Accessible Requires Authentication Published by De Gruyter October 13, 2015

Superior cellulose-protective effects of cosolvent during enhanced dissolution in imidazolium ionic liquid

Juan Tao, Takao Kishimoto, Satoshi Suzuki, Masahiro Hamada and Noriyuki Nakajima
From the journal Holzforschung

Abstract

To improve the solubility of cellulose at lower temperatures, several polar organic solvents were examined as cosolvents in imidazolium ionic liquid (IL). All tested cosolvents increased the solubilization efficiency of ILs at lower temperatures. Among these, N-methylimidazole, N-methyl-2-pyrrolidone, and dimethyl sulfoxide (DMSO) were notably efficient; in case of Avicel the solubility was increased, with 12–15% cellulose dissolution in 1-allyl-3-methylimidazolium chloride ([Amim]Cl) at 30°C. IR spectra of the regenerated celluloses from IL/cosolvent systems showed characteristic features of cellulose II and/or amorphous cellulose. Thermogravimetric analyses showed significantly higher thermal stability of regenerated cellulose from [Amim]Cl/DMSO compared with that without DMSO. Moreover, dimethylacetamide (DMAc) increased the solubility of filter paper pulp in 1-ethyl-3-methylimidazolium acetate ([Emim]OAc), with 12% pulp dissolution at 30°C. No decrease in the degree of polymerization (DP) of cellulose was observed with [Emim]OAc/DMAc, whereas 8–9% DP decrease was observed with [Emim]OAc, even at 30°C. These results indicate that some cosolvents including DMSO and DMAc increase solubilization efficiency and have superior cellulose-protective effects during enhanced dissolution in ILs.


Corresponding author: Takao Kishimoto, Faculty of Engineering, Department of Biotechnology, Toyama Prefectural University, 939-0398 Imizu, Japan, e-mail:

Acknowledgments

Part of this work was supported by JSPS KAKENHI Grant 25292106.

References

Abushammala, H., Pontes, J.F., Gomes, G.H., Osorio-Madrazo, A., Thiré, R.M.S.M., Pereira, F.V., Laborie, M.-P.G. (2015) Swelling, viscoelastic, and anatomical studies on ionic liquid-swollen Norway spruce as a screening tool toward ionosolv pulping. Holzforschung 69:1059–1067. Search in Google Scholar

Azubuike, C.P., Rodríguez, H., Okhamafe, A.O., Rogers, R.D. (2012) Physicochemical properties of maize cob cellulose powders reconstituted from ionic liquid solution. Cellulose 19:425–433. Search in Google Scholar

Fukaya, Y., Sugimoto, A., Ohno, H. (2006) Superior solubility of polysaccharides in low viscosity, polar, and halogen-free 1,3-dialkylimidazolium formates. Biomacromolecules 7:3295–3297. Search in Google Scholar

Fukaya, Y., Hayashi, K., Wada, M., Ohno, H. (2008) Cellulose dissolution with polar ionic liquids under mild conditions: required factors for anions. Green Chem. 10:44–46. Search in Google Scholar

George, A., Tran, K., Morgan, T.J., Benke, P.I., Berrueco, C., Lorente, E., Wu, B.C. Keasling, J.D., Simmons, B.A., Holmes, B.M. (2011) The effect of ionic liquid cation and anion combinations on the macromolecular structure of lignins. Green Chem. 13:3375–3385. Search in Google Scholar

Gericke, M., Liebert, T., El Seoud, O.A., Heinze, T. (2011) Tailored media for homogeneous cellulose chemistry: ionic liquid/cosolvent mixtures. Macromol. Mater. Eng. 296:483–493. Search in Google Scholar

Heinze, T., Schwikal, K., Barthel, S. (2005) Ionic liquids as reaction medium in cellulose functionalization. Macromol. Biosci. 5:520–525. Search in Google Scholar

Kanbayashi, T., Miyafuji, H. (2015) Raman microscopic analysis of wood after treatment with the ionic liquid, 1-ethyl-3-methylimidazolium chloride. Holzforschung 69:273–279. Search in Google Scholar

Kosan, B., Michels, C., Meister, F. (2008) Dissolution and forming cellulose with ionic liquids. Cellulose 15:59–66. Search in Google Scholar

Li, D., Sevastyanova, O., Ek, M. (2012) Pretreatment of softwood dissolving pulp with ionic liquids. Holzforschung 66(8):935–943. Search in Google Scholar

Liang, C.Y., Marchessault, R.H. (1959a) Infrared spectra of crystalline polysaccharides. I. Hydrogen bonds in native celluloses. J. Polym. Sci. 37:385–395. Search in Google Scholar

