Skip to main content
Log in

An Efficient and Recyclable Silica Based Inorganic–Organic Hybrid Zinc Catalyst for Transesterification of β-Ketoesters

  • Published:
Journal of Inorganic and Organometallic Polymers and Materials Aims and scope Submit manuscript

Abstract

A new silica based inorganic–organic hybrid zinc catalyst was synthesized and its catalytic activity was investigated for transesterification of β-ketoesters. Polymer supported catalyst was characterized by various techniques such as surface area (BET), elemental and thermogravimetric analyses, FTIR, 13C CPMAS spectral studies and atomic absorption spectroscopy (AAS). The reaction proceeded smoothly in the presence of 0.04 mmol of catalyst in toluene at refluxing conditions. The catalyst revealed higher catalytic activity compared to homogeneous catalyst and was reused without appreciable loss in catalytic activity.

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

Access this article

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

Instant access to the full article PDF.

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. P.M. Price, J.H. Clark, D.J. Macquarrie, J. Chem. Soc., Dalton Trans., 101 (2000)

  2. Q.H. Fan, Y.M. Li, A.S.C. Chan, Chem. Rev. 102, 3385 (2002)

    Article  CAS  Google Scholar 

  3. N.E. Leadbeater, M. Marco, Chem. Rev. 102, 3217 (2002)

    Article  CAS  Google Scholar 

  4. D. Brunel, N. Belloq, P. Sutra, A. Cauvel, M. Laspéras, P. Moreau, F. Di Renzo, A. Galarneau, F. Fajula, Coord. Chem. Rev. 178–180, 1085 (1998)

