. Neftezavodskaya, 644040, Omsk, Russian Federation

    R. M. Mironenko, O. B. Belskaya, V. P. Talzi, V. A. Rodionov & V. A. Likholobov

  2. Dostoevsky Omsk State University, 55a prosp. Mira, 644077, Omsk, Russian Federation

    R. M. Mironenko

  3. Omsk State Technical University, 11 prosp. Mira, 644050, Omsk, Russian Federation

    O. B. Belskaya & V. A. Likholobov

  4. Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences, 1 ul. Sotsialisticheskaya, 659322, Biysk, Altai Krai, Russian Federation

    S. V. Sysolyatin

  5. Omsk Scientific Center, Siberian Branch of the Russian Academy of Sciences, 15 prosp. K. Marksa, 644024, Omsk, Russian Federation

    V. A. Likholobov

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  1. R. M. Mironenko
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  2. O. B. Belskaya
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Correspondence to R. M. Mironenko.

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Dedicated to the memory of Professor G. V. Plaksin.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1535—1540, June, 2016.

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Mironenko, R.M., Belskaya, O.B., Talzi, V.P. et al. An unusual reduction route of 2,4,6-trinitrobenzoic acid under conditions of aqueous-phase hydrogenation over Pd/Sibunit catalyst. Russ Chem Bull 65, 1535–1540 (2016). https://doi.org/10.1007/s11172-016-1479-8

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  • DOI: https://doi.org/10.1007/s11172-016-1479-8

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