Skip to main content
SpringerLink
Log in

Interaction characteristics controlling catalytic performances of Ni (II) and Cu (II) phthalocyanines immobilized on bentonite clay surface in redox-initiated polymerization of methyl methacrylate in aqueous medium

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

Abstract

Different catalytic performances have been shown for nickel (II) phthalocyanine (1.8 wt%)/bentonite/HSO3 − and copper (II) phthalocyanine (1.8 wt%)/bentonite/HSO3 − initiating systems in the early stage of methyl methacrylate polymerization in aqueous medium, in the temperature range, 40–60 °C. Redox–free radical mechanisms, suggesting dual-site initiation in presence of nickel phthalocyanine system and single-site initiation by using copper phthalocyanine system, were discussed in view of different interaction and dispersion profiles of the immobilized complex systems. Both complexes exhibited strong interaction with bentonite, assisted by n-butyl amine solvent, during the immobilization process. This amine could modify bentonite surface through eliminating its narrower pores, expanding its sheet structure and using up its strongest Brönsted acid sites. Nickel phthalocyanine molecules, intercalated into bentonite clay galleries by n-butyl amine, could be located parallel to silicate layer planes in an even distribution and higher dispersion. Cation exchange or substitution mechanism involving stronger interaction between Ni2+ ions and Al3+ sites in the octahedral sheet encouraged dual-site initiation; two active Ni sites, accessible from one side each, coordinated with two monomer molecules. Copper phthalocyanine molecules, drawn in an inclined edge-on orientation, displayed a strong interaction between N’s of the macro-ring system and the clay external edge OH sites (asymmetric Brönsted interactions). This allowed facile access of Cu sites to the monomer and HSO3 − cocatalyst from both sides, resulting in smoother initiation effect.

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.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Schemes 1
Schemes 2
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  1. B.B. Wayland, G. Poszmik, S.L. Mukerjee, J. Am. Chem. Soc. 116, 7943 (1994)

    Article  CAS  Google Scholar 

  2. V. Percec, B. Barboiu, H.J. Kim, J. Am. Chem. Soc. 120, 305 (1998)

    Article  CAS  Google Scholar 

  3. F. Ueda, M. Matsuyama, M. Kamigaito, M. Sawamoto, Macromolecules 31, 557 (1998)

    Article  CAS  Google Scholar 

  4. A.K. Nanda, K. Kishore, Macromolecules 34, 1558 (2001)

    Article  CAS  Google Scholar 

  5. E.M. Sadek, M.A. Mekewi, F.Z. Yehia, S.M. Solyman, S.A. Hassan, Macromol. Chem. Phys. 202, 1505 (2001)

    Article  CAS  Google Scholar 

  6. M.R. Nabid, R. Sedghi, P.R. Jamaat, N. Safari, A.A. Entezami, Appl. Catal. A Gen. 328, 52 (2007)

    Article  CAS  Google Scholar 

  7. Y.I. Yermakov, N. Kuznetsov, V.A. Zakharov, Catalysis by supported complexes. (Elsevier Sci. Publ. Comp., New York, 1981)

