Skip to main content
SpringerLink
Log in

Intermetallic Pd1–Zn1 nanoparticles in the selective liquid-phase hydrogenation of substituted alkynes

  • Published:
Kinetics and Catalysis Aims and scope Submit manuscript

Abstract

A comparative study of the catalytic characteristics of monometallic Pd/α-Al2O3 and bimetallic Pd–Zn/α-Al2O3catalysts in the liquid-phase hydrogenation of structurally different substituted alkynes (terminal and internal, symmetrical and asymmetrical) was carried out. It was established that an increase in the reduction temperature from 200 to 400 and 600°C led to a primary decrease in the activity of Pd–Zn/α-Al2O3 due to the formation and agglomeration of Pd1–Zn1 intermetallic nanoparticles. The Pd–Zn/α-Al2O3 catalyst containing Pd1–Zn1 nanoparticles exhibited increased selectivity to the target alkene formation, as compared with that of Pd/α-Al2O3. Furthermore, the use of the Pd–Zn/α-Al2O3 catalyst made it possible to more effectively perform the kinetic process control of hydrogenation because the rate of an undesirable complete hydrogenation stage decreased on this catalyst.

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.

Institutional subscriptions

Similar content being viewed by others

References

  1. Borodzinski, A. and Bond, G.C., Catal. Rev., 2006, vol. 48, p. 91.

    Article  CAS  Google Scholar 

  2. Ananikov, V.P., Khemchyan, L.L., Ivanova, Yu.V., Bukhtiyarov, V.I., Sorokin, A.M., Prosvirin, I.P., Vatsadze, S.Z., Medved’ko, A.V., Nuriev, V.N., Dil’man, A.D., Levin, V.V., Koptyug, I.V., Kovtunov, K.V., Zhivonitko, V.V., Likholobov, V.A., et al., Russ. Chem. Rev., 2014, vol. 83, p. 885.

    Article  Google Scholar 

  3. Nikolaev, S.A., Zanaveskin, L.N., Smirnov, V.V., Aver’yanov, V.A., and Zanaveskin, K.L., Russ. Chem. Rev., 2009, vol. 78, p. 231.

    Article  CAS  Google Scholar 

  4. Bonrath, W., Medlock, J., Schütz, J., Wüstenberg, B., and Netscher, T., Hydrogenation Overview, Karamé, I., Ed., InTech, 2012. http://www.intechopen.com/ books/hydrogenation/hydrogenation-in-the-vitaminsand-fine-chemicals-industry-an-overview.

    Google Scholar 

  5. Ichimura, K., Chem. Rev., 2000, vol. 100, p. 1847.

    Article  CAS  Google Scholar 

  6. Halim, M., Samuel, I.D.W., Pillow, J.N.G., Monkman, A.P., and Burn, P.L., Synth. Met., 1999, vol. 102, p. 1571.

    Article  CAS  Google Scholar 

  7. Furukawa, Sh., Yokoyama, A., and Komatsu, T., ACS Catal., 2014, vol. 4, p. 3581.

    Article  CAS  Google Scholar 

  8. Blaser, H.-U., Schnyder, A., Steiner, H., Rossler, F., and Baumeister, P., in Handbook of Heterogeneous Catalysis, Ertl, G., Knözinger, H., Schüth, F., and Weitkamp, J., Eds., Weinheim, Germany: Wiley–VCH, 2008, vol. 8, p. 3298.

    Google Scholar 

  9. Ananikov, V.P., Galkin, K.I., Egorov, M.P., Sakharov, A.M., Zlotin, S.G., Redina, E.A., Isaeva, V.I., Kustov, L.M., Gening, M.L., and Nifantiev, N.E., Mendeleev Commun., 2016, vol. 26, p. 365.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  11. Karunananda, M.K. and Mankad, N.P., J. Am. Chem. Soc., 2015, vol. 137, p. 14598.

    Article  CAS  Google Scholar 

  12. Pei, G.X., Yan, LiuX., Wang, A., Lee, A.F., Isaacs, M.A., Li, L., Pan, X., Yang, X., Wang, X., Tai, Z., Wilson, K., and Zhang, T., ACS Catal., 2015, vol. 5, p. 3717.

