Skip to main content
SpringerLink
Log in

Fe-amino acid complexes immobilized on silica gel as active and highly selective catalysts in cyclohexene epoxidation

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

In this work, the syntheses, structure, superoxide dismutase (SOD) activity, and the catalytic use in the oxidative transformations of cyclohexene of covalently grafted Fe(III)-complexes formed with various or various combinations of C-protected amino acid (l-histidine, l-tyrosine, l-cysteine and l-cystine) ligands are presented. The structural features of the surface complexes were studied by XANES/EXAFS and mid/far-IR spectroscopies. The compositions of the complexes were determined by ICP-MS and the Kjeldahl method. The SOD activities of the materials were evaluated in a biochemical test reaction. The obtained materials were used as catalysts for the oxidation of cyclohexene with peracetic acid in acetone. Both covalent grafting and building the complex onto the surface of the chloropropylated silica gel were successful in most cases. In many instances, the obtained structures and the coordinating groups were found to substantially vary upon changing the conditions of the syntheses. All the covalently immobilized Fe(III)-complexes displayed SOD activities, and most of them were found to be capable of catalyzing the oxidation of cyclohexene with appreciably high activities and outstanding epoxide selectivities.

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
Scheme 1

Similar content being viewed by others

References

  1. K.M. Koeller, C.H. Wong, Nature 409, 232 (2001)

    Article  CAS  Google Scholar 

  2. U. Hanefeld, L. Gardossi, E. Magner, Chem. Soc. Rev. 38, 453 (2009)

    Article  CAS  Google Scholar 

  3. U.T. Bornscheuer, Angew. Chem. Int. Ed. 42, 3336 (2003)

    Article  CAS  Google Scholar 

  4. D.J. Xuereb, R. Raja, Catal. Sci. Technol. 1, 517 (2011)

    Article  CAS  Google Scholar 

  5. J.A. Labinger, J. Mol. Catal. A Chem. 220, 27 (2004)

    Article  CAS  Google Scholar 

  6. M. Luechinger, A. Kienhöfer, G.D. Pirngruber, Chem. Mater. 18, 1330 (2006)

    Article  CAS  Google Scholar 

  7. K. Suzuki, P.D. Oldenburg, L. Que Jr, Angew. Chem. Int. Ed. 47, 1887 (2008)

    Article  CAS  Google Scholar 

  8. B.M. Weckhuysen, J. Am. Chem. Soc. 128, 3208 (2006)

    Article  Google Scholar 

  9. A.-F. Miller, in Handbook of Metalloproteins, ed. by A. Messerschmidt, R. Huber, K. Wieghardt, T. Poulos (Wiley, Chichester, 2001), pp. 668–682

  10. M.L. Ludwig, A.L. Metzger, K.A. Pattridge, W.C. Stallings, J. Mol. Biol. 219, 335 (1991)

    Article  CAS  Google Scholar 

  11. M.S. Lath, M.M. Dixon, K.A. Pattridge, W.C. Stallings, J.A. Fee, M.L. Ludwig, Biochem. 34, 1646 (1995)

    Article  Google Scholar 

  12. F. Farzaneh, S. Sohrabi, M. Ghiasi, M. Ghandi, V. Mehdi Ghandi, J. Porous Mater. 20, 267 (2013)

    Article  CAS  Google Scholar 

  13. M. Halma, K.A.D. de Freitas Castro, C. Taviot-Gueho, V. Prévot, C. Forano, F. Wypych, S. Nakagaki, J. Catal. 257, 233 (2008)

