Advertisement

Anchoring of Copper(II) Schiff Base Complex into Aminopropyl-Functionalised MCM-41: A Novel, Efficient and Reusable Catalyst for Selective Oxidation of Alcohols

  • Mehdi Hatefi Ardakani
  • Samira Saeednia
  • Parvaneh Iranmanesh
  • Behnam Konani
Article

Abstract

A copper(II) complex containing tetradentate N2O2 Schiff base ligand immobilized into aminopropyl-functionalised MCM-41 (mobile crystalline material number 41), was prepared and characterized by Fourier-transform infrared, X-ray diffraction, scanning electron microscopy, thermogravimetric analysis, N2 adsorption–desorption and inductively coupled plasma analysis techniques. The novel heterogeneous catalyst, MCM-41-pr-NH2-CuL, can be successfully applied for efficient and selective oxidation of different primary and secondary alcohols to the corresponding carbonyl compounds using hydrogen peroxide as an oxidant in acetonitrile at 60 °C. The effect of reaction parameters such as solvent, amount of catalyst, temperature and kind of oxidant on the oxidation of benzyl alcohol was also studied. The prepared catalyst could be recovered and reused four times without important loss of its catalytic performance. The heterogeneous MCM-41-pr-NH2-CuL catalyst was found to be catalytically more active in the oxidation of alcohols compared to the similar type of copper(II) Schiff base complex in homogeneous media under the same reaction conditions.

Keywords

Tetradentate Schiff base Copper(II) complex MCM-41 Heterogeneous catalyst Alcohol oxidation Hydrogen peroxide 

Notes

Acknowledgements

The support of this work by Vali-e-Asr University of Rafsanjan is acknowledged. The authors also thank Prof. Majid Moghadam from University of Isfahan, Dr. Atena Naeimi from Jiroft University and Dr. Masoud Karimi-Pour from Vali-e-Asr University of Rafsanjan for their valuable helps.

Supplementary material

10904_2017_647_MOESM1_ESM.docx (132 kb)
Supplementary material 1 (DOCX 132 KB)

