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Liquid-phase Hydrogenation of Phenol to Cyclohexanone over Supported Palladium Catalysts

Department of Chemical Engineering, Shenyang University of Chemical Technology,, China

Received: 29 Jun 2016; Published: 11 Oct 2016.
Open Access Copyright (c) 2016 Bulletin of Chemical Reaction Engineering & Catalysis under

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The ZSM-5, g-Al2O3, SiO2 and MgO supported Pd-catalysts were prepared for the phenol hydrogenation to cyclohexanone in liquid-phase. The natures of these catalysts were characterized by XRD, N2 adsorption-desorption analysis, H2-TPR, CO2-TPD and NH3-TPD. The catalytic performance of the supported Pd-catalyst for phenol hydrogenation to cyclohexanone is closely related to nature of the support and the size of Pd nanoparticles. The Pd/MgO catalyst which possesses higher basicity shows higher cyclohexanone selectivity, but lower phenol conversion owing to the lower specific surface area. The Pd/SiO2 catalyst prepared by precipitation gives higher cyclohexanone selectivity and phenol conversion, due to the moderate amount of Lewis acidic sites, and the smaller size and higher dispersion of Pd nanoparticles on the surface. Under the reaction temperature of 135 oC and H2 pressure of 1 MPa, after reacting for 3.5 h, the phenol conversion of 71.62% and the cyclohexanone selectivity of 90.77% can be obtained over 0.5 wt% Pd/SiO2 catalyst. Copyright © 2016 BCREC GROUP. All rights reserved

Received: 7th March 2016; Revised: 13rd May 2016; Accepted: 7th June 2016

How to Cite: Fan, L., Zhang, L., Shen, Y., Liu, D., Wahab, N., Hasan, M.M. (2016). Liquid-phase Hydrogenation of Phenol to Cyclohexanone over Supported Palladium Catalysts. Bulletin of Chemical Reaction Engineering & Catalysis, 11 (3): 354-362 (doi: 10.9767/bcrec.11.3.575.354-362)


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Keywords: cyclohexanone; phenol; hydrogenation; Pd-catalyst; liquid-phase