    Article  CAS  Google Scholar 

  13. Tan, L., Wu, X., Chen, D., Liu, H., Menga, X., and Tang, F., J. Mater. Chem. A, 2013, vol. 1, p. 10382.

    Article  CAS  Google Scholar 

  14. McCue, A.J., Gibson, A., and Anderson, J.A., Chem. Eng. J., 2016, vol. 285, p. 384.

    Article  CAS  Google Scholar 

  15. Chinayon, S., Mekasuwandumrong, O., Praserthdam, P., and Panpranot, J., Catal. Commun., 2008, vol. 9, p. 2297.

    Article  CAS  Google Scholar 

  16. Mashkovskii, I.S., Tkachenko, O.P., Baeva, G.N., and Stakheev, A.Yu., Kinet. Catal., 2009, vol. 50, no. 50, p. 768.

    Article  CAS  Google Scholar 

  17. Zhou, H., Yang, X., Wang, A., Miao, Sh., Liu, X., Pan, X., Su, Y., Li, L., Tan, Y., and Zhang, T., Chin. J. Catal., 2016, vol. 37, p. 692.

    Article  CAS  Google Scholar 

  18. Mashkovsky, I.S., Baeva, G.N., Stakheev, A.Yu., Vargaftik, M.N., Kozitsyna, N.Yu., and Moiseev, I.I., Mendeleev Commun., 2014, vol. 24, p. 355.

    Article  CAS  Google Scholar 

  19. Föttinger, K., Catalysis, 2013, vol. 25, p. 77.

    Article  Google Scholar 

  20. Armbrüster, M., Behrens, M., Föttinger, K., Friedrich, M., Gaudry, É., Matam, S.K., and Sharma, H.R., Catal. Rev. Sci. Eng., 2013, vol. 55, p. 289.

    Article  Google Scholar 

  21. Studt, F., Abild-Pedersen, F., Bligaard, T., Sørensen, R.Z., Christensen, C.H., and Nørskov, J.K., Science, 2008, vol. 320, p. 1320.

    Article  CAS  Google Scholar 

  22. Furukawa, S. and Komatsu, T., ACS Catal., 2017, vol. 7, p. 735.

    Article  CAS  Google Scholar 

  23. Zhou, H., Yang, X., Li, L., Liu, X., Huang, Y., Pan, X., Wang, A., Li, J., and Zhang, T., ACS Catal., 2016, vol. 6, p. 1054.

    Article  CAS  Google Scholar 

  24. Yoshida, H., Zama, T., Fujita, S., Panpranot, J., and Arai, M., RSC Adv., 2014, vol. 4, p. 24922.

    Article  CAS  Google Scholar 

  25. Wang, Z., Yang, L., Zhang, R., Li, L., Cheng, Z., and Zhou, Z., Catal. Today, 2016, vol. 264, p. 37.

    Article  CAS  Google Scholar 

  26. Mashkovsky, I.S., Markov, P.V., Bragina, G.O., Baeva, G.N., Bukhtiyarov, A.V., Prosvirin, I.P., Bukhtiyarov, V.I., and Stakheev, A.Yu., Kinet. Catal., 2017, vol. 58, p. 471.

    Article  Google Scholar 

  27. Markov, P.V., Bragina, G.O., Baeva, G.N., Tkachenko, O.P., Mashkovskii, I.S., Yakushev, I.A., Kozytsyna, N.Yu., Vargaftik, M.N., and Stakheev, A.Yu., Kinet. Catal., 2015, vol. 56, p. 591.

    Article  CAS  Google Scholar 

  28. Spee, J., Boersma, J., Meijer, M.D., Slagt, M.Q., van Koten, G., and Geus, J.W., J. Org. Chem., 2001, vol. 66, p. 1647.

    Article  CAS  Google Scholar 

  29. Mashkovsky, I.S., Markov, P.V., Bragina, G.O., Tkachenko, O.P., Yakushev, I.A., Kozitsyna, N.Yu., Vargaftik, M.N., and Stakheev, A.Yu., Russ. Chem. Bull., 2016, vol. 65, no. 2, p. 425.