  14. A. Baso, L.D. Martin, C. Ebert, L. Gardossi, P. Linda, F. Sibilla, Tetrahedron Lett. 44, 5889 (2003)

    Article  Google Scholar 

  15. H.H.P. Yiu, P.A. Wright, J. Mater. Chem. 15, 3690 (2005)

    Article  CAS  Google Scholar 

  16. C. Ispas, I. Sokolov, S. Andreescu, Anal. Bioanal. Chem. 393, 543 (2009)

    Article  CAS  Google Scholar 

  17. G.D. Pirngruber, L. Frunz, M. Lüchinger, Phys. Chem. Chem. Phys. 11, 2928 (2009)

    Article  CAS  Google Scholar 

  18. Y. Zhang, J. Zhao, L. He, D. Zhao, S. Zhang, Mic. Mes. Mater. 94, 159 (2006)

    Article  CAS  Google Scholar 

  19. J. Gao, Y. Chen, B. Han, Z. Feng, C. Li, N. Zhou, Z. Gao, J. Mol. Catal., A 210, 197 (2004)

  20. S. Samantaray, K. Parida, Catal. Commun. 6, 578 (2005)

    Article  CAS  Google Scholar 

  21. S. Bhattacharjee, J.A. Anderson, J. Mol. Catal. A 249, 103 (2006)

    Article  CAS  Google Scholar 

  22. C. Marchi-Delapierre, A. Jorge-Robin, A. Thibon, S. Ménage, Chem. Commun. 1166 (2007)

  23. J. Jiang, K. Ma, Y. Zheng, S. Cai, R. Li, J. Ma, Appl. Clay Sci. 45, 117 (2009)

    Article  CAS  Google Scholar 

  24. R. Noyori, M. Aoki, K. Sato, Chem. Commun. 1977 (2003)

  25. T. Punniyamurthy, L. Rout, Coord. Chem. Rev. 252, 134 (2008)

    Article  CAS  Google Scholar 

  26. H. Shi, Z. Zhang, Y. Wang, J. Mol. Catal. A 238, 13 (2005)

  27. K.-P. Ho, W.-L. Wong, K.-M. Lam, C.-P. Lai, T.H. Chan, K.-Y. Wong, Chem. Eur. J. 14, 7988 (2008)

    Article  CAS  Google Scholar 

  28. Z. Csendes, Cs. Dudás, G. Varga, É.G. Bajnóczi, S.E. Canton, P. Sipos, I. Pálinkó, J. Mol. Struct. 1044, 39 (2013)

  29. Z. Csendes, N. Földi, J.T. Kiss, P. Sipos, I. Pálinkó, J. Mol. Struct. 993, 203 (2011)

    Article  CAS  Google Scholar 

  30. S. Carlson, M. Clausen, L. Gridneva, B. Sommarin, C.J. Svensson, J. Synchrotron Radiat. 13, 359 (2006)

    Article  CAS  Google Scholar 

  31. S.K. Papageorgiou, E.P. Kouvelos, E.P. Favvas, A.A. Sapadilis, G.E. Romanos, F.K. Katsaros, Carbohydr. Res. 345, 469 (2010)

    Article  CAS  Google Scholar 

  32. S.A. Abdel-Latif, H.B. Hassib, Y.M. Issa, Spectrochim Acta Part A 67, 950 (2007)

    Article  CAS  Google Scholar 

  33. T. Miura, T. Satoh, H. Takeuchi, Biochim. Biophys. Acta 1384, 171 (1998)

    Article  CAS  Google Scholar 

  34. C. Beauchamp, I. Fridovich, Anal. Biochem. 44, 276 (1971)

    Article  CAS  Google Scholar 

  35. P. Chutia, S. Kato, T. Kojima, S. Satokawa, Polyhedron 28, 370 (2009)

    Article  CAS  Google Scholar 

  36. G. Bilis, K.C. Christoforidis, Y. Deligiannakis, M. Louloudi, Catal. Today 157, 101 (2010)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This research was financed by the TÁMOP 4.2.2.A-11/1/KONV-2012-0047 and the OTKA 83889 Grants. The support is highly appreciated.

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged, 6720, Hungary

    Gábor Varga, Zita Csendes & István Pálinkó

  2. Department of Inorganic and Analytical Chemistry, University of Szeged, Dóm tér 7, Szeged, 6720, Hungary

    Éva G. Bajnóczi & Pál Sipos

  3. Material and Solution Structure Research Group, Institute of Chemistry, University of Szeged, Dóm tér 7-8, Szeged, 6720, Hungary

    Gábor Varga, Zita Csendes, Éva G. Bajnóczi, Pál Sipos & István Pálinkó

  4. MaxIV-Lab, Lund University, 223 63, Lund, Sweden

    Stefan Carlson

Authors
  1. Gábor Varga
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zita Csendes
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Éva G. Bajnóczi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Stefan Carlson
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Pál Sipos
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. István Pálinkó
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to István Pálinkó.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Varga, G., Csendes, Z., Bajnóczi, É.G. et al. Fe-amino acid complexes immobilized on silica gel as active and highly selective catalysts in cyclohexene epoxidation. Res Chem Intermed 41, 9155–9169 (2015). https://doi.org/10.1007/s11164-015-1920-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-015-1920-x

Keywords

Search

Navigation