  8. S.A. Hassan, A.A. Zahran, F.Z. Yehia, Adsorption Sci. Technol. 20, 269 (2002)

    Article  CAS  Google Scholar 

  9. S.A. Hassan, S.A. Sadek, S.M. Faramawy, M.A. Mekewi, Stud. Surf. Sci. Catal. 100, 407 (1996)

    Article  CAS  Google Scholar 

  10. J.S. Yadav, B.V.S. Reddy, G. Satheesh, Tetrahedron Lett. 45, 3673 (2004)

    Article  CAS  Google Scholar 

  11. S. Lu, E. Ruth, I.R. Kaplan, Org. Geochem. 14, 491 (1989)

    Article  CAS  Google Scholar 

  12. S.A. Hassan, A.M. Mousa, M. Abdel Khalik, A.A. Abdel Azim, J. Catal. 53, 175 (1978)

    Article  CAS  Google Scholar 

  13. A. Harrane, N. Naar, M. Belbachir, Mater. Lett. 61, 3555 (2007)

    Article  CAS  Google Scholar 

  14. H. Datta, N.K. Singha, A.K. Bhowmick, Macromolecules 41, 50 (2008)

    Article  CAS  Google Scholar 

  15. H. Akat, M.A. Tasdelen, F. Du Prez, Y. Yagci, Eur. Polym. J. 44, 1949 (2008)

    Article  CAS  Google Scholar 

  16. T. Agag, T. Takeichi, Polymer 41, 7083 (2000)

    Article  CAS  Google Scholar 

  17. Z. Qian, G. Hu, S. Zhang, M. Yang, Phys. B Condens. 403, 3231 (2008)

    Article  CAS  Google Scholar 

  18. S.A. Hassan, H.A. Hassan, K.M. Hashem, H.M. Abdel Dayem, Appl. Catal. A Gen. 300, 14 (2006)

    Article  CAS  Google Scholar 

  19. H. Kameyama, F. Narumi, T. Hattori, H. Kameyama, J. Mol. A Catal. Chem. 258, 172 (2006)

    Article  CAS  Google Scholar 

  20. A.M. Machado, F. Wypych, S.M. Drechsel, S. Nagaki, J. Colloid Interface Sci. 254, 158 (2002)

    Article  CAS  Google Scholar 

  21. M.S.M. Moriera, P.R. Martins, R.B. Curi, O.R. Nascimento, Y. Iamamoto, J. Mol. Catal. A Chem. 233, 73 (2005)

    Article  Google Scholar 

  22. K.G. Suddaby, D.M. Haddleton, J.J. Hastings, S.N. Richards, P.J. O’Donnel, Macromolecules 29, 8083 (1996)

    Article  CAS  Google Scholar 

  23. T. Nishikawa, T. Ando, M. Kamigaito, M. Sawamoto, Macromolecules 30, 2244 (1997)

    Article  CAS  Google Scholar 

  24. K. Shivakumar, M.K. Veeraiah, K.S. Rai, B.S. Sherigara, N.M.M. Gowda, J. Mol. A Catal. Chem. 273, 218 (2007)

    Article  CAS  Google Scholar 

  25. T. Ando, M. Kato, M. Kamigaito, M. Sawamoto, Macromolecules 29, 1070 (1996)

    Article  CAS  Google Scholar 

  26. F.H. Moser, A.L. Thomas, Phthalocyanine compounds (Reinhold Publishing Corp, New York, 1963)

    Google Scholar 

  27. K.S.W. Sing, D.H. Everret, R.A.W. Haul, L. Moscou, R.A. Pierotti, J. Rouquerol, T. Siemieniewska, IUPAC Pure Appl. Chem. 57, 603 (1985)

