Deep eutectic solvents (DESs) for cellulose dissolution: a mini-review

Deep eutectic solvents (DESs), which are a novel class of sustainable designer solvents, have attracted considerable attentions in the field of cellulose chemistry. Due to their low cost and analogous physico-chemical properties to ionic liquids, DESs are expected to be alternative solvents for dissolving cellulose. However, at present, the solubility of cellulose in DESs is much lower than in most ionic liquids. In this mini-review, we briefly summarize the current state of knowledge about cellulose dissolution in DESs. By comparing with similar solvents, it was found that the components of current DESs are usually involved in hydrogen bond interaction making difficult their interaction with the hydrogen bond network of cellulose. Accordingly, we propose a strategy that the components which have good hydrogen bond accepting ability, such as Cl-, OAc-, HCOO-, (MeO)2PO2-, morpholine and imidazole, are promising choices to form DESs for cellulose dissolution. Ultrasound-assisted treatment and adding a surfactant are effective ways to promote cellulose solubility by enhancing the permeability of DESs.

[1]  Jiasong He,et al.  Determination of intrinsic viscosity-molecular weight relationship for cellulose in BmimAc/DMSO solutions , 2016, Cellulose.

[2]  R. Rogers,et al.  Ionic liquid processing of cellulose. , 2012, Chemical Society reviews.

[3]  A. Abbott,et al.  Electrodeposition of copper–tin alloys using deep eutectic solvents , 2016 .

[4]  Jianji Wang,et al.  Cation does matter: how cationic structure affects the dissolution of cellulose in ionic liquids , 2014 .

[5]  J. Barrault,et al.  Green and inexpensive choline-derived solvents for cellulose decrystallization. , 2012, Chemistry.

[6]  G. Voth,et al.  IONIC LIQUIDS , 2004 .

[7]  Arthur J. Ragauskas,et al.  Natural deep eutectic solvents for lignocellulosic biomass pretreatment: Recent developments, challenges and novel opportunities. , 2018, Biotechnology advances.

[8]  Narendra Kumar,et al.  Deep eutectic solvents' ability to solubilize lignin, cellulose, and hemicellulose; thermal stability; and density. , 2017, Bioresource technology.

[9]  T. Itoh Design of Ionic Liquids for Cellulose Dissolution , 2014 .

[10]  Alistair W. T. King,et al.  Sustainability of cellulose dissolution and regeneration in 1,5-diazabicyclo[4.3.0]non-5-enium acetate: a batch simulation of the IONCELL-F process , 2015 .

[11]  Lu Lin,et al.  Green Processing of Lignocellulosic Biomass and Its Derivatives in Deep Eutectic Solvents. , 2017, ChemSusChem.

[12]  P. Alexandridis,et al.  Cellulose dissolution: insights on the contributions of solvent-induced decrystallization and chain disentanglement , 2017, Cellulose.

[13]  Shrikant I Bangdiwala,et al.  Understanding interactions , 2015, International journal of injury control and safety promotion.

[14]  Antje Potthast,et al.  The chemistry of side reactions and byproduct formation in the system NMMO/cellulose (Lyocell process) , 2001 .

[15]  Qinghong Wang,et al.  Synthesis of a Novel Allyl-Functionalized Deep Eutectic Solvent to Promote Dissolution of Cellulose , 2016 .

[16]  Christoph Michels,et al.  Dissolution and forming of cellulose with ionic liquids , 2008 .

[17]  Raymond K. Rasheed,et al.  Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains. , 2001, Chemical communications.

[18]  P. Fardim,et al.  Enhancement of cellulose dissolution in water-based solvent via ethanol–hydrochloric acid pretreatment , 2011 .

[19]  Michael E Himmel,et al.  The maize primary cell wall microfibril: a new model derived from direct visualization. , 2006, Journal of agricultural and food chemistry.

[20]  D. Argyropoulos,et al.  Review of Cellulose Non-Derivatizing Solvent Interactions with Emphasis on Activity in Inorganic Molten Salt Hydrates , 2013 .

[21]  Jun Zhang,et al.  SYNTHESIS OF 1-ALLYL,3-METHYLIMIDAZOLIUM-BASED ROOM- TEMPERATURE IONIC LIQUID AND PRELIMINARY STUDY OF ITS DISSOLVING CELLULOSE , 2003 .

[22]  Robin D. Rogers,et al.  Dissolution of Cellose with Ionic Liquids , 2002 .

