Skip to main content
Log in

Highly selective catalysts for liquid-phase hydrogenation of substituted alkynes based on Pd—Cu bimetallic nanoparticles

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Catalytic properties of Pd—Cu bimetallic catalysts supported on SiO2 and Al2O3 were studied in a model reaction of selective hydrogenation of diphenylacetylene. Application of PdCu2(AcO)6 heterobimetallic acetate complex as a precursor made it possible to obtain homogeneous Pd—Cu bimetallic nanoparticles. This result was supported by the data of IR spectroscopy of adsorbed CO. The Pd-Cu catalysts showed considerably higher selectivity than monometallic samples. Moreover, the introduction of copper decreases the hydrogenation rate of diphenylethylene (DPE) to diphenylethane. As a result, the maximum yield of the target product, DPE, increased from 78 to 93% in the presence of Pd—Cu catalysts.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. H. U. Blaser, A. Schnyder, H. Steiner, F. Rossler, P. Baumeister, in Handbook of Heterogeneous Catalysis, Eds G. Ertl, H. Knözinger, F. Schüth, J. Weitkamp, WileyVCH Verlag GmbH&Co. KGaA, Weinheim, Germany, 2008, vol. 8, p. 3298.

  2. V. P. Ananikov, L. L. Khemchyan, Yu. V. Ivanova, V. I. Bukhtiyarov, A. M. Sorokin, I. P. Prosvirin, S. Z. Vatsadze, A. V. Medved´ko, V. N. Nuriev, A. D. Dilman, V. V. Levin, I. V. Koptyug, K. V. Kovtunov, V. V. Zhivonitko, V. A. Likholobov, A. V. Romanenko, P. A. Simonov, V. G. Nenajdenko, O. I. Shmatova, V. M. Muzalevskiy, M. S. Nechaev, A. F. Asachenko, O. S. Morozov, P. B. Dzhevakov, S. N. Osipov, D. V. Vorobyeva, M. A. Topchiy, M. A. Zotova, S. A. Ponomarenko, O. V. Borshchev, Yu. N. Luponosov, A. A. Rempel, A. A. Valeeva, A. Yu. Stakheev, O. V. Turova, I. S. Mashkovsky, S. V. Sysolyatin, V. V. Malykhin, G. A. Bukhtiyarova, A. O. Terent´ev, I. B. Krylov, Russ. Chem. Rev., 2014, 83, 885.

    Article  Google Scholar 

  3. V. P. Ananikov, E. A. Khokhlova, M. P. Egorov, A. M. Sakharov, S. G. Zlotin, A. V. Kucherov, L. M. Kustov, M. L. Gening, N. E. Nifantiev, Mendeleev Commun., 2015, 25, 75.

    Article  CAS  Google Scholar 

  4. A. Borodzinski, G. C. Bond, Catal. Rev., 2006, 48, 91.

    Article  CAS  Google Scholar 

  5. K. R. Campos, D. Cai, M. Journet, J. J. Kowal, R. D. Larsen, P. J. Reider, J. Org. Chem., 2001, 66, 3634.

    Article  CAS  Google Scholar 

  6. G. C. Bond, in Metal-Catalysed Reactions of Hydrocarbons, Springer Science + Business Media, Inc., New York, 2005, p. 395.

    Google Scholar 

  7. N. A. Khan, S. Shaikhutdinov, H.-J. Freund, Catal. Lett., 2006, 108, 159.

    Article  CAS  Google Scholar 

  8. A. A. Lamberov, S. R. Egorova, I. R. Il´yasov, Kh. Kh. Gil´manov, S. V. Trifonov, V. M. Shatilov, Sh. Ziyatdinov, Kinet. Catal. (Int. Ed.), 2007, 48, 136 [Kinetika i Kataliz, 2007, 48, 143].

    Article  CAS  Google Scholar 

  9. I. S. Mashkovskii, O. P. Tkachenko, G. N. Baeva, A. Yu. Stakheev, Kinet. Catal. (Int. Ed.), 2009, 50, 768 [Kinetika i Kataliz, 2009, 50, 798].

    Article  CAS  Google Scholar 

  10. I. S. Mashkovsky, G. N. Baeva, A. Yu. Stakheev, M. N. Vargaftik, N. Yu. Kozitsyna, I. I. Moiseev, Mendeleev Com-mun., 2014, 24, 355.

    Article  CAS  Google Scholar 

  11. T. V. Choudhary, C. Sivadinarayana, A. K. Datye, D. Kumar, D. W. Goodman, Catal. Lett., 2003, 86, 1.

    Article  CAS  Google Scholar 

  12. A. Yu. Stakheev, B. L. Moroz, I. S. Mashkovsky, P. V. Markov, O. V. Turova, O. P. Tkachenko, P. A. Pyryaev, V. I. Bukhtiyarov, Russ. Chem. Bull. (Int. Ed.), 2015, 64, 53 [Izv. Akad. Nauk, Ser. Khim., 2015, 53].

