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Dissolution and regeneration behavior of chitosan in 3-methyl-1-(ethylacetyl)imidazolium chloride

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Abstract

3-methyl-1-(ethylacetyl)imidazolium chloride ([EtMIM]Cl), was synthesized for chitosan dissolution, and the dissolution and regeneration behaviors of chitosan in [EtMIM]Cl were thoroughly investigated. The solubility of chitosan in [EtMIM]Cl was measured at temperatures ranging from 40 °C to 110 °C, based on which the thermodynamic parameters of chitosan in [EtMIM]Cl were calculated. The polarizability and hydrogen bond accepting ability was determined by solvatochromic UV/vis spectroscopy. The regenerated chitosan from [EtMIM]Cl by adding methanol was characterized by thermogravimetric analysis (TGA), Fourier transform infrared spectroscopy (FTIR), X-ray diffraction (XRD) and scanning electron microscopy (SEM). Density functional theory (DFT) computations were performed to study the interactions between [EtMIM]Cl and chitobiose. Five kinds of hydrogen bonds, C-H/O, O-H/O, O-H/Cl, C-H/Cl, N-H/Cl were found, suggesting strong interactions between [EtMIM]Cl and chitobiose. In particular, the oxygen atom and the active methylene group of carboxylic ester in [EtMIM]+, formed strong hydrogen bonding with chitobiose. The molecular simulation results indicated that both the Cl− anions and [EtMIM]+ cation played important roles in the chitosan dissolution process, by the disruption of native hydrogen bonds of chitosan.

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References

  1. A. M. Dias, A. R. Cortez, M. Barsan, J. Santos, and C. M. Brett, ACS Sustain. Chem. Eng., 1, 1480 (2013).

    Article  CAS  Google Scholar 

  2. F. B. Lv, C. X. Wang, P. Zhu, and C. J. Zhang, Cellulose, 21, 4405 (2014).

    Article  CAS  Google Scholar 

  3. W. Jiang, Z. M. Zhou, D. Wang, X. H. Zhou, R. Y. Tao, Y. Yang, Y. X. Shi, G. L. Zhang, D. Y. Wang, and Z. Zhou, Carbohydr. Polym., 153, 105 (2016).

    Article  CAS  Google Scholar 

  4. M. Dash, F. Chiellini, R. Ottenbrite, and E. Chiellini, Prog. Polym. Sci., 36, 981 (2011).

    Article  CAS  Google Scholar 

  5. X. F. Sun, Q. Q. Tian, and Z. M. Xue, RSC Adv., 4, 30282 (2014).

    Article  CAS  Google Scholar 

  6. A. Ayoub, R. A. Venditti, J. J. Pawlak, A. Salam, and M. A. Hubbe, ACS Sustain. Chem. Eng., 1, 1102 (2013).

    Article  CAS  Google Scholar 

  7. L. Qian and H. F. Zhang, Green Chem., 12, 1207 (2010).

    Article  CAS  Google Scholar 

  8. R. Hirase, Y. Higashiyama, M. Mori, Y. Takahara, and C. Yamane, Carbohydr. Polym., 80, 993 (2010).

    Article  CAS  Google Scholar 

  9. Z. Zhang, A. A. M. Salih, M. T. Li, and B. L. Yang, Energ. Fuel., 28, 2802 (2014).

    Article  CAS  Google Scholar 

  10. E. B. Silva, D. Santos, D. R. M. Alves, M. S. Barbosa, R. C. L.Guimaraes, B. M. S. Ferreira, R. A. Guarnieri, E. Franceschi, C. Dariva, and A. F. Santos, Energ. Fuel., 27, 6311 (2013).

    Article  CAS  Google Scholar 

  11. Z. W. Wu, C. Chen, Q. Guo, B. X. Li, Y. G. Que, L. Wang, H. Wan, and G. F. Guan, Fuel, 184, 128 (2016).

    Article  CAS  Google Scholar 

  12. J. P. Hallett and T. Welton, Chem. Rev., 111, 3508 (2011).

    Article  CAS  Google Scholar 

  13. I. Anugwom, V. Eta, P. Virtanen, P. M. Arvela, M Hedenstrcm, M. Hummel, H. Sixta, and J. P. Mikkola, ChemSusChem, 7, 1170 (2014).

