Skip to main content
Log in

Knoevenagel condensation reactions catalyzed by nitrogen-containing mesoporous carbon materials under mild reaction conditions

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

Abstract

A series of nitrogen-containing ordered mesoporous carbon (NOMC) materials have been prepared by a convenient soft-templating method. The physicochemical properties of the NOMC samples were characterized by N2 adsorption and desorption, small-angle XRD, FT-IR, XPS, and TEM. As solid base catalysts, NOMCs exhibited remarkable catalytic activities for Knoevenagel condensation reactions under mild reaction conditions, depending on their synthetic calcination temperature. Among them, NOMC-500 showed the highest catalytic activity. For Knoevenagel condensation of benzaldehyde and malononitrile, the conversion of aldehyde was higher than 85% under 50 °C. Moreover, the catalysts had good catalytic applicability for wide substrates. The catalytic activity obtained on NOMC catalyst is compared with other nitrogen-containing carbon-based materials.

Graphical abstract

Nitrogen-containing ordered mesoporous carbon materials, prepared by a soft-templating method under aqueous solution and as solid base catalysts, demonstrated high catalytic activity in Knoevenagel condensation reactions under mild reaction conditions.

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
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. X. Zhang, E.S. Man Lai, R. Martin-Aranda, K.L. Yeung, Appl. Catal. A 261, 109 (2004)

    Article  CAS  Google Scholar 

  2. F. Ouyang, Y. Zhou, Z. Li, N. Hu, D. Tao, Korean J. Chem. Eng. 31, 1377 (2014)

    Article  CAS  Google Scholar 

  3. S. Saravanamurugan, M. Palanichamy, M. Hartmann, V. Murugesan, Appl. Catal. A 298, 8 (2006)

    Article  CAS  Google Scholar 

  4. M.B. Ansari, H. Jin, M.N. Parvin, S.-E. Park, Catal. Today 185, 211 (2012)

    Article  CAS  Google Scholar 

  5. S. van Dommele, K.P. de Jong, J.H. Bitter, Topic. Catal. 52, 1575 (2009)

    Article  CAS  Google Scholar 

  6. S.-E. Park, D.-S. Han, S.-C. Han, M.-J. Jin, T. Ohsuna, Chem. Commun. 39, 4131–4133 (2006)

    Google Scholar 

  7. M.N. Parvin, H. Jin, M.B. Ansari, S.-M. Oh, S.-E. Park, Appl. Catal. A 413–414, 205 (2012)

    Article  Google Scholar 

  8. S.N. Talapaneni, S. Anandan, G.P. Mane, C. Anand, D.S. Dhawale, S. Varghese, A. Mano, T. Mori, A. Vinu, J. Mater. Chem. 22, 9831 (2012)

    Article  CAS  Google Scholar 

  9. J. Xu, Y. Wang, J.-K. Shang, Q. Jiang, Y.-X. Li, Catal. Sci. Technol. 6, 4192 (2016)

    Article  CAS  Google Scholar 

  10. J. Xu, K. Shen, B. Xue, Y.-X. Li, Y. Cao, Catal. Lett. 143, 600 (2013)

    Article  CAS  Google Scholar 

  11. N.D. Shcherban, P. Mäki-Arvela, A. Aho, S.A. Sergiienko, P.S. Yaremov, K. Eränen, D.Y. Murzin, Catal. Sci. Technol. 8, 2928 (2018)

    Article  CAS  Google Scholar 

  12. X. Jin, V.V. Balasubramanian, S.T. Selvan, D.P. Sawant, M.A. Chari, G.Q. Lu, A. Vinu, Angew. Chem. Int. Ed. 48, 7884 (2009)

    Article  CAS  Google Scholar 

  13. J. Xu, K.-Z. Long, T. Chen, B. Xue, Y.-X. Li, Y. Cao, Catal. Sci. Technol. 3, 3192 (2013)

    Article  CAS  Google Scholar 

  14. C. Anand, S.V. Priya, G. Lawrence, G.P. Mane, D.S. Dhawale, K.S. Prasad, V.V. Balasubramanian, M.A. Wahab, A. Vinu, Catal. Today 204, 164 (2013)

