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Studying the Three-Phase Hydrogenation of Nitrobenzene to Aniline in the Presense of a Ruthenium Catalyst

  • CATALYSIS IN CHEMICAL AND PETROCHEMICAL INDUSTRY
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Abstract

The catalytic hydrogenation of nitrobenzene (NB) is an important technological stage in the production of aniline (AN). The catalytic behavior of hypercrosslinked polystyrene based ruthenium catalyst 3%Ru/MN270 in the three-phase hydrogenation of NB to AN is considered in this work. The following parameters are varied: 0.12 to 0.24 mol/L of NB; 1.11 × 10−4 to 11.12 × 10−4 mol/L of catalyst; temperatures of 160 to 190°C; and partial hydrogen pressures of 0.113 to 1.013 MPa. The optimum process parameters are determined to ensure 98% selectivity toward aniline with 97% conversion of nitrobenzene.

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REFERENCES

  1. Shokouhimehr, M., Catalysts, 2015, vol. 5, no. 2, pp. 534–560.

    Article  CAS  Google Scholar 

  2. Blaser, H.-U., Malan, C., Pugin, B., Spindler, F., Steiner, H., and Studer, M., Adv. Synth. Catal., 2003, vol. 345, nos. 1–2, pp. 103–151.

  3. Wu, H., Zhuo, L., He, Q., Liao, X., and Shi, B., Appl. Catal., A, 2009, vol. 366, no. 1, pp. 44–56.

  4. Haber, F., Z. Elektrochem., 1898, vol. 4, pp. 506–514.

    Article  CAS  Google Scholar 

  5. Gelder, E.A., Jackson, S.D., and Lok, C.M., Chem. Commun., 2005, vol. 41, no. 4, pp. 522–524.

    Article  CAS  Google Scholar 

  6. Polotnyuk, O.-V.Ya., Katal. Prom-sti, 2013, no. 4, pp. 55–80.

  7. Verho, O., Gustaffson, K.P.J., Nagendiran, A., Tai, C.-W., and Bäckvall, J.-E., ChemCatChem, 2014, vol. 6, no. 11, pp. 3153–3159.

    Article  CAS  Google Scholar 

  8. Westerhaus, F.A., Jagadeesh, R.V., Wienhöfer, G., Pohl, M.M., Radnik, J., Surkus, A.E., Rabeah, J., Junge, K., Junge, H., Nielsen, M., Brückner, A., and Beller, M., Nat. Chem., 2013, vol. 5, no. 6, pp. 527–543.

    Article  CAS  Google Scholar 

  9. Sangeetha, P., Seetharamulu, P., Shanthi, K.., Narayanan, S., and Rama Rao, K.S., J. Mol. Catal. A: Chem., 2007, vol. 273, nos. 1–2, pp. 244–249.

  10. Rahaim, R.J. and Maleczka, R.E., Org. Lett., 2005, vol. 7, no. 22, pp. 5087–5090.

    Article  CAS  PubMed  Google Scholar 

  11. Shil, A.K. and Das, P., Green Chem., 2013, vol. 15, no. 12, pp. 3421–3428.

    Article  CAS  Google Scholar 

  12. Schabel, T., Belger, C., and Plietker, B., Org. Lett., 2013, vol. 15, no. 11, pp. 2858–2861.

    Article  CAS  PubMed  Google Scholar 

  13. Copéret, C., Chabanas, M., Petroff Saint-Arroman, R., and Basset, J.M., Angew. Chem., Int. Ed. Engl., 2003, vol. 42, no. 2, pp. 156–181.

    Article  Google Scholar 

  14. Shokouhimehr, M., Kim, J.-H., and Lee, Y.-S., Synlett, 2006, vol. 4, no. 4, pp. 618–620.

    Google Scholar 

  15. Janssen, M., Müller, C., and Vogt, D., Green Chem., 2011, vol. 13, no. 9, pp. 2247–2257.

    Article  CAS  Google Scholar 

  16. Kim, J.-H., Kim, J.-W., Shokouhimehr, M., and Lee, Y.-S., J. Org. Chem., 2005, vol. 70, no. 17, pp. 6714–6720.

    Article  CAS  PubMed  Google Scholar 

  17. Höller, V., Wegricht, D., Yuranov, I., Kiwi-Minsker, L., and Renken, A., Chem. Eng. Technol., 2000, vol. 23, no. 3, pp. 251–255.

    Article  Google Scholar 

  18. Rakitin, M.Yu., Doluda, V.Yu., Tereshchenkov, A.Yu., Demidenko, G.N., Lakina, N.V., Matveeva, V.G., Sul’man, M.G., and Sul’man, E.M., Catal. Ind., 2015, vol. 7, no. 1, pp. 1–5.

    Article  Google Scholar 

  19. Tobe, M.L. and Burgess, J., Inorganic Reaction Mechanisms, Harlow, UK: Longman, 1999.

    Google Scholar 

  20. Zhao, F., Ikushima, Y., and Arai, M., J. Catal., 2004, vol. 224, no. 2, pp. 479–483.

    Article  CAS  Google Scholar 

  21. Li, C.-H., Yu, Z.-X., Yao, K.-F., Ji, S.-F, and Liang, J., J. Mol. Catal. A: Chem., 2005, vol. 226, no. 1, pp. 101–105.