    Article  Google Scholar 

  5. M.H. Valkenberg, W.F. Hölderich, Catal. Rev. 44, 321 (2002)

    Article  CAS  Google Scholar 

  6. D.E. De Vos, M. Dams, B.F. Sels, P.A. Jacobs, Chem. Rev. 102, 3615 (2002)

    Article  Google Scholar 

  7. B.M.L. Dioos, I.F.J. Vankelecom, P.A. Jacobs, Adv. Synth. Catal. 348, 1413 (2006)

    Article  CAS  Google Scholar 

  8. A. Corma, H. Garcia, Adv. Synth. Catal. 348, 1391 (2006)

    Article  CAS  Google Scholar 

  9. Z.L. Lu, E. Lindner, H.A. Mayer, Chem. Rev. 102, 3543 (2002)

    Article  CAS  Google Scholar 

  10. A.P. Wight, M.E. Davis, Chem. Rev. 102, 3589 (2002)

    Article  CAS  Google Scholar 

  11. R.K. Sharma, C. Sharma, J. Macromol. Sci. Pure Appl. Chem. Part A 48, 155 (2011)

    Article  CAS  Google Scholar 

  12. R.K. Sharma, C. Sharma, Tetrahedron Lett. 51, 4415 (2010)

    Article  CAS  Google Scholar 

  13. R.K. Sharma, D. Rawat, P. Pant, J. Macromol. Sci. Pure Appl. Chem. Part A 45, 394 (2008)

    Article  CAS  Google Scholar 

  14. R.K. Sharma, D. Rawat, J. Inorg. Organomet. Polym. 20, 698 (2010)

    Article  CAS  Google Scholar 

  15. R.K. Sharma, C. Sharma, J. Mol. Catal. A: Chem. 332, 53 (2010)

    Article  CAS  Google Scholar 

  16. R.K. Sharma, C. Sharma, Catal. Commun. 12, 327 (2011)

    Article  CAS  Google Scholar 

  17. J. Otera, Chem. Rev. 93, 1449 (1993)

    Article  CAS  Google Scholar 

  18. U. Schuchardt, R. Sercheli, R.M. Vargas, J. Braz. Chem. Soc. 9, 199 (1998)

    Article  CAS  Google Scholar 

  19. H. Hagiwara, A. Koseki, K. Isobe, K. Shimizu, T. Hoshi, T. Susuki, Synlett, 2188 (2004)

  20. F.C. Da Silva, V.F. Ferreira, R.S. Rianelli, W.C. Perreira, Tetrahedron Lett. 43, 1165 (2002)

    Article  CAS  Google Scholar 

  21. S. Benetti, R. Romagnoli, C. De Risi, G. Spalluto, V. Zanirato, Chem. Rev. 9, 1065 (1995)

    Article  Google Scholar 

  22. C.E. Rehberg, C.H. Fischer, J. Am. Chem. Soc. 66, 1203 (1944)

    Article  CAS  Google Scholar 

  23. S.P. Chavan, P.K. Zubaidha, N.R. Ayyangar, Tetrahedron Lett. 33, 4589 (1992)

    Article  Google Scholar 

  24. D.F. Taber, J.C. Amedio Jr., Y.K. Patel, J. Org. Chem. 50, 3618 (1985)

    Article  CAS  Google Scholar 

  25. D. Seebach, A. Thaler, D. Blaser, S.Y. Ko, Helv. Chim. Acta 74, 1102 (1991)

    Article  CAS  Google Scholar 

  26. C. Blandy, J.L. Pellegatta, P. Cassoux, Catal. Lett. 43, 139 (1997)

    Article  CAS  Google Scholar 

  27. L. Osipow, F.D. Snell, A. Finchler, J. Am. Oil Chem. Soc. 34, 185 (1957)

    Article  CAS  Google Scholar 

  28. E. Santaniello, P. Ferraboschi, P. Grisenti, Enzyme Microb. Technol. 15, 367 (1993)

    Article  CAS  Google Scholar 

  29. J. Otera, N. Dan-Oh, J. Nozaki, J. Org. Chem. 56, 5307 (1991)

    Article  CAS  Google Scholar 

  30. B.C. Ranu, P. Dutta, A. Sarkar, J. Org. Chem. 63, 6027 (1998)

    Article  CAS  Google Scholar 

  31. K. Pradeep, R.K. Pandey, Synlett, 251 (2000)

  32. B.M. Reddy, V.R. Reddy, B. Manohar, Synth. Commun. 29, 1235 (1999)

    Article  CAS  Google Scholar 

  33. B.P. Bandgar, V.S. Sadavarte, L.S. Uppalla, Synlett, 1338 (2001)

  34. B.P. Bandgar. J. Chem. Res. (S), 16 (2001)

  35. G. Shapiro, M. Marzi, J. Org. Chem. 62, 7096 (1997)

    Article  CAS  Google Scholar 

  36. S.P. Chavan, R. Anand, K. Pasupathy, B.S. Rao, Green Chem., 320 (2001)

  37. B.P. Bandgar, V.S. Sadavarte, L.S. Uppalla, Chem. Lett. 9, 894 (2001)

    Article  Google Scholar 

  38. M.I. de Sairre, E.S. Bronze-Uhle, P.M. Donate, Tetrahedron Lett. 46, 2705 (2005)

    Article  Google Scholar 

  39. P. Goswami, S.K. Bharadwaj, Catal. Lett. 124, 100 (2008)

    Article  CAS  Google Scholar 

  40. Y.V.S. Rao, D.E. De Vos, P.A. Jacobs, Angew. Chem. Int. Ed. Engl. 36, 2661 (1997)

    Article  CAS  Google Scholar 

  41. R.K. Sharma, S. Mittal, M. Koel, Crit. Rev. Anal. Chem. 3, 183 (2003)

    Article  Google Scholar 

  42. J.S. Yadav, B.V.S. Reddy, A.D. Krishna, C.S. Reddy, A.V. Narsaiah, J. Mol. Catal. A: Chem. 261, 93 (2007)

    Article  CAS  Google Scholar 

  43. B.S. Balaji, B.M. Chanda, Tetrahedron 54, 13237 (1998)

    Article  CAS  Google Scholar 

  44. D.E. Ponde, V.H. Deshpande, V.J. Bulbule, A. Sudalai, A.S. Gajare, J. Org. Chem. 63, 1058 (1998)

    Article  Google Scholar 

  45. W. Kamel, A.C. Cope, J. Am. Chem. Soc. 65, 1992 (1943)

    Article  Google Scholar 

  46. D.S. Campbell, C.W. Lawrie, J. Chem. Soc. Chem. Commun., 355 (1971)

Download references

Acknowledgment

Authors gratefully acknowledge IISc Bangalore for carrying out solid state NMR analyses.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to R. K. Sharma.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 29 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sharma, R.K., Rawat, D. An Efficient and Recyclable Silica Based Inorganic–Organic Hybrid Zinc Catalyst for Transesterification of β-Ketoesters. J Inorg Organomet Polym 21, 619–626 (2011). https://doi.org/10.1007/s10904-011-9525-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-011-9525-3

Keywords

Navigation