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One-pot synthesis of nitrogen-doped highly ordered mesoporous polymer nanospheres as a highly efficient catalyst for the water-medium Knoevenagel reactions

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Abstract

Nitrogen-doped mesoporous polymer nanospheres (3HP-MPS) with short channel structures were prepared by a template strategy using 3-hydroxypyridine as a nitrogen source. The nitrogen basic active sites are incorporated into the framework of mesoporous polymer. The nitrogen amount of 3HP-MPS sample could be adjusted up to 1.87%. The as-made 3HP-MPS sample possesses the unique amphiphilic property, which enables the effective reaction in the water medium even without organic solvents. As demonstrated experimentally, the unique 3HP-MPS catalyst displays the approximate efficiencies to 3-hydroxypyridine homogenous catalyst in water-medium Knoevenagel reactions. Moreover, the robust 3HP-MPS catalyst could be easily recycled and reused for at least five times without obvious decrease of catalytic performance. The result shows the catalyst has important application in green chemistry in the future.

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References

  1. F. Freeman, Chem. Rev. 80, 329 (1980)

    Article  CAS  Google Scholar 

  2. L.F. Tietze, Chem. Rev. 96, 115 (1996)

    Article  CAS  PubMed  Google Scholar 

  3. L. Pan, Y. Ni, Z. Yao, Z. Yu, W. Wu, A. Ying, Chem. J. Chin. Uni. 36, 81 (2015)

    Google Scholar 

  4. G.A. Kraus, M.E. Krolski, J. Org. Chem. 51, 3347 (1986)

    Article  CAS  Google Scholar 

  5. R. Banerjee, S. Mondal, P. Purkayastha, RSC Adv. 6, 105347 (2016)

  6. M. Zahouily, M. Salah, B. Bahlaouane, A. Rayadh, A. Houmam, E. Hamed, S. Sebti, Tetrahedron 60, 1631 (2004)

    Article  CAS  Google Scholar 

  7. D.W. Shawn, C. DiVirgilio, E. Huang, L. Liu, P. Morrison, H. Sugi, K. Tanaka, M. Woo, J. Faul, Org. Process Res. Dev. 15, 570 (2011)

    Article  Google Scholar 

  8. K. Jain, S. Chaudhuri, K. Pal, K. Das, New J. Chem. 43, 1299 (2019)

    Article  CAS  Google Scholar 

  9. A. Lee, A. Michrowska, S.B. Sulzer-Mosse, Angew Chem. Int. Ed. 50, 1707 (2011)

    Article  CAS  Google Scholar 

  10. X. Gu, Y. Tang, X. Zhang, Z. Lu, H. Lu, New J. Chem. 40, 6580 (2016)

    Article  CAS  Google Scholar 

  11. S.K. Panja, N. Dwivedi, S. Saha, RSC Adv. 5, 65526 (2015)

    Article  CAS  Google Scholar 

  12. T.M. Suzuki, M. Yamamoto, K. Fukumoto, Y. Akimoto, K. Yano, J. Catal. 251, 249 (2007)

    Article  CAS  Google Scholar 

  13. R.A. Sheldon, Green Chem. 7, 267 (2005)

    Article  CAS  Google Scholar 

  14. Z. An, Y. Dai, Y. Jiang, J. He, Asian. J. Org. Chem. 8, 1539 (2019)

    CAS  Google Scholar 

  15. I. Kohei, H. Takashi, S. Toshio, H. Hisahiro, Mol. Divers 9, 317 (2005)

    Article  Google Scholar 

  16. X. Wang, K.S.K. Lin, J.C.C. Chan, S. Cheng, J. Phys. Chem. B 109, 1763 (2005)

    Article  CAS  PubMed  Google Scholar 

  17. F. Zhu, D. Yang, F. Zhang, H. Li, J. Mol. Catal. A: Chemical 363–364, 387 (2012)

    Article  Google Scholar 

  18. N. Yao, J. Tan, X. Liu, Y. Liu, Y. Hu, J. Saudi Chem. Soc. 23, 740 (2019)

    Article  Google Scholar 

  19. D. Elhamifar, S. Kazempoor, B. Karimi, Catal. Sci. Technol. 6, 4318 (2016)

    CAS  Google Scholar 

  20. N. Lolak, E. Kuyuldar, H. Burhan, H. Goksu, S. Akocak, F. Sen, ACS Omega 4, 6848 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. J. Zhu, F. Wang, D. Li, J. Zhai, P. Liu, W. Zhang, Y. Li, Catal. Lett. 150, 1909 (2020)

    Article  CAS  Google Scholar 

  22. N. Barrios-Bermúdez, J. Santos-Granados, V. Calvino-Casilda, M.L. A. Cerpa-Naranjo Rojas-Cervantes, Catal. Lett. 149, 2279 (2019)

  23. X. Hu, Y. Long, M. Fan, M. Yuan, H. Zhao, J. Ma, Z. Dong, App. Catal. B: Environ. 244, 25 (2019)

    Article  CAS  Google Scholar 

  24. Y. Jiang, F. Jiang, X. Liao, S. Lai, S. Wang, X. Xiong, J. Zheng, Y. Liu, J. Porous Mater. 27, 779 (2020)

    Article  CAS  Google Scholar 

  25. Z. Liu, L. Ning, K. Wang, L. Feng, W. Gu, X. Liu, J. Mol. Struct. 1221, 128744 (2020)

  26. B, Qiu, S, Fan, Y, Wang, J, Chen, Z, Xiao, Y, Wang, Y, Chen, J, Liu, Y, Qin, S, Jian, Chem. Eng. J. 400, 125910 (2020)

