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Fe3O4@zeolite-SO3H as a magnetically bifunctional and retrievable nanocatalyst for green synthesis of perimidines

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Abstract

In the current study, a new catalytic system based on Fe3O4 nanoparticles immobilized on zeolite-SO3H (Fe3O4@zeolite-SO3H) is introduced. In the first stage, zeolite@SO3H was synthesized from the reaction of zeolite-NaY with chlorosulfonic acid to produce zeolo sulfuric acid. Then, Fe3O4@zeolite-SO3H was prepared via immobilizing magnetic nanoparticles on the surface of functionalized zeolite-NaY as a support. Fe3O4@zeolite-SO3H as a multifunctional nanoplatform system was recognized by FT-IR, FE-SEM, XRD, EDS, BET, and VSM techniques. This nanocomposite demonstrated high activity in the catalytic synthesis of perimidine derivatives under solvent-free conditions. Combining the advantages of solid acids based nanocomposites and magnetic separation, this method provides an efficient and much improved modification of the general synthesis of perimidines. Recycling experiments confirmed the good stability of the nanocatalyst for six times and its constant activity.

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References

  1. C. Hou, Z. Tai, L. Zhao, Y. Zhai, Y. Hou, Y. Fan, F.J. Wang, H. Lio, J. Mater. Chem. A. 7, 13460 (2019)

    CAS  Google Scholar 

  2. H. Sun, Z. Yang, Y. Pu, W. Dou, C. Wang, W. Wang, X. Hao, S. Chen, Q. Shao, M. Dong, S. Wu, T. Ding, Z. Guo, J. Colloid Interf. Sci. 547, 40 (2019)

    CAS  Google Scholar 

  3. B. Lin, Z. Lin, S. Chen, M. Yu, W. Li, Q. Gao, M. Dong, Q. Shao, S. Wu, T. Ding, Z. Guo, Dalton Trans. 48, 8279 (2019)

    CAS  PubMed  Google Scholar 

  4. G. Zhu, X. Cui, Y. Zhang, S. Chen, M. Dong, H. Liu, Q. Shao, T. Ding, S. Wu, Z. Guo, Polymer 172, 415 (2019)

    CAS  Google Scholar 

  5. C. Wang, V. Murugadoss, J. Kong, Z. He, X. Mai, Q. Shao, Y. Chen, L. Guo, C. Liu, S. Angaiah, Z. Guo, Carbon 140, 696 (2018)

    CAS  Google Scholar 

  6. X. Gong, Y. Liu, Y. Wang, Z. Xie, Q. Dong, M. Dong, H. Liu, Q. Shao, N. Lu, V. Murugadoss, T. Ding, Z. Guo, Polymer 168, 131 (2019)

    CAS  Google Scholar 

  7. Z. Lin, B. Line, Z. Wang, S. Chen, C. Wang, M. Dong, Q. Gao, Q. Shao, T. Ding, H. Liu, Z. Gao, Chemcatchem. 11, 2217 (2019)

    CAS  Google Scholar 

  8. N. Wu, D. Xu, Z. Wang, F. Wang, J. Liu, W. Liu, Q. Shao, H. Liu, Q. Gao, Z. Guo, Carbon 145, 433 (2019)

    CAS  Google Scholar 

  9. K. Li, Z. Wang, Q. Wang, Q. Shao, V. Murugadoss, S. Wu, W. Liu, J. Liu, Q. Gao, Z. Gao, Dalton Trans. 48, 5193 (2019)

    Google Scholar 

  10. X.L. Luo, F. Pei, W. Wang, H.M. Qian, K.K. Miao, Z. Pan, Y.S. Chen, G.D. Feng, Micropor. Mesopor. Mater. 262, 148 (2018)

    CAS  Google Scholar 

  11. Z. Shi, C. Wu, Y. Wu, H. Liu, G. Xu, J. Deng, H. Gu, H. Liu, J. Zhang, A. Umar, Y. Ma, Z. Guo, Sci. Adv. Mater. 11, 699 (2019)

