Reflections on the Solubility of Cellulose

Pinkert, André; Marsh, Kenneth N.; Pang, Shusheng

doi:10.1021/ie1006596

Cited by 197 publications

(162 citation statements)

References 62 publications

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“…The essence of cellulose dissolving was the breaking of hydrogen bonds in the supramolecular structure. Based on the "electro donor-electron acceptor" mechanism (Pinkert et al 2010;Liu et al 2011), the accessibility of hydrogen bonds for a solvent is positively related to its dissolving ability. Therefore, the hydrogen bond basicity (β) of ChCl-DESs controls the solubility of cellulose compared to the dipolarity/polarizability effects (π*).…”

Section: Properties Of Chcl-dess Thermostability Of Chcl-dessmentioning

confidence: 99%

The Properties of Choline Chloride-based Deep Eutectic Solvents and their Performance in the Dissolution of Cellulose

et al. 2016

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A series of choline chloride-based deep eutectic solvents (ChCl-DESs) were synthesized and characterized, and their performance in the dissolution of cellulose was investigated. The hydrogen-bond donors significantly (β-value) affected the properties of ChCl-DESs, causing differentiated dissolution performances. ChCl-imidazole (Im) showed the highest Hammett acidity function (1.869), hydrogen bond basicity (0.864), and dipolarity/polarizability effect (0.382) among the ChCl-DESs. The ChCl-Im showed the lowest pseudo-activation energy for viscous flow (31.76 kJ mol -1 ) among the ChCl-DESs. The properties of ChCl-Im caused the highest solubility of cellulose (2.48 wt.%) relative to the other ChClDESs. Polyethylene glycol (PEG), as a co-solvent, significantly (β-value) enhanced the accessibility of ChCl-Im to cellulose by breaking the supramolecular structure of cellulose, promoting its dissolution. The decrystallization of ChCl-Im-coupled PEG approximately doubled the dissolving capabilities, and the solubility increased by more than 80% in comparison with only ChCl-Im. The cellulose was directly dissolved by ChCl-Im-coupled PEG, and no other derivatives were produced.

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Section: Properties Of Chcl-dess Thermostability Of Chcl-dessmentioning

confidence: 99%

The Properties of Choline Chloride-based Deep Eutectic Solvents and their Performance in the Dissolution of Cellulose

et al. 2016

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“…Electron donor-acceptor (EDA) theory could explain this phenomenon. N-methyl imidazolium cation and dimethyl phosphate anion of the ionic liquid [Mmim]DMP, respectively, as electron acceptor and electron donor centers, interacted with H and O atoms of cellulosic -OH to produce EDA complexes (Pinkert et al 2010;Gupta and Jiang 2015;Zhang et al 2015). They led to hydrogen bond fracture between cellulosic macromolecules, which deteriorated crystalline regularity.…”

Section: Plm Observation Of Wood Powder Microwave Dissolving Processmentioning

confidence: 99%

Dissolution of Eucalyptus Powder with Alkaline Ionic Liquid [Mmim]DMP under Microwave Conditions

