Skip to main content
SpringerLink
Log in

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

  • CATALYSIS IN CHEMICAL AND PETROCHEMICAL INDUSTRY
  • Published:
Catalysis in Industry Aims and scope Submit manuscript

Abstract

The results are presented from studying the catalytic properties of ruthenium catalyst 3% Ru/MN270 based on hypercrosslinked polystyrene in the reaction of three-phase hydrogenation of nitrobenzene to aniline. The following parameters are varied in the study: the NB concentration in the range from 0.12 to 0.24 mol/L, the catalyst concentration in the range from 1.11 × 10−4 to 11.12 × 10−4 mol/L, the temperature in the range from 160 to 190°C, and the partial hydrogen pressure in the range from 1.013 to 0.113 MPa. The optimum parameters of the process are determined, allowing 97% conversion of nitrobenzene and a selectivity of 98% towards aniline to be achieved.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.
Fig. 8.

Similar content being viewed by others

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.

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

  6. Polotnyuk, O.-V.Ya., Katal. Prom-sti, 2013, no. 5, pp. 55–80.

  7. Verho, O., Gustaffson, K.P.J., Nagendiran, A., Tai, C.-W., and Backvall, 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, 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., 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., Saint-Arroman, R.P., 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, no. 4, pp. 618–620.

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

    Article  CAS  Google Scholar 

  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 

Download references

FUNDING

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

Author information

Authors and Affiliations

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

    V. Yu. Doluda, A. E. Filatova, E. M. Sulman, 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
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. E. Filatova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. M. Sulman
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. G. Matveeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. P. Mikhailov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. I. Sidorov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yu. Yu. Kosivtsov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. E. Filatova.

Additional information

Translated by O. Kadkin

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Doluda, V.Y., Filatova, A.E., Sulman, E.M. et al. Studying the Three-Phase Hydrogenation of Nitrobenzene to Aniline in the Presence of a Ruthenium Catalyst. Catal. Ind. 11, 147–153 (2019). https://doi.org/10.1134/S2070050419020041

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S2070050419020041

Keywords:

Search

Navigation