Skip to main content
Log in

Preparation and characterization of multi-walled carbon nanotubes (MWCNTs), functionalized with phosphonic acid (MWCNTs–C–PO3H2) and its application as a novel, efficient, heterogeneous, highly selective and reusable catalyst for acetylation of alcohols, phenols, aromatic amines, and thiols

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

A novel, efficient, heterogeneous, and reusable multi-walled carbon nanotubes (MWCNTs), functionalized with phosphonic acid (MWCNTs–C–PO3H2) has been synthesized. The synthesized CNTs were characterized using some electron microscopic techniques such as scanning electron microscopy (SEM), atomic force microscopy (AFM), Energy dispersive X-ray spectroscopy (EDAX), and also some thermal and spectroscopic methods such as thermogravimetry (TG). The nitrogen adsorption behavior of the MWCNTs–C–PO3H2 catalyst was evaluated using the TG instrumentation system at 25 °C. The catalyst was applied successfully for highly efficient and selective acetylation of alcohols, phenols, thiols and aromatic amines with acetic anhydride at room temperature under solvent-free conditions. The reusability of the catalyst was checked and the recovered catalyst was reused for five runs without significant loss in activity.

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.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Scheme 1
Fig. 5
Scheme2
Fig. 6

Similar content being viewed by others

References

  1. J.L. Bahr, J. Yang, D.M. Kosynkin, M.J. Bronikowski, R.E. Smalley, J.M. Tour, J. Am. Chem. Soc. 123, 6536 (2001)

    Article  CAS  Google Scholar 

  2. F. Pompeo, D. Reasaco, Nano Lett. 2, 369 (2002)

    Article  CAS  Google Scholar 

  3. C.A. Dyke, J.M. Tour, Nano Lett. 3, 1215 (2003)

    Article  CAS  Google Scholar 

  4. M.S. Strano, C.A. Dyke, M.L. Usrey, P.W. Barone, M.J. Allen, H. Shan, C. Kittrell, R.H. Hauge, J.M. Tour, R.E. Smalley, Science 301, 1519 (2003)

    Article  CAS  Google Scholar 

  5. J. Chen, A.M. Rao, S. Lyuksyutov, M.E. Itkis, M.A. Hamon, H. Hu, R.W. Cohn, P.C. Eklund, D.T. Colbert, R.E. Smalley, R.C. Haddon, J. Phys. Chem. 105, 2525 (2001)

    Article  CAS  Google Scholar 

  6. M.C. O’Connell, P. Boul, L.M. Ericson, C. Huffman, Y. Wang, E. Haroz, C. Kuper, J. Tour, K.D. Ausman, R.E. Smalley, Chem. Phys. Lett. 342, 265 (2001)

    Article  Google Scholar 

  7. D. Chattopadhyay, S. Lastella, S. Kim, F. Papadimitrikapoulos, J. Am. Chem. Soc. 124, 728 (2002)

    Article  CAS  Google Scholar 

  8. D. Chattopadhyay, I. Galeska, F. Papadimitrikapoulos, J. Am. Chem. Soc. 125, 3370 (2003)

    Article  CAS  Google Scholar 

  9. N. Karousis, N. Tagmatarchis, D. Tasis, Chem. Rev. 110, 5366 (2010)

    Article  CAS  Google Scholar 

  10. M. Salavati-Niasari, M. Bazarganipour, Appl. Surf. Sci. 255, 2963 (2008)

    Article  CAS  Google Scholar 

  11. M. Salavati-Niasari, S.N. Mirsattari, M. Bazarganipour, Polyhedron 27, 3653 (2008)

    Article  CAS  Google Scholar 

  12. H. Sharghi, S. Ebrahimpourmoghaddam, M.M. Doroodmand, A. Purkhosrow, Asian J. Org. Chem. 1, 377 (2012)

    Article  CAS  Google Scholar 

  13. H. Steininger, M. Schuster, K.D. Kreuer, A. Kaltbeitzel, B. Bingol, W.H. Meyer, S. Schauff, G. Brunklaus, J. Maier, H.W. Spiess, Phys. Chem. Chem. Phys. 9, 1764 (2007)

    Article  CAS  Google Scholar 

  14. B. Lafitte, P. Jannasch, in Advances in Fuel Cells, ed. by T.S. Zhao, K.D. Kreuer, T.V. Nguyen (Elsevier, Amsterdam, 2007), p. 120

    Google Scholar 

  15. M. Nogami, R. Nagao, G. Wong, T. Kasuga, T. Hayakawa, J. Phys. Chem. B. 103, 9468 (1999)

    Article  CAS  Google Scholar 

  16. Y. Nishiyama, K. Ochi, N. Nishiyama, Y. Egashira, K. Ueyama, Electrochem. Solid-State Lett. 11, 86 (2008)

    Article  Google Scholar 

  17. M. Yoshizawa-Fujita, K. Fujita, M. Forsyth, D.R. MacFarlane, Electrochem. Commun. 9, 1202 (2007)

    Article  CAS  Google Scholar 

  18. H. Steininger, M. Schuster, K.D. Kreuer, A. Kaltbeitzel, B. Bingol, W.H. Meyer, S. Schauff, G. Brunklaus, J. Maier, H.W. Spiess, Phys. Chem. Chem. Phys. 9, 1764 (2007)

