DOI: https://doi.org/10.9767/bcrec.13.1.1226.24-35

Catalytic Properties of Alumina-Supported Ruthenium, Platinum, and Cobalt Nanoparticles towards the Oxidation of Cyclohexane to Cyclohexanol and Cyclohexanone

Laboratoire de Catalyse et Synthèse en Chimie Organique, Faculté des Sciences, Université de Tlemcen, Algeria

Received: 26 May 2017; Revised: 17 Jul 2017; Accepted: 18 Jul 2017; Published: 2 Apr 2018; Available online: 22 Jan 2018.
Open Access Copyright (c) 2018 by Authors, Published by BCREC Group under http://creativecommons.org/licenses/by-sa/4.0.

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Abstract

A series of metal-loaded (Ru, Pt, Co) alumina catalysts were evaluated for the catalytic oxidation of cyclohexane using tertbutylhydroperoxide (TBHP) as oxidant and acetonitrile or acetic acid as solvent. These materials were prepared by the impregnation method and then characterized by Inductively Coupled Plasma-Optical Emission Spectroscopy (ICP-OES), H2 chemisorption, Fourier Transformed Infrared Spectroscopy (FTIR), High-Resolution Transmission Electron Microscopy (HRTEM), and X-ray Diffraction (XRD). All the prepared materials acted as efficient catalysts. Among them, Ru/Al2O3 was found to have the best catalytic activity with enhanced cyclohexane conversion of 36 %, selectivity to cyclohexanol and cyclohexanone of 96 % (57.6 mmol), and cyclohexane turnover frequency (TOF) of 288 h-1. 

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Keywords: Cyclohexane oxidation, Alumina, TBHP, Metal.
Funding: Algerian Ministry of Higher Education and Scientific Research

