Skip to main content
SpringerLink
Log in

Comparison of the acylation of chitosan with succinic anhydride in aqueous suspension and in solution

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A homogeneous reaction in 1% AcOH and a heterogeneous reaction in aqueous suspension were used to obtain N-succinylchitosan from chitosan and succinic anhydride. The 1H NMR data indicated that both reactions resulted in selective acylation of the free amino group. Further experiments examined the effects of the main reaction parameters (temperature, reaction time, the ratio of the reagents, and chitosan preactivation) on the degree of succinylation of the product.

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

Similar content being viewed by others

References

  1. A. S. Berezin, E. A. Lomkova, Y. A. Skorik, Russ. Chem. Bull. (Int. Ed.), 2012, 61, 781 [Izv. Akad. Nauk, Ser. Khim., 2012, 778].

    Article  CAS  Google Scholar 

  2. M. Izume, Chitin Chitosan Res., 1998, 4, 12.

    CAS  Google Scholar 

  3. Y. H. Song, H. Onishi, T. Nagai, Int. J. Pharm., 1993, 98, 121.

    Article  CAS  Google Scholar 

  4. K. Kamiyama, H. Onishi, Y. Machida, Biol. Pharm. Bull., 1999, 22, 179.

    Article  CAS  Google Scholar 

  5. Y. Kato, H. Onishi, Y. Machida, Biomaterials, 2000, 21, 1579.

    Article  CAS  Google Scholar 

  6. D. L. Sonin, L. V. Vasina, E. I. Pochkaeva, M. L. Vasyutina, D. V. Korolev, Y. A. Skorik, M. M. Galagudza, Byull. Eksp. Biol. Med. [Bulletin of Experimental Biology and Medicine], 2015 (in press).

    Google Scholar 

  7. H. Luo, J. Li, X. Chen, Biomed. Pharmacother., 2010, 64, 521.

    Article  CAS  Google Scholar 

  8. Y. Dai, P. Li, J. Zhang, A. Wang, Q. Wei, Biopharm. Drug Dispos., 2008, 29, 173.

    Article  CAS  Google Scholar 

  9. P. Mukhopadhyay, K. Sarkar, S. Bhattacharya, A. Bhattacharyya, R. Mishra, P. P. Kundu, Carbohydr. Polym., 2014, 112, 627.

    Article  CAS  Google Scholar 

  10. A. Zubareva, A. Ilyina, A. Prokhorov, D. Kurek, M. Efremov, V. Varlamov, S. Senel, P. Ignatyev, E. Svirshchevskaya, Molecules, 2013, 18, 7848.

    Article  CAS  Google Scholar 

  11. Q. Zhu, Y. Zhou, M. Guan, X. Zhou, S. Yang, Y. Liu, W. Chen, C. Zhang, Z. Yuan, C. Liu, A. Zhu, X. Zhang, Biomaterials, 2014, 35, 5965.

    Article  CAS  Google Scholar 

  12. C. Yan, D. Chen, J. Gu, J. Qin, J. Pharm. Pharmacol., 2006, 58, 1177.

    Article  CAS  Google Scholar 

  13. X. Xu, L. Li, H. Zhou, S. Lu, H. Yang, X. Yin, J. Ren, Colloid Surf. B: Biointerfaces, 2007, 55, 222.

    Article  CAS  Google Scholar 

  14. T. Woraphatphadung, W. Sajomsang, P. Gonil, S. Saesoo, P. Opanasopit, Carbohydr. Polym., 2015, 121, 99.

    Article  CAS  Google Scholar 

  15. Y. Wang, S. Tu, R. Li, X. Yang, L. Liu, Q. Zhang, Nanomed.-Nanotechnol. Biol. Med., 2010, 6, 471.

    Article  CAS  Google Scholar 

  16. Y. Kato, H. Onishi, Y. Machida, Biomaterials, 2004, 25, 907.

    Article  CAS  Google Scholar 

  17. C. Yan, J. Gu, D. Hou, H. Jing, J. Wang, Y. Guo, H. Katsumi, T. Sakane, A. Yamamoto, Int. J. Biol. Macromol., 2015, 72, 751.

