Table of Contents Author Guidelines Submit a Manuscript
Journal of Nanomaterials
Volume 2015 (2015), Article ID 738089, 9 pages
http://dx.doi.org/10.1155/2015/738089
Research Article

Fe3+-Exchanged Titanate Nanotubes: A New Kind of Highly Active Heterogeneous Catalyst for Friedel-Crafts Type Benzylation

1State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology, Harbin 150090, China
2Department of Chemistry, Harbin Institute of Technology, Harbin 150001, China

Received 6 January 2015; Accepted 20 April 2015

Academic Editor: Takuya Tsuzuki

Copyright © 2015 Yunchen Du et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. K. Mertins, I. Iovel, J. Kischel, A. Zapf, and M. Beller, “Transition-metal-catalyzed benzylation of arenes and heteroarenes,” Angewandte Chemie International Edition, vol. 44, no. 2, pp. 238–242, 2004. View at Publisher · View at Google Scholar · View at Scopus
  2. Y. Li, Y. Chen, L. Li et al., “A simple co-impregnation route to load highly dispersed Fe(III) centers into the pore structure of SBA-15 and the extraordinarily high catalytic performance,” Applied Catalysis A: General, vol. 366, no. 1, pp. 57–64, 2009. View at Publisher · View at Google Scholar · View at Scopus
  3. V. R. Choudhary, S. K. Jana, and B. P. Kiran, “Alkylation of benzene by benzyl chloride over H-ZSM-5 zeolite with its framework Al completely or partially substituted by Fe or Ga,” Catalysis Letters, vol. 59, no. 2-4, pp. 217–219, 1999. View at Publisher · View at Google Scholar · View at Scopus
  4. B. Coq, V. Gourves, and F. Figuéras, “Benzylation of toluene by benzyl chloride over protonic zeolites,” Applied Catalysis A, General, vol. 100, no. 1, pp. 69–75, 1993. View at Publisher · View at Google Scholar · View at Scopus
  5. V. R. Choudhary, S. K. Jana, and B. P. Kiran, “Highly active Si-MCM-41-supported Ga2O3 and In2O3 catalysts for friedel-crafts-type benzylation and acylation reactions in the presence or absence of moisture,” Journal of Catalysis, vol. 192, no. 2, pp. 257–261, 2000. View at Publisher · View at Google Scholar · View at Scopus
  6. S. K. Das, M. K. Bhunia, A. K. Sinha, and A. Bhaumik, “Self-assembled mesoporous zirconia and sulfated zirconia nanoparticles synthesized by triblock copolymer as template,” Journal of Physical Chemistry C, vol. 113, no. 20, pp. 8918–8923, 2009. View at Publisher · View at Google Scholar · View at Scopus
  7. N. B. Shrigadi, A. B. Shinde, and S. D. Samant, “Study of catalytic activity of free and K10-supported iron oxyhydroxides and oxides in the Friedel-Crafts benzylation reaction using benzyl chloride/alcohol to understand their role in the catalysis by the Fe-exchanged/impregnated K10 catalysts,” Applied Catalysis A: General, vol. 252, no. 1, pp. 23–35, 2003. View at Publisher · View at Google Scholar · View at Scopus
  8. T. Cseri, S. Békássy, F. Figueras, and S. Rizner, “Benzylation of aromatics on ion-exchanged clays,” Journal of Molecular Catalysis. A, Chemical, vol. 98, no. 2, pp. 101–107, 1995. View at Publisher · View at Google Scholar · View at Scopus
  9. Y. Q. Jiang, K. F. Lin, Y. N. Zhang et al., “Fe-MCM-41 nanoparticles as versatile catalysts for phenol hydroxylation and for Friedel-Crafts alkylation,” Applied Catalysis A: General, vol. 445-446, pp. 172–179, 2012. View at Publisher · View at Google Scholar · View at Scopus