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  1. Sheldon, R.A. (1981) Metal-catalyzed Epoxidation of Olefins with Hydroperoxides, in Aspects of Homogeneous Catalysis, R. Ugo (Ed.); Reidel, Dordrecht, Volume 4, pp. 3-70
  2. Hao, J., Liu, B., Cheng, H., Wang, Wang, Q.J., Cai, S., Zhao, F. (2009). Cyclohexane Oxidation on A Novel Ti70Zr10Co20 Catalyst Containing Quasicrystal. Chemical Communications, 23: 3460-3462
  3. Sato, K., Aoki, M., Noyori, R. (1998). A "Green" Route to Adipic Acid: Direct Oxidation of Cyclohexenes with 30 Percent Hydrogen Peroxide. Science, 281: 1646-1647
  4. Cavani, F., Centi, G., Perathoner, S., Trifiro, F. (2009). Sustainable Industrial Processes, WILEY-VCH Verlag GmbH & Co, KGaA, Weinheim
  5. Zhou, L., Xu, J., Miao, H., Wang, F., Li, X. (2005). Catalytic Oxidation of Cyclohexane to Cyclohexanol and Cyclohexanone over Co3O4 Nanocrystals with Molecular Oxygen. Applied Catalysis A: General, 292: 223-228
  6. Chen, C., Xu, J., Zhang, Q., Ma, H., Miao, H., Zhou, L. (2009). Direct Synthesis of Bifunctionalized Hexagonal Mesoporous Silicas and Its Catalytic Performance for Aerobic Oxidation of Cyclohexane. The Journal of Physical Chemistry C, 113: 2855-2860
  7. Deng, Y., Ma, Z., Wang, K., Chen, J. (1999). Clean Synthesis of Adipic Acid by Direct Oxidation of Cyclohexene with H2O2 over Peroxytungstate-Organic Complex Catalysts. Green Chemistry, 1: 275-276
  8. Thomas, J.M., Raja, R. (2006). Innovations in Oxidation Catalysis Leading to A Sustainable Society. Catalysis Today, 117: 22-31
  9. Guo, C.C., Chu, M.F., Liu, Q., Liu, Y., Guo, D.C., Liu, X.Q. (2003). Effective Catalysis of Simple Metalloporphyrins for Cyclohexane Oxidation with Air in the Absence of Additives and Solvents. Applied Catalysis A: General, 246: 303-309
  10. Burda, C., Chen, X., Narayanan, R., El-Sayed, M.A. (2005). Chemistry and Properties of Nanocrystals of Different Shapes. Chemical Reviews, 105: 1025-1102
  11. Wang, C., Chen, L., Qi, Z. (2013). One-pot Synthesis of Gold Nanoparticles Embedded in Silica for Cyclohexane Oxidation. Catalysis Science & Technology, 3: 1123-1128
  12. Wu, P., Xiong, Z., Loh, K.P., Zhao, X.S. (2011). Selective Oxidation of Cyclohexane over Gold Nanoparticles Supported on Mesoporous Silica Prepared in the Presence of Thioether Functionality. Catalysis Science & Technology, 1: 285-294
  13. Bradley, J.S. In: Schmidt G., editor. (1994). Clusters and Colloids from Theory to Applications, VCH, Weinheim, Germany
  14. Liu, X., Conte, M., Sankar, M., He, Q., Murphy, D.M., Morgan, D., Jenkins, R.L., Knight, D., Whiston, K., Kiely, C.J., Hutchings, G.J. (2015). Liquid Phase Oxidation of Cyclohexane Using Bimetallic Au-Pd/MgO Catalysts. Applied Catalysis A: General, 504: 373-380
  15. Mahdavi, V., Hasheminasab, H.R. (2015). Liquid-phase Efficient Oxidation of Cyclohexane over Cobalt Promoted VPO Catalyst Using Tert-butylhydroperoxide. Journal of the Taiwan Institute of Chemical Engineers, 51: 53-62
  16. Makgwane, P.R., Ray, S.S. (2014). Efficient Room Temperature Oxidation of Cyclohexane over Highly Active Hetero-mixed WO3/V2O5 Oxide Catalyst. Catalysis Communications, 54: 118-123
  17. Bellifa, A., Choukchou-Braham, A., Kappenstein, C., Pirault-Roy, L. (2014). Preparation and Characterization of MTiX for the Catalytic Oxidation of Cyclohexane. RSC Advances, 4: 22374-22379
  18. Hayati, F., Chandren, S., Hamdan, H., Nur, H. (2014). The Role of Ti and Lewis Acidity in Manganese Oxide Octahedral Molecular Sieves Impregnated with Titanium in Oxidation Reactions. Bulletin of Chemical Reaction Engineering & Catalysis, 9: 28-38
  19. Carabineiro, S.A.C., Martins, L.M., Avalos-Borja, M., Buijnsters, J.G., Pombeiro, A.J.L., Figueiredo, J.L. (2013). Gold Nanoparticles Supported on Carbon Materials for Cyclohexane Oxidation with Hydrogen Peroxide. Applied Catalysis A: General, 467: 279-290
