Skip to main content
SpringerLink
Log in

Multi SO3H supported on carbon nanotubes: a practical, reusable, and regioselective catalysts for the tert-butylation of p-cresol under solvent-free conditions

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

Abstract

The present study describes the synthesis, characterization, and catalytic activity of sulfonated multi-walled carbon nanotubes and sulfonated single-walled carbon nanotubes in the tert-butylation of p-cresol. The catalysts were prepared using a chemical and simple process and it characterized by scanning electron microscopy, Fourier transform infrared, and Raman spectroscopy, thermogravimetric analysis, and acid–base titration. The sulfonated multi-walled carbon nanotubes and sulfonated single-walled carbon nanotubes have been used as practical heterogeneous catalytic systems in the tert-butylation of p-cresol under solvent-free conditions. Sulfonated multi-walled carbon nanotubes with the highest total density of SO3H groups possessed high activity for p-cresol conversion and high selectivity than the sulfonated single-walled carbon nanotubes. This methodology offers some advantages of high selectivity, and high yields, easy work-up, solvent-free conditions, and reusable catalyst. Moreover, the catalytic system was used in scale-up under similar optimized reaction conditions.

Graphical Abstract

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
Scheme 1
Scheme 2
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Scheme 3

Similar content being viewed by others

References

  1. P.T. Anastas, M.M. Kirchhoff, Acc. Chem. Res. 35, 686 (2002)

    Article  CAS  Google Scholar 

  2. J.H. Clark, Acc. Chem. Res. 35, 791 (2002)

    Article  CAS  Google Scholar 

  3. H.T. Gomes, S.M. Miranda, M.J. Sampaio, A.M.T. Silva, J.L. Faria, Catal. Today 151, 153 (2010)

    Article  CAS  Google Scholar 

  4. A. Takagaki, M. Toda, M. Okamura, J.N. Kondo, S. Hayashi, K. Domen, M. Hara, Catal. Today 116, 157 (2006)

    Article  CAS  Google Scholar 

  5. X. Liang, M. Zeng, C. Qi, Carbon 48, 1844 (2010)

    Article  CAS  Google Scholar 

  6. H. Xiao, Y. Guo, X. Liang, C. Qi, J. Solid State Chem. 183, 1721 (2010)

    Article  CAS  Google Scholar 

  7. Y. Zhao, H. Wang, Y. Zhao, J. Shen, Catal. Commun. 11, 824 (2010)

    Article  CAS  Google Scholar 

  8. V. Mirkhani, M. Moghadam, S. Tangestaninejad, I. Mohammadpoor-Baltork, M. Mahdavi, Monatsh. Chem. 140, 1489 (2009)

    Article  CAS  Google Scholar 

  9. J. Safari, S. Gandomi-Ravandi, J. Mol. Catal. A: Chem. 373, 72 (2013)

    Article  CAS  Google Scholar 

  10. X. Hu, Y.-Y. Zhang, K. Tang, G.-L. Zou, Synth. Met. 150, 1 (2005)

    Article  CAS  Google Scholar 

  11. Y. Wang, Z. Iqbal, S. Mitra, J. Am. Chem. Soc. 128, 95 (2005)

    Article  Google Scholar 

  12. H. Yu, Y. Jin, Z. Li, F. Peng, H. Wang, J. Solid State Chem. 181, 432 (2008)

    Article  CAS  Google Scholar 

  13. L. Adams, A. Oki, T. Grady, H. McWhinney, Z. Luo, Phys E41, 723 (2009)

    Google Scholar 

  14. M.M. Doroodmand, S. Sobhani, A. Ashoori, Can. J. Chem. 90, 701 (2012)

    Article  CAS  Google Scholar 

  15. F. Peng, L. Zhang, H. Wang, P. Lv, H. Yu, Carbon 43, 2405 (2005)

    Article  CAS  Google Scholar 

  16. J. Pospíšil, Polym. Degrad. Stab. 20, 181 (1988)

    Article  Google Scholar 

  17. J. Murphy, in Additives for Plastics Handbook, 2nd edn., ed. by J. Murphy (Elsevier Science, Amsterdam, 2001)

    Google Scholar 

  18. N. Platzer, J. Polym. Sci. Pol. Lett. 24, 659 (1986)

    Article  Google Scholar 

  19. S.E. Dapurkar, P. Selvam, Appl. Catal. A254, 239 (2003)

    Article  Google Scholar 

  20. A.B. Shinde, N.B. Shrigadi, S.D. Samant, Appl. Catal. A276, 5 (2004)

    Article  Google Scholar 

  21. D. Mravec, P. Zavadan, A. Kaszonyi, J. Joffre, P. Moreau, Appl. Catal. A257, 49 (2004)

    Article  Google Scholar 

  22. G. Kostrab, M. Lovič, I. Janotka, M. Bajus, D. Mravec, Appl. Catal. A323, 210 (2007)

    Article  Google Scholar 

  23. E. Dumitriu, V. Hulea, J. Catal. 218, 249 (2003)

    Article  CAS  Google Scholar 

  24. G. Kostrab, M. Lovič, A. Turan, P. Hudec, A. Kaszonyi, M. Bajus, J. Uhlár, P. Lehocký, D. Mravec, Catal. Commun. 18, 176 (2012)

