Effect of anion in carboxylate-based ionic liquids on catalytic activity of transesterification with vinyl esters and the solubility of cellulose

Hirose, Daisuke; Kusuma, Samuel Budi Wardhana; Nomura, Seiichi; Yamaguchi, Makoto; Yasaka, Yoshiro; Kakuchi, Ryohei; Takahashi, Kenji

doi:10.1039/c8ra10042j

Cited by 26 publications

(27 citation statements)

References 41 publications

(27 reference statements)

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“…The introduction of acetate groups via an undesired side reaction during the esterification of cellulose in EmimOAc using acyl chloride and vinyl esters has previously been reported. 28,37,38 Subsequently, the degree of substitution (DS) of the resulting product was determined. In order to enhance its solubility in acetone-d 6 and avoid overlap of sample and solvent peaks, the obtained cellulose ester was completely acetylated with acetic acid and condensation reagent.…”

Section: Resultsmentioning

confidence: 99%

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Direct one-step synthesis of a formally fully bio-based polymer from cellulose and cinnamon flavor

et al. 2019

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Section: Resultsmentioning

confidence: 99%

“…4, left). 38 To avoid the undesired introduction of acetate anions to the cellulose ester, the reaction was carried out using Emim phenylpropionate (EmimPPA) (Fig. 3), in which the anion corresponds to the cellulose phenylpropionate structure.…”

Section: Resultsmentioning

confidence: 99%

Direct one-step synthesis of a formally fully bio-based polymer from cellulose and cinnamon flavor

et al. 2019

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“…The ionic liquids 1-ethyl-3-methylimidazolium benzoate ([EMIm][OBz]) and 1-ethyl-3-methylimidazolium salicylate ([EMIm][OSc]) were synthesized from 1-ethyl-3-methylimidazolium chloride ([EMIm][Cl]) [ 23 , 61 ]. At first, [EMIm][Cl] (20.46 mmol) was dissolved in 10 mL methanol and added to a solution of silver benzoate (20.46 mmol) in 10 mL methanol.…”

Section: Methodsmentioning

confidence: 99%

Dissolving Cellulose in 1,2,3-Triazolium- and Imidazolium-Based Ionic Liquids with Aromatic Anions

et al. 2020

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We present 1,2,3-triazolium- and imidazolium-based ionic liquids (ILs) with aromatic anions as a new class of cellulose solvents. The two anions in our study, benzoate and salicylate, possess a lower basicity when compared to acetate and therefore should lead to a lower amount of N-heterocyclic carbenes (NHCs) in the ILs. We characterize their physicochemical properties and find that all of them are liquids at room temperature. By applying force field molecular dynamics (MD) simulations, we investigate the structure and dynamics of the liquids and find strong and long-lived hydrogen bonds, as well as significant π–π stacking between the aromatic anion and cation. Our ILs dissolve up to 8.5 wt.-% cellulose. Via NMR spectroscopy of the solution, we rule out chain degradation or derivatization, even after several weeks at elevated temperature. Based on our MD simulations, we estimate the enthalpy of solvation and derive a simple model for semi-quantitative prediction of cellulose solubility in ILs. With the help of Sankey diagrams, we illustrate the hydrogen bond network topology of the solutions, which is characterized by competing hydrogen bond donors and acceptors. The hydrogen bonds between cellulose and the anions possess average lifetimes in the nanosecond range, which is longer than found in common pure ILs.

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“…Hirose and co-workers [ 47 ] proposed a transesterification reaction based on vinyl ester when studying the esterification reaction of cellulose. Compared with traditional esterification of anhydride or acyl chloride, ethylene ester-based esterification is a mild acid-free reaction.…”

Section: Modification Of Hemicellulosementioning

confidence: 99%

Hemicellulose-Based Film: Potential Green Films for Food Packaging

et al. 2020

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Globally increasing environmental awareness and the possibility of increasing price and dwindling supply of traditional petroleum-based plastics have led to a breadth of research currently addressing environmentally friendly bioplastics as an alternative solution. In this context, hemicellulose, as the second richest polysaccharide, has attracted extensive attention due to its combination of such advantages as abundance, biodegradability, and renewability. Herein, in this review, the latest research progress in development of hemicellulose film with regard to application in the field of food packaging is presented with particular emphasis on various physical and chemical modification approaches aimed at performance improvement, primarily for enhancement of mechanical, barrier properties, and hydrophobicity that are essential to food packing materials. The development highlights of hemicellulose film substrate are outlined and research prospects in the field are described.

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Effect of anion in carboxylate-based ionic liquids on catalytic activity of transesterification with vinyl esters and the solubility of cellulose

Abstract: The role of 1-ethyl-3-methylimidazolium carboxylate-type ionic liquid as the solvent and organocatalyst for transesterification reaction of cellulose was investigated.

Cited by 26 publications

References 41 publications

Direct one-step synthesis of a formally fully bio-based polymer from cellulose and cinnamon flavor

Direct one-step synthesis of a formally fully bio-based polymer from cellulose and cinnamon flavor

Dissolving Cellulose in 1,2,3-Triazolium- and Imidazolium-Based Ionic Liquids with Aromatic Anions

Hemicellulose-Based Film: Potential Green Films for Food Packaging

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