Skip to main content
Log in

Nanomagnet-Bound Imidazole as a Heterogeneous Axial Ligand for MnIII(salophen)Cl: An Efficient, Recoverable and Recyclable Catalyst for Epoxidation of Alkenes with Sodium Periodate

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

An Erratum to this article was published on 23 July 2013

Abstract

Efficient alkene epoxidation with sodium periodate catalyzed by manganese(III) salophen supported on nanomagnetic materials is reported. First, the iron nanomagnets were silica coated, functionalized with imidazole and then manganese salophen was successfully bonded to their surface. The catalyst, [MnIII(salophen)Cl]@SiIm-Fe, was characterized by elemental analysis, FT-IR and UV/Vis spectroscopic techniques, SEM and ICP. The [MnIII(salophen)Cl]@SiIm-Fe was used for alkene epoxidation with sodium periodate at room temperature. Different aromatic and aliphatic terminal alkenes were epoxidized efficiently using sodium periodate as an oxidant. The effect of reaction parameters such as solvent and oxidant in the epoxidation of cis-cyclooctene was investigated. This new heterogenized epoxidation catalyst is easily recovered with a magnet and showed no appreciable loss of activity even after four consecutive runs.

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. V. A. de la pena O’shea, J. M. Campos-Martin, J. L. G. Fierro, Catal. Commun. 5, 635–638 (2004)

  2. X. Guo, F. Chen, Environ. Sci. Technol. 39, 6808–6818 (2005)

    Article  CAS  Google Scholar 

  3. P. Couvreur, C. Vauthier, Pharm. Res. 23, 1417–1450 (2006)

    Article  CAS  Google Scholar 

  4. T. Hayashi, S. Hirono, M. Tomita, S. Umemura, Nature 381, 772–774 (1996)

    Article  Google Scholar 

  5. P. Gambardella, S. Rusponi, M. Veronese, S.S. Dhesi, C. Grazioli, A. Dallmeyer, I. Cabria, R. Zeller, P.H. Dederichs, K. Kern, C. Carbone, H. Brune, Science 300, 1130–1131 (2003)

