Abstract
A comparative catalytic study of Pd–Ag bimetallic catalysts and the commercial Lindlar catalyst (Pd–Pb/CaCO3) has been carried out in the hydrogenation of phenylacetylene (PA) and diphenylacetylene (DPA). The Pd–Ag catalysts have been prepared using the heterobimetallic complex PdAg2(OAc)4(HOAc)4 supported on MgAl2O4 and aluminas (α-Al2O3 and γ-Al2O3). Physicochemical studies have demonstrated that the reduction of supported Pd–Ag complex with hydrogen results in homogeneous Pd–Ag nanoparticles. Equal in selectivity to the Lindlar catalyst, the Pd–Ag catalysts are more active in DPA hydrogenation. The synthesized Pd–Ag catalysts are active and selective in PA hydrogenation as well, but the unfavorable ratio of the rates of the first and second stages of the process makes it difficult to kinetically control the reaction. The most promising results have been obtained for the Pd–Ag2/α-Al2O3 catalyst. Although this catalyst is less active, it is very selective and allows efficient kinetic control of the process to be carried out owing to the fact that, with this catalyst, the rate of hydrogenation of the resulting styrene is much lower than the rate of hydrogenation of the initial PA.
Similar content being viewed by others
References
Mitsudome, T., Takahashi, Y., Ichikawa, S., Mizugaki, T., Jitsukawa, K., and Kaneda, K., Angew. Chem., Int. Ed. Engl., 2013, vol. 52, p. 1481.
Oger, C., Balas, L., Durand, T., and Galano, J.-M., Chem. Rev., 2013, vol. 113, p. 1313.
Karakhanov, E.A., Maksimov, A.L., Aksenov, I.A., Kuznetsov, V.S., Filippova, T.Yu., Kardashev, S.V., and Volkov, D.S., Russ. Chem. Bull., 2014, vol. 63, no. 8, p. 1710.
Wilhite, B.A., McCready, M.J., and Varma, A., Ind. Eng. Chem. Res., 2002, vol. 41, p. 3345.
Domínguez-Domínguez, S., Berenguer-Murcia, A., Linares-Solano, A., and Cazorla-Amorós, D., J. Catal., 2008, vol. 257, p. 87.
Nikolaev, S.A., Zanaveskin, L.N., Smirnov, V.V., Averyanov, V.A., and Zanaveskin, K.L., Russ. Chem. Rev., 2009, vol. 78, p. 231.
Bond, G.C., Metal-Catalysed Reactions of Hydrocarbons, New York Springer Science + Business Media, 2005.
Borodzinski, A. and Bond, G.C., Catal. Rev., 2006, vol. 48, p. 91.
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.
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.
Ponec, V. and Bond, G.C., Stud. Surf. Sci. Catal., 1995, vol. 95, p. 1.
Pei, G.X., Yan Liu, X., 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.
Yang, B., Burch, R., Hardacre, C., Headdock, G., and Hu, P., J. Catal., 2013, vol. 305, p. 264.
Studt, F., Abild-Pedersen, F., Bligaard, T., Sørensen, R.Z., Hviid Christensen, C., and Nørskov, J. K., Science, 2008, vol. 320, p. 1320.
Karakhanov, E.A., Maximov, A.L., Zolotukhina, A.V., Yatmanova, N., and Rosenberg, E., Appl. Organomet. Chem., 2015, vol. 29, p. 777.
Nikolaev, S.A. and Krotova, I.N., Pet. Chem., 2013, vol. 53, no. 6, p. 394.
Chen, Yu-Z., Zhou, Yu-X., Wang, H., Lu, J., Uchida, T., Xu, Q., Yu, S.-H., and Jiang, H.-L., ACS Catal., 2015, vol. 5, p. 2062.
Wang, Z., Yang, L., Zhang, R., Li, L., Cheng, Z., and Zhou, Z., Catal. Today, 2016, vol. 264, p. 37.
Kozitsyna, N.Yu., Nefedov, S.E., Dobrokhotova, Zh.V., Ikorskii, V.N., Stolyarov, I.P., Vargaftik, M.N., and Moiseev, I.I., Nanotechnol. Russ., 2008, vol. 3, nos. 3–4, p. 166.
Mashkovsky, I.S., Baeva, G.N., Stakheev, A.Yu., Vargaftik, M.N., Kozitsyna, N.Yu., and Moiseev, I.I., Mendeleev Commun., 2014, vol. 24, no. 6, p. 355.
Markov, P.V., Bragina, G.O., Baeva, G.N., Tkachenko, O.P., Mashkovskii, I.S., Yakushev, I.A., Kozitsyna, N.Yu., Vargaftik, M.N., and Stakheev, A.Yu., Kinet. Catal., 2015, vol. 56, p. 591.
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.
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.
Stakheev, A.Yu., Isaeva, V.I., Markov, P.V., Turova, O.V., Mashkovskii, I.S., Kapustin, G.I., Saifutdinov, B.R., and Kustov, L.M., Russ. Chem. Bull., 2015, vol. 64, p. 284.
MSD ChemStation Data Analysis Software, B.07.03.2129, Santa Clara, Calif. Agilent Technologies, 2015.
NIST14 Mass Spectral Library & Search Software, Ringoes, M.J.,: Scientific Instrument Services, 2014.
Spee, M.P.R., Boersma, J., Meijer, M.D., Slagt, M.Q., van Koten, G., and Geus, J.W., J. Org. Chem., 2001, vol. 66, p. 1647.
Bond, G.C., Metal-Catalysed Reactions of Hydrocarbons, New York Springer Science + Business Media, 2005.
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. 629.
Markov, P.V., Bragina, G.O., Rassolov, A.V., Mashkovsky, I.S., Baeva, G.N., Tkachenko, O.P., Yakushev, I.A., Vargaftik, M.N., Stakheev, A.Yu., Mendeleev Commun. (in press).
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © A.V. Rassolov, P.V. Markov, G.O. Bragina, G.N. Baeva, I.S. Mashkovskii, I.A. Yakushev, M.N. Vargaftik, A.Yu. Stakheev, 2016, published in Kinetika i Kataliz, 2016, Vol. 57, No. 6, pp. 857–864.
Rights and permissions
About this article
Cite this article
Rassolov, A.V., Markov, P.V., Bragina, G.O. et al. Catalytic properties of nanostructured Pd–Ag catalysts in the liquid-phase hydrogenation of terminal and internal alkynes. Kinet Catal 57, 853–858 (2016). https://doi.org/10.1134/S0023158416060124
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0023158416060124