Abstract
The properties of phosphorus-modified palladium catalysts in the liquid-phase hydrogenation of nitrobenzene and o-nitrochlorobenzene have been investigated. A general regularity in the reduction of the nitro compounds in the presence of the phosphorus-containing palladium catalysts is an autoacceleration observed at large P: Pd ratios of 0.7–1.5. The autoacceleration is due to a redox process between the intermediate (azoxy derivative) and PdP2, a component of the catalyst nanoparticles. A promoting effect of elemental phosphorus on the chemoselectivity of the Pd-P catalysts in o-nitrochlorobenzene hydrogenation has been discovered. The main factors responsible for the changes in the quantitative characteristics of the phosphorus-modified palladium nanoparticles are considered. Among these factors there are the nature of the nanoparticles, their size, and the state of the surface layer. The properties of the Pd-P catalysts are determined by the proportions of palladium clusters and palladium phosphides (Pd(0) and Pd x P) in the nanoparticles. The formation of the clusters and phosphides has been confirmed by X-ray diffraction and X-ray photoelectron spectroscopy.
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Coq, B. and Figueras, F., Coord. Chem. Rev., 1998, vols. 178–180, p. 1753.
Wang, X., Liang, M., Zhang, J., and Wang, Y., Curr. Org. Chem., 2007, vol. 11, p. 299.
Blaser, H.U., Science, 2006, vol. 313, p. 312.
Eur. Patent 0842920, 2004.
Baumeister, P., Blaser, P.U., Siegrist, U., and Studer, M., Catal. Org. React., 1998, vol. 75, p. 207.
Corma, A., Serna, P., Concepcion, P., and Calvino, J.J., J. Am. Chem. Soc., 2008, vol. 130, p. 8748.
Simagina, V.I., Netskina, V.I., Tayban, E.S., Komova, O.V., Grayfer, E.D., Ischenko, A.V., and Pazhetnov, E.M., Appl. Catal., A, 2010, vol. 379, p. 87.
Cárdenas-Lizana, F., Gómez-Quero, S., and Keane, M., Catal. Commun., 2008, vol. 9, p. 475.
Chen, Y., Qiu, J., Wang, X., and Xiu, J., J. Catal., 2006, vol. 242, p. 227.
Cárdenas-Lizana, F., Pedro, Z.M., Gómez-Quero, S., and Keane, M.A., J. Mol. Catal. A: Chem., 2010, vol. 326, p. 48.
Serna, P. and Corma, A., J. Catal., 2009, vol. 265, p. 19.
Corma, A., González-Arellano, C., Iglesias, M., and Sánchez, F., Appl. Catal., A, 2009, vol. 356, p. 99.
Boronat, M., Concepción, P., Corma, A., González, S., Illas, S., and Serna, P., J. Am. Chem. Soc., 2007, vol. 129, p. 16230.
Yang, P., Jiang, Z., Ying, P., and Li, C., J. Catal., 2008, vol. 253, p. 66.
Ni, Y., Li, J., Zhang, L., Yang, S., and Wei, X., Mater. Res. Bull., 2009, vol. 44, p. 1166.
Cecilia, J.A., Jiménez-Morales, I., Infantes-Molina, A., Rodríguez-Castellón, E., and Jiménez-López, A., J. Mol. Catal. A: Chem., 2013, vols. 368–369, p. 78.
Oyama, S.T., Gott, T., Zhao, H., and Lee, Y.-K., Catal. Today, 2009, vol. 143, p. 94.
Belykh, L.B., Skripov, N.I., Belonogova, L.N., Umanets, V.A., and Shmidt, F.K., Kinet. Catal., 2010, vol. 51, no. 1, p. 42.
Gordon, A.J. and Ford, R.A., The Chemist’s Companion, New York: Wiley, 1972.
Mitchell, J. and Smith, D., Aquametry, New York: Wiley, 1977.
US Patent 3474464, 1969.
