Fe3O4@FSM-16-SO3H as a novel magnetically recoverable nanostructured catalyst: preparation, characterization and catalytic application

  • Somayeh Hashemi-Uderji
  • Mohammad Abdollahi-Alibeik
  • Reza Ranjbar-Karimi


Fe3O4@FSM-16-SO3H was prepared as new magnetically recoverable catalyst and characterized by SEM, BET, XRD, EDS, VSM and FT-IR techniques. The catalytic activity was investigated in the reaction of various aldehydes, ethyl cyanoacetate, dimedone and ammonium acetate for the preparation of Polyhydroquinolines in one pot. This protocol suggests benefits in terms of higher yields and short reaction time. In addition, the catalyst could be separated using an external magnet and is reusable many times without significant loss of activity.


Magnetic nanoparticle Folded sheet mesoporous silica Polyhydroquinoline Hantzsch reaction Recoverable catalyst FSM-16 



We are thankful to the Yazd University Research Council for partial support of this work.


  1. 1.
    O. Veiseh, C. Sun, A. Sze, Hallahan, J. Gunn, N. Kohler, P. Gabikian, D. Lee, N. Bhattarai, R. Ellenbogen, R. Sze, Nano Lett. 5, 1003–1008 (2005)CrossRefGoogle Scholar
  2. 2.
    A.H. Latham, A.N. Tarpara, M.E. Williams, Anal. Chem. 79, 5746–5752 (2007)CrossRefGoogle Scholar
  3. 3.
    N. Shamim, L. Hong, K. Hidajat, M. Uddin, Sep. Purif. Technol. 53, 164–170 (2007)CrossRefGoogle Scholar
  4. 4.
    B. Gilbert, J.E. Katz, J.D. Denlinger, Y. Yin, R. Falcone, G.A. Waychunas, J. Phys. Chem. C 114, 21994–22001 (2010)CrossRefGoogle Scholar
  5. 5.
    X. Zhou, Y. Shi, L. Ren, S. Bao, Y. Han, S. Wu, H. Zhang, L. Zhong, Q. Zhang, J. Solid State Chem. 196, 138–144 (2012)CrossRefGoogle Scholar
  6. 6.
    Y. Guan, C. Jiang, C. Hu, L. Jia, Talanta 83, 337–343 (2010)CrossRefGoogle Scholar
  7. 7.
    Y. Arum, Y. Song, J. Oh, Appl. Nanosci. 1, 237–246 (2011)CrossRefGoogle Scholar
  8. 8.
    J. Wang, S. Zheng, Y. Shao, J. Liu, Z. Xu, D. Zhu, J. Colloid Interface Sci. 349, 293–299 (2010)CrossRefGoogle Scholar
  9. 9.
    P. Lu, J.-L. Zhang, Y.-L. Liu, J.-Z. Ni, D.-H. Sun, G.-X. Liu, G.-Y. Hong, Talanta 82, 450–457 (2010)CrossRefGoogle Scholar
  10. 10.
    S. Rostamnia, E. Doustkhah, J. Magn. Magn. Mater. 386, 111–116 (2015)CrossRefGoogle Scholar
  11. 11.
    A. Shoshi, J. Schotter, P. Schroeder, H. Brueckl, M. Milnera, P. Ertl, R. Heer, G. Reiss, Biosens. Bioelectron. 40, 82–88 (2013)CrossRefGoogle Scholar
  12. 12.
    Y. Yao, S. Miao, S. Yu, L.P. Ma, H. Sun, S. Wang, J. Colloid Interface Sci. 379, 20–26 (2012)CrossRefGoogle Scholar
  13. 13.
    G.G. Utkan, F. Sayar, P. Batat, S. Ide, M. Kriechbaum, E. Pişkin, J. Colloid Interface Sci. 353, 372–379 (2011)CrossRefGoogle Scholar
  14. 14.
    N. Mizutani, T. Iwasaki, S. Watano, T. Yanagida, H. Tanaka, T. Kawai, Bull. Mater. Sci. 31, 713–717 (2008)CrossRefGoogle Scholar
  15. 15.