  10. Y. Izumi, M. Ogawa, and K. Urabe, “Alkali metal salts and ammonium salts of Keggin-type heteropolyacids as solid acid catalysts for liquid-phase Friedel-Crafts reactions,” Applied Catalysis A: General, vol. 132, no. 1, pp. 127–140, 1995. View at Publisher · View at Google Scholar · View at Scopus
  11. Y. C. Du, S. Liu, Y. Y. Ji et al., “Highly efficient synthesis of Fe-containing mesoporous materials by using semi-fluorinated surfactant and their high activities in Friedel-Crafts alkylations,” Catalysis Today, vol. 131, no. 1–4, pp. 70–75, 2008. View at Publisher · View at Google Scholar · View at Scopus
  12. N. D. Cuong, N. D. Hoa, T. T. Hoa et al., “Nanoporous hematite nanoparticles: Synthesis and applications for benzylation of benzene and aromatic compounds,” Journal of Alloys and Compounds, vol. 582, pp. 83–87, 2014. View at Publisher · View at Google Scholar · View at Scopus
  13. M. S. Hamdy and G. Mul, “TUD-1-encapsulated HY zeolite: a new hierarchical microporous/mesoporous composite with extraordinary performance in benzylation reactions,” ChemCatChem, vol. 5, no. 10, pp. 3156–3163, 2013. View at Publisher · View at Google Scholar · View at Scopus
  14. K. Y. Leng, Y. Wang, C. M. Hou et al., “Enhancement of catalytic performance in the benzylation of benzene with benzyl alcohol over hierarchical mordenite,” Journal of Catalysis, vol. 306, pp. 100–108, 2013. View at Publisher · View at Google Scholar · View at Scopus
  15. Z. C. Miao, H. L. Song, H. H. Zhao, L. L. Xu, and L. J. Chou, “One-pot synthesis of mesoporous ZrPW solid acid catalyst for liquid phase benzylation of anisole,” Catalysis Science & Technology, vol. 4, no. 3, pp. 838–850, 2014. View at Publisher · View at Google Scholar · View at Scopus
  16. V. R. Choudhary and S. K. Jana, “Benzylation of benzene by benzyl chloride over Fe-, Zn-, Ga- and In-modified ZSM-5 type zeolite catalysts,” Applied Catalysis A: General, vol. 224, no. 1-2, pp. 51–62, 2002. View at Publisher · View at Google Scholar · View at Scopus
  17. M. Salavati-Niasari, J. Hasanalian, and H. Najafian, “Alumina-supported FeCl3, MnCl2, CoCl2, NiCl2, CuCl2, and ZnCl2 as catalysts for the benzylation of benzene by benzyl chloride,” Journal of Molecular Catalysis A: Chemical, vol. 209, no. 1-2, pp. 209–214, 2004. View at Publisher · View at Google Scholar · View at Scopus
  18. A. Vinu, D. P. Sawant, K. Ariga et al., “Direct synthesis of well-ordered and unusually reactive FeSBA-15 mesoporous molecular sieves,” Chemistry of Materials, vol. 17, no. 21, pp. 5339–5345, 2005. View at Publisher · View at Google Scholar · View at Scopus
  19. Y. Y. Sun, S. Walspurger, J.-P. Tessonnier, B. Louis, and J. Sommer, “Highly dispersed iron oxide nanoclusters supported on ordered mesoporous SBA-15: a very active catalyst for Friedel-Crafts alkylations,” Applied Catalysis A: General, vol. 300, no. 1, pp. 1–7, 2006. View at Publisher · View at Google Scholar · View at Scopus
  20. Z. B. Lei, S. Y. Bai, L. Q. Dang et al., “Fe2O3/SBA-15 catalyst synthesized by chemical vapor infiltration for Friedel-Crafts alkylation reaction,” Microporous and Mesoporous Materials, vol. 123, no. 1–3, pp. 306–313, 2009. View at Publisher · View at Google Scholar · View at Scopus
