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Preparation and testing of ceasium Brønsted ion-exchanged Al-SBA-15 supported heteropoly acid as heterogeneous catalyst in the fructone fragrancy synthesis

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Abstract

Here we report a new ceasium Brønsted ion-exchanged Al-SBA-15 (Cs/AS15) supported heteropoly acid (HPA) H3PW12O40 (HPA-Cs/AS15) material which can be prepared and used as heterogeneous catalyst for the fructone fragrancy synthesis. It was demonstrated that Cs+ was more effective than NH4+ as counter cation of ion-exchanged AS15 support for preparing HPA/AS15 catalyst with higher acidity and HPA leaching stability. HPA-Cs/AS15 material showed high acidity with the maximum NH3 desorption peak appeared at 759.6 °C in the NH3-TPD spectrum, stronger than pure HPA (635.7 °C) and the ammonium Brønsted ion-exchanged Al-SBA-15 supported HPA (HPA-NH4/AS15) (559.1 °C) materials. The HPA leaching stability test showed that the HPA content of HPA-Cs/AS15 catalyst reduced only by 2.55% after five washing times, much less than that of HPA-NH4/AS15 catalyst (49.22%).

The higher acidity helped improve the HPA-Cs/AS15 catalyst performance in the fructone fragrancy synthesis. The ethyl acetoacetate conversion over this catalyst was 94.82%, better than those over HPA-NH4/AS15 (93.49%) and pure HPA (89.52%) catalysts, although HPA-Cs/AS15 catalyst had lower HPA content (23.16 wt%) than HPA-NH4/AS15 (24.28 wt%). In addition, it was shown that the reaction conditions such as ethyl acetoacetate:ethanediol reactant molar ratio of 1:1.5, ethanediol used as the diol reactant, and toluene used as the solvent, the fructone fragrancy synthesis reaction over HPA-Cs/AS15 catalyst reached the highest ethyl acetoacetate conversion (95.58%). The toluene’s boiling temperature of 110.6 °C can promote the dispersion and contact abilities of the reactants with HPA molecules presented inside the pores of HPA-Cs/AS15 catalyst.

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References

  1. K. Kakaei, M.D. Esrafili, A. Ehsani, Interface Sci. Technol. 27, 1 (2019)

    Article  Google Scholar 

  2. E. Rafiee, S. Eavani, RSC Adv. 6, 46433 (2016)

    Article  CAS  Google Scholar 

  3. B. Hu, C. Li, S.X. Zhao, L.M. Rong, S.Q. Lv, X. Liang, C. Qi, Molecules 15, 5369 (2010)

    Article  CAS  Google Scholar 

  4. S. Gao, X.Z. Liang, J.G. Yang, M.Y. He, Sci. China Ser. B 51, 646 (2008)

    Article  CAS  Google Scholar 

  5. A. Vinu, J. Justus, V.V. Balasubramanian, S.B. Halligudi, K. Ariga, T. Mori, Collect. Czech. Chem. Commun. 73, 1112 (2008)

