Skip to main content
SpringerLink
Log in

α-Zirconium phosphate supported metal–salen complex: synthesis, characterization and catalytic activity for cyclohexane oxidation

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

Abstract

Metal–salen intercalated α-zirconium phosphate, abbreviated as {α-ZrP·M(Salen), where M = Fe(III) and Mn(II)} was synthesized insitu by the flexible ligand method. The structure of resulting compounds was characterized by BET surface area, powder X-ray diffraction, Fourier transform infrared spectroscopy, scanning electron microscopy, energy dispersive X-ray analysis, X-ray photoelectron spectroscopy, thermogravimetric analysis and UV–visible spectroscopy. The catalytic activity of α-ZrP·M(Salen) was tested for the oxidation of cyclohexane using dry tert-butylhydroperoxide as an oxidant. In the oxidation reaction, cyclohexane was oxidized to cyclohexanol (A), cyclohexanone (K) and some unidentified products. It was found that the reactivity of α-ZrP·Fe(Salen) is greater than α-ZrP·Mn(Salen) in the oxidation reaction. Influence of various reaction parameters viz. reaction temperature, catalyst concentration, substrate to oxidant molar ratio was studied using α-ZrP·Fe(Salen) catalyst to obtain maximum conversion (29.30%) of cyclohexane. The catalyst was reused for five cycles without significant loss of catalytic activity.

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
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. J.A. Labinger, J.E. Bercaw, Nature 417, 507 (2002)

    Article  CAS  Google Scholar 

  2. T. Newhouse, P.S. Baran, Angew. Chem. Int. Ed. 50, 3362 (2011)

    Article  CAS  Google Scholar 

  3. U. Neuenschwander, N. Turra, C. Aellig, P. Mania, I. Hermans, Chimia 64, 225 (2010)

    Article  CAS  Google Scholar 

  4. R.A. Sheldon, J.K. Kochi, Metal-Catalyzed Oxidation of Organic Compounds (Academic Press, New York, 1981), p. 34

    Google Scholar 

  5. C.L. Hill, Activation and Functionalization of Alkanes (Wiley, New York, 1989), p. 372

    Google Scholar 

  6. U. Schuchardt, D. Cardoso, R. Serchelic, R. Pereira, R.S. Da Cruz, M.C. Guerreiro, D.E.V. Spinacé, V. Pires, Appl. Catal. A Gen. 211, 1 (2001)