    Article  CAS  Google Scholar 

  25. G. Kamalakar, K. Komura, Y. Sugi, Ind. Eng. Chem. Res. 45, 6118 (2006)

    Article  CAS  Google Scholar 

  26. H.-J. Dong, L. Shi, Ind. Eng. Chem. Res. 49, 2091 (2010)

    Article  CAS  Google Scholar 

  27. L.-B. Chen, H.-j Dong, L. Shi, Ind. Eng. Chem. Res. 49, 7234 (2010)

    Article  CAS  Google Scholar 

  28. A. Vinu, K.U. Nandhini, V. Murugesan, W. Böhlmann, V. Umamaheswari, A. Pöppl, M. Hartmann, Appl. Catal. A265, 1 (2004)

    Article  Google Scholar 

  29. T. Mathew, S. Shylesh, B.M. Devassy, M. Vijayaraj, C.V.V. Satyanarayana, B.S. Rao, C.S. Gopinath, Appl. Catal. A273, 35 (2004)

    Article  Google Scholar 

  30. A. Vinu, B.M. Devassy, S.B. Halligudi, W. Böhlmann, M. Hartmann, Appl. Catal. A281, 207 (2005)

    Article  Google Scholar 

  31. G.S. Kumar, M. Vishnuvarthan, M. Palanichamy, V. Murugesan, J. Mol. Catal. A: Chem. 260, 49 (2006)

    Article  CAS  Google Scholar 

  32. B. Rác, M. Nagy, I. Pálinkó, Á. Molnár, Appl. Catal. A316, 152 (2007)

    Article  Google Scholar 

  33. E.-P. Ng, H. Nur, K.-L. Wong, M.N.M. Muhid, H. Hamdan, Appl. Catal. A323, 58 (2007)

    Article  Google Scholar 

  34. E.-P. Ng, S.N. Mohd Subari, O. Marie, R.R. Mukti, J.-C. Juan, Appl. Catal. A450, 34 (2013)

    Article  Google Scholar 

  35. X. Liu, M. Liu, X. Guo, J. Zhou, Catal. Commun. 9, 1 (2008)

    Article  CAS  Google Scholar 

  36. K. Kondamudi, P. Elavarasan, P.J. Dyson, S. Upadhyayula, J. Mol. Catal. A: Chem. 321, 34 (2010)

    Article  CAS  Google Scholar 

  37. P. Elavarasan, K. Kondamudi, S. Upadhyayula, Chem. Eng. J. 166, 340 (2011)

    Article  CAS  Google Scholar 

  38. X. Liu, J. Zhou, X. Guo, M. Liu, X. Ma, C. Song, C. Wang, Ind. Eng. Chem. Res. 47, 5298 (2008)

    Article  CAS  Google Scholar 

  39. F. Adam, K.M. Hello, T.H. Ali, Appl. Catal. A399, 42 (2011)

    Article  Google Scholar 

  40. S.M. Kumbar, G.V. Shanbhag, F. Lefebvre, S.B. Halligudi, J. Mol. Catal. A: Chem. 256, 324 (2006)

    Article  CAS  Google Scholar 

  41. B.M. Reddy, M.K. Patil, G.K. Reddy, B.T. Reddy, K.N. Rao, Appl. Catal. A332, 183 (2007)

    Article  Google Scholar 

  42. B.M. Devassy, G.V. Shanbhag, S.P. Mirajkar, W. Böhringer, J. Fletcher, S.B. Halligudi, J. Mol. Catal. A: Chem. 233, 141 (2005)