[23]  Qinghong Wang,et al.  The Properties of Choline Chloride-based Deep Eutectic Solvents and their Performance in the Dissolution of Cellulose , 2016 .

[24]  Héctor Rodríguez,et al.  Where are ionic liquid strategies most suited in the pursuit of chemicals and energy from lignocellulosic biomass? , 2011, Chemical communications.

[25]  Mingzhu Pan,et al.  Physicochemical transformation of rice straw after pretreatment with a deep eutectic solvent of choline chloride/urea. , 2017, Carbohydrate polymers.

[26]  T. Welton,et al.  Determination of Kamlet-Taft parameters for selected solvate ionic liquids. , 2016, Physical chemistry chemical physics : PCCP.

[27]  Y. Marcus Deep Eutectic Solvents , 2018 .

[28]  S. Desobry,et al.  Cellulose derivative based active coatings: Effects of nisin and plasticizer on physico-chemical and antimicrobial properties of hydroxypropyl methylcellulose films , 2010 .

[29]  R. Taft,et al.  The solvatochromic comparison method. I. The .beta.-scale of solvent hydrogen-bond acceptor (HBA) basicities , 1976 .

[30]  Andreas Koschella,et al.  Solvents applied in the field of cellulose chemistry - a mini review , 2005 .

[31]  Raymond K. Rasheed,et al.  Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids. , 2004, Journal of the American Chemical Society.

[32]  Lina Zhang,et al.  Recent advances in regenerated cellulose materials , 2016 .

[33]  K. Wilpiszewska,et al.  Deep eutectic solvents for polysaccharides processing. A review. , 2018, Carbohydrate polymers.

[34]  Emma L. Smith,et al.  Deep eutectic solvents (DESs) and their applications. , 2014, Chemical reviews.

[35]  Monica Ek,et al.  Pulping chemistry and technology , 2009 .

[36]  M. Izadyar,et al.  Deep eutectic solvent as an efficient molecular liquid for lignin solubilization and wood delignification , 2018, Journal of Molecular Liquids.

[37]  J. O. Baker,et al.  How Does Plant Cell Wall Nanoscale Architecture Correlate with Enzymatic Digestibility? , 2012, Science.

[38]  David L Davies,et al.  Novel solvent properties of choline chloride/urea mixtures. , 2003, Chemical communications.

[39]  T. Rosenau,et al.  Kinetic and chemical studies on the isomerization of monosaccharides in N-methylmorpholine-N-oxide (NMMO) under Lyocell conditions. , 2004, Carbohydrate research.

[40]  H. Ohno,et al.  Extraction of polysaccharides from bran with phosphonate or phosphinate-derived ionic liquids under short mixing time and low temperature , 2010 .

[41]  François Jérôme,et al.  Deep eutectic solvents: syntheses, properties and applications. , 2012, Chemical Society reviews.

[42]  Maaike C. Kroon,et al.  New natural and renewable low transition temperature mixtures (LTTMs): screening as solvents for lignocellulosic biomass processing , 2012 .

[43]  S. Kongruang Bacterial Cellulose Production by Acetobacter xylinum Strains from Agricultural Waste Products , 2008, Applied biochemistry and biotechnology.

[44]  C. Felby,et al.  Enzymatic conversion of lignocellulose into fermentable sugars: challenges and opportunities , 2007 .

[45]  P. Wasserscheid,et al.  Ionic liquids in chemical engineering. , 2010, Annual review of chemical and biomolecular engineering.

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

[47]  Hua Zhao Review: Current studies on some physical properties of ionic liquids , 2003 .

[48]  Raymond K. Rasheed,et al.  Ionic liquids based upon metal halide/substituted quaternary ammonium salt mixtures. , 2004, Inorganic chemistry.

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

[50]  H. Ohno,et al.  Task Specific Ionic Liquids for Cellulose Technology , 2009 .

[51]  A. Bell,et al.  Preferential interactions between lithium chloride and glucan chains in N,N-dimethylacetamide drive cellulose dissolution. , 2013, The journal of physical chemistry. B.

[52]  Geert-Jan Witkamp,et al.  Natural deep eutectic solvents as new potential media for green technology. , 2013, Analytica chimica acta.

[53]  S. Eichhorn,et al.  Understanding the interactions of cellulose fibres and deep eutectic solvent of choline chloride and urea , 2017, Cellulose.