    Article  CAS  Google Scholar 

  30. Domínguez-Domínguez, S., Berenguer-Murcia, A., Cazorla-Amorós, D., and Linares-Solano, A., J. Catal., 2006, vol. 243, p. 74.

    Article  Google Scholar 

  31. Karakhanov, E.A., Aksenov, I.A., Kardashev, S.V., Maksimov, A.L., Putilin, F.N., Shatokhin, A.N., and Savilov, S.V., Appl. Catal., A, 2013, vols. 464–465, p. 253.

    Google Scholar 

  32. Marin-Astorga, N., Alvez-Manoli, G., and Reyes, P., J. Mol. Catal. A: Chem., 2005, vol. 226, p. 81.

    Article  CAS  Google Scholar 

  33. Jung, A., Jess, A., Schubert, T., and Schütz, W., Appl. Catal., A, 2009, vol. 362, p. 95.

    Article  CAS  Google Scholar 

  34. Segura, Y., López, N., and Pérez-Ramírez, J., J. Catal., 2007, vol. 247, p. 383.

    Article  CAS  Google Scholar 

  35. Teschner, D., Borsodi, J., and Wootsch, A., Science, 2008, vol. 320, p. 86.

    Article  CAS  Google Scholar 

  36. Vilé, G., Almora-Barrios, N., Mitchell, Sh., Lóopez, N., and Pérez-Ramírez, J., Chem. Eur. J., 2014, vol. 20, p. 5926.

    Article  Google Scholar 

  37. Markov, P.V., Bragina, G.O., Baeva, G.N., Tkachenko, O.P., Mashkovskii, I.S., Yakushev, I.A., Vargaftik, M.N., and Stakheev, A.Yu., Kinet. Catal., 2016, vol. 57, no. 5, p. 617.

    Article  CAS  Google Scholar 

  38. Markov, P.V., Bragina, G.O., Baeva, G.N., Mashkovskii, I.S., Rassolov, A.V., Yakushev, I.A., Vargaftik, M.N., and Stakheev, A.Yu., Kinet. Catal., 2016, vol. 57, no. 5, p. 625.

    Article  CAS  Google Scholar 

  39. Rassolov, A.V., Markov, P.V., Bragina, G.O., Baeva, G.N., Krivoruchenko, D.S., Mashkovskii, I.S., Yakushev, I.A., Vargaftik, M.N., and Stakheev, A.Yu., Kinet. Catal., 2016, vol. 57, no. 6, p. 859.

    Article  CAS  Google Scholar 

  40. Osswald, J., Giedigkeit, R., Jentoft, R.E., Armbrüster, M., Girgsdies, F., Kovnir, K., Ressler, T., Grin, Yu., and Schlögl, R., J. Catal., 2008, vol. 258, p. 210.

    Article  CAS  Google Scholar 

  41. Armbrüster, M., Kovnir, K., Behrens, M., Teschner, D., Grin, Yu., and Schlögl, R., J. Am. Chem. Soc., 2010, vol. 132, p. 14745.

    Article  Google Scholar 

  42. Holzapfel, H.H., Wolfbeisser, A., Rameshan, C., Weilach, C., and Rupprechter, G., Top. Catal., 2014, vol. 57, p. 1218.

    Article  CAS  Google Scholar 

  43. Gabasch, H., Knop-Gericke, A., Schlögl, R., Penner, S., Jenewein, B., and Hayek, K., and Klötzer, B., J. Phys. Chem. B, 2006, vol. 110, p. 11391.

    Article  CAS  Google Scholar 

  44. Palczewska, W., Adv. Catal., 1975, vol. 24, p. 245.

    CAS  Google Scholar 

  45. García-Mota, M., Gómez-Díaz, J., Novell-Leruth, G., Vargas-Fuentes, C., Bellarosa, L., and Pérez-Ramírez, J., and López, N., Theor. Chem. Acc., 2011, vol. 128, p. 663.