  20. Huang, G., Shen, L., Luo, Z.C., Hu, Y.D., Guo, Y.A., Wei, S.J. (2013). Use of A Boehmite Immobilized Cobalt Tetra(4-carboxyl) Phenylporphyrin Catalyst for the Aerobic Oxidation of Cyclohexane to Ketone and Alcohol. Catalysis Communications, 32: 108-112
  21. Lu, X.H., Yuan, H.X., Lei, J., Zhang, J.L., Yu, A.A., Zhou, D., Xia, Q.H. (2012). Selective Oxidation of Cyclohexane to KA-oil with Oxygen over Active Co3O4 in A Solvent-free System. Indian Journal of Chemistry, 51A: 420-427
  22. Bernas, A., Kumar, N., Laukkanen, P., Vayrynen, J., Salmi, T., Murzin, D.Y. (2004). Influence of Ruthenium Precursor on Catalytic Activity of Ru/Al2O3 Catalyst in Selective Isomerization of Linoleic Acid to Cis-9,trans-11- and Trans-10,cis-12-conjugated Linoleic Acid. Applied Catalysis A: General, 267: 121-133
  23. Perkas, N., Minh, D.P., Gallezot, P., Gedanken, A., Besson, M. (2005). Platinum and Ruthenium Catalysts on Mesoporous Titanium and Zirconium Oxides for the Catalytic Wet Air Oxidation of Model Compounds. Applied Catalysis B: Environmental, 59: 121-130
  24. Bergeret, G., Gallezot, P. (1997). In: Handbook of Heterogeneous Catalysis. Wiley-VCH, Weinheim
  25. Coloma, F., Sepulveda-Escribano, A., Fierro, J.L., Rodriguez- Reinoso, F. (1997). Gas Phase Hydrogenation of Crotonaldehyde over Pt/Activated Carbon Catalysts: Influence of the Oxygen Surface Groups on the Support. Applied Catalysis A: General, 150: 165-183
  26. Rekkab-Hammoumraoui, I., Choukchou-Braham, A., Pirault-Roy, L., Kappenstein, C. (2011). Catalytic Oxidation of Cyclohexane to Cyclohexanone and Cyclohexanol by Tert-Butyl Hydroperoxide over Pt/oxide Catalysts. Bulletin of Materials Science, 34: 1127-1135
  27. Kumar, R., Sithambaram, S., Suib, S.L. (2009). Cyclohexane Oxidation Catalyzed by Manganese Oxide Octahedral Molecular Sieves-Effect of Acidity of the Catalyst. Journal of Catalysis, 262: 304-313
  28. Bellifa, A., Lahcene, D., Tchenar, Y.N., Choukchou-Braham, A., Bachir, R., Bedrane, S., Kappenstein, C. (2006). Preparation and Characterization of 20 wt.% V2O5-TiO2 Catalyst Oxidation of Cyclohexane. Applied Catalysis A: General, 305: 1-6
  29. Zhao, R., Wang, Y., Guo, Y., Guo, Y., Liu, X., Zhang, Z., Wang, Y., Zhan, W., Lu, G. (2006). A Novel Ce/AlPO-5 Catalyst for Solvent-free Liquid Phase Oxidation of Cyclohexane by Oxygen. Green Chemistry, 8: 459-466
  30. Wangcheng, Z., Guanzhong, L., Yanglong, G., Yun, G., Yanqin, W., Yunsong, W., Zhigang, Z., Xiaohui, L. (2008). Synthesis of Cerium-doped MCM-48 Molecular Sieves and Its Catalytic Performance for Selective Oxidation of Cyclohexane. Journal of Rare Earths, 26: 515-522
  31. Lu, G., Zhao, R., Qian, G., Qia, Y., Wang, X., Suo, J. (2004). A Highly Efficient Catalyst Au/MCM-41 for Selective Oxidation Cyclohexane Using Oxygen. Catalysis Letters, 97: 115-118
  32. Li, H., She, Y., Wang, T. (2012). Advances and Perspectives in Catalysts for Liquid-phase Oxidation of Cyclohexane. Frontiers of Chemical Science and Engineering, 6: 356-368
  33. Liu, Y., Tsunoyama, H., Akita, T., Xie, S., Tsukuda, T. (2011). Aerobic Oxidation of Cyclohexane Catalyzed by Size-Controlled Au Clusters on Hydroxyapatite: Size Effect in the Sub-2 nm Regime. ACS Catalysis, 1: 2-6
  34. Rekkab-Hammoumraoui, I., Benabadji-Soulimane, R., El Korso-Hamza Reguig, S., Choukchou-Brabam, A., Bachir, R. (2010). Preparation and Characterization of X wt-%Ru/Al2O3 Catalysts for Cyclohexane Oxidation Using Tert-butyl Hydroperoxide. Research Journal of Pharmaceutical, Biological and Chemical Sciences, 1: 240-239
  35. Sooknoi, T., Limtrakul, J., (2002). Activity Enhancement by Acetic Acid in Cyclohexane Oxidation Using Ti-containing Zeolite Catalyst. Applied Catalysis A: General, 233: 227-237