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  1. Jianliang, L., Hui, L., Hexing, L. (2007). Liquid-phase selective hydrogenation of phenol to cyclohexanone over Pd-Ce-B/hydrotalcite catalyst. Chinese Journal of Catalysis 28(4): 312-316
  2. Li, H., Liu, J., Li, H. (2008). Liquid-phase selective hydrogenation of phenol to cyclohexanone over the Ce-doped Pd–B amorphous alloy catalyst. Materials Letters 62(2): 297-300
  3. Lin, C.-J., Huang, S.-H., Lai, N.-C., Yang, C.-M. (2015). Efficient Room-Temperature Aqueous-Phase Hydrogenation of Phenol to Cyclohexanone Catalyzed by Pd Nanoparticles Supported on Mesoporous MMT-1 Silica with Unevenly Distributed Functionalities. ACS Catalysis 5(7): 4121-4129
  4. Galvagno, S., Donato, A., Neri, G., Pietropaolo, R. (1991). Hydrogenation of phenol to cyclohexanone over Pd/MgO. Journal of Chemical Technology and Biotechnology 51(2): 145-153
  5. Claus, P., Berndt, H., Mohr, C., Radnik, J., Shin, E.-J., Keane, M. A. (2000). Pd/MgO: catalyst characterization and phenol hydrogenation activity. Journal of Catalysis 192(1): 88-97
  6. Scire, S., Crisafulli, C., Maggiore, R., Minicò, S., Galvagno, S. (1998). Effect of the acid–base properties of Pd–Ca/Al2O3 catalysts on the selective hydrogenation of phenol to cyclohexanone: FT-IR and TPD characterization. Applied Surface Science 136(4): 311-320
  7. Xiang, Y.-z., Kong, L.-n., Lu, C.-s., Ma, L., Li, X.-n. (2010). Lanthanum-promoted Pd/Al2O3 catalysts for liquid phase in situ hydrogenation of phenol to cyclohexanone. Reaction Kinetics, Mechanisms and Catalysis 100(1): 227-235
  8. Watanabe, S., Arunajatesan, V. (2010). Influence of acid modification on selective phenol hydrogenation over Pd/activated carbon catalysts. Topics in Catalysis 53(15-18): 1150-1152
  9. Xiang, Y., Kong, L., Xie, P., Xu, T., Wang, J., Li, X. (2014). Carbon Nanotubes and Activated Carbons Supported Catalysts for Phenol in Situ Hydrogenation: Hydrophobic/Hydrophilic Effect. Industrial & Engineering Chemistry Research 53(6): 2197-2203
  10. Neri, G., Visco, A., Donato, A., Milone, C., Malentacchi, M., Gubitosa, G. (1994). Hydrogenation of phenol to cyclohexanone over palladium and alkali-doped palladium catalysts. Applied Catalysis A: General 110(1): 49-59
  11. Narayanan, S., Krishna, K. (1996). Highly active hydrotalcite supported palladium catalyst for selective synthesis of cyclohexanone from phenol. Applied Catalysis A: General 147(2): L253-L258
  12. Chen, Y., Liaw, C., Lee, L. (1999). Selective hydrogenation of phenol to cyclohexanone over palladium supported on calcined Mg/Al hydrotalcite. Applied Catalysis A: General 177(1): 1-8
  13. Cheng, L., Dai, Q., Li, H., Wang, X. (2014). Highly selective hydrogenation of phenol and derivatives over Pd catalysts supported on SiO2 and g-Al2O3 in aqueous media. Catalysis Communications 57: 23-28
  14. Zhao, M., Shi, J., Hou, Z. (2016). Selective hydrogenation of phenol to cyclohexanone in water over Pd catalysts supported on Amberlyst-45. Chinese Journal of Catalysis 37(2): 234-239
  15. Liu, H., Jiang, T., Han, B., Liang, S., Zhou, Y. (2009). Selective Phenol Hydrogenation to Cyclohexanone Over a Dual Supported Pd–Lewis Acid Catalyst. Science 326(5957): 1250-1252
  16. Ratanathavorn, W., Samart, C., Reubroycharoen, P. (2015). Tinospora crispa-like ZSM-5/silica fibers synthesized by electrospinning and hydrothermal method. Materials Letters 159: 135-137
  17. Amorim, C., Keane, M.A. (2012). Catalytic hydrodechlorination of chloroaromatic gas streams promoted by Pd and Ni: The role of hydrogen spillover. Journal of Hazardous Materials 211–212: 208-217
  18. Fessi, S., Mamede, A.S., Ghorbel, A., Rives, A. (2012). Sol-gel synthesis combined with solid–solid exchange method, a new alternative process to prepare improved Pd/SiO2-Al2O3 catalysts for methane combustion. Catalysis Communications 27: 109-113
  19. Zheng, J., Guo, M., Song, C. (2008). Characterization of Pd catalysts supported on USY zeolites with different SiO2/Al2O3 ratios for the hydrogenation of naphthalene in the presence of benzothiophene. Fuel Processing Technology 89(4): 467-474
  20. Dixit, M., Mishra, M., Joshi, P.A., Shah, D.O. (2013). Physico-chemical and catalytic properties of Mg-Al hydrotalcite and Mg-Al mixed oxide supported copper catalysts. Journal of Industrial and Engineering Chemistry 19(2): 458-468
  21. Kuśtrowski, P., Sułkowska, D., Chmielarz, L., Rafalska-Łasocha, A., Dudek, B., Dziembaj, R. (2005). Influence of thermal treatment conditions on the activity of hydrotalcite-derived Mg-Al oxides in the aldol condensation of acetone. Microporous and Mesoporous Materials 78(1): 11-22
  22. Lónyi, F., Valyon, J. (2001). On the interpretation of the NH3-TPD patterns of H-ZSM-5 and H-mordenite. Microporous and Mesoporous Materials 47(2-3): 293-301
  23. Rodríguez-González, L., Rodríguez-Castellón, E., Jiménez-López, A., Simon, U. (2008). Correlation of TPD and impedance measurements on the desorption of NH3 from zeolite H-ZSM-5. Solid State Ionics 179(35-36): 1968-1973
  24. Chen, J., Tian, S., Lu, J., Xiong, Y. (2015). Catalytic performance of MgO with different exposed crystal facets towards the ozonation of 4-chlorophenol. Applied Catalysis A: General 506: 118-125
  25. Scirè, S., Minicò, S., Crisafulli, C. (2002). Selective hydrogenation of phenol to cyclohexanone over supported Pd and Pd-Ca catalysts: an investigation on the influence of different supports and Pd precursors. Applied Catalysis A: General 235(1): 21-31
  26. Zhang, J., Huang, G., Zhang, C., He, Q., Huang, C., Yang, X., Song, H., Liang, Z., Du, L., Liao, S. (2013). Immobilization of highly active Pd nano-catalysts on functionalized mesoporous silica supports using mercapto groups as anchoring sites and their catalytic performance for phenol hydrogenation. Chinese Journal of Catalysis 34(8): 1519-1526
  27. Pérez, Y., Fajardo, M., Corma, A. (2011). Highly selective palladium supported catalyst for hydrogenation of phenol in aqueous phase. Catalysis Communications 12(12): 1071-1074
  28. Velu, S., Kapoor, M. P., Inagaki, S., Suzuki, K. (2003). Vapor phase hydrogenation of phenol over palladium supported on mesoporous CeO2 and ZrO2. Applied Catalysis A: General 245(2): 317-331

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