Abstract
The effect of ionic liquids (ILs) on the solubility of cellulose was investigated by changing their anions and cations. The structural variation included 11 kinds of cations in combination with 4 kinds of anions. The interaction between the IL and cellobiose, the repeating unit of cellulose, was clarified through nuclear magnetic resonance (NMR) spectroscopy. The reason for different dissolving capabilities of various ILs was revealed. The hydrogen bonding interaction between the IL and hydroxyl was the major force for cellulose dissolution. Both the anion and cation in the IL formed hydrogen bonds with cellulose. Anions associated with hydrogen atoms of hydroxyls, and cations favored the formation of hydrogen bonds with oxygen atoms of hydroxyls by utilizing activated protons in imidazolium ring. Weakening of either the hydrogen bonding interaction between the anion and cellulose, or that between the cation and cellulose, or both, decreases the capability of ILs to dissolve cellulose.
Similar content being viewed by others
References
Klemm D, Heublein B, Fink HP, Bohn A. Angew Chem Int Ed, 2005, 44: 3358–3393
Zhang JM, Zhang J. Acta Polymerica Sinica, 2010, 12: 1376–1398
Ranke J, Stolte S, Störmann R, Arning J, Jastorff B. Chem Rev, 2007, 107: 2183–2206
Wang H, Gurau G, Rogers RD. Chem Soc Rev, 2012, 41: 1519–1537
Mai NL, Koo YM. ACS Sustain Chem Eng, 2016, 4: 541–547
Badgujar KC, Bhanage BM. Bioresour Technol, 2015, 178: 2–18
Miao JJ, Sun HB, Yu YQ, Song XL, Zhang LP. RSC Adv, 2014, 4: 36721–36724
Yang YL, Song LC, Peng C, Liu EH, Xie HB. Green Chem, 2015, 17: 2758–2763
Hauru LKJ, Hummel M, Nieminen K, Michud A, Sixta H. Soft Matter, 2016, 12: 1487–1495
Kostag M, Liebert T, Heinze T. Macromol Rapid Commun, 2014, 35: 1419–1422
Raut DG, Sundman O, Su WQ, Virtanen P, Sugano Y, Kordas K, Mikkola JP. Carbohyd Polym, 2015, 130: 18–25
Schenzel A, Hufendiek A, Barner-Kowollik C, Meier MAR. Green Chem, 2014, 16: 3266–3271
Ma Y, Hummel M, Määttänen M, Särkilahti A, Harlin A, Sixta H. Green Chem, 2016, 18: 858–866
Xie HB, Yu X, Yang YL, Zhao ZBK. Green Chem, 2014, 16: 2422–2427
Zhang JM, Lv YX, Luo N, Wu J, Yu J, He JS, Zhang J. Chinese Polym Bull, 2011, 10: 138–153
Swatloski RP, Spear SK, Holbrey JD, Rogers RD. J Am Chem Soc, 2002, 124: 4974–4975
Remsing RC, Swatloski RP, Rogers RD, Moyna G. Chem Commun, 2006, 1271–1273
Remsing RC, Hernandez G, Swatloski RP, Massefski WW, Rogers RD, Moyna G. J Phys Chem B, 2008, 112: 11071–11078
Youngs TGA, Holbrey JD, Deetlefs M, Nieuwenhuyzen M, Costa Gomes MF, Hardacre C. ChemPhysChem, 2006, 7: 2279–2281
Youngs TGA, Hardacre C, Holbrey JD. J Phys Chem B, 2007, 111: 13765–13774
Youngs TGA, Holbrey JD, Mullan CL, Norman SE, Lagunas MC, D’Agostino C, Mantle MD, Gladden LF, Bowron DT, Hardacre C. Chem Sci, 2011, 2: 1594–1605
de Oliveira HFN, Rinaldi R. ChemSusChem, 2015, 8: 1577–1584
Liu HB, Cheng G, Kent M, Stavila V, Simmons BA, Sale KL, Singh S. J Phys Chem B, 2012, 116: 8131–8138
Pinkert A. J Chem Eng Data, 2012, 57: 1338–1340