    Article  CAS  Google Scholar 

  6. F. Zhang, C. Yuan, J. Wang, Y. Kong, H. Zhu, C. Wang, J. Mol. Catal. A Chem. 247, 130 (2006)

    Article  CAS  Google Scholar 

  7. Y. Liu, Y.T. Wang, T. Liu, D.J. Tao, RSC Adv. 4, 22520 (2014)

    Article  CAS  Google Scholar 

  8. V.Z. Sasca, O. Verdes, L. Avram, A. Popa, A. Erdȍhelyi, A. Oszko, Appl. Catal. A Gen. 451, 50 (2013)

    Article  CAS  Google Scholar 

  9. E.Y. Safronova, A.K. Osipov, A.E. Baranchikov, A.B. Yaroslavtsev, Inorg. Mater. 51, 1157 (2015)

    Article  CAS  Google Scholar 

  10. E. Rafiee, F. Rahimi, Monatsh. Chem. 144, 361 (2013)

    Article  CAS  Google Scholar 

  11. Y. Iwase, S. Sano, L. Mahardiani, R. Abe, Y. Kamiya, J. Catal. 318, 34 (2014)

    Article  CAS  Google Scholar 

  12. T. Okuhara, H. Watanabe, T. Nishimura, K. Inumaru, M. Misono, Chem. Mater. 12, 2230 (2000)

    Article  CAS  Google Scholar 

  13. Z. Huo, J. Zhao, Z. Bu, P. Ma, Q. Liu, J. Niu, J. Wang, Chem. Cat. Chem. 6, 3096 (2014)

    CAS  Google Scholar 

  14. X. Lia, R. Cao, Q. Lin, Catal. Commun. 69, 5 (2015)

    Article  Google Scholar 

  15. E. Rafiee, F. Mirnezami, J. Mol. Liq. 199, 156 (2014)

    Article  CAS  Google Scholar 

  16. Y. Leng, J. Liu, P. Jiang, J. Wang, Chem. Eng. J. 239, 1 (2014)

    Article  CAS  Google Scholar 

  17. E. Rafiee, M. Kahrizi, Res. Chem. Intermed. 41, 2833 (2015)

    Article  CAS  Google Scholar 

  18. Y. Chen, Y. Cao, G.P. Zheng, B.B. Dong, X.C. Zheng, Adv. Powder Technol. 25, 1351 (2014)

    Article  CAS  Google Scholar 

  19. E. Rafiee, S.H. Shahebrahimi, M. Feyzi, M. Shaterzadeh, Inter. Nano Lett. 2, 29 (2012)

    Article  Google Scholar 

  20. A. Popa, V. Sasca, D. Bajuk-Bogdanović, I. HolclajtnerAntunović, J. Porous. Mater. 23, 211 (2016)

    Article  CAS  Google Scholar 

  21. R.M. Ladera, M. Ojeda, J.L.G. Fierro, S. Rojas, Catal. Sci. Technol. 5, 484 (2015)

    Article  CAS  Google Scholar 

  22. S.R. Mukai, T. Masuda, I. Ogino, K. Hashimoto, Appl. Catal. A: Gen. 165, 219 (1997)

    Article  CAS  Google Scholar 

  23. S.R. Mukai, L. Lin, T. Masuda, K. Hashimoto, Chem. Eng. Sci. 56, 799 (2001)

    Article  CAS  Google Scholar 

  24. L. Zhao, Y. Chi, Q. Yuan, N. Li, W. Yan, X. Li, J. Colloid Interface Sci. 390, 70 (2013)

    Article  CAS  Google Scholar 

  25. X. Zheng, L. Zhang, J. Li, S. Luo, J.P. Cheng, Chem. Commun. 47, 12325 (2011)

    Article  CAS  Google Scholar 

  26. R. Tayebee, M.M. Amini, M. Akbari, A. Aliakbari, Dalton Trans. 44, 9596 (2015)

    Article  CAS  Google Scholar 

  27. E. Grinenval, F. Bayard, J.M. Basset, F. Lefebvre, Inorg. Chem. 53, 2022 (2014)

    Article  CAS  Google Scholar 

  28. X. Chen, H. Li, P. Yin, T. Liu, Chem. Commun. 51, 6104 (2015)

    Article  CAS  Google Scholar 

  29. T.H. Truong, V.C. Do, N.M. Do, T.Q. Hung, H.V. Doan, T.N. Nguyen, T.H. Doan, T.H.N. Le, T.V. Nguyen, L.G. Bach, Q.V. Tran, Mol. Catal. 478, 110571 (2019). https://doi.org/10.1016/j.mcat.2019.110571

    Article  CAS  Google Scholar 

  30. M. Chamack, A.R. Mahjoub, H. Aghayan, Chem. Eng. J. 255, 686 (2014)

    Article  CAS  Google Scholar 

  31. Z. Zhang, K.G. Marek, J.S. Watson, J. Tian, M.R. Ryder, K.A. Tarach, L.L. Pérez, J.M. Triguero, I.M. Cabrera, Nat. Sus. 2, 39 (2019)

    Article  Google Scholar 

  32. M.J. Nash, A.M. Shough, D.W. Fickel, D.J. Doren, R.F. Lobo, J. Am. Chem. Soc. 130, 2460 (2008)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by Vietnam’s National Foundation for Science and Technology Development (NAFOSTED) under Grant Number 104.05-2016.38.

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Authors and Affiliations

  1. Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet Street, Cau Giay District, Hanoi City, Vietnam

    Quang Vinh Tran, Tran Quang Hung, Nam Thi Hoai Le & Van Tuyen Nguyen

  2. Graduate University of Science and Technology, 18 Hoang Quoc Viet Street, Cau Giay District, Hanoi City, Vietnam

    Quang Vinh Tran, Thi Hanh Truong, Tran Quang Hung & Van Tuyen Nguyen

  3. Vietnam Maritime University, 484 Lach Tray Street, Le Chan District, Haiphong City, Vietnam

    Thi Hanh Truong

  4. Department of Mechanical Engineering, University of Bristol, Bristol, BS8 1TH, UK

    Huan V. Doan

  5. Department of Oil Refining and Petrochemistry, Hanoi University of Mining and Geology, Duc Thang, Bac Tu Liem, Hanoi, Vietnam

    Huan V. Doan & Xuan Nui Pham

  6. NTT Hi-Tech Institute, Nguyen Tat Thanh University, Ho Chi Minh City, Vietnam

    Long Giang Bach

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  1. Quang Vinh Tran
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Tran, Q.V., Truong, T.H., Hung, T.Q. et al. Preparation and testing of ceasium Brønsted ion-exchanged Al-SBA-15 supported heteropoly acid as heterogeneous catalyst in the fructone fragrancy synthesis. J Porous Mater 27, 1745–1754 (2020). https://doi.org/10.1007/s10934-020-00948-3

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