Catalysis Letters

, Volume 139, Issue 1–2, pp 17–25 | Cite as

Assessment of the Catalytic Activities of Novel Brönsted Acidic Ionic Liquid Catalysts



Brönsted acidic ionic liquids (BILs) were synthesized by a two step synthetic protocol. Catalytic activities of BILs were assessed by means of suitable catalytic reactions such as acylation of 2-methoxynapthalene with acetic anhydride, Biginelli reaction to synthesize 3,4-dihydropyrimidin-2(1H)-one, stereoselective synthesis of β-amino ketone via direct Mannich-type reaction and esterification of hexanoic acid with benzyl alcohol. Catalytic activities of BILs were high when compared with those of solid acid catalysts such as ZSM-5, beta, dealuminated beta and Al-SBA-15. BILs catalysts were found to be highly stereo/regio-selective for above mentioned reactions. Novel BILs catalyst offers several attractive features such as low cost, high catalytic activity/selectivity and recyclability.

Graphical Abstract

N-methylimidazole and pyridine derived Brönsted acidic ionic liquids were found to be highly active and stereo/regio-selective compared to various solid acid catalysts in fine chemicals (1–5) synthesis.


Brönsted acidic ionic liquids Acylation Biginelli reaction β-Amino ketone Esterification 



Author thanks Mr. Anu Prathap for his help in NMR and IR measurements. Author thanks Prof. M. K. Surappa, Director, IIT Ropar and Prof. B. D. Gupta, Head, Department of Chemistry, IIT Ropar for their constant encouragements.


  1. 1.
    Corma A, Garcia H (2003) Chem Rev 103:4307CrossRefGoogle Scholar
  2. 2.
    Corma A, Garcia H (2002) Chem Rev 102:3837CrossRefGoogle Scholar
  3. 3.
    Corma A (1997) Chem Rev 97:2373CrossRefGoogle Scholar
  4. 4.
    Corma A (1995) Chem Rev 95:559CrossRefGoogle Scholar
  5. 5.
    Smith MB, March J (2001) March’s advanced organic chemistry, chap 8. Wiley-Interscience, New YorkGoogle Scholar
  6. 6.
    Ritter SK (2001) Chem Eng News 79:63Google Scholar
  7. 7.
    Stöcker M (2005) Microporous Mesoporous Mater 82:257CrossRefGoogle Scholar
  8. 8.
    Ishihara K, Hasegama A, Yamamoto H (2001) Angew Chem Int Ed 40:4077CrossRefGoogle Scholar
  9. 9.
    Srivastava R, Choi M, Ryoo R (2006) Chem Commun:4489Google Scholar
  10. 10.
    Earle MJ, Seddon KR (2000) Pure Appl Chem 72:1391CrossRefGoogle Scholar
  11. 11.
    Welton T (1999) Chem Rev 99:2073CrossRefGoogle Scholar
  12. 12.
    Boon JA, Levisky JA, Pflug JL, Wilkes JS (1986) J Org Chem 51:480CrossRefGoogle Scholar
  13. 13.
    Abbott AP, Capper G, Davies DL, Munro HL, Rasheed RK, Tambyrajah V (2001) Chem Commun:2010Google Scholar
  14. 14.
    Kim YJ, Varma RS (2005) J Org Chem 70:7882CrossRefGoogle Scholar
  15. 15.
    Cole AC, Jensen JL, Ntai L, Loan K, Tran T, Weaver KJ, Forbes DC, Davis JH Jr (2002) J Am Chem Soc 124:5962CrossRefGoogle Scholar
  16. 16.
    Huang JF, Baker GA, Luo H, Hong K, Li QF, Bjerrum NJ, Dai S (2006) Green Chem 8:599CrossRefGoogle Scholar
  17. 17.
    Li X, Eli W (2008) J Mol Catal A 279:159CrossRefGoogle Scholar
  18. 18.
    Srivastava R, Iwasa N, Fujita SI, Arai M (2009) Catal Lett 130:655CrossRefGoogle Scholar
  19. 19.
    Srivastava R, Srinivas D, Ratnasamy P (2006) Microporous Mesoporous Mater 90:314CrossRefGoogle Scholar
  20. 20.
    Gazz, Biginelli P (1893) Chem Ital 23:360Google Scholar
  21. 21.
    Chen X, Xu X, Liu H, Cun L, Gong L (2006) J Am Chem Soc 128:14802CrossRefGoogle Scholar
  22. 22.
    Nilsson BL, Overman LE (2006) J Org Chem 71:7706CrossRefGoogle Scholar
  23. 23.
    Ahmed N, van Lier JE (2007) Tetrahedron Lett 48:5407CrossRefGoogle Scholar
  24. 24.
    Hassani Z, Islami MR, Kalantari M (2006) Biorg Med Chem Lett 16:4479CrossRefGoogle Scholar
  25. 25.
    Suzuki I, Suzumura Y, Takeda K (2006) Tetrahedron Lett 47:7861CrossRefGoogle Scholar
  26. 26.
    Muller R, Goesmann H, Waldmann H (1999) Angew Chem Int Ed 38:184CrossRefGoogle Scholar
  27. 27.
    Arend M, Westerman B (1998) Angew Chem Int Ed 37:1044CrossRefGoogle Scholar
  28. 28.
    Kobyashi S, Ishitani H (1999) Chem Rev 99:1069CrossRefGoogle Scholar
  29. 29.
    Wang YG, Yang YY, Shou WG (2006) Tetrahedron 62:10079CrossRefGoogle Scholar
  30. 30.
    Wang YG, Yang YY, Shou WG (2006) Tetrahedron Lett 47:1845CrossRefGoogle Scholar
  31. 31.
    Azizi N, Torkiyan L, Saidi MR (2006) Org Lett 8:2079CrossRefGoogle Scholar
  32. 32.
    Eftekhari-Sis B, Abdollahifa A, Hashemi MM, Zirak M (2006) Eur J Org Chem 51:52Google Scholar
  33. 33.
    Iimura S, Nobutou D, Manabe K, Kobayashi S (2003) Chem Commun:1644Google Scholar
  34. 34.
    Hayashi Y, Tsuboi W, Ashimine I, Urushima T, Shoji M, Sakai K (2003) Angew Chem Int Ed 42:3677CrossRefGoogle Scholar
  35. 35.
    Bigdeli MA, Nemati F, Mahdavinia GH (2007) Tetrahedron Lett 48:6801CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  1. 1.Department of ChemistryIndian Institute of Technology RoparRupnaharIndia

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