    Article  CAS  Google Scholar 

  19. M. Schuster, K.D. Kreuer, H. Steininger, J. Maier, Solid State Ionics 179, 523 (2008)

    Article  CAS  Google Scholar 

  20. E. Parcero, R. Herrera, S.P. Nunes, J. Membr. Sci. 285, 206 (2006)

    Article  CAS  Google Scholar 

  21. M. Schuster, T. Rager, A. Noda, K.D. Kreuer, J. Maier, Fuel Cells 5, 355 (2005)

    Article  CAS  Google Scholar 

  22. A. Oki, L. Adams, V. Khabashesku, Y. Edigin, P. Biney, Zh Luo, Materials Lett. 62, 918 (2008)

    Article  CAS  Google Scholar 

  23. P. Li, H. Liu, Y. Ding, Y. Wang, Y. Chen, Y. Zhou, Y. Tang, H. Wei, Ch. Cai, T. Lu, J. Mater. Chem. 22, 15370 (2012)

    Article  CAS  Google Scholar 

  24. M. Zheng, P. Li, G. Fu, Y. Chen, Y. Zhou, Y. Tang, T. Lu, Appl. Catal. B 129, 394 (2013)

    Article  CAS  Google Scholar 

  25. T.W. Greene, P.G.M. Wutz, Protective Groups in Organic Synthesis, 2nd edn. (Wiley, New York, 1991), p. 50

    Google Scholar 

  26. D.B. Mawhinney, V. Naumenko, A. Kuznetsova, J.T. Yates, J. Liu, R.E. Smalley, J. Am. Chem. Soc. 122, 2383 (2000)

    Article  CAS  Google Scholar 

  27. L.T. Cai, J.L. Bahr, Y.X. Yao, J.M. Tour, Chem. Mater. 14, 4235 (2002)

    Article  CAS  Google Scholar 

  28. H. Kuzmany, A. Kukovecz, F. Simon, M. Holzwebe, Ch. Kramberger, T. Pichler, Synth. Met. 141, 113 (2004)

    Article  CAS  Google Scholar 

  29. Zhu Hongwei, Ci Lijie, Xu Cailu, Ji Liang, Wu Dehai, Diam. Relat. Mater. 11, 1349 (2002)

    Article  Google Scholar 

  30. L.D. Freeman, G.O. Doak, Chem. Rev. 57, 479 (1959)

    Article  Google Scholar 

  31. X. Lu, J. Zhu, J. Huang, X. Tao, J. Mol. Catal. 41, 235 (1987)

    Article  CAS  Google Scholar 

  32. J. Zhu, X. Lu, J. Chem. Soc. Commun. 17, 1318 (1987)

    Article  Google Scholar 

  33. M. Salavati-Niasari, S. Hydrazadeh, A. Amiri, S. Salavati, J. Mol. Catal. A: Chem. 231, 191 (2005)

    Article  CAS  Google Scholar 

  34. H. Firouzabadi, N. Iranpoor, S. Farahi, J. Mol. Catal. A: Chem. 289, 61 (2008)

    Article  CAS  Google Scholar 

  35. M. Moghadam, Sh Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, S. Abdolmanaf Taghavi, J. Mol. Catal. A: Chem. 274, 217 (2007)

    Article  CAS  Google Scholar 

  36. A.K. Chakraborti, R. Gulhane, Tetrahedron Lett. 44l, 3521 (2003)

    Article  CAS  Google Scholar 

  37. R. Dalpozzo, A. De Nino, L. Maiuolo, A. Procopio, M. Nardi, G. Bartoli, R. Romeo, Tetrahedron Lett. 44, 5621 (2003)

    Article  CAS  Google Scholar 

  38. K. Chakraborti, L. Sharma, R. Gulhane, Shivani, Tetrahedron 59, 7661 (2003)

    Article  CAS  Google Scholar 

  39. M.M. Heravi, F.K. Behbahani, F.F. Bamoharram, J. Mol. Catal. A: Chem. 253, 16 (2006)

    Article  CAS  Google Scholar 

  40. M. Araghi, V. Mirkhani, M. Moghadam, Sh Tangestaninejad, I. Mohammdpoor-Baltork, Dalton Trans. 41, 11745 (2012)

    Article  CAS  Google Scholar 

  41. S.A. Taghavi, M. Moghadam, I. Mohammadpoor-Baltork, Sh Tangestaninejad, V. Mirkhani, A.R. Khosropour, Inorg. Chim. Acta 377, 159 (2011)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to research council of Shiraz University for the financial support of this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ali Reza Sardarian.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dehghani, F., Sardarian, A.R. & Doroodmand, M.M. Preparation and characterization of multi-walled carbon nanotubes (MWCNTs), functionalized with phosphonic acid (MWCNTs–C–PO3H2) and its application as a novel, efficient, heterogeneous, highly selective and reusable catalyst for acetylation of alcohols, phenols, aromatic amines, and thiols. J IRAN CHEM SOC 11, 673–684 (2014). https://doi.org/10.1007/s13738-013-0339-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-013-0339-9

Keywords

Navigation