    Article  CAS  Google Scholar 

  43. B.M. Devassy, G.V. Shanbhag, F. Lefebvre, S.B. Halligudi, J. Mol. Catal. A: Chem. 210, 125 (2004)

    Article  CAS  Google Scholar 

  44. S. Sarish, B.M. Devassy, S.B. Halligudi, J. Mol. Catal. A: Chem. 235, 44 (2005)

    Article  CAS  Google Scholar 

  45. B.M. Devassy, G.V. Shanbhag, S.B. Halligudi, J. Mol. Catal. A: Chem. 247, 162 (2006)

    Article  CAS  Google Scholar 

  46. N. Bhatt, P. Sharma, A. Patel, P. Selvam, Catal. Commun. 9, 1545 (2008)

    Article  CAS  Google Scholar 

  47. G. Kamalakar, K. Komura, Y. Sugi, Appl. Catal. A310, 155 (2006)

    Article  Google Scholar 

  48. M. Selvaraj, P.K. Sinha, J. Mol. Catal. A: Chem. 264, 44 (2007)

    Article  CAS  Google Scholar 

  49. M. Selvaraj, S. Kawi, Micropor. Mesopor. Mat. 98, 143 (2007)

    Article  CAS  Google Scholar 

  50. R.C. Huston, W.C. Lewis, J. Am. Chem. Soc. 53, 2379 (1931)

    Article  CAS  Google Scholar 

  51. H. Hart, E.A. Haglund, J. Org. Chem. 15, 396 (1950)

    Article  CAS  Google Scholar 

  52. R. Alamdari, Z. Hosseinabadi, M. Khouzani, J. Chem. Sci. 124, 827 (2012)

    Article  CAS  Google Scholar 

  53. R. Fareghi-Alamdari, M. Golestanzadeh, F. Agend, N. Zekri, J. Chem. Sci. 125, 1185 (2013)

    Article  CAS  Google Scholar 

  54. R. Fareghi-Alamdari, M. Golestanzadeh, F. Agend, N. Zekri, C. R. Chimie 16, 878 (2013)

    Article  CAS  Google Scholar 

  55. R. Fareghi-Alamdari, M. Golestanzadeh, F. Agend, N. Zekri, Can. J. Chem. 91, 982 (2013)

    Article  CAS  Google Scholar 

  56. H. Hu, P. Bhowmik, B. Zhao, M.A. Hamon, M.E. Itkis, R.C. Haddon, Chem. Phys. Lett. 345, 25 (2001)

    Article  CAS  Google Scholar 

  57. N.P. Blanchard, R.A. Hatton, S.R.P. Silva, Chem. Phys. Lett. 434, 92 (2007)

    Article  CAS  Google Scholar 

  58. A.G. Osorio, I.C.L. Silveira, V.L. Bueno, C.P. Bergmann, Appl. Surf. Sci. 255, 2485 (2008)

    Article  CAS  Google Scholar 

  59. H. Peng, L.B. Alemany, J.L. Margrave, V.N. Khabashesku, J. Am. Chem. Soc. 125, 15174 (2003)

    Article  CAS  Google Scholar 

  60. H. Hu, B. Zhao, M.E. Itkis, R.C. Haddon, J. Phys. Chem. B107, 13838 (2003)

    Article  Google Scholar 

  61. S. Goyanes, G.R. Rubiolo, A. Salazar, A. Jimeno, M.A. Corcuera, I. Mondragon, Diamond Relat. Mater. 16, 412 (2007)

    Article  CAS  Google Scholar 

  62. A. Jorio, M.A. Pimenta, A.G.S. Filho, R. Saito, G. Dresselhaus, M.S. Dresselhaus, New J. Phys. 5, 139 (2003)

    Article  Google Scholar 

  63. E. Flahaut, C. Laurent, A. Peigney, Carbon 43, 375 (2005)

    Article  CAS  Google Scholar 

  64. J.J. Stephenson, J.L. Hudson, S. Azad, J.M. Tour, Chem. Mater. 18, 374 (2005)

    Article  Google Scholar 

  65. J.M. González-Domínguez, M. González, A. Ansón-Casaos, A.M. Díez-Pascual, M.A. Gómez, M.T. Martínez, J. Phys. Chem. C115, 7238 (2011)

    Google Scholar 

Download references

Acknowledgments

We gratefully acknowledge the financial support by Malek-Ashtar University of Technology (MUT). We thank Dr. Rashidi in Research Institute of Petroleum Industry (RIPI) for useful help.

Author information

Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Malek-Ashtar University of Technology, 16765-3454, Tehran, Iran

    Reza Fareghi-Alamdari, Negar Zekri & Zeinab Mavedatpoor

  2. Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, 87317-51167, Kashan, Iran

    Mohsen Golestanzadeh

Authors
  1. Reza Fareghi-Alamdari
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mohsen Golestanzadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Negar Zekri
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Zeinab Mavedatpoor
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Reza Fareghi-Alamdari.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Fareghi-Alamdari, R., Golestanzadeh, M., Zekri, N. et al. Multi SO3H supported on carbon nanotubes: a practical, reusable, and regioselective catalysts for the tert-butylation of p-cresol under solvent-free conditions. J IRAN CHEM SOC 12, 537–549 (2015). https://doi.org/10.1007/s13738-014-0511-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-014-0511-x

Keywords

Search

Navigation