Skip to main content
SpringerLink
Log in

Catalytic activity of SBA-15-grafted indium tri-isopropoxide in chemoselective MPV reductions

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

Abstract

Indium tri-isopropoxide-containing heterogeneous In(OiPr)3–SBA-15 catalyst were synthesized by grafting method and were then used as catalyst in the Meerwein–Ponndorf–Verley (MPV) reduction of various carbonyl compounds using 2-propanol as the hydrogen transfer agent. The prepared new heterogeneous catalyst, In(OiPr)3–SBA-15, was characterized in details by using XRD, 29Si NMR,13C NMR, TEM, N2 adsorption and ICP-OES. New heterogeneous catalyst has been studied in the chemoselective MPV reduction of unsaturated aldehydes and ketones. Good activity and selectivity to the reduced unsaturated alcohols, citronellol, cinnamalcohol, α-ionol, 3-methyl-2-butanol, geraniol, nerol were observed over indium tri-isopropoxide supported on silica. The In(OiPr)3–SBA-15 catalyst is recyclable up to six cycles without any significant loss in its catalytic activity. Eventually, In(OiPr)3–SBA-15 has been found that active catalyst in the MPV reactions of carbonyl compounds including unsaturated aldehydes and ketones with excellent conversion, selectivity and reusability.

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

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 3
Scheme 4

Similar content being viewed by others

References

  1. G. Brieger, T.J. Nestrick, Chem. Rev. 74, 567–580 (1974)

    Article  CAS  Google Scholar 

  2. E.J. Creyghton, R.S. Downing, J. Mol. Catal. A Chem. 134, 47–61 (1998)

    Article  CAS  Google Scholar 

  3. E.J. Creyghton, J. Huskens, J.C. van der Waal, H. van Bekkum, in Heterogeneous Catalysis and Fine Chemicals IV, ed. by H.U. Blaser, A. Baiker, R. Prins (Elsevier, Amsterdam, 1997)

    Google Scholar 

  4. J.E. Bailey, M. Bohnet, J. Brinker, Ullmann’s Encyclopedia of Technical Chemistry, 6th edn. (Wiley-VCH, London, 2000)

    Google Scholar 

  5. E.J. Creyghton, S.D. Ganeshie, R.S. Downing, H. van Bekkum, J. Mol. Catal. A 115, 457–472 (1997)

    Article  CAS  Google Scholar 

  6. P.J. Kunkeler, B.J. Zuurdeeg, J.C. van der Waal, J.A. van Bokhoven, D.C. Koningsberger, H. van Bekkum, J. Catal. 180, 234 (1998)

    Article  CAS  Google Scholar 

  7. A. Corma, M.E. Domine, S. Valencia, J. Catal. 215, 294 (2003)

    Article  CAS  Google Scholar 

  8. R. Anwander, C. Palm, Stud. Surface Sci. 117, 413 (1999)

    Google Scholar 

  9. R. Anwander, C. Palm, G. Gerstberger, O. Groeger, G. Engelhardt, Chem. Commun. 1811–1812 (1998)

  10. V.A. Ivanov, J. Bachelier, F. Audry, J.C. Lavalley, J. Mol. Catal. 91, 45 (1994)

    Article  CAS  Google Scholar 

  11. P. Leyrit, C. Mc Gill, F. Quignard, A. Choplin, J. Mol. Catal. A Chem. 112, 395–400 (1996)

    Article  CAS  Google Scholar 

  12. J.C. Van der Waal, E.J. Creyghton, P.J. Kunkeler, K. Tan, H. Van Bekkum, Top. Catal. 4, 261–268 (1997)

    Article  Google Scholar 

  13. C.T. Kresge, M.E. Leonowicz, W.J. Roth, J.C. Vartuli, J.S. Beck, Nature 359, 710–712 (1992)

    Article  CAS  Google Scholar 

  14. J.Y. Ying, C.P. Mehnert, M.S. Wong, Angew. Chem. Int. Ed. 38, 56–77 (1999)

    Article  CAS  Google Scholar 

  15. F. Schüth, Chem. Mater. 13, 3184–3195 (2001)

    Article  Google Scholar 

  16. Y. Wan, D.Y. Zhao, Chem. Rev. 107, 2821–2860 (2007)

    Article  CAS  Google Scholar 

  17. Y. Han, D. Zhang, Curr. Opin. Chem. Eng. 1, 129–137 (2012)

    Article  CAS  Google Scholar 

  18. W.J.J. Stevens, K. Lebeau, M. Mertens, G. van Tendeloo, P. Cool, E.F. Vansant, J. Phys. Chem. B 110, 9183–9187 (2006)

