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Efficient cyclohexyl acrylate production by direct addition of acrylic acid and cyclohexene over SBA-15-SO3H

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Abstract

A set of propysulfonic acid modified mesostructured silica materials (SBA-15-SO3H) were prepared by a convenient one-pot co-condensation method. Samples were characterized by XRD, FT-IR, Py-FTIR, N2 adsorption–desorption, elemental analysis and acid–base titration. The catalysts exhibited excellent activities and selectivities for addition esterification of acrylic acid and cyclohexene. The highest catalytic activity (82.8 %) and selectivity (92.6 %) were obtained over SBA-15-SO3H (15 %). The efficient catalytic performance of SBA-15-SO3H (15 %) was attributed to the high surface area, proper mesopore texture and presence of sulfonic acid groups in its structure. SBA-15-SO3H catalyst was easily separated and recycled with high stability.

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References

  1. A. Bulai, M.L. Jimeno, J.S. Roman, Macromolecules 28, 7363 (1995)

    Article  CAS  Google Scholar 

  2. J. Lilja, D.Y. Murzin, T. Salmi, J. Aumo, P.M. Arvela, M. Sundell, J. Mol. Catal. A Chem. 182, 555 (2002)

    Article  Google Scholar 

  3. K. Tanabe, Appl. Catal. A Gen. 113, 147 (1994)

    Article  CAS  Google Scholar 

  4. E.V. Spinacé, J.M. Vaz, Catal. Commun. 4, 91 (2003)

    Article  Google Scholar 

  5. H. Nagahara, M. Ono, M. Konishi, Appl. Surf. Sci. 121, 48 (1997)

    Google Scholar 

  6. J.C. Choi, K. Kohno, D. Masuda, H. Yasuda, T. Sakakura. Chem. Commun. 44, 777 (2008)

    Article  Google Scholar 

  7. G. Jignesh, M. Surendra, M. Sanjay, Ind. Eng. Chem. Res. 42, 2146 (2003)

    Article  Google Scholar 

  8. R. Kumar, A. Katariya, H. Freund, Org. Process Res. Dev. 15, 527 (2011)

    Article  CAS  Google Scholar 

  9. Y. Yamamoto, S. Hatanaka, K. Tsuji, Appl. Catal. A Gen. 344, 55 (2008)

    Article  CAS  Google Scholar 

  10. V. Hugues, M.E. Road, Pluakdaeng, W.O. Patent 2006087297A1 (2006)

  11. J.A. Melero, R.V. Grieken, G. Morales, Chem. Rev. 106, 3790 (2006)

    Article  CAS  Google Scholar 

  12. R.I. Kureshy, I. Ahmad, N.H. Khan, S.H.R. Abdi, K. Pathak, R.V. Jasra, J. Catal. 238, 134 (2006)

    Article  CAS  Google Scholar 

  13. M.E. Davis, Nature 417, 813 (2002)

    Article  CAS  Google Scholar 

  14. B.P. Wu, Z.W. Tong, X.D. Yuan, J. Porous Mater. 18, 475 (2011)

    Article  Google Scholar 

  15. S. Park, T.J. Kim, Y.M. Chung, S.H. Oh, I.K. Song, Catal. Lett. 130, 296 (2009)

    Article  CAS  Google Scholar 

  16. J.A. Melero, R.V. Grieken, G. Morales, V. Nuno, Catal. Commun. 5, 131 (2004)

    Article  CAS  Google Scholar 

  17. J. Pérez-Pariente, I. D′ıaz, F. Mohino, E. Sastre, Appl. Catal. A Gen. 254, 173 (2003)

    Article  Google Scholar 

  18. X.C. Guo, Z.F. Qin, W.B. Fan, G.F. Wang, R.H. Zhao, S.Y. Peng, J.G. Wang, Catal. Lett. 128, 405 (2009)

    Article  CAS  Google Scholar 

  19. J.P. Dacquin, A.F. Lee, C. Pirez, K. Wilson, Chem. Commun. 48, 212 (2012)

    Article  CAS  Google Scholar 

  20. M.A. Naik, D. Sachdev, A. Dubey, Catal. Commun. 11, 1148 (2010)

    Article  CAS  Google Scholar 

  21. R.I. Kureshy, I. Ahmad, K. Pathak, N.K. Khan, S.H.R. Abdi, R.V. Jasra, Catal. Commun. 10, 572 (2009)

    Article  CAS  Google Scholar 