    Article  CAS  Google Scholar 

  28. J.A. Van Veen, F. Van Bar, K.J. Kroese, J. Chem. Soc. Farad. Trans. 77, 2827 (1981)

    Article  Google Scholar 

  29. H. Kita, N. Henmi, K. Shimazu, H. Hattori, J. Tanabe, J. Chem. Soc. Farad. Trans. 77, 2451 (1981)

    Article  CAS  Google Scholar 

  30. H.M. AbdelDayem, H.A. Hassan, S.A. Hassan, J. Dispers. Sci. Technol. 28, 892 (2007)

    Article  CAS  Google Scholar 

  31. H. Uegaki, Y. Kotani, M. Kamigaito, M. Sawamoto, Macromolecules 30, 2249 (1997)

    Article  CAS  Google Scholar 

  32. M. Kato, M. Kamigaito, M. Sawamoto, T. Higashimura, Macromolecules 28, 1721 (1995)

    Article  CAS  Google Scholar 

  33. Y. Nakayama, T. Shibahara, H. Fukumoto, A. Nakamura, Macromolecules 29, 8014 (1996)

    Article  CAS  Google Scholar 

  34. S.A. Hassan, S.A. Selim, M.A. Mekewi, S. Hanafi, J. Mater. Sci. 24, 1095 (1989)

    Article  CAS  Google Scholar 

  35. A.B. Moustafa, M.A. Abd El-Ghaffar, A.S. Badran, J. Polym. Sci. Polym. Chem. Ed. 19, 719 (1981)

    Article  CAS  Google Scholar 

  36. S.P.S. Khalsa, H.S. Chahabra, H.C. Roy, Advances in Catalysis, Proc. 6th Int. Congr. Catal., ed. by G.C. Bond, P.B. Wells, F.C. Tompkins, (John Wiley, New York, 1985), pp. 675–684

  37. J.C. Brown, J. Chem. Soc. A 2488, 25 (1968)

    Google Scholar 

  38. D.M.C. MacEwan, The montmorillonite minerals (Mineralogical Society of Great Britain, London, 1961), pp. 143–207

    Google Scholar 

  39. C. Paluszkiewicz, M. Holtzer, A. Bobrowski, J. Mol. Struct. 880, 109 (2008)

    Article  CAS  Google Scholar 

  40. T.S. Anirudhan, P.S. Suchithra, S. Rijith, Colloids Surf. A Physicochem. Eng. Asp. 326, 147 (2008)

    Article  CAS  Google Scholar 

  41. V.C. Farmer, The infrared spectra of minerals (Minerological Society, London, 1994)

    Google Scholar 

  42. Y. Komori, Y. Sugahara, K. Kuroda, Appl. Clay Sci. 15, 241 (1999)

    Article  CAS  Google Scholar 

  43. J. Wang, Z. Liu, X. Tang, K. Ooi, J. Colloid Interf. Sci. 307, 524 (2007)

    Article  CAS  Google Scholar 

  44. J.H. Zagal, M. Paez, J. Stum, S.U. Zanartu, J. Electroanal. Chem. 181, 295 (1984)

    Article  CAS  Google Scholar 

  45. J.R. Fryer, R.B. Mckay, R.R. Mather, K.S.W. Sing, J. Chem. Technol. Biotechnol. 31, 371 (1981)

    Article  CAS  Google Scholar 

  46. V.Yu. Zakharov, O.M. Zakharov, B.V. Romanovskii, R.E. Mardaleishvili, React. Kint. Catal. Lett. 6, 133 (1977)

    Article  CAS  Google Scholar 

  47. F. Steinbach, H.H. Schmidt, J. Catal. 39, 190 (1975)

    Article  CAS  Google Scholar 

  48. I. Mochida, A. Yasutaka, H. Fujitsu, K. Takeshita, J. Phys. Chem. 86, 3468 (1982)

    Article  CAS  Google Scholar 

  49. P. Kumar, R.V. Jasra, T.S.G. Bhat, Ind. Eng. Chem. Res. 34, 1440 (1995)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ain Shams University, Cairo, Egypt

    Salah A. Hassan, Ashraf A. Hamed & Afaf A. Zahran

  2. Department of Petrochemicals, Egyptian Petroleum Research Institute, Cairo, Egypt

    Fatma Z. Yehia & Sanaa M. Solyman

Authors
  1. Salah A. Hassan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Fatma Z. Yehia
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ashraf A. Hamed
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Afaf A. Zahran
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sanaa M. Solyman
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Salah A. Hassan.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hassan, S.A., Yehia, F.Z., Hamed, A.A. et al. Interaction characteristics controlling catalytic performances of Ni (II) and Cu (II) phthalocyanines immobilized on bentonite clay surface in redox-initiated polymerization of methyl methacrylate in aqueous medium. J Porous Mater 18, 1–11 (2011). https://doi.org/10.1007/s10934-009-9350-z

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10934-009-9350-z

Keywords

Search

Navigation