    Article  CAS  Google Scholar 

  13. M. P. R. Spee, J. Boersma, M. D. Meijer, M. Q. Slagt, G. van Koten, J. W. Geus, J.Org. Chem., 2001, 66, 1647.

    Article  CAS  Google Scholar 

  14. L. Guczi, Z. Schay, Gy. Stefler, L. F. Liotta, G. Deganello, A. M. Venezia, J. Catal., 1999, 182, 456.

    Article  CAS  Google Scholar 

  15. P. V. Markov, G. O. Bragina, G. N. Baeva, O. P. Tkachenko, I. S. Mashkovsky, I. A. Yakushev, N. Yu. Kozitsyna, M. N. Vargaftik, A. Yu. Stakheev, Kinet. Catal. (Int. Ed.), 2015, 56, 591 [Kinetika i Kataliz, 2015, 56, 599].

    Article  CAS  Google Scholar 

  16. O. P. Tkachenko, A. Yu. Stakheev, L. M. Kustov, I. S. Mashkovsky, M. van den Berg, W. Grünert, N. Yu. Kozitsyna, S. E. Nefedov, Zh. V. Dobrokhotova, V. I. Zhilov, M. N. Vargaftik, I. I. Moiseev, Catal. Lett., 2006, 112, 155.

    Article  CAS  Google Scholar 

  17. N. Yu. Kozitsyna, S. E. Nefedov, F. M. Dolgushin, N. V. Cherkashina, M. N. Vargaftik, I. I. Moiseev, Inorg. Chim. Acta, 2006, 359, 2072.

    Article  CAS  Google Scholar 

  18. V. V. Kachala, L. L. Khemchyan, A. S. Kashin, N. V. Orlov, A. A. Grachev, S. S. Zalesskiy, V. P. Ananikov, Russ. Chem. Rev., 2013, 82, 648.

    Article  Google Scholar 

  19. A. S. Kashin, V. P. Ananikov, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 2602 [Izv. Akad. Nauk, Ser. Khim., 2011, 2551].

    Article  CAS  Google Scholar 

  20. N. Marin-Astorga, G. Alvez-Manoli, P. Reyes, J. Mol. Catal. A Chem., 2005, 226, 81.

    Article  CAS  Google Scholar 

  21. B. M. Choudary, M. Lakshmi Kantam, N. Mahender Reddy, K. Koteswara Rao, Y. Haritha, V. Bhaskar, F. Figueras, A. Tuel, Appl. Catal. A, 1999, 181, 139.

    Article  CAS  Google Scholar 

  22. X.-Y. Quek, Y. Guan, E. J. M. Hensen, Catal. Today, 2012, 183, 72.

    Article  CAS  Google Scholar 

  23. A. Yu. Stakheev, P. V. Markov, A. S. Taranenko, G. O. Bragina, G. N. Baeva, O. P. Tkachenko, I. S. Mashkovsky, A. S. Kashin, Kinet. Catal. (Ind. Ed.), 2015, 56, 733 [Kinetika i Katal., 2015, 56, 721].

    Article  CAS  Google Scholar 

  24. A. Davidov, in Molecular Spectroscopy of Oxide Catalyst Surfaces, Wiley, New York, 2003, 691 pp.

    Book  Google Scholar 

  25. K. I. Hadjiivanov, G. N. Vayssilov, Adv. Catal., 2002, 47, 307.

    CAS  Google Scholar 

  26. S. Sitthisa, T. Pham, T. Prasomsri, T. Sooknoi, R. G. Mallinson, D. E. Resasco, J. Catal., 2011, 280, 17.

    Article  CAS  Google Scholar 

  27. B. T. Meshesha, N. Barrabes, J. Llorca, A. Dafinov, F. Medina, K. Föttinger, Appl. Catal. A: General, 2013, 453, 130.

    Article  CAS  Google Scholar 

  28. P. Benito, M. Gregori, S. Andreoli, G. Fornasari, F. Ospitali, S. Millefanti, M. S. Avila, T. F. Garett, S. Albonetti, Catal. Today, 2015, 246, 108.

    Article  CAS  Google Scholar 

  29. M. Fernandez-Garcia, A. Martinez-Arias, A. Iglesias-Juez, A. B. Hungria, J. A. Anderson, J. C. Conesa, J. Soria, Appl. Catal. B: Environmental, 2001, 31, 39.

    Article  CAS  Google Scholar 

  30. A. B. Hungria, A. Iglesias-Juez, A. Martinez-Arias, M. Fernandez-Garcia, J. A. Anderson, J. C. Conesa, J. Soria, J. Catal., 2002, 206, 281.

    Article  CAS  Google Scholar 

  31. V. Yu. Borovkov, D. R. Luebke, V. I. Kovalchuk, J. L. d´Itri, J. Phys. Chem. B, 2003, 107, 5568.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. Yu. Stakheev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0425—0431, February, 2016.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mashkovsky, I.S., Markov, P.V., Bragina, G.O. et al. Highly selective catalysts for liquid-phase hydrogenation of substituted alkynes based on Pd—Cu bimetallic nanoparticles. Russ Chem Bull 65, 425–431 (2016). https://doi.org/10.1007/s11172-016-1316-0

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-016-1316-0

Key words

Navigation