Facile Cellulose Dissolution and Characterization in the Newly Synthesized 1,3-Diallyl-2-ethylimidazolium Acetate Ionic Liquid

A facile cellulose solvent 1,3-diallyl-2-ethylimidazolium acetate ([AAeim][OAc]) with high electrical conductivity has been designed and synthesized for the first time, via a quaternization reaction and ion exchange method. The dissolution characteristics of cellulose in this solvent were studied in detail. Meanwhile, the co-solvent system was designed by adding an aprotic polar solvent dimethyl sulfoxide (DMSO) in [AAeim][OAc]. The effects of temperature and the mass ratio of DMSO to [AAeim][OAc] on the solubility of cellulose were studied. Furthermore, the effects of regeneration on the molecular structure and thermal stability of cellulose were determined by Fourier transform infrared spectroscopy (FT-IR), thermal gravity analysis (TGA) and X-ray diffraction (XRD). The findings revealed that the synthesized ionic liquid (IL) has a relatively low viscosity, high conductivity and a good dissolving capacity for bamboo dissolving pulp cellulose (Degree of Polymerization: DP = 650). The macromolecular chain of the cellulose is less damaged during the dissolution and regeneration process. Due to the increased number of "free" anions [OAc]- and cations [AAeim]⁺, the addition of DMSO can significantly increase the solubility of the cellulose up to 12 wt % at the mass ratio of 3:1, indicating that the synthesized IL has a potential application in the electrospinning field.

[1]  Qinghong Wang,et al.  The role and potential of morpholinium-based ionic liquids in dissolution of cellulose , 2017 .

[2]  Ronghui Shi,et al.  Highly efficient synthesis of biodiesel catalyzed by CF3SO3H-functionalized ionic liquids: experimental design and study with response surface methodology , 2017, Reaction Kinetics, Mechanisms and Catalysis.

[3]  Lihui Chen,et al.  Versatile fabrication of a superhydrophobic and ultralight cellulose-based aerogel for oil spillage clean-up. , 2016, Physical chemistry chemical physics : PCCP.

[4]  Luís M. N. B. F. Santos,et al.  The Effect of n vs. iso Isomerization on the Thermophysical Properties of Aromatic and Non-aromatic Ionic Liquids. , 2016, Fluid phase equilibria.

[5]  Siqun Wang,et al.  Efficient liquefaction of woody biomass in polyhydric alcohol with acidic ionic liquid as a green catalyst , 2015 .

[6]  Bingjun Wang,et al.  Facile cellulose dissolution without heating in [C₄mim][CH ₃COO]/DMF solvent. , 2015, Carbohydrate polymers.

[7]  Xueming Zhang,et al.  Comparison of physical properties of regenerated cellulose films fabricated with different cellulose feedstocks in ionic liquid. , 2015, Carbohydrate polymers.

[8]  K. Reddy,et al.  Preparation and properties of self-reinforced cellulose composite films from Agave microfibrils using an ionic liquid. , 2014, Carbohydrate polymers.

[9]  J. Chen,et al.  Densities and viscosities for ionic liquids mixtures containing [eOHmim][BF4], [bmim][BF4] and [bpy][BF4] , 2014 .

[10]  Alexander Kuhn,et al.  Electropolymerization of polypyrrole by bipolar electrochemistry in an ionic liquid. , 2014, Langmuir : the ACS journal of surfaces and colloids.

[11]  Shengfu Wang,et al.  Direct electrochemistry and electrocatalysis of heme proteins immobilised in carbon-coated nickel magnetic nanoparticle-chitosan-dimethylformamide composite films in room-temperature ionic liquids. , 2013, Bioelectrochemistry.

[12]  Zehui Zhang,et al.  Conversion of carbohydrates into 5-hydroxymethylfurfural catalyzed by acidic ionic liquids in dimethyl sulfoxide , 2013 .

[13]  Xiaomin Liu,et al.  Insight into the cosolvent effect of cellulose dissolution in imidazolium-based ionic liquid systems. , 2013, The journal of physical chemistry. B.

[14]  K. Binnemans,et al.  Homogeneous Liquid-Liquid Extraction of Metal Ions with a Functionalized Ionic Liquid. , 2013, The journal of physical chemistry letters.