References

  1. 1.
    X. Wang, G. Wu, W. Wei, Y. Sun, Trans. Met. Chem. 35, 213 (2010)CrossRefGoogle Scholar
  2. 2.
    P. Wang, Z. Dong, Y. Lei, Y. Du, H. Li, H. Yang, Y. Nie, J. Ma, J. Porous Mater. 20, 277 (2013)CrossRefGoogle Scholar
  3. 3.
    S. Farhadi, M. Zaidi, Appl. Catal. A 354, 119 (2009)CrossRefGoogle Scholar
  4. 4.
    A. Dewan, T. Sarma, U. Bora, D.K. Kakati, Tetrahedron Lett. 52, 2563 (2011)CrossRefGoogle Scholar
  5. 5.
    F. Adam, I. Sugiarmawan, J. Porous Mater. 16, 321 (2009)CrossRefGoogle Scholar
  6. 6.
    S. Velusamy, A. Srinivasan, T. Punniyamurthy, Teteahedron Lett. 47, 923 (2006)CrossRefGoogle Scholar
  7. 7.
    R.A. Sheldon, I.W.C.E. Arends, H.E.B. Lempers, Catal. Today 41, 387 (1998)CrossRefGoogle Scholar
  8. 8.
    R.K. Grasselli, Catal. Today 49, 141 (1999)CrossRefGoogle Scholar
  9. 9.
    D. Srinivas, S. Sivasanker, Catal. Surv. Asia 7, 121 (2003)CrossRefGoogle Scholar
  10. 10.
    M. Hajjami, S. Rahmani, J. Porous Mater. 22, 1265 (2015)CrossRefGoogle Scholar
  11. 11.
    A. Hamza, D. Srinivas, Catal. Lett. 128, 434 (2009)CrossRefGoogle Scholar
  12. 12.
    V. Mahdavi, M. Mardani, J. Chem. Sci. 124, 1107 (2012)CrossRefGoogle Scholar
  13. 13.
    J. Guan, J. Lie, Trans. Met. Chem. 39, 233 (2014)CrossRefGoogle Scholar
  14. 14.
    V.K. Bansala, P.P. Thankachana, R. Prasad, Appl. Catal. A 381, 8 (2010)CrossRefGoogle Scholar
  15. 15.
    P.J. Figiel, A.M. Kirillov, Y.Y. Karabach, M.N. Kopylovich, A.J.L. Pombeiro, J. Mol. Catal. A 305, 178 (2009)CrossRefGoogle Scholar
  16. 16.
    Z. Rezvani, M.A. Ghanea, K. Nejati, S.A. Baghaei, Polyhedron 28, 2913 (2009)CrossRefGoogle Scholar
  17. 17.
    Ě. Balogh-Hergovich, G. Speier, J. Mol. Catal. A 44, 79 (2005)CrossRefGoogle Scholar
  18. 18.
    R. Afrasiabi, F. Jalilian, B. Yadollahi, M. Riahi-Farsani, Inorg. Chem. Commun. 50, 113 (2014)CrossRefGoogle Scholar
  19. 19.
    V. Mirkhani, M. Moghadam, S. Tangestaninejad, I. Mohammadpour-Baltork, N. Rasouli, Catal. Commun. 9, 2411 (2008)CrossRefGoogle Scholar
  20. 20.
    B.B. De, B.B. Lohray, S. Sivaram, P.K. Dhal, J. Polym. Sci. A 35, 1809 (1997)CrossRefGoogle Scholar
  21. 21.
    H. Zhang, S. Xiang, C. Li, Chem. Commun. 9, 1209 (2005)CrossRefGoogle Scholar
  22. 22.
    H.M. Berends, T. Homburg, I. Kunz, P. Kurz, Appl. Clay Sci. 53, 174 (2011)CrossRefGoogle Scholar
  23. 23.
    P. Sharma, A.P. Singh, Catal. Today 198, 184 (2012)CrossRefGoogle Scholar
  24. 24.
    J.S. Rafelt, J.H. Clark, Catal. Today 57, 33 (2000)CrossRefGoogle Scholar
  25. 25.
    N.E. Leadbeater, M. Marco, Chem. Rev. 102, 3217 (2002)CrossRefGoogle Scholar
  26. 26.
    X. Wang, G. Wu, J. Li, N. Zhao, W. Wei, Y. Sun, Catal. Lett. 119, 87 (2007)CrossRefGoogle Scholar
  27. 27.
    V. Mirkhani, M. Moghadam, S. Tangestaninejad, I. Mohammadpour-Baltork, N. Rasouli, Catal. Commun. 9, 2171 (2008)CrossRefGoogle Scholar
  28. 28.
    C.T. Kresge, M.E. Leonowicz, W.J. Roth, J.C. Vartuli, J.S. Beck, Nature 359, 710 (1992)CrossRefGoogle Scholar
  29. 29.
    J.S. Beck, J.C. Vartuli, W.J. Roth, M.E. Leonowicz, C.T. Kresge, K.D. Schmitt, C.T.W. Chu, D.H. Olson, E.E. Sheppard, S.B. Mc Cullen, J.B. Higgins, J.L. Schlenker, J. Am. Chem. Soc. 114, 10834 (1992)CrossRefGoogle Scholar
