Skip to main content
SpringerLink
Log in

Fabrication of activated carbon sulfuric acid as an excellent and novel solid acid catalyst, evaluating its catalytic activity in synthesizing 1,8-dioxo-octahydroxanthenes and 14-aryl-14H-dibenzo[a,j]xanthenes

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

In this work, for the first time, a novel and innovative procedure has been utilized to chemically functionalize activated carbon (AC) based on the sulfonation reaction, which can be used in catalytic reactions as a strong solid acid. For this aim, AC must pass three steps of oxidation, reduction, and sulfonation, respectively. Therefore, the AC first was oxidized, then reduced by lithium aluminum hydride, and eventually participate in the sulfonation reaction with chlorosulfonic acid. We utilized diverse analytical techniques such as FT-IR, XRD, TGA, XPS, and neutralization titration to characterize and confirm our claim that activated carbon was functionalized. The analysis results indicate that sulfonic acid groups were successfully anchored with covalent bonds on the AC's surface. The resulting catalyst was used to synthesize 1,8-dioxo-octahydroxanthenes and 14-aryl-14H-dibenzo[a,j]xanthenes and showed good activity and stability in these reactions. Also, the produced products showed acceptable and good yields (87–97%). Reusability without loss of catalytic activity and simple fabrication method are other advantages of this catalyst.

Graphic 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
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Scheme 1
Scheme 2

Similar content being viewed by others

Availability of data and material

The manuscript has data included as electronic supplementary material.

References

  1. P. Gupta, S. Paul, Catal. Today 236, 153 (2014)

    Article  CAS  Google Scholar 

  2. P. T. Anastas and C. A. Farris, Benign by Design: Alternative Synthetic Design for Pollution Prevention (ACS Publications, 1994)

  3. P. Anastas, Green Chem. Theory Pract. 30 (1998)

  4. P. T. Anastas, L. G. Heine, and T. C. Williamson, Green Chemical Syntheses and Processes: Introduction (ACS Publications, 2000)

  5. M. Lancaster, Green Chemistry: An Introductory Text (Royal society of chemistry, 2020)

  6. Subodh, K. Prakash, and D. T. Masram, ACS Appl. Polym. Mater. (2020)

  7. K. Chaudhary, K. Prakash, N.K. Mogha, D.T. Masram, Arab. J. Chem. 13, 4869 (2020)

    Article  CAS  Google Scholar 

  8. D. Yadav, A.K. Dixit, S. Raghothama, S.K. Awasthi, Dalt. Trans. 49, 12266 (2020)

    Article  CAS  Google Scholar 

  9. K. Prakash, D.T. Masram, J. Mater. Chem. C 8, 9201 (2020)

    Article  Google Scholar 

  10. K. Prakash, D.T. Masram, Dalt. Trans. 49, 1007 (2020)

    Article  Google Scholar 

  11. Shagufta, I. Ahmad, R. Dhar, Catal. Surv. Asia 21, 53 (2017)

  12. A. Corma, H. Garcia, Chem. Rev. 103, 4307 (2003)

    Article  CAS  PubMed  Google Scholar 

  13. R. Rinaldi, F. Schüth, Chemsuschem 2, 1096 (2009)

    Article  CAS  PubMed  Google Scholar 

  14. F. Liu, A. Zheng, I. Noshadi, F.-S. Xiao, Appl. Catal. B Environ. 136, 193 (2013)

    Article  CAS  Google Scholar 

  15. A. Corma, S. Iborra, A. Velty, Chem. Rev. 107, 2411 (2007)

    Article  CAS  PubMed  Google Scholar 

  16. A.C. Cole, J.L. Jensen, I. Ntai, K.L.T. Tran, K.J. Weaver, D.C. Forbes, J.H. Davis, J. Am. Chem. Soc. 124, 5962 (2002)