Chen

et al. 2016

BioResources

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An orthogonal design was used to study three factors-melting temperature, time, and solid-liquid ratio-and how they affected the dissolution rate of eucalyptus powder. The optimum solution conditions were 170 °C, 20 min, and a solid-liquid ratio of 1:25. Composition analysis of the residue indicated that, in the dissolving process, acidinsoluble lignin was converted into acid-soluble lignin, and a part of the lignin was degraded or modified. After dissolution, the crystalline structure of cellulose deteriorated, the relative crystallinity decreased, and the crystal form changed from type I into amorphous. Wood powder degradation occurred during dissolution, and a higher dissolution rate led to greater degradation. In a low-temperature environment below 225 °C, the residue thermal stability decreased slightly with increasing dissolution rates, but it greatly improved in a high-temperature environment of 225 to 600 °C. Keywords INTRODUCTIONLignocellulose is the most abundant renewable resource on the planet. Its main components of cellulose, hemicellulose, and lignin are important chemical raw materials (Zhang 2008;King et al. 2009;Kuo and Lee 2009;Zhang et al. 2009). However, due to the complex structure of lignocellulosic cell wall, its components are difficult to separate, which is a great obstacle in using lignocellulose (Chen and Kuo 2010). Traditional separation methods are cooking with inorganic acid or alkali and extraction with organic solvents. These methods not only change lignocellulosic structure but also have the problems of high cost and serious pollution. Ionic liquids are green solvents with low vapor pressure, adjustable nature, good solubility, and high thermal stability (Rehman and Zeng 2012;Lozano et al. 2014;Findrik et al. 2016), and they have broad application prospects in the dissolution and separation of lignocellulose (Cole et al. 2002;Fang et al. 2006;Ren et al. 2013).Previous literature includes studies of the dissolution of a single component with ionic liquids. Some alkyl-substituted imidazolium ionic liquids effectively dissolve cellulose (Swatloski et al. 2002) (Pu et al. 2007). However, because of the complicated structure of lignocellulose, the dissolution rate of whole components with ionic liquids is not high. In a study on the dissolution of Masson pine, PEER-REVIEWED ARTICLE bioresources.com Chen et al. (2016). "Dissolving eucalyptus in ionic liquid," BioResources 11(4), 9710-9722. 9711 poplar, eucalyptus, and oak in the [C4mim]Cl/DMSO solvent system, non-pretreated lignocellulose heated to 100 °C for 24 h could be partially dissolved (Fort et al. 2007). The low dissolution rate of all components is an urgent problem hindering the use of biomass resources.To promote the application of ionic liquids in biomass materials and improve the dissolution rate of whole components, the present work involves an orthogonal design for the lignocellulosic dissolution factors of melting temperature, time, and solid-liquid ratio under microwave conditions, and the optimized solution scheme w...

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“…However, other opinions exist about how ionic liquids are dissolving cellulose. In essence, it was proposed that small ions capable of hydrogen bonding as well as the delocalization ability of the positive charge within the cation of ionic liquids can assist in the dissolution process [69]. In a recent publication [70], hydrogen-bonding basic media (ionic liquids) were observed to break intra-and intermolecular hydrogen bonds in crystalline cellulose.…”

Section: Synthesis Of 5-hydroxymethylfurfural From Lignocellulosic Mamentioning

confidence: 99%

The Challenge of Efficient Synthesis of Biofuels from Lignocellulose for Future Renewable Transportation Fuels

Mäki‐Arvela

Salminen

Riittonen

et al. 2012

International Journal of Chemical Engineering

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Dehydration of sugars to 5-hydroxymethylfurfural (HMF) has recently been under intensive study by a multitude of research groups. On the other hand, when lignocellulosic biomass is applied as the starting material, very few studies can be found in the open literature. The direct synthesis of HMF, in line with the idea of “one-pot” synthesis strategy from lignocellulose, is demanding since the overall process should encompass dissolution, hydrolysis, and dehydration steps in a single processing unit. Ionic liquid-assisted methods to produce hydroxymethyl-furfural directly from lignocellulosic biomass are reported here together with a short overview of the most important biofuels. In reality, HMF is not suitable to be used as a single-component fuel as such, and, consequently, methods to produce HMF derivatives suitable as liquid fuels are reported.

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Reflections on the Solubility of Cellulose

Cited by 197 publications

References 62 publications

The Properties of Choline Chloride-based Deep Eutectic Solvents and their Performance in the Dissolution of Cellulose

The Properties of Choline Chloride-based Deep Eutectic Solvents and their Performance in the Dissolution of Cellulose

Dissolution of Eucalyptus Powder with Alkaline Ionic Liquid [Mmim]DMP under Microwave Conditions

The Challenge of Efficient Synthesis of Biofuels from Lignocellulose for Future Renewable Transportation Fuels

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