  21. J. L. Gu, X. Dong, S. P. Elangovan et al., “Simultaneous pore enlargement and introduction of highly dispersed Fe active sites in MSNs for enhanced catalytic activity,” Journal of Solid State Chemistry, vol. 186, pp. 208–216, 2012. View at Publisher · View at Google Scholar · View at Scopus
  22. M. E. L. Preethi, T. Sivakumar, and M. Palanichami, “Room temperature efficacious synthesis of diphenylmethane over Fe/Al-MCM-41 catalysts,” Catalysis Communications, vol. 11, no. 10, pp. 876–879, 2010. View at Publisher · View at Google Scholar · View at Scopus
  23. K. Bachari, J. M. M. Millet, B. Benaïchouba, O. Cherifi, and F. Figueras, “Benzylation of benzene by benzyl chloride over iron mesoporous molecular sieves materials,” Journal of Catalysis, vol. 221, no. 1, pp. 55–61, 2004. View at Publisher · View at Google Scholar · View at Scopus
  24. A. Arafat and Y. Alhamed, “Catalytic activity of mesoporous catalysts in Friedel-Crafts benzylation of benzene,” Journal of Porous Materials, vol. 16, no. 5, pp. 565–572, 2009. View at Publisher · View at Google Scholar · View at Scopus
  25. C. Anand, G. Lawrence, A. A. Elzatahry et al., “Highly dispersed and active iron oxide nanoparticles in SBA-15 with different pore sizes for the synthesis of diphenylmethane,” Science of Advanced Materials, vol. 6, no. 7, pp. 1618–1626, 2014. View at Publisher · View at Google Scholar
  26. C. Anand, S. V. Priya, G. Lawrence et al., “Cage type mesoporous ferrosilicate catalysts with 3D structure for benzylation of aromatics,” Catalysis Today, vol. 204, pp. 125–131, 2013. View at Publisher · View at Google Scholar · View at Scopus
  27. T. Kasuga, M. Hiramatsu, A. Hoson, T. Sekino, and K. Niihara, “Formation of titanium oxide nanotube,” Langmuir, vol. 14, no. 12, pp. 3160–3163, 1998. View at Publisher · View at Google Scholar · View at Scopus
  28. X. Sun and Y. Li, “Synthesis and characterization of ion-exchangeable titanate nanotubes,” Chemistry: A European Journal, vol. 9, no. 10, pp. 2229–2238, 2003. View at Publisher · View at Google Scholar · View at Scopus
  29. Z. S. Hong, X. Z. Zheng, X. K. Ding, L. L. Jiang, M. D. Wei, and K. M. Wei, “Complex spinel titanate nanowires for a high rate lithium-ion battery,” Energy and Environmental Science, vol. 4, no. 5, pp. 1886–1891, 2011. View at Publisher · View at Google Scholar · View at Scopus
  30. D. V. Bavykin, A. A. Lapkin, P. K. Plucinski, J. M. Friedrich, and F. C. Walsh, “Reversible storage of molecular hydrogen by sorption into multilayered TiO2 nanotubes,” The Journal of Physical Chemistry B, vol. 109, no. 41, pp. 19422–19427, 2005. View at Publisher · View at Google Scholar · View at Scopus
  31. H.-H. Ou, C.-H. Liao, Y.-H. Liou, J.-H. Hong, and S.-L. Lo, “Photocatalytic oxidation of aqueous ammonia over microwave-induced titanate nanotubes,” Environmental Science & Technology, vol. 42, no. 12, pp. 4507–4512, 2008. View at Publisher · View at Google Scholar · View at Scopus
  32. T. Wang, W. Liu, N. Xu, and J. Ni, “Adsorption and desorption of Cd(II) onto titanate nanotubes and efficient regeneration of tubular structures,” Journal of Hazardous Materials, vol. 250-251, pp. 379–386, 2013. View at Publisher · View at Google Scholar · View at Scopus