    Article  CAS  Google Scholar 

  15. J. Zhu, P. Xiao, H. Li, S.A.C. Carabineiro, A.C.S. Appl, Mater. Inter. 6, 16449 (2014)

    Article  CAS  Google Scholar 

  16. Y. Wang, Q. Jiang, J.-K. Shang, J. Xu, Y.-X. Li, Acta Phys. -Chim. Sin. 32, 1913 (2016)

    CAS  Google Scholar 

  17. J. Xu, K.-Z. Long, Y. Wang, B. Xue, Y.-X. Li, Appl. Catal. A 496, 1 (2015)

    Article  CAS  Google Scholar 

  18. T. Tanabe, Y. Yamada, J. Kim, M. Koinuma, S. Kubo, N. Shimano, S. Sato, Carbon 109, 208 (2016)

    Article  CAS  Google Scholar 

  19. D.P. Bezerra, D.C.S. Azevedo, L.G. Pinheiro, J.M. Filho, A.C. Oliveira, Chem. Eng. J. 264, 565 (2015)

    Article  CAS  Google Scholar 

  20. S. Fujita, A. Katagiri, H. Watanabe, S. Asano, H. Yoshida, M. Arai, ChemCatChem 7, 2965 (2015)

    Article  CAS  Google Scholar 

  21. J. Yu, M. Guo, F. Muhammad, A. Wang, F. Zhang, Q. Li, G. Zhu, Carbon 69, 502 (2014)

    Article  CAS  Google Scholar 

  22. J. Wei, D. Zhou, Z. Sun, Y. Deng, Y. Xia, D. Zhao, Adv. Funct. Mater. 23, 2322 (2013)

    Article  CAS  Google Scholar 

  23. J. Wang, H. Liu, J. Diao, X. Gu, H. Wang, J. Rong, B. Zong, D.S. Su, J. Mater. Chem. A 3, 2305 (2015)

    Article  CAS  Google Scholar 

  24. J. Wang, H. Liu, X. Gu, H. Wang, D.S. Su, Chem. Commun. 50, 9182 (2014)

    Article  CAS  Google Scholar 

  25. D. Ma, H. Zheng, H.-M. Wan, Y. Chen, J. Xu, B. Xue, Micropor. Mesopor. Mater. 258, 244 (2018)

    Article  CAS  Google Scholar 

  26. J. Xu, D. Ma, Y. Chen, Y. Wang, Y.-X. Li, Micropor. Mesopor. Mater. 241, 72 (2017)

    Article  CAS  Google Scholar 

  27. N.D. Shcherban, P.S. Yaremov, V.G. Ilyin, M.V. Ovcharova, J. Anal. Appl. Pyrol. 107, 155 (2014)

    Article  CAS  Google Scholar 

  28. N. Liu, L. Yin, C. Wang, L. Zhang, N. Lun, D. Xiang, Y. Qi, R. Gao, Carbon 48, 3579 (2010)

    Article  CAS  Google Scholar 

  29. Q. Li, J. Yang, D. Feng, Z. Wu, Q. Wu, S.S. Park, C.-S. Ha, D. Zhao, Nano Res. 3, 632 (2010)

    Article  CAS  Google Scholar 

  30. L. Zhang, H. Wang, Z. Qin, J. Wang, W. Fan, RSC Adv. 5, 22838 (2015)

    Article  CAS  Google Scholar 

  31. G.-P. Hao, W.-C. Li, D. Qian, A.-H. Lu, Adv. Mater. 22, 853 (2010)

    Article  CAS  Google Scholar 

  32. J. Jiang, Q. Gao, Z. Zheng, K. Xia, J. Hu, Int. J. Hydrogen Energy 35, 210 (2010)

    Article  CAS  Google Scholar 

  33. D.-H. Lan, F.-M. Yang, S.-L. Luo, C.-T. Au, S.-F. Yin, Carbon 73, 351 (2014)

    Article  CAS  Google Scholar 

  34. J. Xu, Y. Wang, J.-K. Shang, D. Ma, Y.-X. Li, Appl. Catal. A 538, 221 (2017)

    Article  CAS  Google Scholar 

  35. N. Kan-Nari, S. Okamura, S.-I. Fujita, J.-I. Ozaki, M. Arai, Adv. Synth. Catal. 352, 1476 (2010)

    Article  CAS  Google Scholar 

  36. P. Makowski, J. Weber, A. Thomas, F. Goettmann, Catal. Commun. 10, 243 (2008)

    Article  CAS  Google Scholar 

  37. Y. Zhang, C. Chen, G. Wu, N. Guan, L. Li, J. Zhang, Chem. Commun. 50, 4305 (2014)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The work was supported by PetroChina Innovation Foundation (2018D-5007-0508), Advanced Catalysis and Green Manufacturing Collaborative Innovation Center (ACGM2016-06-28), Foundation of State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering (2017-K28), the Top-notch Academic Programs Project of Jiangsu Higher Education Institutions (PPZY2015B145), and the Priority Academic Program Development of Jiangsu Higher Education Institutions.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jie Xu.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 827 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Xue, B., Wen, LZ., Ma, D. et al. Knoevenagel condensation reactions catalyzed by nitrogen-containing mesoporous carbon materials under mild reaction conditions. Res Chem Intermed 44, 7641–7655 (2018). https://doi.org/10.1007/s11164-018-3578-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-018-3578-7

Keywords

Navigation