    Article  CAS  Google Scholar 

  6. S.I. Nikitenko, Y. Koltypin, O. Palchik, I. Felner, X.N. Xu, A. Gedanken, Angew. Chem. Int. Ed. 40, 4447–4449 (2001)

    Article  CAS  Google Scholar 

  7. A.H. Latham, M.E. Williams, Acc. Chem. Res. 41, 411–420 (2008)

    Article  CAS  Google Scholar 

  8. M. Palucki, G.J. McCormick, E.N. Jacobsen, Tetrahedron Lett. 36, 5457–5460 (1995)

    CAS  Google Scholar 

  9. T. Yamada, K. Imagawa, T. Nagata, T. Mukaiyama, Bull. Chem. Soc. Jpn. 67, 2248–2526 (1994)

    Article  CAS  Google Scholar 

  10. E.N. Jacobsen, W. Zhang, M.L. Guler, J. Am. Chem. Soc. 113, 6703–6704 (1991)

    Article  CAS  Google Scholar 

  11. R. Irie, T. Hashihayata, T. Katsuki, M. Akita, M. Moro-Oka, Chem. Lett. 1041–1042 (1998)

  12. V. Mirkhani, M. Moghadam, S. Tangestaninejad, B. Bahramian, J. Iran. Chem. Soc. 5, 375–383 (2008)

    Article  CAS  Google Scholar 

  13. P. Pietikainen, Tetrahedron Lett. 36, 319–322 (1995)

    Article  Google Scholar 

  14. A. Scheurer, P. Mosset, M. Spiegel, R.W. Saalfrank, Tetrahedron 55, 1063–1078 (1999)

    Article  CAS  Google Scholar 

  15. K. Srinivasan, P. Michaud, J. K. Kochi, J. Am. Chem. Soc. 108, 2309–2320 (1986)

    Article  CAS  Google Scholar 

  16. J.P. Collman, V.J. Lee, C.J. Kellen-Yuen, X. Zhang, J.A. Ibers, J.I. Brauman, J. Am. Chem. Soc. 117, 692–703 (1995)

    Article  CAS  Google Scholar 

  17. J.M. Fraile, J.I. Garcia, J. Massam, J.A. Mayoral, J. Mol. Catal. A: Chem. 136, 47–57 (1998)

    Article  CAS  Google Scholar 

  18. M.R. Maurya, S.J.J. Titinchi, S. Chand, J. Mol. Catal. A: Chem. 228, 177–187 (2002)

    Article  CAS  Google Scholar 

  19. A. Heckel, D. Seebach, Helv. Chim. Acta 85, 913–926 (2002)

    Article  CAS  Google Scholar 

  20. H. Zhang, S. Xiang, C. Li, Chem. Commun. 1209–1210 (2005)

  21. S. Xiang, Y. Zhang, Q. Xin, C. Li, Chem. Commun. 2696–2697 (2002)

  22. G.-J. Kim, S.-H. Kim, Catal. Lett. 57, 139–143 (1999)

    Article  CAS  Google Scholar 

  23. L. Canali, D.C. Sherrington, H. Deleuze, React. Funct. Polym. 40, 155–168 (1999)

    Article  CAS  Google Scholar 

  24. B. Bahramian, V. Mirkhani, M. Moghadam, S. Tangestaninejad, Appl. Catal. A: Gen. 301, 169–175 (2006)

    Article  CAS  Google Scholar 

  25. V. Mirkhani, M. Moghadam, S. Tangestaninejad, B. Bahramian, Monats. Chem. 138, 1303–1308 (2007)

    Article  CAS  Google Scholar 

  26. V. Mirkhani, M. Moghadam, S. Tangestaninejad, B. Bahramian, Polyhedron 25, 2904–2914 (2006)

    Article  CAS  Google Scholar 

  27. S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, M.S. Saeedi, Appl. Catal. A: Gen. 381, 233–241 (2010)

    Article  CAS  Google Scholar 

  28. V. La Paglia Fragola, F. Lupo, A. Pappalardo, G. Trusso Sfrazzetto, R.M. Toscano, F.P. Ballistreri, G.A. Tomaselli, A. Gulino, J. Mater. Chem. 22, 20561–20565 (2012)

    Article  Google Scholar 

  29. R. Ji, K. Yu, L. Lou, C. Zhang, Y. Han, S. Pan, S. Liu, Inorg. Chem. Commun. 25, 65–69, (2012)

    Article  CAS  Google Scholar 

  30. P. Sharma, A. Lazar, A.P. Singh, Appl. Catal. A: Gen. 101, 439–440 (2012)

    Google Scholar 

  31. P. Sharma, A.P. Singh, Catal. Today 198, 184–188 (2012)

    Article  CAS  Google Scholar 

  32. H. Gaspar, M. Andrade, C. Pereira, A.M. Pereira, S.L.H. Rebelo, J.P. Araújo, J. Pires, A.P. Carvalho, C. Freire, Catal. Today 203, 103–110 (2013)

    Article  CAS  Google Scholar 

  33. C.B. Wang, W.X. Zhang, Environ. Sci. Technol. 31, 2154–2156 (1997)

    Article  CAS  Google Scholar 

  34. G. N. Glavee, K. J. Klabunde, C. M. Sorensen, G. C. Hadjipanayis, Inorg. Chem. 34, 28–35 (1995)

    Article  CAS  Google Scholar 

  35. B.M. Trivedi, P.K. Bhattacharya, P.A. Ganeshpure, S. Satish, J. Mol. Catal. 75, 109–115 (1992)

    Article  CAS  Google Scholar 

  36. M.L. Yuan, J.H. Tao, G.J. Yan, M.Y. Tan, G.Z. Qiu, Trans. Nonferrous Met. Soc. China 20, 632–636 (2010)

    Article  CAS  Google Scholar 

  37. P. R. Cooke, J. R. Lindsay Smith, J. Chem. Soc. Perkin Trans. 1, 1913–1923 (1994)

    Article  Google Scholar 

  38. J.P. Collman, L. Zeng, J.I. Brauman, Inorg. Chem. 43, 2672–2679 (2004)

    Article  CAS  Google Scholar 

  39. Z. Groos, S. Ini, J. Org. Chem. 62, 5514–5521 (1997)

    Article  Google Scholar 

  40. M. Zakeri, M. Moghadam, I. Mohammadpoor-Baltork, S. Tangestaninejad, V. Mirkhani, A.R. Khosropour, J. Coord. Chem. 65, 1144–1157 (2012)

    Article  CAS  Google Scholar 

  41. M. Zakeri, M. Moghadam, I. Mohammadpoor-Baltork, S. Tangestaninejad, V. Mirkhani, A.R. Khosropour, M. Alizadeh, Transition Met. Chem. 37, 45–53 (2012)

    Article  CAS  Google Scholar 

  42. R. Hajian, S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, A.R. Khosropour, J. Coord. Chem. 64, 4134–4144 (2011)

    Article  CAS  Google Scholar 

  43. M. Nooraeipour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, S.M. Nabavizadeh, Transition Met. Chem. 36, 861–866 (2011)

    Article  CAS  Google Scholar 

  44. M. Nooraeipour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, N. Iravani, J. Coord. Chem. 65, 226–238 (2012)

    Article  CAS  Google Scholar 

  45. M. Moghadam, I. Mohammadpoor-Baltork, S. Tangestaninejad, V. Mirkhani, H. Kargar, N. Zeini-Isfahani, Polyhedron 28, 3816–3822 (2009)

    Article  CAS  Google Scholar 

  46. M.S. Saeedi, S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, A.R. Khosropour, Polyhedron 49, 158–166 (2013)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We acknowledge the support of this work by Research Council of the University of Isfahan.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Shahram Tangestaninejad, Valiollah Mirkhani or Majid Moghadam.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Torki, M., Tangestaninejad, S., Mirkhani, V. et al. Nanomagnet-Bound Imidazole as a Heterogeneous Axial Ligand for MnIII(salophen)Cl: An Efficient, Recoverable and Recyclable Catalyst for Epoxidation of Alkenes with Sodium Periodate. J Inorg Organomet Polym 23, 923–929 (2013). https://doi.org/10.1007/s10904-013-9865-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-013-9865-2

Keywords

Navigation