  33. D. V. Bavykin, A. A. Lapkin, P. K. Plucinski, L. Torrente-Murciano, J. M. Friedrich, and F. C. Walsh, “Deposition of Pt, Pd, Ru and Au on the surfaces of titanate nanotubes,” Topics in Catalysis, vol. 39, no. 3-4, pp. 151–160, 2006. View at Publisher · View at Google Scholar
  34. M. Kitano, E. Wada, K. Nakajima et al., “Protonated titanate nanotubes with Lewis and Brønsted acidity: relationship between nanotube structure and catalytic activity,” Chemistry of Materials, vol. 25, no. 3, pp. 385–393, 2013. View at Publisher · View at Google Scholar · View at Scopus
  35. E. Wada, M. Kitano, K. Nakajima, and M. Hara, “Effect of preparation conditions on the structural and acid catalytic properties of protonated titanate nanotubes,” Journal of Materials Chemistry A, vol. 1, no. 41, pp. 12768–12774, 2013. View at Publisher · View at Google Scholar · View at Scopus
  36. Q. Chen, G. H. Du, S. Zhang, and L. M. Peng, “The structure of trititanate nanotubes,” Acta Crystallographica Section B: Structural Science, vol. 58, no. 4, pp. 587–593, 2002. View at Publisher · View at Google Scholar · View at Scopus
  37. W. Liu, T. Wang, A. G. L. Borthwick et al., “Adsorption of Pb2+, Cd2+, Cu2+ and Cr3+ onto titanate nanotubes: competition and effect of inorganic ions,” Science of the Total Environment, vol. 456-457, pp. 171–180, 2013. View at Publisher · View at Google Scholar · View at Scopus
  38. C.-K. Lee, K.-S. Lin, C.-F. Wu, M.-D. Lyu, and C.-C. Lo, “Effects of synthesis temperature on the microstructures and basic dyes adsorption of titanate nanotubes,” Journal of Hazardous Materials, vol. 150, no. 3, pp. 494–503, 2008. View at Publisher · View at Google Scholar · View at Scopus
  39. X. K. Li and Y. S. Zhong, “Ion-exchangeable titanate nanotubes with visible light responsive photocatalytic activities for dyes degradation,” Journal of Nanoscience and Nanotechnology, vol. 14, no. 9, pp. 7151–7156, 2014. View at Publisher · View at Google Scholar
  40. Y. X. Tang, D. G. Gong, Y. K. Lai et al., “Hierarchical layered titanate microspherulite: formation by electrochemical spark discharge spallation and application in aqueous pollutant treatment,” Journal of Materials Chemistry, vol. 20, no. 45, pp. 10169–10178, 2010. View at Publisher · View at Google Scholar · View at Scopus
  41. M. Qamar, S. J. Kim, and A. K. Ganguli, “TiO2-based nanotubes modified with nickel: synthesis, properties, and improved photocatalytic activity,” Nanotechnology, vol. 20, no. 45, Article ID 455703, 2009. View at Publisher · View at Google Scholar · View at Scopus
  42. B. C. Viana, O. P. Ferreira, A. G. Souza Filho et al., “Decorating titanate nanotubes with CeO2 nanoparticles,” Journal of Physical Chemistry C, vol. 113, no. 47, pp. 20234–20239, 2009. View at Publisher · View at Google Scholar · View at Scopus
  43. S.-T. Myung, N. Takahashi, S. Komaba et al., “Nanostructured TiO2 and its application in lithium-ion storage,” Advanced Functional Materials, vol. 21, no. 17, pp. 3231–3241, 2011. View at Publisher · View at Google Scholar · View at Scopus
