Skip to main content
SpringerLink
Log in

Deactivation aspect of BEA zeolite in microwave assisted synthesis of 2-cyclohexyl-4-methyl phenol by cyclohexylation of p-cresol

  • Published:
Journal of Porous Materials Aims and scope Submit manuscript

Abstract

Selective synthesis of 2-cyclohexyl-4-methyl phenol (2-CH-4-MP) by liquid phase alkylation of p-cresol with cyclohexanol and cyclohexene over BEA zeolite has been investigated under microwave as well as conventional heating. Significant acceleration of reaction rate was observed under microwave heating. However, no difference in conversion or selectivity was noticed between the two modes of heating. Various reaction parameters like catalyst amount, mole ratio of reactants, temperature and reaction time showed a significant influence on the distribution of products. With cyclohexanol as alkylating agent, initially formed cyclohexene and O-alkylated product were converted to 2-CH-4-MP with increase in temperature, catalyst amount and reaction time. When cyclohexene is used directly as alkylating agent, C-/O-product ratio also increased with increase in temperature, catalyst amount and reaction time. However, in both the cases, selectivity to 2-CH-4-MP was almost same. Deactivation of BEA zeolite was observed during the reaction possibly due to coking constituents. In an attempt to stabilize the catalytic activity of BEA zeolite, it was dealuminated to different extents by treating with 0.1, 0.2 and 0.5 M solutions of p-toluene sulphonic acid. The catalytic activity and deactivation behaviour of dealuminated samples in the alkylation reaction were investigated.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 1
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13

Similar content being viewed by others

References

  1. J.W. Horvath, C. Falls, Ohio, C.A. Markley, US patent 3,661,825 (1972)

  2. F.X O’Shea, W.B. Von Schmeling, H.M.D. Dudarevitch, US patent 3,301,748 (1967)

  3. Katsumi Inomata, Katsuji douki, Tooru Mizumachi, Shin-ichiro iwanaga, US patent US 6,171,750 B1 (2001)

  4. R. Aiello, G. Giordano, F. Testa (Editors), G. Moon, K. P. Moller, W. Bohringer, C. T. O’Connor, Stud. Surf. Sci. Catal. 142, 635 (2002)

    Google Scholar 

  5. M. Bregolato, V. Bolis, C. Busco, P. Ugliengo, S. Bordiga, F. Cavani, N. Ballarini, L. Maselli, S. Passeri, I. Rossetti, L. Forni, J. Catal. 245, 285 (2007)

    Article  CAS  Google Scholar 

  6. M.E. Sad, C.L. Padro, C.R. Apestegufa, Catal. Today 133–135, 720 (2008)

    Article  Google Scholar 

  7. K.G. Bhattacharyya, A.K. Talukdar, P. Das, S. Sivasanker, J. Mol. Catal. A: Chem. 197, 255 (2003)

    Article  CAS  Google Scholar 

  8. G. Moon, W. Boehringer, C.T. O’Connor, Catal. Today 97, 291 (2004)

    Article  CAS  Google Scholar 

  9. K. Song, J. Guan, S. Wu, Y. Yang, B. Liu, Q. Kan, Catal. Lett. 126, 333 (2008)

    Article  CAS  Google Scholar 

  10. E. Dumitriu, D. Meloni, R. Monaci, V. Solinas, C. R. Chimie 8, 441 (2005)

    Article  CAS  Google Scholar 

  11. R. Anand, T. Daniel, R.J. Lahoti, K.V. Srinivasan, B.S. Rao, Catal. Lett. 81, 241 (2002)

    Article  CAS  Google Scholar 

  12. A. Klein, Duesseldorf, H. Fiege, L. Puppe, Burscheid, W. Jeblick, US patent 4,990,687 (1991)

  13. J.B. Higgins, R.B. LaPierre, J.L. Schlenker, A.C. Rohrman, J.D. Wood, G.T. Kerr, W.J. Rohrbaugh, Zeolites 8, 446 (1988)

