Skip to main content
SpringerLink
Log in

Alkylation of aromatic compounds with multi-component Lewis acid catalysts of ZnCl2 and ionic liquids with different organic cations

  • Published:
Reaction Kinetics and Catalysis Letters Aims and scope Submit manuscript

Abstract

Alkylation of aromatic compounds with various alkylating agents such as benzyl chloride, benzyl alcohol and isopropyl chloride were investigated using ZnCl2 based ionic liquid (ILs) Lewis acid catalysts. Multi-component Lewis acid catalysts of ZnCl2 and ionic liquids such as 1-butyl-3-methylimidazolium bromide, 1-butylpyridinium bromide, cholin chloride and tetrabutylammonium bromide were prepared, supported on silica gel, and compared for alkylation reactions with various alkylating agents. Among the IL-based catalysts, 1-butyl-3-methyl imidazolium-bromide-ZnCl2 and 1-butylpyridinium bromide-ZnCl2 are highly active.

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

Similar content being viewed by others

References

  1. A. Corma, H. Garcia: Chem. Rev., 103, 4307 (2003).

    Article  CAS  Google Scholar 

  2. A. Corma: Chem. Rev., 97, 2373 (1997).

    Article  CAS  Google Scholar 

  3. S.K. Sikdar, S.G. Howell: J. Cleaner Prod., 6, 253 (1998).

    Article  Google Scholar 

  4. G.A. Olah: Friedel-Crafts and Related Reactions, p. II. Interscience Publishers, New York, 1963.

    Google Scholar 

  5. Y. Sugi, Y. Kubota, K. Komura, N. Sugiyama, M. Hayashi, J.-H. Kim, G. Seo: Appl. Catal. A: Gen., 299, 157 (2006).

    Article  CAS  Google Scholar 

  6. G.D. Yadav, P. Kumar: Appl. Catal. A: Gen., 286, 61 (2005).

    Article  CAS  Google Scholar 

  7. R. Srivastava, M. Choi, R. Ryoo: Chem. Comm., 4889 (2006).

  8. L. Xiao, K. E. Johnson, R.G. Treble: J. Mol. Catal. A: Chem., 214, 121 (2004).

    Article  CAS  Google Scholar 

  9. M.K. Potdar, S.S. Mohile, M.M. Salunkhe: Tetrahedron Lett., 42, 9285 (2001)

    Article  CAS  Google Scholar 

  10. D. Yin, C. Li, L. Tao, N. Yu, S. Hu, D. Yin: J. Mol. Catal. A: Chem., 245, 260 (2006).

    Article  CAS  Google Scholar 

  11. H. Xin, Q. Wu, M. Han, D. Wang, Y. Jin: Appl. Catal. A: Gen., 292, 354 (2005).

    Article  CAS  Google Scholar 

  12. S. Cui, B. Lu, Q. Cai, X. Cai, X. Li, X. Xiao, L. Hou, Y. Han: Ind. Eng. Chem. Res. 45, 1571 (2006).

    Article  CAS  Google Scholar 

  13. Y.J. Kim, R.S. Verma: J. Org. Chem., 70, 7882 (2005).

    Article  CAS  Google Scholar 

  14. T.W. Bastock, J.H. Clark: Speciality Chemicals, Elsevier, London, 1991.

    Google Scholar 

  15. A.D. Harford, H.W. Vernon: US Patent 2 897 112 (1956).

  16. J. Howarth, K. Hanlon, D. Fayne, P. McCormac: Tetrahedron Lett., 38, 3097 (1997).

    Article  CAS  Google Scholar 

  17. S. Tait, R.A. Osteryoung: Inorg. Chem., 23, 4352 (1984).

    Article  CAS  Google Scholar 

  18. K.M. Dieter, C.J. Dymek, Jr., N.E. Heimer, J.W. Rovang, J.S. Wilkes: J. Am. Chem. Soc., 110, 2722 (1988).

    Article  CAS  Google Scholar 

  19. J-L. Thomas, J. Howarth, K. Hanlon, D. Mc Guirk: Tetrahedron Lett., 41, 413 (2000).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Division of Chemical Process Engineering, Graduate School of Engineering Hokkaido University, Sapporo, 060-8628, Japan

    Rajendra Srivastava, Shin-Ichiro Fujita, Shuhei Okamura & Masahiko Arai

Authors
  1. Rajendra Srivastava
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shin-Ichiro Fujita
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shuhei Okamura
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Masahiko Arai
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Masahiko Arai.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Srivastava, R., Fujita, SI., Okamura, S. et al. Alkylation of aromatic compounds with multi-component Lewis acid catalysts of ZnCl2 and ionic liquids with different organic cations. React Kinet Catal Lett 96, 55–64 (2009). https://doi.org/10.1007/s11144-009-5422-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11144-009-5422-y

Keywords

Search

Navigation