Skip to main content
SpringerLink
Log in

Customized three-dimensional porous catalyst for Knoevenagel reaction

  • Published:
Journal of Porous Materials Aims and scope Submit manuscript

Abstract

Despite the success in the fabrication of various arbitrary-sized one-dimensional architectures, researches still face specific disadvantages of uncontrollable porosity and disordered structures, leading to a deficiency in micro-sized porous for efficient catalytic performance. To improve these limitations, herein, fabricating controllable microstructures based on three-dimensional (3D) printing technology was conducted for catalysis applications. Initially, a multi-channel organized structure printed by silica (SiO2) powder was as the support, onto which different organic functional groups were immobilized. Prior to exploring the catalytic efficiency, different techniques were used to investigate the characterization of 3D-SiO2 systematically. Amongst various immobilized functional groups, the 3D-SiO2 modified with diethylenetriamine showed the best catalytic activity for Knoevenagel condensation reaction. Moreover, the results showed that 3D-SiO2 enhanced catalytic activities of over 90% in only 30 min and could be reused more than ten times with high-performance efficiency while transforming various aldehydes in the presence of malononitrile.

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.

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

Similar content being viewed by others

References

  1. S. Swami, A. Agarwala, R. Shrivastava, Sulfonic acid functionalized silica-coated CuFe2O4 core-shell nanoparticles: an efficient and magnetically separable heterogeneous catalyst for the synthesis of 2-pyrazole-3-amino-imidazo-fused polyheterocycles. New. J. Chem. 40(11), 9788–9794 (2016)

    Article  CAS  Google Scholar 

  2. E. Yavuz, N. Cherkasov, V. Degirmenci, Acid and base catalysed reactions in one pot with site-isolated polyHIPE catalysts. RSC Adv. 9(15), 8175–8183 (2019)

    Article  CAS  Google Scholar 

  3. Y. Huang, L. Yang, M. Huang, J. Wang, L. Xu, W. Li, H. Zhou, X. Sun, H. Xing, H. Liu, Polystyrene microsphere-immobilized palladium(II) porphyrin as mild, reusable, and highly efficient catalyst for Heck reaction. Particuology 22, 128–133 (2015)

    Article  CAS  Google Scholar 

  4. X.G. Wang, K.S.K. Lin, J.C.C. Chan, S.F. Cheng, Direct synthesis and catalytic applications of ordered large pore aminopropyl-functionalized SBA-15 mesoporous materials. J. Phys. Chem. B 109(5), 1763–1769 (2005)

    Article  CAS  Google Scholar 

  5. S. Couck, J. Lefevere, S. Mullens, L. Protasova, V. Meynen, G. Desmet, G.V. Baron, J.F.M. Denayer, CO2, CH4 and N2 separation with a 3DFD-printed ZSM-5 monolith. Chem. Eng. J. 308, 719–726 (2017)

    Article  CAS  Google Scholar 

  6. J. Azuaje, C.R. Tubio, L. Escalante, M. Gomez, F. Guitian, A. Coelho, O. Caamano, A. Gil, E. Sotelo, An efficient and recyclable 3D printed alpha-Al2O3 catalyst for the multicomponent assembly of bioactive heterocycles. Appl. Catal. A 530, 203–210 (2017)

    Article  CAS  Google Scholar 

  7. M. Pourghasemi-Lati, F. Shirini, M. Alinia-Asli, M.A. Rezvani, Butane-1-sulfonic acid immobilized on magnetic Fe3O4@SiO2 nanoparticles: a novel and heterogeneous catalyst for the one-pot synthesis of barbituric acid and pyrano 2,3-d pyrimidine derivatives in aqueous media. Appl. Organomet. Chem. 32(10), e4455 (2018)

    Article  Google Scholar 

  8. S. Abdolmohammadi, M. Mohammadnejad, F. Shafaei, TiO2 nanoparticles as an efficient catalyst for the one-pot preparation of tetrahydrobenzo c acridines in aqueous media. Z. Naturforsch. B 68(4), 362–366 (2013)

    Article  CAS  Google Scholar 

  9. J. Zhao, B. Lin, Y. Zhu, Y. Zhou, H. Liu, Phosphor-doped hexagonal boron nitride nanosheets as effective acid-base bifunctional catalysts for one-pot deacetalization-Knoevenagel cascade reactions. Catal. Sci. Technol. 8(22), 5900–5905 (2018)

    Article  CAS  Google Scholar 

  10. S. Ishikawa, Y. Maegawa, M. Waki, S. Inagaki, Immobilization of a molybdenum complex on bipyridine-based periodic mesoporous organosilica and its catalytic activity for epoxidation of olefins. Acs Catal. 8(5), 4160–4169 (2018)

    Article  CAS  Google Scholar 

  11. S. Rossi, A. Puglisi, M. Benaglia, Additive manufacturing technologies: 3D printing in organic synthesis. Chemcatchem 1(7), 1512–1525 (2018)

    Article  Google Scholar 

  12. E.G. Gordeev, E.S. Degtyareva, V.P. Ananikov, Analysis of 3D printing possibilities for the development of practical applications in synthetic organic chemistry. Russ. Chem. B + 65(6), 1637–1643 (2016)

    Article  Google Scholar 

  13. X. Li, B. Lin, H. Li, Q. Yu, Y. Ge, X. Jin, X. Liu, Y. Zhou, J. Xiao, Carbon doped hexagonal BN as a highly efficient metal-free base catalyst for Knoevenagel condensation reaction. Appl. Catal. B 239, 254–259 (2018)

