Skip to main content
Log in

Synthesis of Sulfonated Carbon Nanocage and Its Performance as Solid Acid Catalyst

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

A carbon nanocage material (CKT) was first successfully sulfonated by introducing sulfophenyl groups on the surface of pore channels through benzenesulfonic acid-containing aryl radical in situ generated from the reaction of 4-aminobenzenesulfonic acid and isoamyl nitrite in water. The sulfonated carbon nanocage material (S-CKT) was characterized by Fourier transform infrared spectroscopy, transmission electron microscopy, powder small-angle X-ray diffraction and nitrogen sorption measurements. The results showed that the S-CKT still possess the high specific surface area (787 m2/g) and uniform mesoporous (pore diameter 4.7 nm) structures, although the structure of S-CKT is slightly disorder, compared with its unsulfonated precursor. S-CKT, as a carbon-based solid acid catalyst, showed good catalytic performance and reusability in the cross-Aldol condensation of ketones with aromatic aldehydes under solvent-free condition.

Graphical Abstract

[Dispersibility of S-CKT in H2O, DMF, EtOH (from left to right) after 6 month]

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
Fig. 5
Scheme 1

Similar content being viewed by others

References

  1. Clark JH (2002) Acc Chem Res 35:791

    Article  CAS  Google Scholar 

  2. Van Rhijn WM, De Vos DE, Sels BF, Bossaert WD, Jacobs PA (1998) Chem Commun 317

  3. Melero JA, Stucky GD, van Grieken R, Morales G (2002) J Mater Chem 12:1664

    Article  CAS  Google Scholar 

  4. Das D, Lee JF, Cheng S (2004) J Catal 223:152

    Article  CAS  Google Scholar 

  5. Dufaud V, Davis ME (2003) J Am Chem Soc 125:9403

    Article  CAS  Google Scholar 

  6. Yang Q, Kapoo MP, Inagaki S, Shirokura N, Kondo JN, Domen K (2005) J Mol Catal A 230:85

    Article  CAS  Google Scholar 

  7. Macquarrie DJ, Tavener SJ, Harmer MA (2005) Chem Commun 2363

  8. Rác B, Molnár Ä, Forgo P, Mohai M, Bertóti I (2006) J Mol Catal A 244:46

    Article  Google Scholar 

  9. Van de Vyver S, Peng L, Geboers J, Schepers H, de Clippel F, Gommes CJ, Goderis B, Jacobs PA, Sels BF (2010) Green Chem 12:1560

    Article  Google Scholar 

  10. Hara M, Yoshida T, Takagaki A, Takata T, Kondo JN, Domen K, Hayashi S (2004) Angew Chem Int Ed 43:2955

    Article  CAS  Google Scholar 

  11. Toda M, Takagaki A, Okamura M, Kondo JN, Hayashi S, Domen K, Hara M (2005) Nature 438:178

    Article  CAS  Google Scholar 

  12. Okamura M, Takagaki A, Toda M, Kondo JN, Domen K, Tatsumi T, Hara M, Hayashi S (2006) Chem Mater 18:3039

    Article  CAS  Google Scholar 

  13. Budarin VL, Clark JH, Luque R, Macquarrie DJ (2007) Chem Commun 634

  14. Ryoo R, Joo SH, Jun S (1999) J Phys Chem B 103:7743

    Article  CAS  Google Scholar 

  15. Lee J, Yoon S, Hyeon T, Oh SM, Kim KB (1999) Chem Commun 2177

  16. Joo SH, Choi J, Oh I, Kwak J, Liu Z, Terasaki O, Ryoo R (2001) Nature 412:169

    Article  CAS  Google Scholar 

  17. Zhang FQ, Meng Y, Gu D, Yan Y, Yu CZ, Tu B, Zhao DY (2005) J Am Chem Soc 127:13508

    Article  CAS  Google Scholar 

  18. Meng Y, Gu D, Zhang FQ, Shi YF, Yang HF, Li Z, Yu CZ, Tu B, Zhao DY (2005) Angew Chem Int Ed 44:7053

    Article  CAS  Google Scholar 

  19. Liang CD, Dai S (2006) J Am Chem Soc 128:5316

    Article  CAS  Google Scholar 

  20. Jun S, Choi M, Ryu S, Lee HY, Ryoo R (2003) Studies in surface science and catalysis, vol 146, Chap.1. Synthesis and Material, Jeju, Korea