  22. X.Y. Liu, L. Zhu, T. Zhao, J.F. Lan, W.F. Yan, H.X. Zhang, Micropor. Mesopor. Mater. 142, 614 (2011)

    Article  CAS  Google Scholar 

  23. S.J. Miao, B.H. Shanks, Appl. Catal. A Gen. 359, 113 (2009)

    Article  CAS  Google Scholar 

  24. J.K. Shon, X.D. Yuan, C.H. Ko, H.I. Lee, S.S. Thakur, M. Kang, M.S. Kang, D.H. Li, J.N. Kim, J. Ind. Eng. Chem. 13, 1201 (2007)

    CAS  Google Scholar 

  25. D. Margolese, J.E. Melero, S.C. Christiansen, B.F. Chmelka, G.D. Stucky, Chem. Mater. 12, 2448 (2000)

    Article  CAS  Google Scholar 

  26. J. Machado, J.E. Castanheiro, I. Matos, A.M. Ramos, J. Vital, I.M. Fonseca, Micropor. Mesopor. Mater. 163, 237 (2012)

    Article  CAS  Google Scholar 

  27. S.J. Miao, B.H. Shanks, J. Catal. 279, 136 (2011)

    Article  CAS  Google Scholar 

  28. B. Sow, S. Hamoudi, M.H. Zahedi-Niaki, S. Kaliaguine, Micropor. Mesopor. Mater. 79, 129 (2005)

    Article  CAS  Google Scholar 

  29. D. Das, J.F. Lee, S. Cheng, Chem. Commun. 21, 2178 (2001)

    Article  Google Scholar 

  30. S. Shylesh, P.P. Samuel, Ch. Srilakshmi, R. Parischa, A.P. Singh, J. Mol. Catal. A Chem. 274, 153 (2007)

    Article  CAS  Google Scholar 

  31. J.C. Juan, J.C. Zhang, M.A. Yarmo, Catal. Lett. 126, 319 (2008)

    Article  CAS  Google Scholar 

  32. S. Brunauer, L.S. Deming, W.E. Deming, E. Teller, J. Am. Chem. Soc. 62, 1723 (1940)

    Article  CAS  Google Scholar 

  33. J.A. Melero, G.D. Stucky, R.V. Grieken, G. Morales, J. Mater. Chem. 12, 1664 (2002)

    Article  CAS  Google Scholar 

  34. B. Dragoi, E. Dumitriu, C. Guimon, A. Auroux, Micropor. Mesopor. Mater. 121, 7 (2009)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was financial supported by National Natural Science Foundation of China (Project No. 21276126), Jiangsu Province Higher Education Natural Science Foundation (Project No. 09KJA530004) and Prospective Joint Research Project of Jiangsu Province (Project No. BY2011105).

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Authors and Affiliations

  1. Jiangsu Key Laboratory of Industrial Water-Conservation and Emission Reduction, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, 210009, People’s Republic of China

    Feng Zhou, Jihai Tang, Xiaoli Zhou, Xian Chen & Mifen Cui

  2. State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, 210009, People’s Republic of China

    Zhaoyang Fei & Xu Qiao

Authors
  1. Feng Zhou
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  2. Jihai Tang
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  3. Zhaoyang Fei
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  4. Xiaoli Zhou
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  5. Xian Chen
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  6. Mifen Cui
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  7. Xu Qiao
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Correspondence to Jihai Tang or Xu Qiao.

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Zhou, F., Tang, J., Fei, Z. et al. Efficient cyclohexyl acrylate production by direct addition of acrylic acid and cyclohexene over SBA-15-SO3H. J Porous Mater 21, 149–155 (2014). https://doi.org/10.1007/s10934-013-9759-2

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  • DOI: https://doi.org/10.1007/s10934-013-9759-2

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