    Article  CAS  Google Scholar 

  22. Makosch, M., Hydrogenation over supported noble metal catalysts: From characterization to design, Dr. Sc. ETH Zürich Dissertation, Augsburg: ETH Zürich, 2012.

  23. Evangelisti, C., Aronica, L.A., Botavina, M., Martra, G., Battocchio, C., and Polzonetti, G., J. Mol. Catal. A: Chem., 2013, vol. 366, pp. 288–293.

    Article  CAS  Google Scholar 

  24. Polshettiwar, V., Len, C., and Fihri, A., Coord. Chem. Rev., 2009, vol. 253, nos. 21–22, pp. 2599–2626.

  25. Toebes, M.L., van Dillen, J.A., and de Jong, K.P., J. Mol. Catal. A: Chem., 2001, vol. 173, nos. 1–2, pp. 75–98.

  26. Matveeva, V.G., Valetskii, P.M., Sulman, M.G., Bronshtein, L.M., Sidorov, A.I., Doluda, V.Yu., Gavrilenko, A.V., Nikoshvili, L.Zh., Bykov, A.V., Grigorjev, M.E., and Sulman, E.M., Catal. Ind., 2011, vol. 3, no. 3, pp. 260–270.

    Article  Google Scholar 

  27. Sulman, E., Matveeva, V., Doluda, V., L. Nikoshvili, L., Bykov, A., Demidenko, G., and Bronstein, L., Stud. Surf. Sci. Catal., 2010, vol. 175, pp. 153–160.

    Article  CAS  Google Scholar 

  28. Sulman, M., Doluda, V., Grigoryev, M., Manaenkov, O., Filatova, A., Molchanov, V., Sidorov, A., Bykov, A., Shkileva, I., Sulman, A., Stein, B., and Matveeva, V., Bull. Chem. React. Eng. Catal., 2015, vol. 10, no. 3, pp. 313–323.

    Article  CAS  Google Scholar 

  29. Tsyurupa, M.P., Tarabaeva, O.G., Pastukhov, A.V., and Davankov, V.A., Int. J. Polym. Mater., 2003, vol. 52, no. 5, pp. 403–414.

    Article  CAS  Google Scholar 

  30. Pavlova, L.A., Davankov, V.A, and Lependina, N.A., Sorbtsionnye Khromatogr. Protsessy, 2014, vol. 14, no. 1, pp. 75–85.

    CAS  Google Scholar 

  31. Qingquan, L., Macromol. Chem. Phys., 2010, vol. 211, no. 9, pp. 1012–1017.

    Article  CAS  Google Scholar 

  32. Rakitin, M.Yu., Doluda, V.Yu., Tyanina, A.A., Petrova, A.I., Sulman, E.M., and Matveeva, V.G., Russ. J. Phys. Chem. B, 2017, vol. 11, no. 7, pp 1113–1116.

    Article  CAS  Google Scholar 

  33. Berezovskii, V.M., Khimiya vitaminov (Chemistry of Vitamins), Moscow: Pishchevaya promyshlennost’, 1973.

  34. Rajashekharam, M.V., Nikalje, D.D., Jaganathan, R., and Chaudhari, R.V., Ind. Eng. Chem. Res., 1997, vol. 36, no. 3, pp. 592–604.

    Article  CAS  Google Scholar 

  35. Sangeetha, P., Shanti, K., Rama Rao, K.S., Viswanathan, B., and Selvam P., Appl. Catal., A, 2009, vol. 353, no. 2, pp. 160–165.

  36. Deshmukh, A.A., Prashar, A.K., Kinage, A.K., Kumar, R., and Meijboom, R., Ind. Eng. Chem. Res., 2010, vol. 49, no. 23, pp. 12 180–12 184.

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

This work was financially supported by the Russian Foundation for Basic Research (project no. 17-08-00659A).

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Authors and Affiliations

  1. Tver State Technical University,, 170026, Tver, Russia

    V. Yu. Doluda, A. E. Filatova, E. M. Sul’man, V. G. Matveeva, A. I. Sidorov & Yu. Yu. Kosivtsov

  2. Tver State University,, 170100, Tver, Russia

    V. G. Matveeva & S. P. Mikhailov

Authors
  1. V. Yu. Doluda
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  2. A. E. Filatova
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  3. E. M. Sul’man
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  4. V. G. Matveeva
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  5. S. P. Mikhailov
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  6. A. I. Sidorov
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  7. Yu. Yu. Kosivtsov
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Correspondence to V. Yu. Doluda.

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Translated by M. Aladina

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Doluda, V.Y., Filatova, A.E., Sul’man, E.M. et al. Studying the Three-Phase Hydrogenation of Nitrobenzene to Aniline in the Presense of a Ruthenium Catalyst. Catal. Ind. 10, 328–334 (2018). https://doi.org/10.1134/S2070050418040049

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  • DOI: https://doi.org/10.1134/S2070050418040049

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