    CAS  Google Scholar 

  12. Z. Shi, C. Jia, D. Wang, J. Deng, G. Xu, C. Wu, M. Dong, Z. Gau, Int. J. Biol. Macromol. 133, 964 (2019)

    CAS  PubMed  Google Scholar 

  13. H. Gu, X. Xu, J. Cai, S. Wei, H. Wei, H. Liu, D.P. Yong, Q. Shao, S. Wu, T. Diang, Z. Gau, Chem. Commun. 53, 11802 (2017)

    Google Scholar 

  14. G. Perot, M. Guisnet, J. Mol. Catal. 61, 173 (1990)

    CAS  Google Scholar 

  15. C.G.S. Lima, N.M. Moreira, M.W. Paixão, A.G. Corrêa, Curr. Opin. Green. Sustain. Chem. 15, 7 (2019)

    Google Scholar 

  16. Z. Shi, C. Wu, Y. Gu, Y. Liang, G. Xu, H. Liu, J. Zhang, H. Hou, J. Zhang, Z. Guo, Sci. Adv. Mater. 11, 1198 (2019)

    CAS  Google Scholar 

  17. A.R. Massah, R. Javad Kalbasi, A. Shafiei, Monatsh. Chem. 143, 643 (2012)

    CAS  Google Scholar 

  18. R. Estevez, I. Iglesias, D. Luna, F.M. Bautista, Molecules 22, 2206 (2017)

    PubMed Central  Google Scholar 

  19. H. Nur, G.L. Kee, H. Hamdan, T.M.I. Mahlia, J. Efendi, H.S.C. Metselaar, Int. J. Hydrogen Energy 37, 12513 (2012)

    CAS  Google Scholar 

  20. N. Krathumkhet, K. Vongjitpimol, T. Chuesutham, S. Changkhamchom, K. Phasuksom, A. Sirivat, K. Wattanakul, Solid State Ion. 319, 278 (2018)

    Google Scholar 

  21. H. Liu, S. Peng, L. Shu, T. Chen, T. Bao, R.L. Frost, Chemosphere 91, 1539 (2013)

    CAS  PubMed  Google Scholar 

  22. A. Gaffer, A.A. Al Kahlawy, D. Aman, Egypt. J. Petrol. 26, 995 (2017)

    Google Scholar 

  23. A. Mesdaghinia, A. Azari, R. Nabizadeh Nodehi, K. Yaghmaeian, A.K. Bharti, S. Agarwal, V.K. Gupta, K. Sharafi, J. Mol. Liq. 233, 378 (2017)

    CAS  Google Scholar 

  24. D. Lin, X. Feng, Y. Wu, B. Ding, T. Lu, Y. Liu, X. Chen, D.C. Yang, Appl. Surf. Sci. 456, 140 (2018)

    CAS  Google Scholar 

  25. P. Abasian, M. Radmansouri, M. Habibi Jouybari, M. Vaez Ghasemi, A. Mohammadi, M. Irani, F. Sharifian Jazi, Int. J. Biol. Macromol. 121, 398 (2019)

    CAS  PubMed  Google Scholar 

  26. S.V.H.S. Bhaskaruni, S. Maddila, K.K. Gangu, S.B. Jonnalagadda, Arab. J. Chem. (2017)

  27. C.V.T. Vo, J.W. Bode, J. Org. Chem. 79, 2809 (2014)

    CAS  PubMed  Google Scholar 

  28. V. Paragamian, M.B. Baker, B.M. Puma, J. Reale, J. Heterocycl. Chem. 5, 591 (1968)

    CAS  Google Scholar 

  29. T.A. Farghaly, M.A. Abdallah, Z.A. Muhammad, Res. Chem. Intermed. 41, 3937 (2015)

    CAS  Google Scholar 

  30. F.A. Bassyouni, S.M. Abu-Bakr, K.H. Hegab, W. El-Eraky, A.A.E. Beih, M.E.A. Rehim, Res. Chem. Intermed. 38, 1527 (2012)

