Skip to main content
SpringerLink
Log in

Synthesis of Crosslinked Chitosan Possessing Schiff Base and Its Use in Metal Removal

  • Published:
Journal of Inorganic and Organometallic Polymers and Materials Aims and scope Submit manuscript

Abstract

A chitosan resin derivatized with Schiff bases was synthesized by using a crosslinked chitosan (CCTS) as base material. We first synthesized N-benzylidene chitosan (CTB) by the reaction of benzaldehyde with chitosan. After this reaction crosslinking was carried out in the usage of epichlorohydrine (ECH) as a crosslinking agent. The Schiff base was removed by reacting diluted ethyl alcohol hydrochloride solution to give crosslinked chitosan (CCTS).The CCTS was suspended in a mixture of ethyl alcohol/deionized water followed by the addition of epichlorohydrine and by this way crosslinked chitosan-epichlorhydrine (CCTS-ECH) resin was synthesized. After the reaction was completed, the product was filtered, washed with ethyl alcohol and deionized water and dried in vacuum. The two novel polymeric ligands (CCTS-ECH-DHSalophen and CCTS-ECH-DHDPE) were synthesized by the reaction of CCTS-ECH with N,N′-bis(2,5 dihydroxybenzylidene)-1,2-diaminobenzene (DHSalophen), and N,N′-bis(2,5 dihydroxybenzylidene)-4,4′-diaminodiphenylether (DHDPE). The structures of the ligands were characterized by elemental analysis, infrared spectroscopy(FT-IR), scanning electron microscopy(SEM) and thermogravimetric analysis (TGA/DTA). Adsorption experiments (pH dependency, kinetics, and equilibrium) of compounds toward Cr(VI) from waste water were carried out at 25 °C.

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
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  1. K.R. Krishnapriya, M. Kandaswamy, Carbohydr. Res. 344, 1632 (2009)