    Article  CAS  Google Scholar 

  7. K.U. Ingold, Aldrichim. Acta 22, 69 (1989)

    CAS  Google Scholar 

  8. M. Breígeault, Dalton Trans., 3289 (2003)

  9. M.R. Ganjali, P. Norouzi, M. Golmohammadi, M. Rezapour, M. Salavati-Niasari, Electroanalysis 16, 910 (2004)

    Article  CAS  Google Scholar 

  10. M. Salavati-Niasari, M. Shaterian, M.R. Ganjali, P. Norouzi, J. Mol. Catal. A Chem. 261, 147 (2007)

    Article  CAS  Google Scholar 

  11. K.C. Gupta, A.K. Sutar, Coord. Chem. Rev. 252, 1420 (2008)

    Article  CAS  Google Scholar 

  12. A. Ebadi, F. Nikbakht, Reac. Kinet. Mech. Cat. 104, 37 (2011)

    Article  CAS  Google Scholar 

  13. L. Zhou, J. Xu, H. Miao, F. Wang, X. Li, Appl. Catal A Gen. 292, 223 (2005)

    Article  CAS  Google Scholar 

  14. M. Salavati-Niasari, A. Amiri, Appl. Catal. A Gen. 290, 46 (2005)

    Article  CAS  Google Scholar 

  15. M. Salavati-Niasari, F. Farzaneh, M. Ghandi, J. Mol. Catal. A Chem. 186, 101 (2002)

    Article  CAS  Google Scholar 

  16. A.P. Singh, N. Torita, S. Shylesh, N. Iwasa, M. Arai, Catal. Lett. 132, 492 (2009)

    Article  CAS  Google Scholar 

  17. K.S. Anisia, A. Kumar, J. Mol. Catal. A Chem. 271, 164 (2007)

    Article  CAS  Google Scholar 

  18. M. Salvati-Niasari, M. Bazarganipour, Bull. Korean Chem. Soc. 30, 355 (2009)

    Article  Google Scholar 

  19. S. Khare, S. Shrivastava, J. Mol. Catal. A Chem. 217, 51 (2004)

    Article  CAS  Google Scholar 

  20. N.V. Maksimchuk, K.A. Kovalenko, V.P. Fedin, O.A. Kholdeeva, Chem. Commun. 48, 6812 (2012)

    Article  CAS  Google Scholar 

  21. G. Huang, C.C. Guo, S.S. Tang, J. Mol. Catal. A Chem. 261, 125 (2007)

    Article  CAS  Google Scholar 

  22. M. Salavati-Niasari, Z. Salimi, M. Bazarganipour, F. Davar, Inorg. Chimi. Acta 362, 3715 (2009)

    Article  CAS  Google Scholar 

  23. W. Trakarnpruk, Int. J. Chem. Eng. Appl. 6, 120 (2015)

    CAS  Google Scholar 

  24. Z. Feng, Y. Xie, F. Hao, P. Liu, H. Luo, J. Mol. Catal. A Chem. 410, 221 (2015)

    Article  CAS  Google Scholar 

  25. Y. Xie, F. Zhang, P. Liu, F. Hao, H. Luo, J. Mol. Catal. A Chem. 386, 95 (2014)

    Article  CAS  Google Scholar 

  26. R. Maheswari, R. Anand, G. Imran, J. Porous Mater. 19, 283 (2012)

    Article  CAS  Google Scholar 

  27. M. Salavati-Niasari, M. Shakouri-Arani, F. Davar, Microporous Mesoporous Mater. 116, 77 (2008)

    Article  CAS  Google Scholar 

  28. M. Salavati-Niasari, A. Sobhani, J. Mol. Catal. A Chem. 285, 58 (2008)

    Article  CAS  Google Scholar 

  29. L. Sun, W.J. Boo, R.L. Browning, H. Sue, A. Clearfield, Chem. Mater. 17, 5606 (2005)

    Article  CAS  Google Scholar 

  30. A. Clearfield, J.A. Stynes, J. Inorg. Nucl. Chem. 26, 117 (1964)

    Article  CAS  Google Scholar 

  31. A. Clearfield (ed.), Inorganic Ion Exchange Materials (CRC Press, Boca Raton, 1982), p. 16

    Google Scholar 

  32. M. Curini, O. Rosati, U. Costantino, Curr. Org. Chem. 8, 591 (2004)

    Article  CAS  Google Scholar 

  33. M. Iwamoto, Y. Nomura, S. Kagawa, J. Catal. 69, 234 (1981)

    Article  CAS  Google Scholar 

  34. A. Clearfield, W.M. Warmuth, R. Schollhorn, E.K. Dordrecht, Progress Intercal. Res. 240 (1994)

  35. Z.G. Sun, Z.M. Liu, Y. Yang, Catal. Today 94, 639 (2004)

    Article  Google Scholar 

  36. A.R. Hajipour, H. Karimi, Chin. J. Catal. 35, 1982 (2014)

    Article  CAS  Google Scholar 

  37. D.D. Agarwal, R. Jain, R.P. Bhatnagar, S. Shrivastava, J. Mol. Catal. 59, 385 (1990)

    Article  CAS  Google Scholar 

  38. D.D. Agarwal, R. Jain, R.P. Bhatnagar, S. Shrivastava, J. Chem. Soc. Perkins Trans. II, 989 (1990)

    Article  Google Scholar 

  39. S. Khare, R. Chokhare, J. Mol. Catal. A Chem. 353, 138 (2012)

    Article  Google Scholar 

  40. S. Khare, S. Shrivastava, J. Ind. Chem. Soc. 83, 813 (2006)

    CAS  Google Scholar 