    Article  CAS  Google Scholar 

  14. A. M. da Costa Lopes and R. Bogel-Lukasik, ChemSusChem, 8, 947 (2015).

    Article  CAS  Google Scholar 

  15. M. E. Zakrzewska, E. Bogel-Lukasik, and R. Bogel-Lukasik, Energ. Fuel., 24, 737 (2010).

    Article  CAS  Google Scholar 

  16. F. Niroomand, A. Khosravani, and H. Younesi, Cellulose, 23, 1311 (2016).

    Article  CAS  Google Scholar 

  17. Z. H. Liu, X. F. Sun, M. Y. Hao, C. Y. Huang, Z. M. Xue, and T. C. Mu, Carbohydr. Polym., 117, 99 (2015).

    Article  CAS  Google Scholar 

  18. J. J. Miao, Y. Q. Yu, Z. M. Jiang, and L. P. Zhang, Cellulose, 23, 1209 (2016).

    Article  CAS  Google Scholar 

  19. N. Sun, H. Rordriguez, M. Rahman, and R. D. Rogers, Chem. Commun., 47, 1405 (2011).

    Article  CAS  Google Scholar 

  20. B. Zhao, L. Greiner, and W. Leitner, RSC Adv., 2, 2476 (2012).

    Article  CAS  Google Scholar 

  21. V. Vladimira and K. Katerina, RSC Adv., 5, 17690 (2015).

    Article  Google Scholar 

  22. Z. Q. Pang, C. H. Dong, and X. J. Pan, Cellulose, 23, 323 (2016).

    Article  CAS  Google Scholar 

  23. X. Y. Liu, P. R. Chang, P. W. Zheng, D. P. Anderson, and X. F. Ma, Cellulose, 22, 709 (2015).

    Article  CAS  Google Scholar 

  24. W. J. Xiao, Q. Chen, Y. Wu, T. Wu, and L. Dai, Carbohydr. Polym., 83, 233 (2011).

    Article  CAS  Google Scholar 

  25. X. F. Sun, Z. M. Xue, and T. Mu, Green Chem., 16, 2102 (2014).

    Article  CAS  Google Scholar 

  26. J. M. Zhang, H. Zhang, J. Wu, J. Zhang, J. S. He, and J. F. Xiang, Phys. Chem. Chem. Phys., 12, 1941 (2010).

    Article  CAS  Google Scholar 

  27. Y. Zhao, X. Liu, J. Wan, and S. Zhang, Phys. Chem. Phys. Chem, 13, 3126 (2012).

    CAS  Google Scholar 

  28. N. Gathergood, M. T. Garcia, and P. J. Scammells, Green Chem., 6, 166 (2004).

    Article  CAS  Google Scholar 

  29. R. Lungwitz and S. Spange, New J. Chem., 32, 392 (2008).

    Article  CAS  Google Scholar 

  30. Y. Fukaya, A. Sugimoto, and H. Ohno, Biomacromolecules, 7, 3295 (2006).

    Article  CAS  Google Scholar 

  31. C. Loerbroks, R. Rinaldi, and W. Thiel, Chem. Eur. J., 19, 16282 (2013).

    Article  CAS  Google Scholar 

  32. Q. Q. Tian, S. Y. Liu, X. F. Sun, H. T. Sun, Z. M. Xue, and T. C. Mu, Carbohydr. Res., 408, 107 (2015).

    Article  CAS  Google Scholar 

  33. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian 09, Revision B.01, Gaussian, Inc., Wallingford CT, 2009.

    Google Scholar 

  34. A. J. Queimada, F. L. Mota, S. P. Pinho, and E. A. Macedo, J. Phys. Chem. B, 113, 3469 (2009).

    Article  CAS  Google Scholar 

  35. Y. Fukaya, A. Sugimoto, and H. Ohno, Biomacromolecules, 7, 3295 (2006).

    Article  CAS  Google Scholar 

  36. L. K. J. Hauru, M. Hummel, A. W. T. King, I. Kilpelainen, and H. Sixta, Biomacromolecules, 13, 2896 (2012).

    Article  CAS  Google Scholar 

  37. C. Reichardt, Green Chem., 7, 339 (2005).

    Article  CAS  Google Scholar 

  38. S. K. Shukla, N. D. Khupse, and A. Kumar, Phys. Chem. Chem. Phys., 14, 2754 (2012).

    Article  CAS  Google Scholar 

  39. C. Chiappe and D. Pieraccini, J. Phys. Org. Chem., 18, 275 (2005).

    Article  CAS  Google Scholar 

  40. Q. T. Chen, A. R. Xu, Z. Y. Li, J. J. Wang, and S. J. Zhang, Green Chem., 13, 3446 (2011).

    Article  CAS  Google Scholar 

  41. C. Stefanescu, W. H. Daly, and I. I. Negulescu, Carbohydr. Polym., 87, 435 (2012).

    Article  CAS  Google Scholar 

  42. B. M. Ma, X. L. Hou, and C. J. He, Fiber. Polym., 16, 2704 (2015).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. College of Food Science and Light Industry, Nanjing Tech University, Nanjing, 211816, China

    Bin Xu, Qiaoping Li & Guowei Wang

  2. College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing, 211816, China

    Linghua Zhuang, Qiang Wang & Chao Li

  3. School of Chemical Engineering, The University of Queensland, Brisbane, Qld, 4072, Australia

    Fengwei Xie & Peter J. Halley

Authors
  1. Bin Xu
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  2. Qiaoping Li
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  3. Linghua Zhuang
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  4. Qiang Wang
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  5. Chao Li
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  6. Guowei Wang
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  7. Fengwei Xie
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  8. Peter J. Halley
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Correspondence to Guowei Wang.

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Xu, B., Li, Q., Zhuang, L. et al. Dissolution and regeneration behavior of chitosan in 3-methyl-1-(ethylacetyl)imidazolium chloride. Fibers Polym 17, 1741–1748 (2016). https://doi.org/10.1007/s12221-016-6747-6

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  • DOI: https://doi.org/10.1007/s12221-016-6747-6

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