  30. 30.
    T. Soundiressane, S. Selvakumar, S. Ménage, o.. Hamelin, M. Fontecave, A.P. Singh, J. Mol. Catal. A 270, 132 (2007)CrossRefGoogle Scholar
  31. 31.
    J. Zhao, W. Wang, Y. Zhang, J. Inorg. Organomet. Polym. 18, 441 (2008)CrossRefGoogle Scholar
  32. 32.
    D. Brunel, N. Bellocq, P. Sutra, A. Cauvel, M. Laspéras, P. Moreau, F.D. Renzo, A. Galarneau, F. Fajula, Coord. Chem. Rev. 178–180, 1085 (1998)CrossRefGoogle Scholar
  33. 33.
    S. Jana, S. Bhunia, B. Dutta, S. Koner, Appl. Catal. A 392, 225 (2011)CrossRefGoogle Scholar
  34. 34.
    M. Nikoorazm, A. Ghorbani-Choghamarani, F. Ghorbani, H. Mahdavi, Z. Karamshahi, J. Porous Mater. 22, 261 (2015)CrossRefGoogle Scholar
  35. 35.
    A. Jabbari, H. Mahdavi, M. Nikoorazm, A. Ghorbani-Choghamarani, Res. Chem. Intermed. 41, 5649 (2015)CrossRefGoogle Scholar
  36. 36.
    H. Mahdavi, M. Nikoorazm, A. Ghorbani-Choghamarani, S. Arshadi, J. Porous Mater. 23, 75 (2016)CrossRefGoogle Scholar
  37. 37.
    G. Grivani, S. Husseinzadeh-Baghan, M. Vakili, A. Dehno-Khalaji, V. Tahmasebi, V. Eigner, M. Dušek, J. Mol. Struct. 1082, 91 (2015)CrossRefGoogle Scholar
  38. 38.
    Q. Cai, W.Y. Lin, F.S. Xiao, W.Q. Pang, X.H. Chen, B.S. Zou, Micropor. Mesopor. Mater. 32, 1 (1999)CrossRefGoogle Scholar
  39. 39.
    V. Mahdavi, M. Mardani, Res. Chem. Intermed. 41, 8907 (2015)CrossRefGoogle Scholar
  40. 40.
    R. Antony, T.D. Manickam, P. Kollu, P.V. Chandrasekar, K. Karuppasamy, S. Balakumar, RSC Adv. 4, 24820 (2014)CrossRefGoogle Scholar
  41. 41.
    U.G. Singh, R.T. Williams, K.R. Hallam, G.C. Alen, J. Solid State Chem. 178, 3405 (2005)CrossRefGoogle Scholar
  42. 42.
    H.Q. Yang, G.Y. Zhang, X.L. Hong, Y.Y. Zhu, J. Mol. Catal. A 210, 143 (2004)CrossRefGoogle Scholar
  43. 43.
    A. Mathew, S. Parambadath, S.S. Park, C.S. Ha, Microporous Mesoporous Mater. 220, 124 (2014)CrossRefGoogle Scholar
  44. 44.
    T. Joseph, M. Hartmannb, S. Ernst, S.B. Halligudi, J. Mol. Catal. A 207, 131 (2004)CrossRefGoogle Scholar
  45. 45.
    Q. Uan, W. Deng, Q. Zhang, Y. Wang, Adv. Synth. Catal. 349, 1199 (2007)CrossRefGoogle Scholar
  46. 46.
    H. Wojtowicz, J. Mlochowski, L. Syper, H.S. Yadav, Synth. Commun. 36, 1991 (2006)CrossRefGoogle Scholar
  47. 47.
    S.N. Azizi, S.E. Tilami, Microporous Mesoporous Mater 167, 89 (2013)CrossRefGoogle Scholar
  48. 48.
    Z. Guo, B. Liu, Q. Zhang, W. Deng, Y. Wang, Y. Yang, Chem. Soc. Rev 43, 3480 (2014)CrossRefGoogle Scholar
  49. 49.
    A.R. Hajipour, H. Karimi, Chin. J. Catal 35, 1529 (2014)CrossRefGoogle Scholar
  50. 50.
    A.R. Hajipour, H. Karimi, A. Koohi, Chin. J. Catal. (2015). doi: 10.1016/S1872-2067(14)60315-6 Google Scholar
  51. 51.
    S. Bhunia, S. Koner, Polyhedron 30, 1857 (2011)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  • Mehdi Hatefi Ardakani
    • 1
  • Samira Saeednia
    • 1
  • Parvaneh Iranmanesh
    • 2
  • Behnam Konani
    • 1
  1. 1.Department of Chemistry, Faculty of ScienceVali-e-Asr University of RafsanjanRafsanjanIran
  2. 2.Department of Physics, Faculty of ScienceVali-e-Asr University of RafsanjanRafsanjanIran

Personalised recommendations