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Friedel–Crafts acylation of pyrrole over ultrasonic-assisted phosphoric acid-modified Hβ zeolite

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Abstract

Friedel–Crafts acylation of pyrrole with acetic anhydride was studied over different zeolites and an ultrasonic-assisted phosphoric acid-modified Hβ (P-Hβ-US) zeolite was found to have the best catalytic performance among all the zeolites examined. The conversion of acetic anhydride reached 98.8% and the selectivity to acetylpyrroles was 97.0% under the optimized conditions. The high activity of the P-Hβ-US zeolite is attributed to the increase of weak acid sites, caused by the synergistic effect between the phosphoric acid modification and ultrasound. Moreover, the carbonaceous deposits, mainly due to the adsorption of reactants and products, on the surface acid sites and the blockage of the pores is believed to be the reason for the deactivation of the reused P-Hβ-US zeolite, confirmed from the Brunauer–Emmett–Teller (BET) method, scanning electron microscopy, and X-ray photoelectron spectroscopy. Furthermore, the catalyst activity can be recovered effectively by a subsequent calcination.

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References

  1. H. Goda, M. Kawamura, K. Kato, M. Sato, US Patent. 4 792 612 (1988)

  2. T. Fujisawa, K. Kondo, K. Sakai, US Patent. 4 266 067 (1981)

  3. L. Zhang, Z.Q. Liu, Y.L. Xu, S.Y. Liu, Res. Chem. Intermed. 33, 535 (2007)

    Article  CAS  Google Scholar 

  4. N.B. Shrigadi, A.B. Shinde, S.D. Samant, Appl. Catal. A Gen. 252, 23 (2003)

    Article  CAS  Google Scholar 

  5. W.B. Fan, S.Q. Wei, T. Yokoi, S. Inagaki, J.F. Li, J.G. Wang, J.N. Kondo, T. Tatsumi, J. Catal. 266, 268 (2009)

    Article  CAS  Google Scholar 

  6. E.G. Derouane, G. Crehan, C.J. Dillon, D. Bethell, H. He, S.B. Derouane-Abd Hamid, J. Catal. 194, 410 (2000)

    Article  CAS  Google Scholar 

  7. G.Y. Bai, H.Y. Dou, M.D. Qiu, X.X. Fan, F. He, L.B. Niu, Z. Ma, Res. Chem. Intermed. 36, 483 (2010)

    Article  CAS  Google Scholar 

  8. J. Klisáková, L. Červený, J. Čejka, Appl. Catal. A Gen. 272, 79 (2004)

    Article  Google Scholar 

  9. C. Venkatesan, T. Jaimol, P. Moreau, A. Finiels, A.V. Ramaswamy, A.P. Singh, Catal. Lett. 75, 119 (2001)

    Article  CAS  Google Scholar 

  10. J.M. Escola, M.E. Davis, Appl. Catal. A Gen. 214, 111 (2001)

    Article  CAS  Google Scholar 

  11. P. Ram Reddy, M. Subrahmanyam, S.J. Kulkarni, Catal. Lett. 54, 95 (1998)

    Article  Google Scholar 

  12. M.L. Kantam, K.V.S. Ranganath, M. Sateesh, K.B.S. Kumar, B.M. Choudary, J. Mol. Catal. A Chem. 225, 15 (2005)

    Article  CAS  Google Scholar 

  13. V.F.D. Álvaro, A.F. Brigas, E.G. Derouane, J.P. Lourenço, B.S. Santos, J. Mol. Catal. A Chem. 305, 100 (2009)

    Article  Google Scholar 

  14. N. Arul Dhas, A. Gedanken, Chem. Mater 9, 3144 (1997)

    Article  Google Scholar 

  15. B.Y. Wang, J.M. Wu, Z.Y. Yuan, N. Li, S.H. Xiang, Ultrason. Sonchem. 15, 334 (2008)

    Article  CAS  Google Scholar 

  16. G.Y. Bai, X.X. Fan, H.L. Wang, J.Z. Xu, F. He, H.S. Ning, Catal. Commun. 10, 2031 (2009)

    Article  CAS  Google Scholar 

  17. H. Kumar, A. Parmar, Ultrason. Sonchem. 15, 129 (2008)

    Article  CAS  Google Scholar 

  18. G.Y. Bai, H.Y. Dou, M.D. Qiu, X.X. Fan, F. He, L.B. Niu, Z. Ma, Catal. Lett. 138, 187 (2010)

    Article  CAS  Google Scholar 

  19. K.K. Cheralathan, I.S. Kumar, M. Palanichamy, V. Murugesan, Appl. Catal. A Gen. 241, 247 (2003)

    Article  CAS  Google Scholar 

  20. C. Gauthier, B. Chiche, A. Finiels, P. Geneste, J. Mol. Catal. 50, 219 (1989)

    Article  CAS  Google Scholar 

  21. N. Narender, K.V.V. Krishna Mohan, S.J. Kulkarni, I. Ajit Kumar Reddy, Catal. Commun. 7, 583 (2006)

    Article  CAS  Google Scholar 

  22. M. Ghiaci, A. Abbaspur, R. Kia, C. Belver, R. Trujillano, V. Rives, M.A. Vicente, Catal. Commun. 8, 49 (2007)

    Article  CAS  Google Scholar 

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Acknowledgments

The authors thank Professor Baoting Liu for his assistance. Financial support by the National Natural Science Foundation of China (20806018), the Natural Science Foundation of Hebei Province (B2011201017), and the Science Project of the Hebei Education Department (ZD200910) are gratefully acknowledged.

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Authors and Affiliations

  1. Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, College of Chemistry and Environmental Science, Hebei University, No.180 Wusi East Road, Baoding, 071002, Hebei, People’s Republic of China

    Guo Yi Bai, Yong Hui Yang, Zheng Ma, Jian Zhong Xu, Man De Qiu & Hai Yang Dou

  2. School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072, People’s Republic of China

    Fei He & Xi Long Yan

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  1. Guo Yi Bai
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  2. Yong Hui Yang
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Correspondence to Guo Yi Bai.

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Bai, G.Y., Yang, Y.H., Ma, Z. et al. Friedel–Crafts acylation of pyrrole over ultrasonic-assisted phosphoric acid-modified Hβ zeolite. Res Chem Intermed 38, 795–806 (2012). https://doi.org/10.1007/s11164-011-0418-4

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  • DOI: https://doi.org/10.1007/s11164-011-0418-4

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