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Imidazole-containing chitosan derivative: a new synthetic approach and sorption properties

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Abstract

A novel method for the synthesis of a hetaryl-containing chelate amino polymer, namely, N-(4(5)-imidazolylmethyl)chitosan (IMC), with a degree of substitution up to 0.3 was proposed. The “synthesis in gel” approach involves direct substitution of the hydroxyl group in 4(5)-imidazolylmethanol. The structures of these polymers were confirmed by 1H NMR data. For sorption studies, IMC samples were crosslinked with epichlorohydrin and diglycidyl ethers of ethylene glycol and diethylene glycol. The degrees of swelling and sorption properties of the polymers largely depend on the crosslinking agent and the degree of crosslinking. The sorption capacities of IMC for AuIII, PtIV, and PdII ions are higher than those of the nonmodified polymer. The extraction of noble metal ions from chloride solutions becomes more selective with increasing degree of crosslinking. The sorption capacity of IMC for CoII and NiII ions is higher than those of chitosan and its known N-heterocyclic derivatives.

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References

  1. R. Jayakumar, M. Prabaharan, S. V. Nair, S. Tokura, H. Tamura, N. Selvamurugan, Prog. Mater. Sci., 2010, 55, 675.

    Article  CAS  Google Scholar 

  2. B. Krajewska, Sep. Purif. Technol., 2005, 41, 305.

    Article  CAS  Google Scholar 

  3. H. Sashiwa, S. I. Aiba, Prog. Polym. Sci., 2004, 29, 887.

    Article  CAS  Google Scholar 

  4. W. Sajomsang, S. Tantayanon, V. Tangpasuthadol, W. H. Daly, Carbohydr. Polym., 2008, 72, 740.

    Article  CAS  Google Scholar 

  5. W. Sajomsang, U. R. Ruktanonchai, P. Gonil, C. Warin, Carbohydr. Polym., 2010, 82, 1143.

    Article  CAS  Google Scholar 

  6. S. Kumar, J. Dutta, P. K. Dutta, Int. J. Biol. Macromol., 2009, 45, 330.

    Article  CAS  Google Scholar 

  7. Y. Baba, K. Masaaki, Y. Kawano, Chem. Lett., 1994, 23, 2389.

    Article  Google Scholar 

  8. Y. Baba, K. Masaaki, Y. Kawano, React. Funct. Polym., 1998, 36, 167.

    Article  CAS  Google Scholar 

  9. C. A. Rodrigues, M. C. M. Laranjeira, V. T. Favere, E. Stadler, Polymer, 1998, 39, 5121.

    Article  CAS  Google Scholar 

  10. Y. Baba, H. Hirakawa, Chem. Lett., 1992, 21, 1905.

    Article  Google Scholar 

  11. R. P. Dhakal, T. Oshima, Y. Baba, React. Funct. Polym., 2008, 68, 1549.

    Article  CAS  Google Scholar 

  12. Y. Baba, Y. Kawano, H. Hirakawa, Bull. Chem. Soc. Jpn, 1996, 69, 1255.

    Article  CAS  Google Scholar 

  13. S. E. S. Leonhardt, A. Stolle, B. Ondruschka, G. Cravotto, C. De Leo, K. D. Jandt, T. F. Keller, Appl. Catal., A, 2010, 379, 30.

    Article  CAS  Google Scholar 

  14. J. Tong, Z. Li, C. Xia, J. Mol. Catal., A, 2005, 231, 197.

    Article  CAS  Google Scholar 

  15. C. A. Rodrigues, M. C. M. Laranjeira, E. Stadler, V. Drago, Carbohydr. Polym., 2000, 42, 311.

    Article  CAS  Google Scholar 

  16. D. Hu, Y. Cui, X. Dong, Y. Fang, React. Funct. Polym., 2001, 48, 201.

    Article  CAS  Google Scholar 

  17. D. Hu, Y. Fang, G. Gao, M. Wang, J. Appl. Polym. Sci., 2006, 101, 2431.

    Article  CAS  Google Scholar 

  18. R. A. A. Muzzarelli, M. Mattioli-Belmonte, C. Tietz, R. Biagini, G. Ferioli, M. A. Brunelli, M. Fini, R. Giardino, P. Ilri, G. Biagini, Biomaterials, 1994, 15, 1075.