Huo F, Liu ZP, Wang WC. J Phys Chem B, 2013, 117, 11780–11792
Payal RS, Balasubramanian S. Phys Chem Chem Phys, 2014, 16: 17458–17465
Rabideau BD, Agarwal A, Ismail AE. J Phys Chem B, 2014, 118, 1621–1629
Hassan ESRE, Mutelet F, Bouroukba. Carbohyd Polym, 2015, 127: 316–324
Benedetto A, Ballone P. ACS Sustain Chem Eng, 2016, 4: 392–412
Zhang H, Wu J, Zhang J, He JS. Macromolecules, 2005, 38: 8272–8277
Zhang JM, Zhang H, Wu J, Zhang J, He JS, Xiang JF. Phys Chem Chem Phys, 2010, 12: 1941–1947
Zhang JM, Zhang H, Wu J, Zhang J, He JS, Xiang JF. Phys Chem Chem Phys, 2010, 12: 14829–14830
Liu Z, Wang H, Li ZX, Lu XM, Zhang XP, Zhang SJ, Zhou KB. Mater Chem Phys, 2011, 128: 220–227
Payal RS, Bharath R, Periyasamy G, Balasubramanian S. J Phys Chem B, 2012, 116: 833–840
Li J, Lu Y, Yang DJ, Sun QF, Liu YX, Zhao HJ. Biomacromolecules, 2011, 12: 1860–1867
Lu BL, Xu AR, Wang JJ. Green Chem, 2014, 16: 1326–1335
Xu AR, Cao LL, Wang BJ. Carbohyd Polym, 2015, 125: 249–254
Annegret S, Martin S, Bernd O, Klemens M. Sci China Chem, 2012, 55: 1663–1670
Pinkert A, Marsh KN, Pang SS. Ind Eng Chem Res, 2010, 49: 11121–11130
Cho HM, Gross AS, Chu JW. J Am Chem Soc, 2011, 133: 14033–14041
Gross AS, Bell AT, Chu JW. J Phys Chem B, 2011, 115: 13433–13440
Muraoka J, Kamiya N, Ito Y. J Mol Liq, 2013, 182: 76–78
Lovell CS, Walker A, Damion RA, Radhi A, Tanner SF, Budtova T, Ries ME. Bomacromolecules, 2010, 11: 2927–2935
Ries ME, Radhi A, Keating AS, Parker O, Budtova T. Biomacromolecules, 2014, 15: 609–617
Sun XF, Tian QQ, Xue ZM, Zhang YW, Mu TC. RSC Adv, 2014, 4: 30282–30291
Kathirgamanathan K, Grigsby WJ, Al-Hakkak J, Edmonds NR. Int J Polym Sci, 2015: 958653
Okushita K, Chikayama E, Kikuchi J. Biomacromolecules, 2012, 13: 1323–1330
Chang HC, Zhang RL, Hsu DT. Phys Chem Chem Phys, 2015, 17: 27573–27578
Ranu BC, Banerjee S. Org Lett, 2005, 7: 3049–3052
Gericke M, Liebert T, El Seoud OA, Heinze T. Macromol Mater Eng, 2011, 296: 483–493
Barthel S, Heinze T. Green Chem, 2006, 8: 301–306
Fukaya Y, Sugimoto A, Ohno H. Biomacromolecules, 2006, 7: 3295–3297
Ohno H, Fukaya Y. Chem Lett, 2009, 38: 2–7
Hauru LKJ, Hummel M, King AWT, Kilpeläinen I, Sixta H. Biomacromolecules, 2012, 13: 2896–2905
Cruz H, Fanselow M, Holbrey JD, Seddon KR. Chem Commun, 2012, 48: 5620–5622
Bonhôte P, Dias AP, Papageorgiou N, Kalyanasundaram K, Grätzel M. Inorg Chem, 1996, 35: 1168–1178
Singh T, Kumar A. J Phys Chem B, 2007, 111: 7843–7851
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
11426_2016_269_MOESM1_ESM.doc
Understanding cellulose dissolution: Effect of the cation and anion structure of ionic liquids on the solubility of cellulose
Rights and permissions
About this article
Cite this article
Zhang, J., Xu, L., Yu, J. et al. Understanding cellulose dissolution: effect of the cation and anion structure of ionic liquids on the solubility of cellulose. Sci. China Chem. 59, 1421–1429 (2016). https://doi.org/10.1007/s11426-016-0269-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-016-0269-5