Skip to main content
SpringerLink
Log in

Clean Preparation Process of Chitosan Oligomers in Gly Series Ionic Liquids Homogeneous System

  • Original Paper
  • Published:
Journal of Polymers and the Environment Aims and scope Submit manuscript

Abstract

Chitosan oligomers because of its water solubility has some special physiological functions, such as binding lipid, affecting the mitogenic response, restraining the growth of tumors, and was widely used in cosmetics and health. H2O2/Gly (Glycine) series ionic liquids system, a new solvable-catalytic system, was an efficient clean process for preparation of chitosan oligomers. The effects of the anions of Gly series ionic liquids on the solubility and degradation for chitosan were investigated, and the results showed that [Gly]Cl aqueous solution was of good solubility and assistant degradation for chitosan. In additional, the mechanism for oxidative degradation of chitosan in ionic liquids (ILs) was studied. The effect on the property of chitosan oligomers catalyzed by H2O2, in two different kinds of solvents (HAc and [Gly]Cl) were compared. It was found that the performance of moisture absorption and retention of chitosan oligomers using ionic liquid aqueous solution as solvent was better than that using HAc aqueous solution as solvent, and even superior to that of hyaluronic acid. Furthermore, [Gly]Cl could be easily separated from the product and reused with only slight loss. It could provide an efficient and environmental friendly method for the preparation of chitosan oligomers in H2O2/ILs system.

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

Similar content being viewed by others

References

  1. Freier T, Kazazian K, Shoichet M (2005) Controlling cell adhesion and degradation of chitosan films by N-acetylation. Biomaterials 26:5872–5878

    Article  CAS  Google Scholar 

  2. Ottoy MH, Varum KM, Smidsord O (1996) Compositional heterogeneity of heterogeneously deacetylated chitosans. Carbohydr Polym 29:17–24

    Article  CAS  Google Scholar 

  3. Laudenslager MJ, Schiffman JD, Schauer CL (2008) Carboxymethyl chitosan as a matrix material for platinum, gold, and silver nanoparticles. Biomacromolecules 9:2682–2685

    Article  CAS  Google Scholar 

  4. Ikeda I, Sugano M, Yoshida K, Eiji Y, Iwamoto Y, Hatano K (1993) Effects of chitosan hydrolyzates on lipid absorption and on serum and liver lipid concentration in rats. J Agric Food Chem 41:431–435

    Article  CAS  Google Scholar 

  5. Chibu H, Shibayama H, Arima S (2002) Effects of chitosan application on the shoot growth of rice and soybean. Jpn J Crop Sci 71:206–211

    Article  CAS  Google Scholar 

  6. Ohta K, Morishita S, Suda K, Kobayashi N, Hosoki T (2004) Effects of chitosan soil mixture treatment in the seedling stage on the growth and flowering of several ornamental plants. J Jpn Soc Hortic Sci 73:66–68

    Article  CAS  Google Scholar 

  7. Park R, Kyu-Jong J, You-Young J, Yu-Lan J, Kil-Yong K, Jae-Hans YK (2002) Variation of antifungal activities of kitosans on plant pathogens. J Microbiol Biotechnol 12:84–88

    CAS  Google Scholar 

  8. Wang SM, Huang QZ, Wang QS (2005) Study on the synergetic degradation of chitosan with ultraviolet light and hydrogen peroxide. Carbohydr Res 340:1143–1147

    Article  CAS  Google Scholar 

  9. Xing RE, Liu S, Yu HH, Guo ZY, Wang PB, Li ZE, Li PC (2005) Salt-assisted acid hydrolysis of chitosan to oligomers under microwave irradiation. Carbohydr Res 340:2150–2153

    Article  CAS  Google Scholar 

  10. Huang QZ, Zhuo LH, Guo YC (2008) Heterogeneous degradation of chitosan with H2O2 catalysed by phosphotungstate. Carbohydr Polym 72:500–505

    Article  CAS  Google Scholar 

  11. Wu Y, Yao P, Wei Y (2009) Influence of ultraviolet-irradiated oxygen on depolymerization of chitosan. Polym Degrad Stab 94:851–858

    Article  Google Scholar 

  12. Kurita K, Ikeda H, Yoshida Y, Shimojoh M, Harata M (2002) Chemoselective protection of the amino groups of chitosan by controlled phthaloylation: facile preparation of a precursor useful for chemical modifications. Biomacromolecules 3:1–4

    Article  CAS  Google Scholar 

  13. Brennecke JF, Maginn EJ (2001) Ionic liquids: innovative fluids for chemical processing. AIChE J 47:2384–2389

    Article  CAS  Google Scholar 

  14. Weingartner H (2008) Understandingionic liquids at the molecular level: facts, problems, and controversies. Angewandte Chemie Int Ed Engl 47:654–670