    Article  CAS  Google Scholar 

  19. J. E. Macor, L. A. M. Cornelius, J. Y. Roberge, Tetrahedron Lett., 2000, 41, 2777.

    Article  CAS  Google Scholar 

  20. T. Kunitake, S. Shinkai, J. Am. Chem. Soc., 1971, 93, 4256.

    Article  CAS  Google Scholar 

  21. A. V. Pestov, N. A. Zhuravlev, Yu. G. Yatluk, Zh. Prikl. Khim., 2007, 80, 1184 [Russ. J. Appl. Chem. (Engl. Transl.), 2007, 80, 1154].

    Google Scholar 

  22. A. V. Pestov, S. Yu. Bratskaya, A. B. Slobodyuk, V. A. Avramenko, Yu. G. Yatluk, Russ. Chem. Bull. (Int. Ed.), 2010, 59, 1303 [Izv. Akad. Nauk, Ser. Khim., 2010, 1273].

    Article  CAS  Google Scholar 

  23. A. V. Pestov, O. V. Koryakova, I. I. Leonidov, Yu. G. Yatluk, Zh. Prikl. Khim., 2010, 83, 787 [Russ. J. Appl. Chem. (Engl. Transl.), 2010, 83, 787].

    CAS  Google Scholar 

  24. A. V. Pestov, S. Yu. Bratskaya, Yu. A. Azarova, M. I. Kodess, Yu. G. Yatluk, Zh. Prikl. Khim., 2011, 84, 678 [Russ. J. Appl. Chem. (Engl. Transl.), 2011, 84, 713].

    Google Scholar 

  25. A. V. Pestov, Yu. A. Skorik, G. Kogan, Yu. G. Yatluk, J. Appl. Polym. Sci., 2008, 108, 119.

    Article  CAS  Google Scholar 

  26. G. V. Myasoedova, P. N. Komozin, Zh. Neorg. Khim., 1994, 39, 280 [Russ. J. Inorg. Chem. (Engl. Transl.), 1994, 39].

    CAS  Google Scholar 

  27. L. A. Sopena, M. Ruiz, A. V. Pestov, A. M. Sastre, Y. Yatluk, E. Guibal, Cellulose, 2011, 18, 309.

    Article  Google Scholar 

  28. Entsiklopediya polimerov [Encyclopedia of Polymers], Sovetskaya Entsiklopediya, Moscow, Vol. 1, 1972 (in Russian).

  29. S. Pramanik, S. Dhara, S. S. Bhattacharyya, P. Chattopadhyay, Anal. Chim. Acta, 2006, 556, 430.

    Article  CAS  Google Scholar 

  30. E. Guibal, Prog. Polym. Sci., 2005, 30, 71.

    Article  CAS  Google Scholar 

  31. J. C. Murphy, D. L. Jewell, K. I. White, G. E. Fox, R. C. Willson, Biotechnol. Prog., 2003, 19, 928.

    Article  Google Scholar 

  32. A. I. Gamzazade, V. M. Slimak, A. M. Skljar, E. V. Stykova, S. A. Pavlova, S. V. Rogozin, Acta Polym., 1985, 36, 420.

    Article  CAS  Google Scholar 

  33. M. Fujinaga, Y. Matsushima, Bull. Chem. Soc. Jpn, 1966, 39, 185.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620041, Ekaterinburg, Russian Federation

    A. V. Pestov & Yu. G. Yatluk

  2. Institute of Chemistry, Far East Branch of the Russian Academy of Sciences, 159 prosp. 100-letiya Vladivostoka, 690022, Vladivostok, Russian Federation

    S. Yu. Bratskaya & Yu. A. Azarova

Authors
  1. A. V. Pestov
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  2. S. Yu. Bratskaya
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  3. Yu. A. Azarova
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  4. Yu. G. Yatluk
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Correspondence to A. V. Pestov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1943–1948, October, 2012.

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Pestov, A.V., Bratskaya, S.Y., Azarova, Y.A. et al. Imidazole-containing chitosan derivative: a new synthetic approach and sorption properties. Russ Chem Bull 61, 1959–1964 (2012). https://doi.org/10.1007/s11172-012-0271-7

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  • DOI: https://doi.org/10.1007/s11172-012-0271-7

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