    S. Rostamizadeh, N. Shadjou, M. Azad, N. Jalali, Catal. Commun. 26, 218–224 (2012)CrossRefGoogle Scholar
  16. 16.
    F. Zhang, J. Jin, X. Zhong, S. Li, J. Li, J. Ma, R. Niu, Green Chem. 13, 1238–1243 (2011)CrossRefGoogle Scholar
  17. 17.
    N. Gharibpour. M. Abdollahi-Alibeik, A. Moaddeli, ChemistrySelect 2, 3137–3146 (2017)CrossRefGoogle Scholar
  18. 18.
    M. Abdollahi-Alibeik, A. Rezaeipoor-Anari, J. Magn. Magn. Mater. 398, 205–214 (2016)CrossRefGoogle Scholar
  19. 19.
    A. Moaddeli, M. Abdollahi-Alibeik, J. Porous. Mater. 25, 147–159 (2017)CrossRefGoogle Scholar
  20. 20.
    H.H. Yiu, M. Keane, Z.A. Lethbridge, M.R. Lees, A.J. El Haj, J. Dobson, Nanotechnology 19, 255606 (2008)CrossRefGoogle Scholar
  21. 21.
    S. Inagaki, Y. Fukushima, K. Kuroda, J. Chem. Soc. Chem. Commun. 8, 680–682 (1993)Google Scholar
  22. 22.
    Y. Sakamoto, S. Inagaki, T. Ohsuna, N. Ohnishi, Y. Fukushima, Y. Nozue, O. Terasaki, Microporous Mesoporous Mater. 21, 589–596 (1998)CrossRefGoogle Scholar
  23. 23.
    K. Bachari, A. Touileb, A. Saadi, D. Halliche, O. Cherifi, J. Porous. Mater. 17, 573–581 (2010)CrossRefGoogle Scholar
  24. 24.
    S. Matsuura, T. Itoh, R. Ishii, T. Tsunoda, K. Sakaguchi, T. Hanaoka, F. Mizukami, Microporous Mesoporous Mater. 131, 245–251 (2010)CrossRefGoogle Scholar
  25. 25.
    T. Selvam, M. Köstner, G.T.P. Mabande, R. Schlögl, W. Schwieger, N. Pfänder, J. Porous. Mater. 14, 263–272 (2007)CrossRefGoogle Scholar
  26. 26.
    K. Hamaguchi, H. Hattori, React. Kinet. Catal. Lett. 61, 13–19 (1997)CrossRefGoogle Scholar
  27. 27.
    Y. Liu, T. Hanaoka, K. Murata, K. Okabe, I. Takahara, K. Sakanishi, React. Kinet. Catal. Lett. 92, 147–154 (2007)CrossRefGoogle Scholar
  28. 28.
    K. Bachari, R.M. Guerroudj, M. Lamouchi, Reac. Kinet. Mech. Catal. 100, 205–215 (2010)Google Scholar
  29. 29.
    C.-Y. Chen, S.-Q. Xiao, M.E. Davis, Microporous Mater. 4, 1–20 (1995)CrossRefGoogle Scholar
  30. 30.
    T. Yamamoto, T. Tanaka, T. Funabiki, S. Yoshida, J. Phys. Chem. B 102, 5830–5839 (1998)CrossRefGoogle Scholar
  31. 31.
    T. Yamamoto, T. Tanaka, S. Inagaki, T. Funabiki, S. Yoshida, J. Phys. Chem. B 103, 6450–6456 (1999)CrossRefGoogle Scholar
  32. 32.
    X. Chen, M. Arruebo, K.L. Yeung, Catal. Today 204, 140–147 (2013)CrossRefGoogle Scholar
  33. 33.
    M. Bayat, H. Yang, F. Ko, Polymer 52, 1645–1653 (2011)CrossRefGoogle Scholar
  34. 34.
    Q.A. Pankhurst, J. Connolly, S. Jones, J. Dobson, J. Phys. D 36, R167 (2003)CrossRefGoogle Scholar
  35. 35.
    R. Brayner, T. Coradin, P. Beaunier, F. Fiévet, J.-M. Grenèche, C. Djediat, C. Yéprémian, A. Couté, Colloids Surf., B 93, 20–23 (2012)CrossRefGoogle Scholar
  36. 36.
    L.G. Bach, M.R. Islam, J.T. Kim, S. Seo, K.T. Lim, Appl. Surf. Sci. 258, 2959–2966 (2012)CrossRefGoogle Scholar
  37. 37.
