Abstract
3-methyl-1-ethoxycarbonylimidazolium chloride ([EtMIM]Cl), was synthesized for white hide powder dissolution. White hide powder was successfully dissolved in [EtMIM]Cl, and regenerated from methanol. The dissolution data and thermodynamic parameter of white hide powder in [EtMIM]Cl and [BMIM]Cl were studied. Hydrogen bond basicity (β) and general polarizability (π*) of ILs were determined. The white hide powders were characterized by FT-IR, XRD, and TGA. The results showed that the maximum solubility of white hide powder in [EtMIM]Cl was higher than that in [BMIM]Cl at same dissolution temperature. At same temperature and same solid content, the dissolution time of white hide powder in [EtMIM]Cl was shorter than that in [BMIM]Cl. Density functional theory (DFT) simulation showed that two kinds of hydrogen bonds (C-H/O and C-H/Cl) and eight strong hydrogen bonds are found in [EtMIM]Cl/GPH, while seven hydrogen bonds are found in [BMIM]Cl/GPH. The carboxylic acid ester cationic group in [EtMIM]+ has more electronegative ester groups and stronger electronic cloud density oxygen atoms than alkyl group in [BMIM]+, [EtMIM]Cl is easier to destroy the intermolecular or intramolecular hydrogen bonds in white hide powder, so as to accelerate the dissolution of white hide powder in [EtMIM]Cl. The molecular simulation results indicated that both Cl− anions and [EtMIM]+ cation played important roles in the white hide powder dissolution.
Similar content being viewed by others
References
R. Vijayaraghavan, B. C. Thompson, D. R. MacFarlane, R. Kumar, M. Surianarayanan, S. Aishwarya, and P. K. Sehgal, Chem. Commun., 46, 294 (2010).
M. D. Shoulders and R. T. Raines, Annu. Rev. Biochem., 78, 929 (2009).
H. L. Tian, Y. H. Chen, C. C. Ding, and G. Y. Li, Carbohydr. Polym., 89, 542 (2012).
V. K. Yadavalli, D. V. Svintradze, and R. M. Pidaparti, Int. J. Biol. Macromol., 46, 458 (2010).
M. C. Gómez-Guillén, B. Giménez, M. E. López-Caballero, and M. P. Montero, Food Hydrocolloids, 25, 1813 (2011).
M. A. Farage, K. W. Miller, P. Elsner, and H. I. Maibach, Int. J. Cosmet. Sci., 30, 87 (2008).
F. Chen, J. Zhang, M. Zhang, Y. An, F. Chen, and Z. Wu, Biomaterials, 31, 7892 (2010).
M. B. Fauzi, Y. Lokanathan, B. S. Aminuddin, B. H. I. Ruszymah, and S. R. Chowdhury, Mater. Sci. Eng. C, 68, 163 (2016).
R. Tylingo, G. Gorczyca, S. Mania, P. Szweda, and S. Milewski, React. Funct. Polym., 103, 131 (2016).
X. H. Liu, S. D. Zheng, W. H. Dan, and N. H. Dan, Fiber. Polym., 17, 1186 (2016).
D. K. Yin, H. Wu, C. X. Liu, J. Zhang, T. Zhou, J. J. Wu, and Y. Wan, React. Funct. Polym., 83, 98 (2014).
F. Gobeaux, E. Belamie, G. Mosser, P. Davidson, and S. Asnacios, Soft Matter, 6, 3769 (2010).
M. Y. Li, M. J. Mondrinos, M. R. Gandhi, F. K. Ko, A. S. Weiss, and P. I. Lelkes, Biomaterials, 26, 5999 (2005).
Z. Zhang, A. A. M. Salih, M. T. Li, and B. L. Yang, Energ. Fuel., 28, 2802 (2014).
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).