    Article  CAS  Google Scholar 

  19. A. Taguchi, F. Schüth, Microporous Mesoporous Mater. 77, 1–45 (2005)

    Article  CAS  Google Scholar 

  20. A. Corma, Chem. Rev. 97, 2373–2419 (1997)

    Article  CAS  Google Scholar 

  21. F. Zhang, Y. Yan, H. Yang, Y. Meng, C. Yu, B. Tu, D. Zhao, J. Phys. Chem. 109, 8723–8732 (2005)

    Article  CAS  Google Scholar 

  22. N. Rahmat, A.A. Zuhairi, A. Rahman Mohamed, Am. J. Appl. Sci. 7, 1579–1586 (2010)

    Article  CAS  Google Scholar 

  23. W. M. Haynes. in: CRC Handbook of Chemistry and Physics: A Ready-Reference Book of Chemical and Physical Data, ed. by David R. Lide (CRC Press, Boca Raton, 2010). ISBN 978-1-4398-2077-3

  24. A.F. Holleman, E. Wiberg, N. Wiberg. “Thallium”. Lehrbuch der Anorganischen Chemie (in German) (91–100 ed.). (Walter de Gruyter, 1985), pp. 892–893. ISBN 3-11-007511-3

  25. D. Zhao, J. Feng, Q. Huo, N. Melosh, G.H. Fredrickson, B.F. Chmelka, G.D. Stucky, Science 279, 548–552 (1998)

    Article  CAS  Google Scholar 

  26. D. Zhao, Q. Huo, J. Feng, B.F. Chmelka, G.D. Stucky, J. Am. Chem. Soc. 120, 6024–6036 (1998)

    Article  CAS  Google Scholar 

  27. D. Zhao, J. Sun, Q. Li, G.D. Stucky, Chem. Mater. 12, 275–279 (2000)

    Article  CAS  Google Scholar 

  28. D. Zhao, Q. Huo, J. Feng, B.F. Chmelka, G.D. Stucky, Am. Chem. Soc. 120, 6024–6036 (1998)

    Article  CAS  Google Scholar 

  29. J.S. Lettow, Y.J. Han, P. Schmidt-Winkel, P.D. Yang, D.Y. Zhao, G.D. Stucky, J.Y. Ying, Langmuir 16, 8291–8295 (2000)

    Article  CAS  Google Scholar 

  30. M. Misono, N. Noijri, Appl. Catal. 64, 1 (1990)

    Article  CAS  Google Scholar 

  31. F.J. Urbano, M.A. Aramendía, A. Marinas, J.M. Marinas, J. Catal. 268, 79–88 (2009)

    Article  CAS  Google Scholar 

  32. J.M. Hidalgo, C.J. Sanchidrián, J.R. Ruiz, Appl. Catal. A 470, 311–317 (2014)

    Article  CAS  Google Scholar 

  33. J.P. Thielemann, F. Girgsdies, R. Schlögl, C. Hess, Beilstein J. Nanotechnol. 2, 110–118 (2011)

    Article  CAS  Google Scholar 

  34. H. Darmstadt, C. Roy, S. Kaliaguine, S.H. Joo, R. Ryoo, Microporous Mesoporous Mater. 60, 139–149 (2003)

    Article  CAS  Google Scholar 

  35. M. Kruk, M. Jaroniec, C.H. Ko, R. Ryoo, Chem. Mater. 12, 1961–1968 (2000)

    Article  CAS  Google Scholar 

  36. A. Sterczynska, A.D. Marczewska, M.S. Bartkowiak, J.Z. Piotrowska, M. Jarek, K. Domin, J. Therm. Anal. Calorim. 118, 263–276 (2014)