  44. M. Kim, S.-H. Hwang, S. K. Lim, and S. Kim, “Effects of ion exchange and calcinations on the structure and photocatalytic activity of hydrothermally prepared titanate nanotubes,” Crystal Research and Technology, vol. 47, no. 11, pp. 1190–1194, 2012. View at Publisher · View at Google Scholar · View at Scopus
  45. L. Shi, L. X. Cao, W. Liu, G. Su, R. J. Gao, and Y. L. Zhao, “A study on partially protonated titanate nanotubes: enhanced thermal stability and improved photocatalytic activity,” Ceramics International, vol. 40, no. 3, pp. 4717–4723, 2014. View at Publisher · View at Google Scholar · View at Scopus
  46. L. Guo, Z. Q. Zhou, and H. M. Yuan, “Hydrothermal synthesis and magnetic properties of Fe3+-doped multiferroic hexagonal rare-earth manganates,” Journal of Alloys and Compounds, vol. 616, pp. 454–460, 2014. View at Publisher · View at Google Scholar
  47. Y. C. Du, Y. Yang, S. Liu, N. Xiao, Y. L. Zhang, and F.-S. Xiao, “Mesoporous aluminophosphates and Fe-aluminophosphates with highly thermal stability and large surface area templated from semi-fluorinated surfactant,” Microporous and Mesoporous Materials, vol. 114, no. 1–3, pp. 250–256, 2008. View at Publisher · View at Google Scholar · View at Scopus
  48. V. R. Choudhary, R. Jha, and V. S. Narkhede, “In-Mg-hydrotalcite anionic clay as catalyst or catalyst precursor for Friedel-Crafts type benzylation reactions,” Journal of Molecular Catalysis A: Chemical, vol. 239, no. 1-2, pp. 76–81, 2005. View at Publisher · View at Google Scholar · View at Scopus
  49. V. R. Choudhary and R. Jha, “GaClx- or GaAlClx-grafted Si-MCM-41: highly active and moisture insensitive/stable catalyst for the acylation and benzylation of benzene, naphthalene and substituted benzenes,” Applied Catalysis A: General, vol. 333, no. 1, pp. 42–48, 2007. View at Publisher · View at Google Scholar · View at Scopus
  50. N. He, S. Bao, and Q. Xu, “Fe-containing mesoporous molecular sieves materials: very active Friedel-Crafts alkylation catalysts,” Applied Catalysis A: General, vol. 169, no. 1, pp. 29–36, 1998. View at Publisher · View at Google Scholar · View at Scopus
  51. K. Y. Leng, S. N. Sun, B. T. Wang, L. Sun, W. Xu, and Y. Y. Sun, “Benzylation of benzene with benzyl chloride on iron-containing mesoporous mordenite,” Catalysis Communications, vol. 28, pp. 64–68, 2012. View at Publisher · View at Google Scholar · View at Scopus
  52. V. R. Choudhary, S. K. Jana, N. S. Patil, and S. K. Bhargava, “Friedel-Crafts type benzylation and benzoylation of aromatic compounds over H beta zeolite modified by oxides or chlorides of gallium and indium,” Microporous and Mesoporous Materials, vol. 57, no. 1, pp. 21–35, 2003. View at Publisher · View at Google Scholar · View at Scopus
  53. Y. C. Du, S. Liu, Y. L. Zhang, F. Nawaz, Y. Y. Ji, and F. S. Xiao, “Urea-assisted synthesis of hydrothermally stable Zr-SBA-15 and catalytic properties over their sulfated samples,” Microporous and Mesoporous Materials, vol. 121, no. 1–3, pp. 185–193, 2009. View at Publisher · View at Google Scholar · View at Scopus
  54. K. Bachari and O. Cherifi, “Study of the benzylation of benzene and other aromatics by benzyl chloride over transition metal chloride supported mesoporous SBA-15 catalysts,” Journal of Molecular Catalysis A: Chemical, vol. 260, no. 1-2, pp. 19–23, 2006. View at Publisher · View at Google Scholar · View at Scopus