    Article  CAS  Google Scholar 

  18. C. Zhang, Q. E. Ping, H. J. Zhang, J. Shen, Eur. Polym. J., 2003, 39, 1629.

    Article  CAS  Google Scholar 

  19. S. Hirano, T. Moriyasu, Carbohydr. Res., 1981, 92, 323.

    Article  CAS  Google Scholar 

  20. R. Yamaguchi, Y. Arai, T. Itoh, S. Hirano, Carbohydr. Res., 1981, 88, 172.

    Article  CAS  Google Scholar 

  21. S. Hirano, T. Moriyasu, Carbohydr. Polym., 2004, 55, 245.

    Article  CAS  Google Scholar 

  22. B. A. Komarov, A. I. Albulov, M. Yu. Belov, A. Ya. Samuilenko, A. S. Fomenko, S. M. Shinkarev, A. M. Trunov, RF Pat. 2144040; Byull. Izobret. [Bulletin of Inventions], 10.01. 2000 (in Russian).

    Google Scholar 

  23. Y. Shigemasa, H. Usui, M. Morimoto, H. Saimoto, Y. Okamoto, S. Minami, H. Sashiwa, Carbohydr. Polym., 1999, 39, 237.

    Article  CAS  Google Scholar 

  24. Khitin i khitozan: Poluchenie, svoistva i primenenie [Chitin and Chitosan: Synthesis, Properties, and Applications], Eds K. G. Skryabin, G. A. Vikhoreva, and V. P. Varlamov, Nauka, Moscow, 2002, 368 pp. (in Russian).

    Google Scholar 

  25. Y. A. Skorik, C. A. R. Gomes, M. Vasconcelos, Y. G. Yatluk, Carbohydr. Res., 2003, 338, 271.

    Article  CAS  Google Scholar 

  26. Y. A. Skorik, A. V. Pestov, M. I. Kodess, Y. G. Yatluk, Carbohydr. Polym., 2012, 90, 1176.

    Article  CAS  Google Scholar 

  27. N. V. Pogodina, G. M. Pavlov, S. V. Bushin, A. B. Mel′nikov, Y. B. Lysenko, L. A. Nud′ga, V. N. Marsheva, G. N. Marchenko, V. N. Tsvetkov, Polym. Sci. USSR, Ser. A, 1986, 28, 251 [Vysokomol. Soedin., Ser. A, 1986, 28, 232].

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State Chemical Pharmaceutical Academy, 14 ul. Prof. Popova, 197022, St. Petersburg, Russian Federation

    A. A. Golyshev

  2. Institute of Macromolecular Compounds of the Russian Academy of Sciences, 31 Bol´shoi prosp. VO, 199004, St. Petersburg, Russian Federation

    A. A. Golyshev, Yu. E. Moskalenko & Yu. A. Skorik

  3. Darmstadt Technical University, 64287, Darmstadt, Germany

    Yu. E. Moskalenko

  4. Institute of Chemistry, St. Petersburg State University, 26 Universitetskii prosp., Petrodvorets, 198504, St. Petersburg, Russian Federation

    Yu. A. Skorik

Authors
  1. A. A. Golyshev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu. E. Moskalenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. A. Skorik
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yu. A. Skorik.

Additional information

On the occasion of the 100th anniversary of the birth of Academician N. K. Kochetkov (1915—2005).

Technische Universität Darmstadt, Deutschland, 64287 Darmstadt, Alarich-Weiss-Str., 16.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1168—1171, May, 2015.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Golyshev, A.A., Moskalenko, Y.E. & Skorik, Y.A. Comparison of the acylation of chitosan with succinic anhydride in aqueous suspension and in solution. Russ Chem Bull 64, 1168–1171 (2015). https://doi.org/10.1007/s11172-015-0994-3

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-015-0994-3

Keywords

Search

Navigation