Trimethylsilylation of Cellulose in Ionic Liquids

Mörmann, Werner; Wezstein, Markus

doi:10.1002/mabi.200800192

Cited by 34 publications

(34 citation statements)

References 23 publications

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“…It has been reported [196] that carboxylate and diethylphosphate counter-ions give better results than chloride. Furthermore, the solubility of HMDS in the IL increases with the increasing extent of CH x groups in the anion.…”

Section: Etherificationmentioning

confidence: 99%

Ionic Liquid as Reaction Media for the Production of Cellulose-Derived Polymers from Cellulosic Biomass

et al. 2017

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Abstract:The most frequent polymer on nature is cellulose that is present together with lignin and hemicellulose in vegetal biomass. Cellulose can be, in the future, sustainable raw matter for chemicals, fuels, and materials. Nevertheless, only 0.3% of cellulose is processed nowadays due to the difficulty in dissolving it, and only a small proportion is used for the production of synthetic cellulosic fibers especially esters and other cellulose derivatives, normally in extremely polluting processes. The efficient and clean dissolution of cellulose is a major objective in cellulose research and development. Ionic liquids (ILs) are considered "green" solvents due to their low vapor pressure, that prevents them evaporating into the atmosphere. In addition, these molten salts present advantages in process intensification, leading to more than 70 patents in lignocellulosic biomass in ILs being published since 2005, most of them related to the production of cellulose derived polymers, e.g., acetates, benzoylates, sulfates, fuorates, phthalates, succinates, tritylates, or silylates. In this work, the use of ILs for production of cellulose derived polymers is thoroughly studied. To do so, in the first place, a brief summary of the state of the art in cellulose derivatives production is presented, as well as the main features of ILs in cellulose processing applications. Later, the main results in the production of cellulose derivatives using ILs are presented, followed by an analysis of the industrial viability of the process, considering aspects such as environmental concerns and ILs' recyclability.

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Section: Etherificationmentioning

confidence: 99%

Ionic Liquid as Reaction Media for the Production of Cellulose-Derived Polymers from Cellulosic Biomass

et al. 2017

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“…A vast range of material properties can be accessed with cellulose derivatives by varying the chemical substituents attached to the polysaccharide backbone and their degree of substitution (DS). To cite just one example, solubility can range from hydrocarbon-soluble (trimethylsilylcellulose) (Mormann and Wezstein 2009), to water-soluble (e.g., cellulose monoacetate) (Buchanan et al 1991a, b;Heinze et al 2006), depending primarily on the type and number of substituents. Cellulose derivatives in general also have unique properties that may be highly beneficial for certain applications, for example high biocompatibility for biomedical applications (Edgar 2007;Liebert et al 2009), good clarity for optical films (Edgar et al 2001;Sata et al 2004), and chirality for the separation of enantiomers (Okamoto 2009;Katoh et al 2011).…”

Section: Introductionmentioning

confidence: 98%

Synthesis of regioselectively brominated cellulose esters and 6-cyano-6-deoxycellulose esters

Fox

Edgar

2011

Cellulose

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The control of regiochemistry in the synthesis of polysaccharide derivatives is one of the most significant scientific challenges in the field. Its importance is only further highlighted by the individual successes in synthesis of regioselectively substituted derivatives, in particular cellulose esters and ethers, over the last 20 years. The availability of these samples and studies of their properties versus randomly substituted analogs has shown clearly that properties like solubility, aggregation phenomena, and optical properties depend heavily on the regiochemistry of substitution. We report here on the onepot synthesis of novel 6-bromo-6-deoxy-2,3-O-acylcellulose derivatives, which as more organic soluble derivatives of 6-bromo-6-deoxycellulose should allow broader exploitation of the highly regioselective cellulose 6-bromination chemistry. We illustrate the potential of these new derivatives by conversion to 6-cyano-6-deoxycellulose esters.Keywords Cellulose ester Á Regioselective synthesis Á 6-Bromo-6-deoxycellulose Á 6-Cyano-6-deoxycellulose Á Polysaccharide derivative

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“…MIM directly facilitates certain reactions and may be successfully used as a cosolvent or additive in derivatization [21,27]. In fact, it has been shown that MIM, which is a precursor for many imidazolium-based ILs, is quite necessary for some reactions to take place at all [28].…”

Section: Introductionmentioning

confidence: 99%

Effect of methylimidazole on cellulose/ionic liquid solutions and regenerated material therefrom

et al. 2014

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Cellulose, especially wood-based cellulose, is increasingly important for making everyday materials such as man-made-regenerated textile fibers, produced via dissolution and subsequent precipitation. In this paper, the effect of cosolvents in ionic liquid-facilitated cellulose dissolution is discussed. Both microcrystalline cellulose and dissolving grade hardwood pulp were studied. Three different cosolvents in combination with ionic liquid were evaluated using turbidity measurements and viscosity. The ionic liquid precursor N-methylimidazole proved to be a promising cosolvent candidate and was thus selected for further studies together with the ionic liquid 1-ethyl-3-methylimidazolium acetate. Results show that dissolution rate can be increased by cosolvent addition, and the viscosity can be significantly reduced. The solutions were stable over time at room temperature and could be converted to regenerated textile fibers with good mechanical properties via airgap spinning and traditional wet spinning.Fibers spun from binary solvents exhibited significantly higher crystallinity than the fibers from neat ionic liquid.

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Trimethylsilylation of Cellulose in Ionic Liquids

Cited by 34 publications

References 23 publications

Ionic Liquid as Reaction Media for the Production of Cellulose-Derived Polymers from Cellulosic Biomass

Ionic Liquid as Reaction Media for the Production of Cellulose-Derived Polymers from Cellulosic Biomass

Synthesis of regioselectively brominated cellulose esters and 6-cyano-6-deoxycellulose esters

Effect of methylimidazole on cellulose/ionic liquid solutions and regenerated material therefrom

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