    Article  CAS  PubMed  Google Scholar 

  17. A. Nouri Parouch, N. Koukabi, E. Abdous, Res. Chem. Intermed. (2020)

  18. F. Liu, K. Huang, A. Zheng, F.S. Xiao, S. Dai, ACS Catal. 8, 372 (2018)

    Article  CAS  Google Scholar 

  19. P. M. Price, J. H. Clark, and D. J. Macquarrie, J. Chem. Soc. Dalt. Trans. 101 (2000)

  20. M. Arghan, N. Koukabi, E. Kolvari, J. Saudi Chem. Soc. 23, 150 (2019)

    Article  CAS  Google Scholar 

  21. C.S. Gill, B.A. Price, C.W. Jones, J. Catal. 251, 145 (2007)

    Article  CAS  Google Scholar 

  22. A. Mahajan, P. Gupta, Environ. Chem. Lett. 18, 299 (2020)

    Article  CAS  Google Scholar 

  23. J.L. White, M.J. Truitt, Prog. Nucl. Magn. Reson. Spectrosc. 51, 139 (2007)

    Article  CAS  Google Scholar 

  24. E. Cano-Serrano, J. M. Campos-Martin, J. L. G. Fierro, Chem. Commun. 246 (2003)

  25. K. Wilson, A.F. Lee, D.J. Macquarrie, J.H. Clark, Appl. Catal. A Gen. 228, 127 (2002)

    Article  CAS  Google Scholar 

  26. S. Inagaki, S. Guan, T. Ohsuna, O. Terasaki, Nature 416, 304 (2002)

    Article  CAS  PubMed  Google Scholar 

  27. G.A. Olah, P.S. Iyer, G.K.S. Prakash, Across Conv Lines Sel. Pap. Georg. A Olah 1, 594 (2003)

    Google Scholar 

  28. K. Tanabe, W.F. Hölderich, Appl. Catal. A Gen. 181, 399 (1999)

    Article  CAS  Google Scholar 

  29. S. Dutta, J. Kim, Y. Ide, J.H. Kim, M.S.A. Hossain, Y. Bando, Y. Yamauchi, K.C.-W. Wu, Mater. Horizons 4, 522 (2017)

    Article  CAS  Google Scholar 

  30. H. Konnerth, B.M. Matsagar, S.S. Chen, M.H.G. Prechtl, F.-K. Shieh, K.C.-W. Wu, Coord. Chem. Rev. 416, 213319 (2020)

    Article  CAS  Google Scholar 

  31. J. Wang, Y. Xu, B. Ding, Z. Chang, X. Zhang, Y. Yamauchi, K.C. Wu, Angew. Chemie Int. Ed. 57, 2894 (2018)

    Article  CAS  Google Scholar 

  32. J. Poupelin, G. Saint‐Ruf, O. Foussard‐Blanpin, G. Narcisse, G. Uchida‐Ernouf, R. Lacroix, Chem. Inform. 9 (1978)

  33. J.G. Waite, A.E. Yousef, J. Food Prot. 71, 1861 (2008)

    Article  CAS  PubMed  Google Scholar 

  34. J.M. Jamison, K. Krabill, A. Hatwalkar, E. Jamison, C. Tsai, Cell Biol. Int. Rep. 14, 1075 (1990)

    Article  CAS  PubMed  Google Scholar 

  35. A.K. Bhattacharya, K.C. Rana, M. Mujahid, I. Sehar, A.K. Saxena, Bioorg. Med. Chem. Lett. 19, 5590 (2009)

    Article  CAS  PubMed  Google Scholar 

  36. A. Banerjee, A.K. Mukherjee, Stain Technol. 56, 83 (1981)

    Article  CAS  PubMed  Google Scholar 

  37. M. Ahmad, T.A. King, D.-K. Ko, B.H. Cha, J. Lee, J. Phys. D. Appl. Phys. 35, 1473 (2002)

    Article  CAS  Google Scholar 

  38. R.-M. Ion, A. Planner, K. Wiktorowicz, D. Frackowiak, ActaBiochim. Pol. 45, 833 (1998)

    CAS  Google Scholar 

  39. B. Wang, P. Li, Y. Zhang, L. Wang, Chinese J. Chem. 28, 2463 (2010)

    Article  CAS  Google Scholar 

  40. A. Khojastehnezhad, A. Davoodnia, M. Bakavoli, N. Tavakoli-Hoseini, M. Zeinali-Dastmalbaf, Chinese J. Chem. 29, 297 (2011)