  27. Y. Yang, D. Wang, P. Jiang, W. Gao, R. Cong, T. Yang, Mol. Catal. 490, 110914 (2020)

  28. F. Wang, K. Hu, Y. Bi, X. Wei, B. Xue, Chem. Phys. 539, 110942. (2020)

  29. A. Das, N. Anbu, A. Dhakshinamoorthy, S. Biswas, Microporous Mesoporous Mater. 284, 459 (2019)

    Article  CAS  Google Scholar 

  30. Y. Huang, L. Yang, M. Huang, J. Wang, L. Xu, W. Li, H. Zhou, X. Sun, H. Xing, H. Liu, Particuology 22, 128 (2015)

    Article  CAS  Google Scholar 

  31. X. Yang, Y. Song, T. Cao, L. Wang, H. Song, W. Lin, Mol. Catal. 492, 110971 (2020)

  32. E. Rahmati, Z. Rafiee, J. Porous. Mater. 28, 1 (2020)

    Google Scholar 

  33. F. Zhu, X. Sun, J. Zhou, P. Zhao, Green Chem Lett Rev 7, 250 (2014)

    Article  Google Scholar 

  34. Z. Sun, Y. Wang, Z. Zhang, F. Zhu, P. Zhao, G. Li, F. Shao, J. Rui, Res. Chem. Intermed. 45, 3107 (2019)

    Article  CAS  Google Scholar 

  35. R.K. Sharma, S. Sharma, S. Dutta, R. Zboril, M.B. Gawande, Green Chem. 17, 3207 (2015)

    Article  CAS  Google Scholar 

  36. I. Muylaert, A. Verberckmoes, J. De Decker, P. Van Der Voort, Adv Colloid Interface Sci. 175, 39 (2012)

    Article  CAS  PubMed  Google Scholar 

  37. I. Muylaert, A. Verberckmoes, J. Spileers, A. Demuynck, L. Peng, F. De Clippel, P. Van Der Voort, Mater. Chem. Phys. 138, 131 (2013)

    Article  CAS  Google Scholar 

  38. F. Zhang, X. Yang, L. Jiang, C. Liang, R. Zhu, H. Li, Green Chem. 15, 1665 (2013)

    Article  CAS  Google Scholar 

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

  40. K. Wang, L. Yang, W. Zhao, L. Cao, Z. Sun, F. Zhang, Green Chem. 19, 1949 (2017)

    Article  CAS  Google Scholar 

  41. Y. Meng, D. Gu, F. Zhang, Y. Shi, H. Yang, Z. Li, C. Yu, B. Tu, D. Zhao, Angew Chem. Intl. Ed. 44, 7053 (2005)

    Article  CAS  Google Scholar 

  42. Z. Wu, Y. Yang, B. Tu, P.A. Webley, D. Zhao, Adsorption 15, 123 (2009)

    Article  CAS  Google Scholar 

  43. J. Yang, Y. Zhai, Y. Deng, D. Gu, Q. Li, Q. Wu, Y. Huang, B. Tu, D. Zhao, J. Colloid Interface Sci. 342, 579 (2010)

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

  45. K.L. Tan, B.T.G. Tan, E.T. Kang, K.G.J. Neoh, Chem Phys. 94, 5382 (1991)

    CAS  Google Scholar 

  46. H. Chen, M. Zhou, Z. Wang, S. Zhao, S. Guan, Electrochim. Acta 148, 187 (2014)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  48. B. Xue, L. Wen, D. Ma, M. Li, J. Xu, Res. Chem. Intermed. 44, 7641 (2018)

    Article  CAS  Google Scholar 

  49. P.H. Yang, Q.Z. Zhang, H.J. Yu, Res. Chem. Intermed. 38, 1403 (2012)

    Article  CAS  Google Scholar 

  50. M.P. Kapoor, S. Inagaki, Chem. Mater. 14, 3509 (2002)

    Article  CAS  Google Scholar 

Download references

Funding

This work was supported the National Natural Science Foundation of China (No. 51872109), the Natural Science Foundation of Jiangsu Provincial Department of Education (No.17KJA150002), and College Students’ Practical Innovation Project of Jiangsu Province (No. 201810323009Z).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huai, 223300, China

    Fengxia Zhu, Xuan Tan & Pusu Zhao

  2. The Education Ministry Key Lab of Resource Chemistry and Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, Shanghai, 200234, China

    Peng Li & Fujian Lv

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  1. Fengxia Zhu
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  2. Xuan Tan
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  3. Peng Li
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  4. Fujian Lv
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  5. Pusu Zhao
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Correspondence to Fengxia Zhu.

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Zhu, F., Tan, X., Li, P. et al. One-pot synthesis of nitrogen-doped highly ordered mesoporous polymer nanospheres as a highly efficient catalyst for the water-medium Knoevenagel reactions. Res Chem Intermed 48, 505–518 (2022). https://doi.org/10.1007/s11164-021-04628-y

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