    CAS  Google Scholar 

  31. M. Kalhor, N. Khodaparast, Res. Chem. Intermed. 41, 3235 (2015)

    CAS  Google Scholar 

  32. M. Kalhor, F. Rezaee-Baroonaghi, A. Dadras, Z. Zarnegar, Appl Organometal Chem. 33, e4784 (2019)

    Google Scholar 

  33. J.J. Vanden-Eynde, F. Delfosse, A. Mayence, Y.V. Haverbeke, Tetrahedron 51, 5813 (1995)

    CAS  Google Scholar 

  34. V.A. Ozeryanskii, E.A. Filatova, V.I. Sorokin, A.F. Pozharskii, Russ. Chem. Bull. 50, 846 (2001)

    CAS  Google Scholar 

  35. M. Kalhor, Org. Chem. Res. 1, 59 (2015)

    Google Scholar 

  36. M. Kalhor, S. Banibairami, S.A. Mirshokraie, Green Chem. Lett. Rev. 11, 334 (2018)

    CAS  Google Scholar 

  37. J. Safari, Z. Zarnegar, New J. Chem. 38, 358 (2014)

    CAS  Google Scholar 

  38. F. Rouquerol, J. Rouquerol, K.S.W. Sing, Adsorption by Powder and Porous Solids (Academic Press, San Diego, 1999), p. 1

    Google Scholar 

  39. M.M. Khakzad-Siuki, M. Bakavoli, H. Eshghi, Appl. Orgmet. Chem. 32, e4290 (2018)

    Google Scholar 

  40. M.A. Bodaghifard, S. Asadbegi, Z. Bahrami, J. Iran. Chem. Soc. 14, 365 (2017)

    CAS  Google Scholar 

  41. O. Maloshitskaya, J. Sinkkonen, V.V. Ovcharenko, K.N. Zelenin, K. Pihlaja, Tetrahedron 60, 6913 (2004)

    CAS  Google Scholar 

  42. F.K. Behbahani, F.M. Golchin, J. Taibah. Univ. Sci. 11, 85 (2017)

    Google Scholar 

  43. A. Mobinikhaledi, N. Foroughifar, Turk. J. Chem. 33, 555 (2009)

    CAS  Google Scholar 

  44. C.K. Wu, T.J. Teau-Jiuan Liou, H.Y. Wei, P.S. Tsai, D.Y. Yang, Tetrahedron 70, 8219 (2014)

    CAS  Google Scholar 

  45. A. Farrokhi, K. Keivan Ghodrati, I. Yavari, Catal. Commun. 63, 41 (2015)

    CAS  Google Scholar 

  46. K.M. Salih, H.J. Azeez, Res. Pharm. Biotechnol. 51, 1 (2014)

    Google Scholar 

  47. A. Mobinikhaledi, P. Steel, Synth. React. Inorg. Metal-Org. Nano-Met. Chem. 39, 133 (2009)

    CAS  Google Scholar 

  48. A. Bamoniri, B.B.F. Mirjalili, S. Saleh, RSC Adv. 8, 6178 (2018)

    Google Scholar 

  49. A. Mobinikhaledi, F. Sasani, A. Hamta, S.M. Shariatzadeh, Bulg. Chem. Commun. 45, 353 (2013)

    CAS  Google Scholar 

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Acknowledgements

We are thankful to the Payame Noor University for the partial support of this work.

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Correspondence to Mehdi Kalhor.

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Kalhor, M., Zarnegar, Z., Janghorban, F. et al. Fe3O4@zeolite-SO3H as a magnetically bifunctional and retrievable nanocatalyst for green synthesis of perimidines. Res Chem Intermed 46, 821–836 (2020). https://doi.org/10.1007/s11164-019-03992-0

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  • DOI: https://doi.org/10.1007/s11164-019-03992-0

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