Effect of 1-butyl-3-methylimidazolium chloride-water mixtures on cellulose

doi:10.11949/j.issn.0438-1157.20141730

Abstract

Abstract:

Dissolution and crystalline structure changes of cellulose treated by 1-butyl-3-methylimidazolium chloride [C₄mim]Cl-water mixtures were investigated at 90℃ under 1.0 MPa. Amorphous cellulose was found to be partial dissolved in the [C₄mim]Cl-water mixtures with [C₄mim]Cl content of 60%—95%, and adding deionized (DI) water into the cellulose-[C₄mim]Cl solution for cellulose regeneration. The crystallinity index (CrI) and the dimension of average crystallite size (D_hkl) for MCC obviously change with increasing treatment duration, but retain the characteristic shapes of cellulose I crystalline structure. There are significant oscillations in the intensities of hydrogen bonds of cellulose for the mixtures with different [C₄mim]Cl content. Different contents of ionic liquid have different effect on microcrystalline cellulose.

Key words: ionic liquids-water, cellulose, solubility, crystallinity

摘要：

在温度90℃, 压力1 MPa条件下, 研究[C₄mim]Cl-水溶液对纤维素的溶解和结构变化的影响。在离子液体含量为60%～95%时, 无定形纤维素可以部分溶解, 并且加去离子水后有纤维素再生。经过[C₄mim]Cl-水溶液处理一段时间后, 微晶纤维素的晶型并没有发生改变, 但纤维素的结晶指数和晶粒尺寸的大小都有明显的变化, 纤维素的分子内和分子间氢键相对强度也有明显变化。离子液体含量不同对微晶纤维素的作用程度不同。

关键词: 离子液体-水, 纤维素, 溶解度, 结晶度

CLC Number:

O636.1⁺1

WANG Linlin, WEI Ligang, MA Yingchong, LI Kunlan, WANG Yantao, DING Shan, WAN Wenying, YAN Bing, ZHAO Deyang, WANG Junmei, WANG Xin. Effect of 1-butyl-3-methylimidazolium chloride-water mixtures on cellulose[J]. CIESC Journal, 2015, 66(S1): 32-37.

王琳琳, 魏立纲, 马英冲, 李坤兰, 王艳涛, 丁珊, 万文英, 闫冰, 赵德扬, 王俊梅, 王鑫. 1-丁基-3-甲基咪唑氯盐离子液体水溶液对纤维素的作用[J]. 化工学报, 2015, 66(S1): 32-37.