  41. M.S. Hamdy, A. Ramanathan, T. Maschmeyer, U. Hanefeld, J.C. Jansen, Chem. Eur. J. 12, 1782 (2006)

    Article  CAS  Google Scholar 

  42. D. Swern, Organic Peroxide, vol. II (Wiley Interscience, New York, 1971), p. 357

    Google Scholar 

  43. L. Sun, W.J. Boo, H.J. Sue, A. Clearfield, New J. Chem. 31, 39 (2007)

    Article  CAS  Google Scholar 

  44. U. Costantino, L. Szirtes, E. Kuzmann, J. Megyeri, K. Lazar, Solid State Ion 141, 359 (2001)

    Article  Google Scholar 

  45. K. Parida, D.P. Das, J. Photochem. Photobiol. A: Chem. 163, 561 (2004)

    Article  CAS  Google Scholar 

  46. K.G. Varshney, A.H. Pandith, U. Gupta, Langmuir 14, 7353 (1998)

    Article  CAS  Google Scholar 

  47. K. Wandelt, Surf. Sci. Rep. 1 (1982)

  48. D. Kothari, V.R. Reddy, A. Gupta, D.M. Phase, N. Lakshmi, S.K. Deshpande, A.M. Awasthi, J. Phys. Condens. Matter 19, 136202 (2007)

    Article  Google Scholar 

  49. P. Oliveriava, A. Machado, A.M. Romas, I.M. Fonseca, F.M.B. Fernandes, A.M.B. Do Rago, J. Vital, Microporous Mesoporous Mater. 120, 432 (2009)

    Article  Google Scholar 

  50. I.K. Biernacka, A.R. Silva, A.P. Carvalho, J. Pires, C. Freire, Langmuir 21, 10825 (2005)

    Article  Google Scholar 

  51. F.J. Pérez-Reina, P. Olivera-Pastor, P. Maireles-Torres, E. Rodríguez-Castellón, A. Jiménez-López, Langmuir 14, 4017 (1998)

    Article  Google Scholar 

  52. V.K. Sivasubramanian, M. Ganesan, S. Rajagopal, R. Ramaraj, J. Org. Chem. 67, 1506 (2002)

    Article  CAS  Google Scholar 

  53. E. Tordin, M. List, U. Monkowius, S. Schindler, G. Knör, Inorg. Chim. Acta 402, 90 (2013)

    Article  CAS  Google Scholar 

  54. M.R. Maurya, A. Kumar, S. Chand, J. Mol. Catal. A Chem. 278, 12 (2007)

    Article  CAS  Google Scholar 

  55. M.R. Maurya, A.K. Chandrakar, S. Chand, J. Mol. Catal. A Chem. 270, 225 (2007)

    Article  CAS  Google Scholar 

  56. W. Jianying, Z. Hua, Z. Xiangjing, L. Runjing, H. Yongqi, Chin. J. Chem. Eng. 16, 373 (2008)

    Article  Google Scholar 

  57. B. Fan, H. Li, W. Fan, C. Jin, R. Li, Appl. Catal. A Gen. 340, 67 (2008)

    Article  CAS  Google Scholar 

  58. R. Zhao, Y. Wang, Y. Guo, X. Liu, Z. Zhang, Y. Wang, W. Zhan, G. Lu, Green Chem. 8, 459 (2006)

    Article  CAS  Google Scholar 

  59. K.A. Lee, W. Nam, Bull. Korean Chem. Soc. 17, 669 (1996)

    Google Scholar 

  60. A.F. Masters, J.K. Beattie, A.L. Roa, Catal. Lett. 75, 3 (2001)

    Article  Google Scholar 

Download references

Acknowledgements

The authors are thankful to UGC-DAU Consortium of Scientific Research, Devi Ahilya University, Indore for providing SEM, XRD, EDAX, XPS and FTIR facilities and Central Salt and Marines Chemical Research Institute (CSMCRI), Bhavnagar, Gujarat for providing BET surface area, GC–MS and TGA analysis facilities.

Author information

Authors and Affiliations

  1. School of Chemical Sciences, Devi Ahilya University, Takshashila Campus, Khandwa Road, Indore, MP, 452 001, India

    Savita Khare, Priti Shrivastava, Rajendra Chokhare, Jagat Singh Kirar & Swati Parashar

Authors
  1. Savita Khare
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Priti Shrivastava
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Rajendra Chokhare
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jagat Singh Kirar
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Swati Parashar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Savita Khare.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 331 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khare, S., Shrivastava, P., Chokhare, R. et al. α-Zirconium phosphate supported metal–salen complex: synthesis, characterization and catalytic activity for cyclohexane oxidation. J Porous Mater 24, 855–866 (2017). https://doi.org/10.1007/s10934-016-0325-6

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10934-016-0325-6

Keywords

Search

Navigation