Ionic liquids have shown great potential in the last two decades as solvents, catalysts, reaction media, additives, lubricants, and in many applications such as electrochemical systems, hydrometallurgy, chromatography, CO2 capture, etc. As solvents, the unlimited combinations of cations and anions have given ionic liquids a remarkably wide range of solvation power covering a variety of organic and inorganic materials. Ionic liquids are also considered "green" solvents due to their negligible vapor pressure, which means no emission of volatile organic compounds. Due to these interesting properties, ionic liquids have been explored as promising solvents for the dissolution and fractionation of wood and cellulose for biofuel production, pulping, extraction of nanocellulose, and for processing all-wood and all-cellulose composites. This review describes, at first, the potential of ionic liquids and the impact of the cation/anion combination on their physiochemical properties and on their solvation power and selectivity to wood polymers. It also elaborates on how the dissolution conditions influence these parameters. It then discusses the different approaches, which are followed for the homogeneous and heterogeneous dissolution and fractionation of wood and cellulose using ionic liquids and categorize them based on the target application. It finally highlights the challenges of using ionic liquids for wood and cellulose dissolution and processing, including side reactions, viscosity, recyclability, and price.

https://www.mdpi.com/2073-4360/12/1/195/pdf

A Review on the Partial and Complete Dissolution and Fractionation of Wood and Lignocelluloses Using Imidazolium Ionic Liquids.

A water-THF biphasic system containing N-methyl-2-pyrrolidone (NMP) was found to enable the efficient synthesis of 5-hydroxymethylfurfural (HMF) from a variety of sugars (simple to complex) using phosphated TiO 2 as a catalyst. Fructose and glucose were selectively converted to HMF resulting in 98 % and 90 % yield, respectively, at 175 °C. Cellobiose and sucrose also gave rise to high HMF yields of 94 % and 98 %, respectively, at 180 °C. Other sugar variants such as starch (potato and rice) and cellulose were also investigated. The yields of HMF from starch (80-85 %) were high, whereas cellulose resulted in a modest yield of 33%. Direct transformation of cellulose to HMF in significant yield (86 %) was assisted by mechanocatalytic depolymerization - ball milling of acid-impregnated cellulose. This effectively reduced cellulose crystallinity and particle size, forming soluble cello-oligomers; this is responsible for the enhanced substrate-catalytic sites contact and subsequent rate of HMF formation. During catalyst recyclability, P-TiO 2 was observed to be reusable for four cycles without any loss in activity. We also investigated the conversion of the cello-oligomers to HMF in a continuous flow reactor. Good HMF yield (53 %) was achieved using a water-methyl isobutyl ketone+NMP biphasic system.

Direct Production of 5-Hydroxymethylfurfural via Catalytic Conversion of Simple and Complex Sugars over Phosphated TiO2.

Designing cellulose hydrogels from non-woody biomass.

Cellulose nanocrystals were prepared using ionic liquids (ILs), 1-ethyl-3-methylimidazolium chloride [EMIM][Cl] and 1-propyl-3-methylimidazolium chloride [PMIM][Cl], from microcrystalline cellulose. The resultant samples were characterized by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FTIR), dynamic light scattering (DLS), scanning electron microscopy (SEM), and transmission electron microscopy (TEM). The XRD results showed that nanocellulose obtained by treatment with both ILs preserved basic cellulose I structure, but crystallinity index of samples (except for Sigmacell treated with [EMIM][Cl]) was lower in comparison to the starting microcrystalline cellulose. The DLS results indicated noticeably smaller particle sizes of prepared cellulose for material treated with [PMIM][Cl] compared to cellulose samples hydrolyzed with [EMIM][Cl], which were prone to agglomeration. The obtained nanocellulose had a rod-like structure that was confirmed by electron microscopy analyses. Moreover, the results described in this paper indicate that cation type of ILs influences particle size and morphology of cellulose after treatment with ionic liquids.

Preparation of Nanocellulose Using Ionic Liquids: 1-Propyl-3-Methylimidazolium Chloride and 1-Ethyl-3-Methylimidazolium Chloride.

Dissolution mechanism of cellulose in quaternary ammonium hydroxide: Revisiting through molecular interactions

We investigated the decomposition of cellulose upon heating in an ionic liquid, 1-ethyl-3-methylimidazolium chloride ([C2mim][Cl]), in air and we studied the reactions of various cellulose decomposition compounds such as cellobiose, cellobiosan, glucose and levoglucosan. We propose two possible decomposition pathways for cellulose during [C2mim][Cl] treatment in air. One pathway is the hydrolysis of cellulose to cellobiose and glucose because [C2mim][Cl] can retain water even at higher than 100 °C, the boiling point of water. The other pathway is the depolymerization of cellulose to cellobiosan by a reaction of the hydroxy group at the C6 position in the glucose residue to form a glycosidic bond. The obtained cellobiosan is then depolymerized to two molecules of levoglucosan by a similar reaction of the hydroxy group at the C6 position. The levoglucosan produced is further hydrolyzed to glucose. Therefore, several products from cellulose decomposition are converted to glucose, which is the final hydrolyzed product. Furthermore, the obtained glucose can be further dehydrated to 5-HMF.

/pdf/decomposition-of-cellulose-in-an-ionic-liquid-1-ethyl-3-3uuuiv2lit.pdf

Decomposition of cellulose in an ionic liquid, 1-ethyl-3-methylimidazolium chloride

The detailed reaction behavior of cellulose in an ionic liquid, 1-ethyl-3-methylimidazolium chloride ([C2mim][Cl]), was investigated. Glucose is a component of cellulose; its oligomerization was studied during treatment with [C2mim][Cl] at around 100 °C. Glucose was polymerized to produce oligosaccharides such as disaccharides and trisaccharides. These oligosaccharides, however, disappeared upon prolonging the treatment time. Maltose, nigerose, kojibiose, laminaribiose, isomaltose, and gentiobiose were identified by gas chromatograph–mass spectrometer in the disaccharides produced. The yield of these disaccharides increased as the initial concentration of glucose in [C2mim][Cl] increased. [C2mim][Cl], therefore, is a reagent capable of producing various oligosaccharides from glucose in the absence of a catalyst.

https://link.springer.com/content/pdf/10.1007%2Fs10086-014-1453-8.pdf

Production of disaccharides from glucose by treatment with an ionic liquid, 1-ethyl-3-methylimidozolium chloride

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Decomposition of cellulose in an ionic liquid, 1-ethyl-3-methylimidazolium chloride

Production of disaccharides from glucose by treatment with an ionic liquid, 1-ethyl-3-methylimidozolium chloride