Z. W. Wu, C. Chen, Q. R. Guo, B. X. Li, Y. G. Que, L. Wang, H. Wan, and G. F. Guan, Fuel, 184, 128 (2016).
J. P. Hallett and T. Welton, Chem. Rev., 111, 3508 (2011).
B. M. Ma, X. L. Hou, and C. J. He, Fiber. Polym., 16, 2704 (2015).
A. M. da Costa Lopes and R. Bogel-Łukasik, ChemSusChem, 8, 947 (2015).
D. T. Liu, K. F. Xia, W. H. Cai, R. D. Yang, L. Q. Wang, and B. Wang, Carbohydr. Polym., 87, 1058 (2012).
H. Wang, G. Gurau, and R. D. Rogers, Chem. Soc. Rev., 41, 1519 (2012).
M. Shibata, N. Teramoto, T. Nakamura, and Y. Saitoh, Carbohydr. Polym., 98, 1532 (2013).
L. K. J. Hauru, M. Hummel, A. W. T. King, I. Kilpeläinen, and H. Sixta, Biomacromolecules, 13, 2896 (2012).
D. M. Phillips, L. F. Drummy, D. G. Conrady, D. M. Fox, R. R. Naik, M. O. Stone, P. C. Trulove, H. C. De Long, and R. A. Mantz, J. Am. Chem. Soc., 126, 14350 (2004).
H. B. Xie, S. H. Li, and S. B. Zhang, Green Chemistry, 7, 606 (2005).
X. F. Sun, Q. Q. Tian, Z. M. Xue, Y. W. Zhang, and T. C. Mu, RSC Adv., 4, 30282 (2014).
S. Mateyawa, D. F. Xie, R. W. Truss, P. J. Halley, T. M. Nicholson, J. L. Shamshina, R. D. Rogers, M. W. Boehm, and T. McNally, Carbohydr. Polym., 94, 520 (2013).
Z. J. Meng, X. J. Zheng, K. Y. Tang, J. Liu, Z. Ma, and Q. L. Zhao, Int. J. Biol. Macromol., 51, 440 (2012).
Y. Hu, L. Liu, W. H. Dan, N. H. Dan, and Z. P. Gu, J. Appl. Polym. Sci., 130, 2245 (2013).
A. Mehta, J. R. Rao, and N. N. Fathima, Colloids and Surf. B: Biointerfaces, 117, 376 (2014).
G. W. Wang, J. R. Guo, L. H. Zhuang, Y. Wang, and B. Xu, Int. J. Biol. Macromol., 76, 70 (2015).
B. Xu, Q. P. Li, L. H. Zhuang, Q. Wang, C. Li, G. W. Wang, and P. J. Halley, Fiber. Polym., 17, 1741 (2016).
R. Lungwitz and S. Spange, New J. Chem., 32, 392 (2008).
L. K. J. Hauru, M. Hummel, A. W. T. King, I. Kilpelainen, and H. Sixta, Biomacromolecules, 13, 2896 (2012).
S. K. Shukla, N. D. Khupse, and A. Kumar, Chem. Phys., 14, 2754 (2012).
A. Tarannum, C. Muvva, A. Mehta, J. R. Rao, and N. N. Fathima, RSC Adv., 6, 4022 (2016).
Q. Q. Tian, S. Y. Liu, X. F. Sun, H. T. Sun, Z. M. Xue, and T. C. Mu, Carbohydr. Res., 408, 107 (2015).
A. Tarannum, C. Muvva, A. Mehta, J. R. Rao, and N. N. Fathima, J. Phys. Chem. B., 120, 6515 (2016).
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, Jr., 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.
C. Chiappe and D. Pieraccini, J. Phys. Org. Chem., 18, 275 (2005).
A. J. Queimada, F. L. Mota, S. P. Pinho, and E. A. Macedo, J. Phys. Chem. B., 113, 3469 (2009).
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Li, Q., Xu, B., Wang, Y. et al. Effect of cationic structure of ionic liquids on dissolution and regeneration of white hide powder. Fibers Polym 18, 1512–1522 (2017). https://doi.org/10.1007/s12221-017-1120-y
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12221-017-1120-y