    Article  CAS  Google Scholar 

  41. E. Soleimani, M.M. Khodaei, A.T.K. Koshvandi, Chinese Chem. Lett. 22, 927 (2011)

    Article  CAS  Google Scholar 

  42. M.A. Naik, D. Sachdev, A. Dubey, Catal. Commun. 11, 1148 (2010)

    Article  CAS  Google Scholar 

  43. B. Maleki, M. Gholizadeh, Z. Sepehr, Bull. Korean Chem. Soc 32, 1697 (2011)

    Article  CAS  Google Scholar 

  44. N.K.M. Subodh, K. Chaudhary, G. Kumar, D.T. Masram, ACS Omega 3, 16377 (2018)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  45. K. Chaudhary, K. Prakash, D.T. Masram, Appl. Surf. Sci. 509, 144902 (2020)

    Article  CAS  Google Scholar 

  46. K. Prakash, K. Chaudhary, D.T. Masram, Appl. Catal. A Gen. 593, 117411 (2020)

    Article  CAS  Google Scholar 

  47. G. Kumar, N.K. Mogha, M. Kumar, D.T. Masram, Dalt. Trans. 49, 1963 (2020)

    Article  CAS  Google Scholar 

  48. M.A. Schwegler, P. Vinke, M. Van der Eijk, H. Van Bekkum, Appl. Catal. A Gen. 80, 41 (1992)

    Article  CAS  Google Scholar 

  49. T. Ramanathan, F.T. Fisher, R.S. Ruoff, L.C. Brinson, Chem. Mater. 17, 1290 (2005)

    Article  CAS  Google Scholar 

  50. L. Vast, G. Philippin, A. Destrée, N. Moreau, A. Fonseca, J.B. Nagy, J. Delhalle, Z. Mekhalif, Nanotechnology 15, 781 (2004)

    Article  CAS  Google Scholar 

  51. H. Ago, T. Kugler, F. Cacialli, W.R. Salaneck, M.S.P. Shaffer, A.H. Windle, R.H. Friend, J. Phys. Chem. B 103, 8116 (1999)

    Article  CAS  Google Scholar 

  52. X. Mo, D.E. López, K. Suwannakarn, Y. Liu, E. Lotero, J.G. Goodwin Jr., C. Lu, J. Catal. 254, 332 (2008)

    Article  CAS  Google Scholar 

  53. B. Rajitha, B.S. Kumar, Y.T. Reddy, P.N. Reddy, N. Sreenivasulu, Tetrahedron Lett. 46, 8691 (2005)

    Article  CAS  Google Scholar 

  54. P.S. Kumar, B.S. Kumar, B. Rajitha, P.N. Reddy, N. Sreenivasulu, Y.T. Reddy, ARKIVOC 12, 46 (2006)

    Article  Google Scholar 

  55. M. Seyyedhamzeh, P. Mirzaei, A. Bazgir, Dye. Pigment. 76, 836 (2008)

    Article  CAS  Google Scholar 

  56. Y. Rajinder, M. Gupta, J. Kour, J. Iran. Chem. Soc. 16, 1977 (2019)

    Article  CAS  Google Scholar 

  57. S. Karhale, Res. Chem. Intermed. 46, 3085 (2020)

    Article  CAS  Google Scholar 

  58. K. Niknam, M. Damya, J. Chinese Chem. Soc. 56, 659 (2009)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors sincerely acknowledge the Research Council of Semnan University for supporting this work.

Funding

Semnan University, Grant Recipient: Dr. Nadiya Koukabi, Associated Professor.

Author information

Authors and Affiliations

  1. Department of Chemistry, Semnan University, 35131-19111, Semnan, Iran

    Alireza Marandi & Nadiya Koukabi

  2. Faculty of Chemistry, Bu-Ali Sina University, 6517838683, Hamedan, Iran

    Mohammad Ali Zolfigol

Authors
  1. Alireza Marandi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nadiya Koukabi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mohammad Ali Zolfigol
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nadiya Koukabi.

Ethics declarations

Conflict of interest

All authors are aware of the submission and agree to its publication, and have no conflicts of interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

The results of elemental analysis and spectral data of some synthesized products were presented in the supplementary information.

Supplementary file1 (DOCX 2993 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Marandi, A., Koukabi, N. & Zolfigol, M.A. Fabrication of activated carbon sulfuric acid as an excellent and novel solid acid catalyst, evaluating its catalytic activity in synthesizing 1,8-dioxo-octahydroxanthenes and 14-aryl-14H-dibenzo[a,j]xanthenes. Res Chem Intermed 47, 3145–3163 (2021). https://doi.org/10.1007/s11164-021-04457-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-021-04457-z

Keywords

Search

Navigation