    Article  CAS  Google Scholar 

  2. G. Karthikeyan, S. Sivailango, E-J. Chem. 5, 666 (2008)

    Article  Google Scholar 

  3. M. Gheju, R. Pode, WASET 66, 996 (2010)

    Google Scholar 

  4. P. Suksabye, N. Akira, T. Paitip, B. Yoshinari, W. Nakbanpote, J. Hazard. Mater. 161, 1103 (2009)

    Article  CAS  Google Scholar 

  5. M. Owlad, M.K. Aroua, W.A.W. Daud, S. Baroutian, Water Air Soil Pollut. 200, 59 (2008)

    Article  Google Scholar 

  6. A.H. Chen, S.C. Liu, C. Yuan Chen, C. Yun Chen, J. Hazard. Mater. 154, 184 (2008)

    Article  CAS  Google Scholar 

  7. M. Kumar, B.P. Tripathi, V.K. Shahi, J. Hazard. Mater. 172, 1041 (2009)

    Article  CAS  Google Scholar 

  8. L. Zhou, Z. Liu, J. Liu, Q. Huang, Desalination 258, 41 (2010)

    Article  CAS  Google Scholar 

  9. S.V. Rodrigo, M.B. Marisa, Adsorption 11, 731 (2005)

    Article  Google Scholar 

  10. V.R. Sinha, A.K. Singla, S. Wadhawan, R. Kaushik, R. Kumria, K. Bansal, S. Dhawan, Int. J. Pharm. 274, 1 (2004)

    Article  CAS  Google Scholar 

  11. Y.K. Twu, H.I. Huang, S.Y. Chang, S.L. Wang, Carbohydr. Polym. 54, 425 (2003)

    Article  CAS  Google Scholar 

  12. K. Yoshizuka, Z. Lou, K. Inoue, React. Funct. Polym. 44, 47 (2000)

    Article  CAS  Google Scholar 

  13. X. Wang, Y. Du, L. Fan, H. Liu, Y. Hu, Polym. Bull. 55, 105 (2005)

    Article  CAS  Google Scholar 

  14. Y. Cui, L. Zhang, Y. Li, Polym. Adv. Technol. 16, 633 (2005)

    Article  CAS  Google Scholar 

  15. S. Chatterjee, D.S. Leeb, M.W. Leec, S.H. Woo, J. Hazard. Mater. 166, 508 (2009)

    Article  CAS  Google Scholar 

  16. P. Miretzky, A. Fernandez Cirelli, J. Hazard. Mater. 167, 10 (2009)

    Article  CAS  Google Scholar 

  17. L.V. Gonçalves, C.M.M. Laranjeira, T.V. Favere, Polimeros 15, 6 (2005)

    Article  Google Scholar 

  18. G.K. Moore, G.A.F. Roberts, Int. J. Biol. Macromol. 3, 337 (1981)

    Article  CAS  Google Scholar 

  19. A.A. Muzzarelli, C. Jeunieux, G.W. Gooday, Chitin in Nature and Technology (Plenum Press, New York, 1985)

    Google Scholar 

  20. F.A.A. Tirkistani, Polym. Degrad. Stabil. 60, 67 (1998)

    Article  CAS  Google Scholar 

  21. Z. Cimermana, N. Galic, B. Bosnerb, Anal. Chim. Acta. 343, 145 (1997)

    Article  Google Scholar 

  22. Y. Zhikuan, Y. Wang, Y. Tang, J. Appl. Polym. Sci. 74, 3053 (1999)

    Article  Google Scholar 

  23. Y. Zhikuan, L. Zhuang, G. Tan, J. Appl. Polym. Sci. 85, 530 (2002)

    Article  Google Scholar 

  24. M. Sahin, N. Kocak, G. Arslan, H.I. Ucan, J. Inorg. Organomet. Polym. 21, 69 (2011)

    Article  CAS  Google Scholar 

  25. S. Qian, G. Huang, J. Jiang, F. He, Y. Wang, J. Appl. Polym. Sci. 77, 3216 (2000)

    Article  CAS  Google Scholar 

  26. W. Tongamp, Q. Zhang, F. Saito, J. Hazard. Mater. 137, 1226 (2006)

    Article  CAS  Google Scholar 

  27. Hİ. Uçan, R. Mirzaoğlu, Synth. React. Inorg. Met. Org. Chem. 20, 437 (1990)

    Article  Google Scholar 

  28. İ. Karataş, Hİ. Uçan, Synth. React. Inorg. Met. Org. Chem. 28, 383 (1998)

    Article  Google Scholar 

  29. M. Sahin, N. Kocak, H.I. Ucan, M.A. Deveci, Russ. J. Coord. Chem. 33, 680 (2007)

    Article  CAS  Google Scholar 

  30. S. Lengvinaite, M. Sangermano, G. Malucelli, A. Priola, S. Grigalevicius, J.V. Grazulevicius, V. Getautis, Eur. Polym. J. 43, 380 (2007)

    Article  CAS  Google Scholar 

  31. J. Zhang, Y. Yuan, J. Shen, S. Lin, Eur. Polym. J. 39, 847 (2003)

    Article  CAS  Google Scholar 

  32. H. Cai, P.Z. Zheng, C.S. Ping, L.H. Bing, X.Z. Xioa, Radiat. Phys. Chem. 74, 26 (2005)

    Article  CAS  Google Scholar 

  33. F.S. Kittur, K.V.H. Prashanth, K.U. Sankar, R.N. Taranathan, Carbohyd. Polym. 49, 185 (2002)

    Article  CAS  Google Scholar 

  34. M. Gümüşderelioğlu, P. Agi, React. Funct. Polym. 61, 211 (2004)

    Article  Google Scholar 

  35. S.P. Ramnani, C.V. Chaudhari, N.D. Patil, S. Sabharwal, J. Polym. Sci. 42, 3897 (2004)

    Article  CAS  Google Scholar 

  36. I. Langmuir, J. Am. Chem. Soc. 38, 2221 (1916)

    Article  CAS  Google Scholar 

  37. M. Rao, A.V. Parwate, A.G. Bhole, Waste Manag. 22, 821 (2002)

    Article  CAS  Google Scholar 

  38. H.M.F. Freundlich, Z. Phys. Chem. 57, 385 (1906)

    CAS  Google Scholar 

  39. R. Sivaraj, C. Namasivayam, K. Kadirvelu, Waste Manag. 21, 105 (2001)

    Article  CAS  Google Scholar 

  40. D.C. Sharma, C.F. Forster, Water S. A. 22, 153 (1996)

    CAS  Google Scholar 

  41. G. Arslan, S. Edebali, E. Pehlivan, Desalination 255, 117 (2010)

    Article  CAS  Google Scholar 

  42. E. Pehlivan, T. Altun, J. Hazard. Mater. 155(1–2), 378 (2008)

    Article  CAS  Google Scholar 

  43. G. Arslan, E. Pehlivan, Bioresour. Technol. 98, 2836 (2007)

    Article  CAS  Google Scholar 

  44. E. Pehlivan, S. Cetin, J. Hazard. Mater. 163, 448 (2009)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are greatly indebted to the Selcuk University Research Foundation (SUAF) for providing financial support (Project number: 2004/082).

Author information

Authors and Affiliations

  1. Department of Science Education, Faculty of Education, Selcuk University, 42031, Konya, Turkey

    Nuriye Kocak

  2. Department of Chemistry, Faculty of Science, Selcuk University, 42075, Konya, Turkey

    Mustafa Sahin, Gulsin Arslan & H. Ismet Ucan

Authors
  1. Nuriye Kocak
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mustafa Sahin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Gulsin Arslan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. H. Ismet Ucan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nuriye Kocak.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kocak, N., Sahin, M., Arslan, G. et al. Synthesis of Crosslinked Chitosan Possessing Schiff Base and Its Use in Metal Removal. J Inorg Organomet Polym 22, 166–177 (2012). https://doi.org/10.1007/s10904-011-9509-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10904-011-9509-3

Keywords

Search

Navigation