Dissolution of cellulose in the mixed solvent of [bmim]Cl–DMAc and its application

Lin, Lianzhen; Yamaguchi, Hideki; Suzuki, Ayami

doi:10.1039/c3ra41299g

Cited by 26 publications

(10 citation statements)

References 14 publications

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“…In this regard, the accessibility of succinic anhydride to the hydroxyl groups on dissolved cellulose would be improved as more cellulose dissolved and more hydroxyl groups were freed, resulting in an increase in the DS value of the modified cellulose. However, further increasing the dosage of TBAA also increased the viscosity of the mixed solvent, which negatively affected the mass transfer of the reaction system and inhibited the succinoylation reaction [ 42 , 43 ]. In addition, a high TBAA dosage in the mixed solvent could also bring a steric hindrance due to the relatively large cation structure of TBAA, which may prevent SA from attacking the hydroxyl groups on cellulose.…”

Section: Resultsmentioning

confidence: 99%

Modification of Cellulose with Succinic Anhydride in TBAA/DMSO Mixed Solvent under Catalyst-Free Conditions

et al. 2017

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Homogeneous modification of cellulose with succinic anhydride was performed using tetrabutylammonium acetate (TBAA)/dimethyl sulfoxide (DMSO) mixed solvent. The molar ratio of succinic anhydride (SA) to free hydroxyl groups in the anhydroglucose units (AGU), TBAA dosage, reaction temperature, and reaction time were investigated. The highest degree of substitution (DS) value of 1.191 was obtained in a 10 wt% TBAA/DMSO mixed solvent at 60 °C for 60 min, and the molar ratio of SA/AGU was 6/1. The molar ratio of SA/AGU and the TBAA dosage showed a significant influence on the reaction. The succinoylated cellulose was characterized by ATR-FTIR, TGA, XRD, solid state CP/MAS 13C NMR spectroscopy (CP/MAS 13C NMR), and SEM. Moreover, the modified cellulose was applied for the adsorption of Cu2+ and Cd2+, and both the DS values of modified cellulose and pH of the heavy metal ion solutions affected the adsorption capacity of succinylated cellulose. The highest capacity for Cu2+ and Cd2+ adsorption was 42.05 mg/g and 49.0 mg/g, respectively.

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Section: Resultsmentioning

confidence: 99%

Modification of Cellulose with Succinic Anhydride in TBAA/DMSO Mixed Solvent under Catalyst-Free Conditions

et al. 2017

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“…26 Previous studies have reported that the addition of a cosolvent to the imidazolium-based ILs can effectively reduce the viscosity of the mixed solvent, which can then facilitate the mobility of ions and increase their dissolution ability. 2,27 On the basis of the results described above, it can be speculated that the dissolution of cellulose in a TBAA/DMSO system is a synergic result from both TBAA and the cosolvent DMSO. Furthermore, the balance between the concentration of free ions and the mobility of the mixed solvent is crucial for the dissolving ability of the TBAA/DMSO system.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Room-Temperature Dissolution and Mechanistic Investigation of Cellulose in a Tetra-Butylammonium Acetate/Dimethyl Sulfoxide System

Huang

Xin

et al. 2016

ACS Sustainable Chem. Eng.

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The dissolution of cellulose in tetrabutylammonium acetate (TBAA) and dimethyl sulfoxide (DMSO) mixed solvent was studied at room temperature (approximately 25 °C). The ratio of TBAA in the mixed solvent system (W TBAA) was found to have great influence on the solubility of cellulose and the corresponding dissolution time. The mixed solvent of W TBAA = 0.15 possessed the highest cellulose solubility and shortest dissolution time. Various cellulosic materials were well-dissolved in the solvent with a maximum solubility up to 8.17 wt %. A mechanistic study regarding the interaction between the solvent system and the model compound cellobiose was conducted using 1H NMR, 13C NMR, ATR-FTIR, conductivity, and viscosity measurements. The results implied that TBAA existed at two different states in the mixed solvent as the ratio of TBAA varied (i.e., ion-split stage (W TBAA ≤ 0.15) and ion-paired stage (W TBAA ≥ 0.15)). W TBAA = 0.15 was the turning point of these two stages, and the mixed solvent displayed the best dissolving ability at this ratio. This finding suggests that a balance between the ion concentration and ion mobility is crucial to the dissolving ability of a mixed solvent. The solvation effect of the cosolvent DMSO helped to dissociate TBAA into free ions and facilitate the ion mobility. The hydroxyl protons of cellobiose were demonstrated to form strong hydrogen bonds with CH3COO–, which was key to the dissolution of cellulose. Finally, the interaction between cellobiose and DMSO in the TBAA/DMSO/cellobiose system was investigated and was demonstrated to be another important factor for the dissolution of cellulose by stabilizing the dissolved cellulose chain from further formation of inter- and intramolecular hydrogen bonds.

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“…In view of the existence of intermolecular and intramolecular hydrogen bonds in cellulose, the formation of highly crystalline supramolecular structures hinders its dissolution. Traditional techniques of dissolving cellulose include the use of copper ammonia, viscose solvents, inorganic acid solvents [4] and non-aqueous system solvents [5]. However, these solvents are unstable, toxic, and difficult to recycle, and therefore fail to satisfy the development requirements of the green chemical industry [6].…”

Section: Introductionmentioning

confidence: 99%

Study on the Dissolution Mechanism of Cellulose by ChCl-Based Deep Eutectic Solvents

et al. 2020

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Four deep eutectic solvents (DESs), namely, glycerol/chlorocholine (glycerol/ChCl), urea/ChCl, citric acid/ChCl, and oxalic acid/ChCl, were synthesized and their performance in the dissolution of cellulose was studied. The results showed that the melting point of the DESs varied with the proportion of the hydrogen bond donor material. The viscosity of the DESs changed considerably with the change in temperature; as the temperature increased, the viscosity decreased and the electrical conductivity increased. Oxalic acid/ChCl exhibited the best dissolution effects on cellulose. The microscopic morphology of cellulose was observed with a microscope. The solvent system effectively dissolved the cellulose, and the dissolution method of the oxalic acid/ChCl solvent on cellulose was preliminarily analyzed. The ChCl solvent formed new hydrogen bonds with the hydroxyl groups of the cellulose through its oxygen atom in the hydroxyl group and its nitrogen atom in the amino group. That is to say, after the deep eutectic melt formed an internal hydrogen bond, a large number of remaining ions formed a hydrogen bond with the hydroxyl groups of the cellulose, resulting in a great dissolution of the cellulose. Although the cellulose and regenerated cellulose had similar structures, the crystal form of cellulose changed from type I to type II.

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Dissolution of cellulose in the mixed solvent of [bmim]Cl–DMAc and its application

Cited by 26 publications

References 14 publications

Modification of Cellulose with Succinic Anhydride in TBAA/DMSO Mixed Solvent under Catalyst-Free Conditions

Modification of Cellulose with Succinic Anhydride in TBAA/DMSO Mixed Solvent under Catalyst-Free Conditions

Room-Temperature Dissolution and Mechanistic Investigation of Cellulose in a Tetra-Butylammonium Acetate/Dimethyl Sulfoxide System

Study on the Dissolution Mechanism of Cellulose by ChCl-Based Deep Eutectic Solvents

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