    Article  Google Scholar 

  46. Caga, I.T., Shutt, E., and Winterbottom, J.M., J. Catal., 1976, vol. 44, p. 271.

    Article  CAS  Google Scholar 

  47. Aduriz, H.R., Bodnariuk, P., Coq, B., and Figueras, F., J. Catal., 1991, vol. 129, p. 47.

    Article  CAS  Google Scholar 

  48. Armbrüster, M., Behrens, M., Cinquini, F., Föttinger, K., Grin, Yu., Haghofer, A., Klötzer, B., Knop-Gericke, A., Lorenz, H., Ota, A., Penner, S., Prinz, J., Rameshan, C., Révay, Z., Rosenthal, D., et al., ChemCatChem, 2012, vol. 4, p. 1048.

    Article  Google Scholar 

  49. Ota, A., Armbrüster, M., Behrens, M., Rosenthal, D., Friedrich, M., Kasatkin, I., Girgsdies, F., Zhang, W., Wagner, R., and Schlögl, R., J. Phys. Chem. C, 2010, vol. 115, p. 1368.

    Article  Google Scholar 

  50. Yang, B., Burch, R., Hardacre, C., Headdock, G., and Hu, P., J. Catal., 2013, vol. 305, p. 264.

    Article  CAS  Google Scholar 

  51. Tew, M.W., Emerich, H., and van Bokhoven, J.A., J. Phys. Chem. C, 2011, vol. 115, p. 8457.

    Article  CAS  Google Scholar 

  52. Rodriguez, J., J. Phys Chem., 1994, vol. 98, p. 5758.

    Article  CAS  Google Scholar 

  53. Araña, J., Homs, N., Sales, J., Fierro, J.L.G., and Ramirez de la Piscina, P., Catal. Lett., 2001, vol. 72, p. 183.

    Article  Google Scholar 

  54. Wowsnick, G., Teschner, D., Armbrüster, M., Kasatkin, I., Girgsdies, F., Grin, Yu., Schlögl, R., and Behrens, M., J. Catal., 2014, vol. 309, p. 221.

    Article  CAS  Google Scholar 

  55. Bond, G.C., Metal-Catalysed Reactions of Hydrocarbons, New York Springer Science + Business Media, 2005.

    Google Scholar 

  56. Markov, P.V., Bragina, G.O., Rassolov, A.V., Mashkovsky, I.S., Baeva, G.N., Tkachenko, O.P., Yakushev, I.A., Vargaftik, M.N., and Stakheev, A.Yu., Mendeleev Commun., 2016, vol. 26, p. 494.

    Article  CAS  Google Scholar 

  57. Chin, Y.H., Dagle, R., Hu, J.L., Dohnalkova, A.C., and Wang, Y., Catal. Today, 2002, vol. 77, p. 79.

    Article  CAS  Google Scholar 

  58. Mitsudome, T., Takahashi, Y., Ichikawa, S., Mizugaki, T., Jitsukawa, K., and Kaneda, K., Angew. Chem., Int. Ed. Engl., 2013, vol. 52, p. 1481.

    Article  CAS  Google Scholar 

  59. Niu, M., Wang, Y., Li, W., Jiang, J., and Jin, Z., Catal. Commun., 2013, vol. 38, p. 77.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 119991, Russia

    I. S. Mashkovsky, P. V. Markov, G. O. Bragina, A. V. Rassolov, G. N. Baeva & A. Yu. Stakheev

Authors
  1. I. S. Mashkovsky
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. P. V. Markov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. O. Bragina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. V. Rassolov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. G. N. Baeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. Yu. Stakheev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. Yu. Stakheev.

Additional information

Original Russian Text © I.S. Mashkovsky, P.V. Markov, G.O. Bragina, A.V. Rassolov, G.N. Baeva, A.Yu. Stakheev, 2017, published in Kinetika i Kataliz, 2017, Vol. 58, No. 4, pp. 508–520.

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. Intermetallic Pd1–Zn1 nanoparticles in the selective liquid-phase hydrogenation of substituted alkynes. Kinet Catal 58, 480–491 (2017). https://doi.org/10.1134/S0023158417040139

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0023158417040139

Keywords

Search

Navigation