Tosylation and acylation of cellulose in 1-allyl-3-methylimidazolium chloride

Granström, Mari; Kavakka, Jari; King, Alistair W. T.; Majoinen, Johanna; Mäkelä, Valtteri; Helaja, Juho; Hietala, Sami; Virtanen, Tommi; Maunu, Sirkka Liisa; Argyropoulos, Dimitris S.; Kilpeläinen, Ilkka

doi:10.1007/s10570-008-9197-5

Cited by 83 publications

(69 citation statements)

References 32 publications

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“…Homogeneous reaction yielding tosylated cellulose can be carried out in [Amim]Cl, and aspects such as the degree of tosylation, the reaction temperature and the base can be varied, e.g., trimethylamine is not fully mixed with [Amim]Cl, however, pyridine works efficiently [172]. The homogeneous reaction produces a predominant conversion of primary hydroxyl groups at DS values up to 1 [173,174].…”

Section: Esterificationmentioning

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: Esterificationmentioning

confidence: 99%

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

et al. 2017

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“…Several methods have been developed to prepare LCCEs. These methods involved heterogeneous acylation by using acyl chloride, acid chlorides under vacuum or aliphatic acids with trifluoroacetic acid [3], and homogeneous acylation in DMAc/LiCl [4][5][6] or in ionic liquids [7,8]. Studies have shown that the maximum degree of substitution (DS) of LCCEs synthesized in ionic liquid system was up to approximately 2.0.…”

Section: Introductionmentioning

confidence: 99%

Thermal Properties and Thermal Degradation of Cellulose Tri-Stearate (CTs)

Huang

2012

Polymers

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Cellulose tri-stearate (CTs) was synthesized employing trifluoroacetic anhydride (TFAA), stearic acid (SA), with microcrystal cellulose (MCC) and characterized with FT-IR and 1 H-NMR. The degree of substitution of CTs was determined by the traditional saponification method and 1 H-NMR. The thermal properties of CTs were investigated by the thermogravimetric analysis (TGA) under Ar flow in dynamic heating conditions. Thermal stability, activation energy, as well as the degradation mechanism of the decomposition process were revealed. The results showed that the thermal stability of CTs is superior to that of raw materials-MCC, and that the degradation of CTs in argon is a first-order weight loss; the initial decomposition temperature and the temperature corresponding to maximum degradation rate (T p ) increase with an increase in heating rate. The activation energy values were calculated with the Ozawa method, Coats-Redfern method and Kinssinger method, respectively. Analyses of experimental results suggest that the degradation mechanism 0.10 < α < 0.80 is F2 type, A3 for α < 0.1, and R3 for α > 0.80. The degradation mechanism of CTs in the whole conversion range is a complex mechanism, and is the combination of A3, F2 and R3.

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“…Acylation of cellulose with linear chain acylation reagents such as anhydride or chloride is the most common method to produce cellulosic bioproducts. Because of the wide application of cellulose acetate, cellulose acetylation with acetic anhydride or acetyl chloride in ILs has been extensively studied, and cellulose acetates with high degree of substitution (DS) were easily prepared (Wu et al, 2004;Abbott et al, 2005;Heinze et al, 2005;Barthel & Heinze, 2006;Granstrom et al, 2008). Furthermore, ILs were also be reported as reaction media for cellulose modification with other liquid reagents, such as carbanilation with phenyl isocyanate (Barthel & Heinze, 2006;Schlufter et al, 2006), acylation with lauroyl chloride (Barthel & Heinze, 2006), and perpropionylation with propionic anhydride (Schlufter et al, 2006).…”

Section: Introductionmentioning

confidence: 99%