    M. Abdollahi-Alibeik, A. Rezaeipoor-Anari, Lett. Org. Chem. 12, 651–658 (2015)CrossRefGoogle Scholar
  38. 38.
    L.-M. Wang, J. Sheng, H. Tian, C.-T. Qian, L. Zhang, J.-W. Han, Z.-Y. Fan, Tetrahedron 61, 1539–1543 (2005)CrossRefGoogle Scholar
  39. 39.
    T. Borowik, M. Przybyło, K. Pala, J. Otlewski, M. Langner, Spectrochim. Acta, Part B 66, 726–732 (2011)CrossRefGoogle Scholar
  40. 40.
    A.Z. Chen, Y.Q. Kang, X.M. Pu, G.F. Yin, Y. Li, J.Y. Hu, J. Colloid Interface Sci. 330, 317–322 (2009)CrossRefGoogle Scholar
  41. 41.
    R. Chen, S. Song, Y. Wei, Colloids Surf. A 395, 137–144 (2012)CrossRefGoogle Scholar
  42. 42.
    B. Cannon, A.R. Campos, Z. Lewitz, K.A. Willets, R. Russell, Anal. Biochem. 431, 40–47 (2012)CrossRefGoogle Scholar
  43. 43.
    M.F. Casula, A. Corrias, P. Arosio, A. Lascialfari, T. Sen, P. Floris, I.J. Bruce, J. Colloid Interface Sci. 357, 50–55 (2011)CrossRefGoogle Scholar
  44. 44.
    P.R. Chang, J. Yu, X. Ma, D.P. Anderson, Carbohydr. Polym. 83, 640–644 (2011)CrossRefGoogle Scholar
  45. 45.
    R. Tafer, R. Boulcina, B. Carboni, A. Debache, J. Chinese Chem. Soc. 59, 1555–1560 (2012)CrossRefGoogle Scholar
  46. 46.
    C. Shundo. H. Zhang. T. Nakanishi, T. Osaka, Colloids Surf., B 97, 221–225 (2012)CrossRefGoogle Scholar
  47. 47.
    M. Abdollahi-Alibeik, F. Nezampour, Reac. Kinet. Mech. Catal. 108, 213–229 (2013)CrossRefGoogle Scholar
  48. 48.
    M. Abdollahi-Alibeik, M. Pouriayevali, Reac. Kinet. Mech. Catal. 104, 235–248 (2011)CrossRefGoogle Scholar
  49. 49.
    A. Kumar, P. Singh, A. Saxena, A. De, R. Chandra, S. Mozumdar, Catal. Commun. 10, 17–22 (2008)CrossRefGoogle Scholar
  50. 50.
    S.H. Chien, M.C. Kuo, C.L. Chen, J. Chinese Chem. Soc. 52, 733–740 (2005)CrossRefGoogle Scholar
  51. 51.
    R. Abu-Reziq, H. Alper, D. Wang, M.L. Post, J. Am. Chem. Soc. 128, 5279–5282 (2006)CrossRefGoogle Scholar
  52. 52.
    H. Araki, A. Fukuoka, Y. Sakamoto, S. Inagaki, N. Sugimoto, Y. Fukushima, M. Ichikawa, J. Mol. Catal. A: Chem. 199, 95–102 (2003)CrossRefGoogle Scholar
  53. 53.
    L.R. Pizzio, P.G. Vázquez, C.V. Cáceres, M.N. Blanco, Appl. Catal. A 256, 125–139 (2003)CrossRefGoogle Scholar
  54. 54.
    M. Saha, A.K. Pal, Tetrahedron Lett. 52, 4872–4877 (2011)CrossRefGoogle Scholar
  55. 55.
    M.Z. Kassaee, H. Masrouri, F. Movahedi, Monatsh. Chem. 141, 317–322 (2010)CrossRefGoogle Scholar
  56. 56.
    M. Abdollahi-Alibeik, S.S. Hoseinikhah, J. Iran. Chem. Soc. 13, 1339–1347 (2016)CrossRefGoogle Scholar
  57. 57.
    M. Saha, T.S. Luireingam, T. Merry, A.K. Pal, J. Heterocycl. Chem. 50, 941–944 (2013)CrossRefGoogle Scholar

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© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of ChemistryYazd UniversityYazdIran
  2. 2.Department of Chemistry, Faculty of ScienceVali-e-Asr UniversityRafsanjanIran

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