    Article  CAS  Google Scholar 

  14. G. Bellussi, G. Pazzuconi, C. Perego, G. Girotti, G. Terzoni, J. Catal. 157, 227 (1995)

    Article  CAS  Google Scholar 

  15. K.S.N. Reddy, B.S. Rao, V.P. Shiralkar, Appl. Catal. A 95, 53 (1993)

    Article  CAS  Google Scholar 

  16. L. Bonetto, M.A. Camblor, A. Corma, J. Perez-Pariente, Appl. Catal. A 8, 37 (1992)

    Google Scholar 

  17. A.J. Hoefnagel, H. van Bekkum, Appl. Catal. A 97, 87 (1993)

    Article  CAS  Google Scholar 

  18. A.E.W. Beers, J.A. van Bokhoven, K.M. de Lathouder, F. Kapteijn, J.A. Moulijn, J. Catal. 218, 239 (2003)

    Article  CAS  Google Scholar 

  19. M. Guisnet, L. Costa, F. Ramoa Ribeiro, J. Mol. Catal. A: Chem. 305, 69 (2009)

    Article  CAS  Google Scholar 

  20. A. Corma, A. Martfnez, P.A. Arroyo, J.L.F. Monteiro, E.F. Sousa-Aguiar, Appl. Catal. A 142, 139 (1996)

    Article  CAS  Google Scholar 

  21. D. Mravec, P. Zavadan, A. Kaszonyi, J. Joffre, P. Moreau, Appl. Catal. A Gen. 257, 49 (2004)

    Article  CAS  Google Scholar 

  22. C. Oliver Kappe, Angew. Chem. Int. Ed. 43, 6250 (2004)

    Google Scholar 

  23. J.P. Tierney, P. Lidstrom (eds.), Microwave Assisted Organic Synthesis (Blackwell, Oxford, 2005)

    Google Scholar 

  24. A. Loupy, Microwaves in Organic Synthesis (Wiley–VCH, Weinheim, 2006)

    Book  Google Scholar 

  25. B. M. Chandra Shekara, B. S. Jai Prakash, Y. S. Bhat, ACS Catal. 1, 193 (2011)

  26. M. Guisnet, P. Magnoux, Appl. Catal. A Gen. 212, 83 (2001)

    Article  CAS  Google Scholar 

  27. M. Bjørgen, S. Kolboe, Appl. Catal. A 225, 285 (2002)

    Article  Google Scholar 

  28. P.A. Parikh, N. Subrahmanyam, Y.S. Bhat, A.B. Halgeri, J. Mol. Catal. A: Chem. 88, 85 (1994)

    Article  CAS  Google Scholar 

  29. J.P. Marques, I. Gener, J.M. Lopes, M. Guisnet, F. Ramoa Ribeiro, Catal. Today 107, 726 (2005)

    Article  Google Scholar 

  30. J.P. Marques, I. Gener, P. Ayrault, J.C. Bordado, J.M. Lopes, F. Ramoa Ribeiro, M. Guisnet, Micropor. Mesopor. Mater. 60, 251 (2003)

    Article  CAS  Google Scholar 

  31. B. Wang, G. Manos, J. Catal. 250, 121 (2007)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors thank the Principal and the Governing Council of Bangalore Institute of Technology for the facilities provided. Thanks are due to Süd chemie India Pvt Ltd. for providing zeolite sample. The authors would like to extend their thanks to Chairman, Chemistry department, BU for TGA, ATR facilities and VTU for financial support.

Author information

Authors and Affiliations

  1. Department of Chemistry, Bangalore Institute of Technology, K.R. Road, Bangalore, 560 004, India

    B. M. Chandra Shekara, B. S. Jai Prakash & Y. S. Bhat

Authors
  1. B. M. Chandra Shekara
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. B. S. Jai Prakash
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Y. S. Bhat
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to B. M. Chandra Shekara.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chandra Shekara, B.M., Jai Prakash, B.S. & Bhat, Y.S. Deactivation aspect of BEA zeolite in microwave assisted synthesis of 2-cyclohexyl-4-methyl phenol by cyclohexylation of p-cresol. J Porous Mater 20, 827–837 (2013). https://doi.org/10.1007/s10934-012-9658-y

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10934-012-9658-y

Keywords

Search

Navigation