    Article  Google Scholar 

  15. Lu X, Hu J, Yao X, Wang Z, Li J (2006) Direct electron transfer of horseradish peroxidase and its biosensor based on chitosan and room temperature ionic liquid. Electrochem Commun 8:874–878

    Article  CAS  Google Scholar 

  16. Xie HB, Zhang SB, Li SH (2006) Chitin and chitosan dissolved in ionic liquids as reversible sorbents of CO2. Green Chem 8:630–633

    Article  CAS  Google Scholar 

  17. Zhang ZH, Li CZ, Wang Q, Zhao ZK (2009) Efficient hydrolysis of chitosan in ionic liquids. Carbohydr Polym 78:685–689

    Article  CAS  Google Scholar 

  18. Laus G, Bentivoglio G, Schottenberger H, Kahlenberg V, Kopacka H, Röer T, Sixta H (2005) Ionic liquids: current developments, potential and drawbacks for industrial applications. Lenzinger Berichte 84:71–85

    CAS  Google Scholar 

  19. Xie Y, Zhou N, Cao J (2008) Effect of chitosans and their derivatives on antiproliferation in humanhepatocellular carcinoma cell lines SMCC7721. J Clin Rehab Tissue Eng Res 12:4579–4582

    Google Scholar 

  20. Imoto T, Yagishita K (1971) A simple activity measurement of lysozyme. Agric Biol Chem 35:1154–1156

    Article  CAS  Google Scholar 

  21. He MJ, Chen WX, Dong XX (2002) Polymer physics. Fudan University Press, Shanghai, China, pp 114–119

    Google Scholar 

  22. Cuissinat C, Navard P, Heinze T (2008) Swelling and dissolution of cellulose, part V: cellulose derivatives fibres in aqueous systems and ionic liquids. Cellulose 15:75–80

    Article  CAS  Google Scholar 

  23. Swatloski RP, Spear SK, Holbrey JD, Rogers RD (2002) Dissolution of cellulose with ionic liquids. J Am Chem Soc 124:4974–4975

    Article  CAS  Google Scholar 

  24. Zhang H, Wu J, Zhang J, He JS (2005) 1-Allyl-3-methylimidazolium chloride room temperature ionic liquid: a new and powerful nonderivatizing solvent for cellulose. Macromolecules 38:8272–8277

    Article  CAS  Google Scholar 

  25. Jiang TD (2006) Chitosan. Chemical Industry Press, Beijing, China

    Google Scholar 

  26. Minke R, Blackwell J (1978) The structure of α-chitin. J Mol Biol 120:167–181

    Article  CAS  Google Scholar 

  27. Cho Y, Jang J, Park C, Ko S (2000) Preparation and solubility in acid and water of partially deacetylated chitins. Biomacromolecules 1(4):609–614

    Article  CAS  Google Scholar 

  28. Damon SE, Rudall KM (1950) Infra-red and X-ray studies of chitin. Discuss Faraday Soc 9:251–260

    Article  Google Scholar 

  29. Focher B, Naggi A, Torri G, Cosani A, Terbojevich M (1992) Structural differences between chitin polymorphs and their precipitates from solutions-evidence from CP-MAS (13)-NMR, FT-IR and FT-Raman spectroscopy. Carbohydr Polym 17:97–102

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors thank Program of 863 (2009AA03Z426), National Natural Science Foundation of China (No.20876080), High-Tech Innovation Project Specialized Plan of Shandong Province(2007ZCB01369) and the Specialized Research Fund for the Doctoral Program of Higher Education of China(20093719110002), Application foundation projects of Qingdao(10-3-4-4-11-jch), Shandong outstanding young and middle-aged scientist research award funded projects(BS2009CL033) for financial support.

Author information

Authors and Affiliations

  1. College of Chemical Engineering, Qingdao University of Science and Technology, 53 Zhengzhou Road, Qingdao, 266042, People’s Republic of China

    Lu Li, Shi-Wei Liu, Shi-Tao Yu, Fu-Sheng Liu & Li-Juan Shan

  2. Key Laboratory of Eco-Chemical Engineering, Ministry of Education, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, 53 Zhengzhou Road, Qingdao, 266042, People’s Republic of China

    Bing Yuan & Cong-Xia Xie

Authors
  1. Lu Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Bing Yuan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shi-Wei Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Shi-Tao Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Cong-Xia Xie
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Fu-Sheng Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Li-Juan Shan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Shi-Tao Yu.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Li, L., Yuan, B., Liu, SW. et al. Clean Preparation Process of Chitosan Oligomers in Gly Series Ionic Liquids Homogeneous System. J Polym Environ 20, 388–394 (2012). https://doi.org/10.1007/s10924-011-0388-z

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10924-011-0388-z

Keywords

Search

Navigation