[15]  R. Sun,et al.  Effect of ionic liquid/organic solvent pretreatment on the enzymatic hydrolysis of corncob for bioethanol production. Part 1: Structural characterization of the lignins , 2013 .

[16]  J. Araújo,et al.  Hydrogen-bonding and the dissolution mechanism of uracil in an acetate ionic liquid: new insights from NMR spectroscopy and quantum chemical calculations. , 2013, The journal of physical chemistry. B.

[17]  Jianzhong Ma,et al.  Long-lived superhydrophobic colorful surfaces. , 2013, Chemical communications.

[18]  Zhiyong Li,et al.  Viscosities and Conductivities of 1-Butyl-3-methylimidazolium Carboxylates Ionic Liquids at Different Temperatures , 2012 .

[19]  W. Leitner,et al.  Cellulose solubilities in carboxylate-based ionic liquids , 2012 .

[20]  Jianji Wang,et al.  Effect of Alkyl Chain Length in Anions on Thermodynamic and Surface Properties of 1-Butyl-3-methylimidazolium Carboxylate Ionic Liquids , 2012 .

[21]  Qilong Ren,et al.  Improved separation efficiency using ionic liquid–cosolvent mixtures as the extractant in liquid–liquid extraction: A multiple adjustment and synergistic effect , 2012 .

[22]  J. Kennedy,et al.  Ultrasound-assisted dissolution of cellulose in ionic liquid , 2011 .

[23]  Roberto Rinaldi,et al.  Instantaneous dissolution of cellulose in organic electrolyte solutions. , 2011, Chemical communications.

[24]  Changmei Jiao,et al.  Dicationic Ionic Liquids as Environmentally Benign Catalysts for Biodiesel Synthesis , 2011 .

[25]  G. Karlström,et al.  On the mechanism of dissolution of cellulose , 2010 .

[26]  Tang Yang,et al.  Electrospinning of polyacrylonitrile fibers from ionic liquid solution , 2010 .

[27]  Jianji Wang,et al.  Effects of anionic structure and lithium salts addition on the dissolution of cellulose in 1-butyl-3-methylimidazolium-based ionic liquid solvent systems , 2010 .

[28]  Jiasong He,et al.  Room temperature ionic liquids (RTILs): A new and versatile platform for cellulose processing and derivatization , 2009 .

[29]  Antje Potthast,et al.  Side reaction of cellulose with common 1-alkyl-3-methylimidazolium-based ionic liquids , 2008 .

[30]  Shanshan Xu,et al.  Electrospinning of native cellulose from nonvolatile solvent system , 2008 .

[31]  M. Frey.  Electrospinning Cellulose and Cellulose Derivatives , 2008 .

[32]  Hiroyuki Ohno,et al.  Cellulose dissolution with polar ionic liquids under mild conditions: required factors for anions , 2008 .

[33]  P. Supaphol,et al.  Electrospun cellulose acetate fibers: effect of solvent system on morphology and fiber diameter , 2007 .

[34]  H. Ohno,et al.  Superior solubility of polysaccharides in low viscosity, polar, and halogen-free 1,3-dialkylimidazolium formates. , 2006, Biomacromolecules.

[35]  Ziniu Yu,et al.  Dissolution of cellulose with ionic liquids and its application : a mini-review , 2006 .

[36]  Michiel Janssen,et al.  Room-temperature ionic liquids that dissolve carbohydrates in high concentrations , 2005 .

[37]  W. Park,et al.  Crystalline structure analysis of cellulose treated with sodium hydroxide and carbon dioxide by means of X-ray diffraction and FTIR spectroscopy. , 2005, Carbohydrate research.

[38]  Jun Zhang,et al.  1-Allyl-3-methylimidazolium chloride room temperature ionic liquid: A new and powerful nonderivatizing solvent for cellulose , 2005 .

[39]  Y. Chu,et al.  Baylis–Hillman reaction in [bdmim][PF6] ionic liquid , 2004 .

[40]  K. Tashiro,et al.  Influence of Water on Structure and Mechanical Properties of Regenerated Cellulose Studied by an Organized Combination of Infrared Spectra, X-ray Diffraction, and Dynamic Viscoelastic Data Measured as Functions of Temperature and Humidity , 2001 .

[41]  Siqun Wang,et al.  Rapid and solvent-saving liquefaction of woody biomass using microwave-ultrasonic assisted technology. , 2016, Bioresource technology.