    Article  CAS  Google Scholar 

  14. B. Xue, L.-Z. Wen, D. Ma, M.-M. Li, J. Xu, Knoevenagel condensation reactions catalyzed by nitrogen-containing mesoporous carbon materials under mild reaction conditions. Res. Chem. Intermediat. 44(12), 7641–7655 (2018)

    Article  CAS  Google Scholar 

  15. I. del Hierro, Y. Perez, M. Fajardo, Supported choline hydroxide (ionic liquid) on mesoporous silica as heterogeneous catalyst for Knoevenagel condensation reactions. Micropor. Mesopor. Mat. 263, 173–180 (2018)

    Article  CAS  Google Scholar 

  16. W. Zhang, C. Feng, G. Yang, G. Li, X. Ding, S. Wang, Y. Dou, Z. Zhang, J. Chang, C. Wu, X. Jiang, 3D-printed scaffolds with synergistic effect of hollow-pipe structure and bioactive ions for vascularized bone regeneration. Biomaterials 135, 85–95 (2017)

    Article  CAS  Google Scholar 

  17. T. Ludwig, J. von Seckendorff, C. Troll, R. Fischer, M. Tonigold, B. Rieger, O. Hinrichsen, Additive manufacturing of Al2O3-Based carriers for heterogeneous catalysis. Chem.-Ing.-Technol. 90(5), 703–707 (2018)

    Article  CAS  Google Scholar 

  18. F. Lucci, A. Della Torre, G. Montenegro, R. Kaufmann, P.D. Eggenschwiler, Comparison of geometrical, momentum and mass transfer characteristics of real foams to Kelvin cell lattices for catalyst applications. Int. J. Heat Mass Tran. 108, 341–350 (2017)

    Article  CAS  Google Scholar 

  19. M. Esmaeilpour, A.R. Sardarian, H. Firouzabadi, Dendrimer-encapsulated Cu(П) nanoparticles immobilized on superparamagnetic Fe3O4@SiO2 nanoparticles as a novel recyclable catalyst for N-arylation of nitrogen heterocycles and green synthesis of 5-substituted 1H-tetrazoles. Appl. Organomet. Chem. 32(4), e4300 (2018)

    Article  Google Scholar 

  20. Y. Qiao, J. Teng, S. Wang, H. Ma, Amine-functionalized sugarcane bagasse: a renewable catalyst for efficient continuous flow Knoevenagel condensation reaction at room temperature. Molecules 23(1), 43 (2018)

    Article  Google Scholar 

  21. M. Honarmand, Green synthesis of a nano salt and its application as multifunctional organocatalyst for Knoevenagel condensation. Res. Chem. Intermediat. 43(11), 6421–6432 (2017)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank the Financial support from the National Marine Economic Innovation and Development Project (16PYY007SF17), the United Fujian Provincial Health and Education Project for Tracking Key Research (WKJ2016-2-22), the Natural Science Foundation of Fujian province (No. 2016J01063) and the Program for Innovative Research Team in Science and Technology at Fujian Province University. We also thank Ranjith Kumar Kankala, Pei Wang and Le-Qing Fan for improvising the revision. The funding was also provided by Natural Science Foundation of Fujian Province of China (2015J05169).

Author information

Author notes

    Authors and Affiliations

    1. College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021, Fujian, People’s Republic of China

      Yan Jiang, Xu Liao, Shi-Lin Lai, Shi-Bin Wang & Xing-Quan Xiong

    2. School of Pharmaceutical Sciences, Fujian Provincial Key Laboratory of Innovative Drug Target Research, Xiamen University, Xiamen, 361102, People’s Republic of China

      Fu-Quan Jiang

    3. College of Chemical Engineering, Huaqiao University, Xiamen, 361021, Fujian, People’s Republic of China

      Yuan-Gang Liu

    4. Institute of Pharmaceutical Engineering, Huaqiao University, Xiamen, 361021, Fujian, People’s Republic of China

      Shi-Bin Wang & Yuan-Gang Liu

    5. Fujian Provincial Key Laboratory of Biochemical Technology, Xiamen, 361021, Fujian, People’s Republic of China

      Shi-Bin Wang & Yuan-Gang Liu

    6. School of Materials Science and Engineering, Xiamen University of Technology, Xiamen, 361021, Fujian, People’s Republic of China

      Jun Zheng

    Authors
    1. Yan Jiang
      View author publications

      You can also search for this author in PubMed Google Scholar

    2. Fu-Quan Jiang
      View author publications

      You can also search for this author in PubMed Google Scholar

    3. Xu Liao
      View author publications

      You can also search for this author in PubMed Google Scholar

    4. Shi-Lin Lai
      View author publications

      You can also search for this author in PubMed Google Scholar

    5. Shi-Bin Wang
      View author publications

      You can also search for this author in PubMed Google Scholar

    6. Xing-Quan Xiong
      View author publications

      You can also search for this author in PubMed Google Scholar

    7. Jun Zheng
      View author publications

      You can also search for this author in PubMed Google Scholar

    8. Yuan-Gang Liu
      View author publications

      You can also search for this author in PubMed Google Scholar

    Corresponding authors

    Correspondence to Xing-Quan Xiong, Jun Zheng or Yuan-Gang Liu.

    Additional information

    Publisher's Note

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

    Rights and permissions

    Reprints and permissions

    About this article

    Check for updates. Verify currency and authenticity via CrossMark

    Cite this article

    Jiang, Y., Jiang, FQ., Liao, X. et al. Customized three-dimensional porous catalyst for Knoevenagel reaction. J Porous Mater 27, 779–788 (2020). https://doi.org/10.1007/s10934-020-00859-3

    Download citation

    • Published:

    • Issue Date:

    • DOI: https://doi.org/10.1007/s10934-020-00859-3

    Keywords

    Search

    Navigation