  36. Adam, F., Wong, J., Ng, E. (2013). Fast Catalytic Oxidation of Phenol over Iron Modified Zeolite L Nanocrystals. Chemical Engineering Journal, 214: 63-67
  37. Arends, I.W.C.E., Sheldon, R.A. (2001). Activities and Stabilities of Heterogeneous Catalysts in Selective Liquid Phase Oxidations: Recent Developments. Applied Catalysis A: General, 212: 175-187
  38. Fraile, J.M., Garcia, J.I., Mayoral, J.A., Vispe, E. (2001). Effect of the Reaction Conditions on the Epoxidation of Alkenes with Hydrogen Peroxide Catalyzed by Silica-Supported Titanium Derivatives. Journal of Catalysis, 204: 146-156
  39. Busca, G., Finocchio, E., Ramis, G., Ricchiardi, G. (1996). On the Role of Acidity In Catalytic Oxidation. Catalysis Today, 32: 133-143
  40. Conte, M., Liu, X., Murphy, D.M., Whiston, K., Hutchings, G.J. (2012). Cyclohexane Oxidation Using Au/MgO: An Investigation of the Reaction Mechanism. Physical Chemistry Chemical Physics, 14: 16279-16285
  41. Yuan, H.X., Xia, Q.H., Zhan, H.J., Lu, X.H., Su, K.X. (2006). Catalytic Oxidation of Cyclohexane to Cyclohexanone and Cyclohexanol by Oxygen in A Solvent-free System over Metal-containing ZSM-5 Catalysts. Applied Catalysis A: General, 304: 178-184
  42. Kharkova, T.V., Arest-Yakubovich, I.L., Lipes, V.V. (1989). Kinetic Model of the Liquid-phase Oxidation of Cyclohexane. I. Homogeneous Proceedings of the Process. Kinetics and Catalysis, 30: 954-958
  43. Loncarevic, D., Krstic, J., Bankovic, P., Anic, S., Cupic, Z. (2007). Temperature Dependence of Catalytic Cyclohexane Partial Oxidation in A Polytetrafluoroethylene Reactor. Russian Journal of Physical Chemistry A., 81: 1398-1401
  44. Akhrem, A.A., Metelitsa, D.I., Skurko, M.E., (1975). Chemical Model of the Enzyme System for Hydroxylating Cyclohexane. Bioorganic Chemistry, 4: 307-316
  45. Larsen, R.G., Saladino, A.C., Hunt, T.A., Mann, J.E., Xu, M., Grassian, V.H., Larsen, S.C. (2001). A Kinetic Study of the Thermal and Photochemical Partial Oxidation of Cyclohexane with Molecular Oxygen in Zeolite Y. Journal of Catalysis, 204: 440-449
  46. Mahajani, S.M., Sharma, M.M., Sridhar, T. (1999). Uncatalyzed Oxidation of Cyclohexene. Chemical Engineering Science, 54: 3967-3976
  47. Suresh, A.K., Sridhar, T., Potter, O.E. (1988). Autocatalytic Oxidation of Cyclohexane-Modeling Reaction Kinetics. AlChE Journal, 34: 69-80
  48. Wang, J., Zhao, H., Zhang, X., Liu, R., Hu, Y. (2008). Oxidation of Cyclohexane Catalyzed by TS-1 in Ionic Liquid with Tert-butyl-hydroperoxide. Chinese Journal of Chemical Engineering, 16: 373-375
  49. Selvam, P., Mohapatra, S.K. (2004). Synthesis, Characterization and Catalytic Properties of Mesoporous TiHMA Molecular Sieves: Selective Oxidation of Cycloalkanes. Microporous and Mesoporous Materials, 73: 137-149
  50. Liu, X., He, J., Yang, L., Wang, Y., Zhang, S., Wang, W., Wang, J. (2010). Liquid-phase Oxidation of Cyclohexane to Cyclohexanone over Cobalt-Doped SBA-3. Catalysis Communications, 11: 710-714
  51. Dapurkar, S.E., Sakthivel, A., Selvam, P. (2004). Mesoporous VMCM-41: Highly Efficient and Remarkable Catalyst for Selective Oxidation of Cyclohexane to Cyclohexanol. Journal of Molecular Catalysis A: Chemical, 223: 241-250
  52. Wu, P., Bai, P., Loh, K.P., Zhao, X.S. (2010). Au Nanoparticles Dispersed on Functionalized Mesoporous Silica for Selective Oxidation of Cyclohexane. Catalysis Today, 158: 220-227
  53. Aboelfetoh, E.F., Fechtelkord, M., Pietschnig, R. (2010). Structure and Catalytic Properties of MgO-supported Vanadium Oxide in the Selective Oxidation of Cyclohexane. Journal of Molecular Catalysis A: Chemical, 318: 51-59
  54. Silva, F.P., Jacinto, M.J., Landers, R., Rossi, L.M. (2011). Selective Allylic Oxidation of Cyclohexene by a Magnetically Recoverable Cobalt Oxide Catalyst. Catalysis Letters, 141: 432-437

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