Rodionov, V.M., Bogoslovskii, B.M., and Fedorova, A.M., Laboratornoe rukovodstvo po khimii promezhutochnykh produktov i krasitelei (Laboratory Guide to the Chemistry of Intermediate Products and Dyes), Moscow: Goskhimizdat, 1948.
Powder Diffraction File Q, Hanawalt Search Manual: Inorganic Phases, Swarthmore, Penn.: Joint Committee on Powder Diffraction Standards, 1992.
Wiehage, G., Weibke, Fr., and Biltz, W., Z. Anorg. Allg. Chem., 1936, vol. 228, p. 357.
Krátky, V., Králik, M., Kaszonyi, A., and Stolcová, M., Zalibera, I., Mecárová, M., and Hronec, M., Collect. Czech. Chem. Commun., 2003, vol. 68, p. 1819.
Coq, B., Tijani, A., and Figueras, F., J. Mol. Catal. A: Chem., 1991, vol. 68, p. 331.
Xi, C., Cheng, H., Hao, J., Cai, S., and Zhao, F., J. Mol. Catal. A: Chem., 2008, vol. 282, p. 80.
Ma, L., Chen, S., Lu, C., Zhang, Q., and Li, X., Catal. Today, 2011, vol. 173, p. 62.
Shimizu, K., Miyamoto, Y., Kawasaki, T., Tanji, T., Tai, Y., and Satsuma, A., J. Phys. Chem. C, 2009, vol. 113, p. 17803.
Belykh, L.B., Skripov, N.I., Akimov, V.V., Tauson, V.L., Stepanova, T.P., and Shmidt, F.K., Russ. J. Gen. Chem., 2013, vol. 83, no. 12, p. 2260.
Gómez-Sainero, L.M., Seoane, X.L., Fierro, J.L.G., and Arcoya, A., J. Catal., 2002, vol. 209, p. 279.
Lokteva, E.S., Golubina, E.V., Kachevskii, S.A., Kharlanov, A.N., Erokhin, A.V., and Lunin, V.V., Kinet. Catal., 2011, vol. 52, no. 1, p. 145.
Finney, E.E. and Finke, R.G., J. Colloid Interface Sci., 2008, vol. 317, p. 351.
Lefedova, O.V., Smirnova, I.V., and Nemtseva, M.P., Russ. J. Phys. Chem. A, 2009, vol. 83, no. 10, p. 1722.
Zilberberg, I., Pelmenschikov, A., McGrath, C.J., Davis, W., Leszczynska, D., and Leszczynski, J., Int. J. Mol. Sci., 2002, vol. 3, p. 801.
Liu, H., Liang, M., Xiao, C., Zheng, N., Feng, X., Liu, Y., Xie, J., and Wang, Y., J. Mol. Catal. A: Chem., 2009, vol. 308, p. 79.
Reutov, O.A., Kurts, A.L., and Butin, K.P., Organicheskaya khimiya (Organic Chemistry), Moscow: BINOM, 2010, vol. 3.
Peruzzini, M., Consalvi, L., and Romerosa, A., Chem. Soc. Rev., 2005, vol. 34, p. 1038.
Barbaro, P., Vaira, M.D., Peruzzini, M., Costantini, S.S., and Stoppioni, P., Angew. Chem., Int. Ed. Engl., 2008, vol. 47, p. 4425.
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Original Russian Text © L.B. Belykh, N.I. Skripov, T.P. Stepanova, F.K. Shmidt, 2015, published in Kinetika i Kataliz, 2015, Vol. 56, No. 2, pp. 182–190.
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Belykh, L.B., Skripov, N.I., Stepanova, T.P. et al. Liquid-phase hydrogenation of nitrobenzene and o-nitrochlorobenzene in the presence of phosphorus-containing palladium nanoparticles. Kinet Catal 56, 181–189 (2015). https://doi.org/10.1134/S0023158415010036
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DOI: https://doi.org/10.1134/S0023158415010036