  21. Wang XQ, Liu R, Waje MM, Chen ZW, Yan YS, Bozhilov KN, Feng PY (2007) Chem Mater 19:2395

    Article  CAS  Google Scholar 

  22. Price BK, Tour JM (2006) J Am Chem Soc 128:12899

    Article  CAS  Google Scholar 

  23. Xing R, Liu YM, Wang Y, Chen L, Wu HH, Jiang YW, He MY, Wu P (2007) Microporous Mesoporous Mater 105:41

    Article  CAS  Google Scholar 

  24. Sun ZP, Zhang XG, Tong H, Liang YY, Li HL (2009) J Colloid Interface Sci 337:614

    Article  CAS  Google Scholar 

  25. Peng L, Philippaerts A, Ke XX, Noyen JV, de Clippel F, Tendeloo GV, Jacobs PA, Sels BF (2010) Catal Today 150:140

    Article  CAS  Google Scholar 

  26. Vinu A, Miyahara M, Sivamurugan V, Mori T, Ariga K (2005) J Mater Chem 15:5122

    Article  CAS  Google Scholar 

  27. Vinu A, Miyahara M, Mori T, Ariga K (2006) J Porous Mater 13:379

    Article  CAS  Google Scholar 

  28. Vinu A, Hossian KZ, Srinivasu P, Miyahara M, Anandan S, Gokulakrishnan N, Mori T, Ariga K, Balasubramanian VV (2007) J Mater Chem 17:1819

    Article  CAS  Google Scholar 

  29. Ariga K, Vinu A, Miyahara M, Hill JP, Mori T (2007) J Am Chem Soc 129:11022

    Article  CAS  Google Scholar 

  30. Yang QH, Liu J, Yang J, Kapoor MP, Inagaki SJ, Li C (2004) J Catal 228:265

    Article  CAS  Google Scholar 

  31. Yadav JS, Subba Reddy BV, Nagaraju A, Sarma JARP (2002) Synth Commun 32:893

    Article  CAS  Google Scholar 

  32. Du ZY, Bao YD, Liu Z, Qiao W, Ma L, Huang ZS, Gu LQ, Chan ASC (2006) Arch Pharm 339:123

    Article  CAS  Google Scholar 

  33. Watanabe K, Imazawa BA (1982) Chem Soc Jpn 55:3208

    Article  CAS  Google Scholar 

  34. Yu H, Jin YG, Li ZL, Peng F, Wang HJ (2008) J Solid State Chem 181:432

    Article  CAS  Google Scholar 

  35. Sun ZP, Zhang XG, Liu RL, Liang YY, Li HL (2008) J Power Sources 185:801

    Article  CAS  Google Scholar 

  36. Sing KSW, Everett DH, Haul RAW, Mosou L, Pierotti RA, Rouquerol J, Siemeniewska T (1985) Pure Appl Chem 57:603

    Article  CAS  Google Scholar 

  37. Yu H, Jin YG, Li ZL, Peng F, Wang HJ (2008) J Solid State Chem 181:432

    Article  CAS  Google Scholar 

  38. Alcaide B, Almendros P (2003) Angew Chem 115:884

    Article  Google Scholar 

  39. Alcaide B, Almendros P (2003) Angew Chem Int Ed 42:858

    Article  CAS  Google Scholar 

  40. Zali A, Ghani K, Shokrolahi A, Keshavarz MH (2009) Chin J Catal 29:602

    Article  Google Scholar 

  41. Mohammadi ZG, Badiei A, Abbasi A, Farahani Z (2009) Chin J Chem 27:1537

    Article  Google Scholar 

  42. An LT, Zou JP, Zhang LL (2008) Catal Commun 9:349

    Article  CAS  Google Scholar 

  43. Li BJ, Xu Z (2009) J Am Chem Soc 131:16380

    Article  CAS  Google Scholar 

  44. Kuang YB, Islam NM, Nabae Y, Hayakawa T, Kakimoto MA (2010) Angew Chem Int Ed 49:436

    CAS  Google Scholar 

  45. Liang CD, Li ZJ, Dai S (2008) Angew Chem Int Ed 47:3696

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are thankful to financial support from the Natural Science Foundation of China (No. 20972090), and grateful to Dr. Kai-qiang Liu for TEM measurements and Dr. Ming-zhen Wang for NMR measurements.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Baolin Li.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lin, P., Li, B., Li, J. et al. Synthesis of Sulfonated Carbon Nanocage and Its Performance as Solid Acid Catalyst. Catal Lett 141, 459–466 (2011). https://doi.org/10.1007/s10562-010-0526-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-010-0526-6

Keywords

Navigation