Liang, C. Y., Marchessault, R. H. (1959b) Infrared spectra of crystalline polysaccharides. II. Native celluloses in the region from 640 to 1700 cm-1 J. Polym. Sci. 39:269–278. Search in Google Scholar

Marchessault, R. H., Liang, C. Y. (1960) Infrared spectra of crystalline polysaccharides. III. Mercerized cellulose. J. Polym. Sci. 43:71–84. Search in Google Scholar

Mikkola, J.P., Kirilin, A., Tuuf, J.C., Pranovich, A., Holmbom, B., Kustov, L.M., Murzin, D.Y., Salmi, T. (2007) Ultrasound enhancement of cellulose processing in ionic liquids: from dissolution towards functionalization. Green Chem. 9:1229–1237. Search in Google Scholar

Nelson, M.L., O’Connor, R.T. (1964) Relation of certain infrared bands to cellulose crystallinity and crystal latticed type. Part I. Spectra of lattice types I, II, III and of amorphous cellulose. J. Appl. Polym. Sci. 8:1311–1324. Search in Google Scholar

Ou, R., Xie, Y., Wang, Q., Sui, S., Wolcott, M.P. (2014) Thermoplastic deformation of poplar wood plasticized by ionic liquids measured by a nonisothermal compression technique. Holzforschung 68:555–566. Search in Google Scholar

Qu, C., Kishimoto, T., Kishino, M., Hamada, M., Nakajima, N. (2011) Heteronuclear single-quantum coherence nuclear magnetic resonance (HSQC NMR) characterization of acetylated fir (Abies sachallnensis MAST) wood regenerated from ionic liquid. J. Agri. Food Chem. 59:5382–5389. Search in Google Scholar

Qu, C., Kishimoto, T., Ogita, S., Hamada, M., Nakajima, N. (2012) Dissolution and acetylation of ball-milled birch (Betula platyphylla) and bamboo (Phyllostachys nigra) in the ionic liquid [Bmim]Cl for HSQC NMR analysis. Holzforschung 66:607–614. Search in Google Scholar

Qu, C., Kishimoto, T., Hamada, M., Nakajima, N. (2013a) Dissolution and acetylation of ball-milled lignocellulosic biomass in ionic liquids at room temperature: Application to NMR analysis of cell-wall components. Holzforschung 67:25–32. Search in Google Scholar

Qu, C., Kishimoto, T., Hamada, M., Nakajima, N. (2013b) Molecular weight distributions of acetylated lignocellulosic biomasses recovered from an ionic liquid system. Holzforschung 67:721–726. Search in Google Scholar

Rinaldi, R. (2011) Instantaneous dissolution of cellulose in organic electrolyte solutions. Chem. Commun. 47:511–513. Search in Google Scholar

Roselli, A., Asikainen, S., Stepan, A., Monshizadeh, A., von Weymarn, N., Kovasin, K., Wang, Y., Xiong, H., Turunen, O., Hummel, M., Sixta, H. (2016) Comparison of pulp species in IONCELL-P: selective hemicellulose extraction method with ionic liquids. Holzforschung 70:291–296 Search in Google Scholar

Schrems, M., Brandt, A., Welton, T., Liebner, F., Rosenau, T., Potthast, A. (2011) Ionic liquid as media for biomass processing: opportunities and restrictions. Holzforschung 65:527–533. Search in Google Scholar

Swatloski, R.P., Spear, S.K., Holbrey, J.D., Rogers, R.D. (2002) Dissolution of cellulose with ionic liquids. J. Am. Chem. Soc. 124:4974–4975. Search in Google Scholar

Viell, J., Marquardt, W. (2011) Disintegration and dissolution kinetics of wood chips in ionic liquids. Holzforschung 65(4):519–525. Search in Google Scholar

Vitz, J., Erdmenger, T., Haensch, C., Schubert, U.S. (2009) Extended dissolution studies of cellulose in imidazolium based ionic liquids. Green Chem. 11:417–424. Search in Google Scholar

Xu, A., Wang, J., Wang, H. (2010) Effects of anionic structure and lithium salts addition on the dissolution of cellulose in 1-butyl-3-methylimidazolium-based ionic liquid solvent systems. Green Chem. 12:268–275. Search in Google Scholar

Xu, A., Zhang, Y., Zhao, Y., Wang, J. (2013) Cellulose dissolution at ambient temperature: Role of preferential salvation of cations of ionic liquids by a cosolvent. Carbohyd. Polym. 92:540–544. Search in Google Scholar

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

Received: 2015-5-14
Accepted: 2015-9-15
Published Online: 2015-10-13
Published in Print: 2016-6-1

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