    Article  CAS  Google Scholar 

  37. J.L. Namy, J. Souppe, J.H.B. Collin Kagan, J. Org. Chem. 49, 2045–2049 (1984)

    Article  CAS  Google Scholar 

  38. B. Uysal, B.S. Buyuktas, Arkıvoc 14, 134–140 (2007)

    Article  Google Scholar 

  39. B. Uysal, B.S. Oksal, J. Chem. Sci. 123, 681–685 (2011)

    Article  CAS  Google Scholar 

  40. J. Lee, T. Ryu, S. Park, P.H. Lee, J. Org. Chem. 77, 4821–4825 (2012)

    Article  CAS  Google Scholar 

  41. B. Uysal, B.S. Oksal, Appl. Catal. A Gen. 435, 204–216 (2012)

    Article  Google Scholar 

  42. S. Shylesh, M.P. Kapoor, L.R. Juneja, P.P. Samuel, C. Srilakshmi, A.P. Singh, J. Mol. Catal. A Chem. 301, 118–126 (2009)

    Article  CAS  Google Scholar 

  43. S. Narayanan, Bull. Catal. Soc. Ind. 2, 107–121 (2003)

    Google Scholar 

  44. W. Bonrath, T. Netscher, Appl. Catal. A 280, 55–73 (2005)

    Article  CAS  Google Scholar 

  45. A. Corma, S. Iborra, A. Velty, Chem. Rev. 107, 2411–2502 (2007)

    Article  CAS  Google Scholar 

  46. A. Stolle, T. Gallert, C. Schmöger, B. Ondruschka, RSC Adv. 3, 2112–2153 (2013)

    Article  CAS  Google Scholar 

  47. Y. Zhu, S. Liu, S. Jaenicke, G. Chuah, Catal. Today 97, 249–255 (2004)

    Article  CAS  Google Scholar 

  48. S. Carnesecchi, Y. Schneider, J. Ceraline, B. Duranton, F. Gosse, N. Seiler, F. Raul, J. Pharmacol. Exp. Ther. 298, 197–200 (2001)

    CAS  Google Scholar 

  49. P. Selvam, S.U. Sonavane, S.K. Mohapatra, R.V. Jayaram, Adv. Synth. Catal. 346, 542–544 (2004)

    Article  CAS  Google Scholar 

  50. B. Uysal, B.S. Oksal, Res. Chem. Intermed. (2013). doi:10.1007/s11164-013-1498-0)

    Google Scholar 

  51. J. Lopez, J.S. Valente, J.M. Clacens, F. Figueras, J. Catal. 208, 30–37 (2002)

    Article  CAS  Google Scholar 

  52. Y. Zhu, S. Jaenicke, G.K. Chuah, J. Catal. 218, 396–404 (2003)

    Article  CAS  Google Scholar 

  53. M. De bruyn, D.E. De Vos, P.A. Jacobs, Adv. Synth. Catal. 344, 1120–1125 (2002)

    Article  CAS  Google Scholar 

  54. Y. Zhu, G.K. Chuah, S. Jaenicke, J. Catal. 241, 25–33 (2006)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The financial support of Scientific and Technical Research Council of Turkey (TUBITAK) under Grant No. 113Z389 is gratefully acknowledged.

Author information

Authors and Affiliations

  1. Technical Sciences Vocational High School, Pamukkale University, Denizli, Turkey

    Burcu Uysal

  2. Department of Chemistry, Art and Science Faculty, Giresun University, Giresun, Turkey

    Birsen S. Oksal

Authors
  1. Burcu Uysal
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Birsen S. Oksal
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Burcu Uysal.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Uysal, B., Oksal, B.S. Catalytic activity of SBA-15-grafted indium tri-isopropoxide in chemoselective MPV reductions. J Porous Mater 22, 1053–1064 (2015). https://doi.org/10.1007/s10934-015-9980-2

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10934-015-9980-2

Keywords

Search

Navigation