References 22

[1]	Gu Yanlong(顾彦龙), Shi Feng(石峰), Deng Youquan(邓友全). Research and application of ionic liquids in catalysis and separation [J]. Journal of Chemical Industry and Engineering(China) (化工学报), 2004, 55(12): 1957-1962.
[2]	Swatloski R P, Spear S K, Holbrey J D. Dissolution of cellulose with ionic liquids [J]. J. Am. Chem. Soc., 2002, 124: 4974-4975.
[3]	Zavrel M, Bross D, Funke M. High-throughput screening for ionic liquids dissolving (ligno-)cellulose [J]. Bioresource Technology, 2009, 100: 2580-2587.
[4]	Wang Y T, Wei L G, Li K L, Ma Y C, Ma N N, Ding S, Wang L L, Zhao D Y, Yan B, Wan W Y, Zhang Q, Wang X, Wang J M, Li H. Lignin dissolution in dialkylimidazolium-based ionic liquid-water mixtures[J]. Bioresource Technology, 2014, 170: 499-505.
[5]	Bendaoud A, Chalamet Y. Effects of relative humidity and ionic liquids on the water content and glass transition of plasticized starch [J]. Carbohydrate Polymers, 2013, 97(2): 665-675.
[6]	Ciolacu D, Kovac J, Kokol V. The effect of the cellulose-binding domain from Clostridium cellulovorans on the supramolecular structure of cellulose fibers [J]. Carbohydrate Research, 2010, 345(5): 621-630.
[7]	Brandt A, Grasvik J, Hallett J P, Welton T. Deconstruction of lignocellulosic biomass with ionic liquids [J]. Green Chem., 2012, 15: 550-583.
[8]	Wei L G, Li K L, Ma Y C, Hou X. Dissolving lignocellulosic biomass in a 1-butyl-3-methylimidazolium chloride-water mixture[J]. Industrial Crops and Products, 2012, 37(1): 227-234.
[9]	Olsson C, Idström A, Nordstierna L, Westman G. Influence of water on swelling and dissolution of cellulose in 1-ethyl-3- methylimidazolium acetate [J]. Carbohydrate Polymers, 2014, 99: 438-446.
[10]	Shi J, Balamurugan K, Parthasarathi R, Sathitsuksanoh N, Zhang S, Stavila V, Subramanian V, Simmons B A, Singh S. Understanding the role of water during ionic liquid pretreatment of lignocellulose: co-solvent or anti-solvent? [J]. Green Chem., 2014, 16: 3830-3840.
[11]	Iguchi M, Aida T M, Watanabe M, Smith Jr R L. Dissolution and recovery of cellulose from 1-butyl-3-methylimidazolium chloride in presence of water [J]. Carbohydrate Polymers, 2013, 92(2): 651-658.
[12]	Mazza M, Catana D A, Vaca-Garcia C, Cecutti C. Influence of water on the dissolution of cellulose in selected ionic liquids [J]. Cellulose, 2009, 16(2): 207-215.
[13]	Schwanninger M, Rodrigues J C, Pereira H, Hinterstoisser B. Effects of short-time vibratory ball milling on the shape of FT-IR spectra of wood and cellulose [J]. Vibrational Spectroscopy, 2004, 36(1): 23-40.
[14]	Fu D B, Mazza G. Aqueous ionic liquid pretreatment of straw [J]. Bioresource Technology, 2011, 102(13): 7008-7011.
[15]	Dai D, Fan M. Investigation of the dislocation of natural fibres by Fourier-transform infrared spectroscopy [J]. Vibrational Spectroscopy, 2011, 55(2): 300-306.
[16]	Wang W C, Zhang P, Zhang S, Li F X, Yu J Y, Lin J Y. Structure and properties of novel regenerated cellulose fibers prepared in NaOH complex solution [J]. Carbohydrate Polymers, 2013, 98(1): 1031-1038.
[17]	Tiwari A K, Sonu, Saha S K. Aggregation behaviour and thermodynamics of mixed micellization of gemini surfactants with a room temperature ionic liquid in water and water-organic solvent mixed media [J]. The Journal of Chemical Thermodynamics, 2013, 60: 29-40.
[18]	Qi X H, Watanabe M, Aida T M, Smith R L. Synergistic conversion of glucose into 5-hydroxymethylfurfural in ionic liquid-water mixtures [J]. Bioresource Technology, 2012, 109: 224-228.
[19]	Zhao H B, Kwak J H, Zhang Z C, Brown H M, Arey B W, Holladay J E. Studying cellulose fiber structure by SEM, XRD, NMR and acid hydrolysis [J]. Carbohydrate Polymers, 2007, 68(2): 235-241.
[20]	Cheng G, Varanasi P, Arora R, Stavila V, Simmons B A, Kent M S, Singh S. Impact of ionic liquid pretreatment conditions on cellulose crystalline structure using 1-ethyl-3-methylimidazolium acetate [J]. The Journal of Physical Chemistry B, 2012, 116 (33): 10049-10054.
[21]	Doherty T V, Mora-Pale M, Foley S E, Linhardt R J, Dordick J S. Ionic liquid solvent properties as predictors of lignocellulose pretreatment efficacy [J]. Green Chemistry, 2010, 12(11): 1967-1975.
[22]	Hauru L K J, Hummel M, King A W T, Kilpeläinen I, Sixta H. Role of solvent parameters in the regeneration of cellulose from ionic liquid solutions [J]. Biomacromolecules, 2012, 13(9): 2896-2905.

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