Homogeneous modification of sugarcane bagasse with maleic anhydride in 1-butyl-3-methylimidazolium chloride without any catalysts

Chen, Mingjie; Chen, Chaoyi; Liu, Chuanfu; Sun, Run‐Cang

doi:10.1016/j.indcrop.2013.02.023

Cited by 36 publications

(40 citation statements)

References 47 publications

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“…These noticeable changes in the absorption bands indicate that butyryl groups were grafted onto the LS, and that the butyration reaction of LS occurred in the butyric anhydride-choline chloride solvent under the given reaction conditions. As expected, the absence of an absorption region between 1840 and 1760 cm -1 in spectra 2b and 2c confirm that the products were free of unreacted butyric anhydride (Chen et al 2012). The lack of a peak representing a carboxylic group at 1700 cm -1 in the spectra of the butyrated products indicates that the LS esters did not contain butyric acid byproducts.…”

Section: Analysessupporting

confidence: 76%

Butyration of Lignosulfonate with Butyric Anhydride in the Presence of Choline Chloride

Cheng

2015

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A novel process was developed for the butyration of lignosulfonate (LS) with butyric anhydride in the presence of choline chloride at elevated temperatures. The degree of substitution (DS) was qualitatively and quantitatively determined by Fourier transform infrared spectroscopy using the baseline method. It was found that the DS of butyrated LS products increased from 0 to the range of 0.41 to 2.14 with the addition of choline chloride, indicating that butyric anhydride-choline chloride is a novel and highly effective solvent for the butyration of LS. The DS of butyrated LS was dependent on choline chloride dosage, reaction temperature, reaction time, and the mass ratio of butyric anhydride to LS. Characterization results by proton nuclear magnetic resonance spectroscopy further demonstrated the occurrence of the butyration reaction. The results of thermogravimetric analysis showed that the thermal stability of the butyrated LS decreased with increasing degree of substitution.

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Section: Analysessupporting

confidence: 76%

Butyration of Lignosulfonate with Butyric Anhydride in the Presence of Choline Chloride

Cheng

2015

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“…In previous studies, ionic liquids were used as excellent solvents for the homogeneous modification of sugarcane bagasse with maleic anhydride, and the WPG was controlled by stoichiometric methods (Chen et al 2013). The carboxylic groups would further react with the O-H groups, resulting in diesters when the temperature reached 100 °C (Matsuda 1987).…”

Section: Preparation Of the Sugarcane Bagasse Derivativesmentioning

confidence: 99%

“…This can be done via the substitution of the hydroxyl groups in the lignin, cellulose, and hemicellulose fractions. The esterification of sugarcane bagasse with cyclic anhydrides is a conventional method to prepare derivatives containing carboxyl groups (Gurgel et al 2008;Chen et al 2013). Thermoplasticization of the esterified sugarcane bagasse with cyclic anhydrides was demonstrated, and very compact self-adhesion esterified sugarcane bagasse composites was formed under hotpressing processing (Hassan et al 2000).…”

Section: Introductionmentioning

confidence: 99%

Thermal Stability of Sugarcane Bagasse Derivatives bearing Carboxyl Groups Synthesized in Ionic Liquid

2016

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To illuminate changes in the thermal stability of lignocellulosic biomass by homogeneous chemical modification in ionic liquids, sugarcane bagasse derivatives bearing carboxyl groups were prepared in ionic liquids. Fourier transform infrared (FT-IR) spectroscopy and solid-state nuclear magnetic resonance (NMR) confirmed the chemical structure of the derivatives. Sugarcane bagasse derivatives with degree of substituted OH as high as 9.93 mmol/g were achieved. The homogeneous esterification was demonstrated to be a more efficient approach than heterogeneous ones. Based on thermogravimetric analysis, the onset degradation temperature of sugarcane bagasse decreased dramatically to 185 °C, 160 °C and 140 °C, using succinic anhydride, maleic anhydride, and phthalic anhydride as reagent, respectively. A first-order degradation kinetic model was applied to obtain the degradation activation energies of sugarcane bagasse. The results showed that homogeneous chemical modification significantly decreased the thermal stability of sugarcane bagasse by reducing the onset degradation temperature and degradation activation energies.

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“…Due to the presence of considerable hydroxyls, the esterification of lignocellulose is easily accomplished, and esterified products can be used as fillers in composites (Paukszta et al 2015). The common esterification reagents conclude linear anhydrides, acyl chloride, cyclic anhydrides (Chen et al 2013;Yuan et al 2010), and so on. Particularly, the esterification of lignocellulose with cyclic anhydrides has received increased attention due to the several advantages, including producing no by-products (e.g.…”

Section: Introductionmentioning

confidence: 99%

“…For example, the esterification of bagasse cellulose with phthalic anhydride in ionic liquid 1-butyl-3-methylimidazium chloride was reported, and the crystallinity of the native cellulosic polymer was completely disrupted after the homogeneous modification (Liu et al 2007). It was also reported that the esterification of bagasse with maleic anhydride occurred in ionic liquid 1-butyl-3-methylimidazium chloride, and the thermal stability of maleated bagasse increased at high temperature (above 300 o C) (Chen et al 2013). Moreover, plastic films directly prepared from phthalated bagasse were reported recently .…”

Section: Introductionmentioning

confidence: 99%

Homogeneous Esterification Mechanism of Bagasse Modified with Phthalic Anhydride in Ionic Liquid, Part 3: Structural Transformation of Lignins

et al. 2017

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The phthalation of bagasse was investigated comparatively with the three main isolated components in 1-allyl-3-methylidazium chloride (AmimCl) to reveal the reaction behavior of bagasse. In the first two parts, the detailed changes of cellulosic and hemicellulosic components in bagasse were elucidated during phthalation. In Part 3, the phthalation of lignins was performed in AmimCl with various ratios of phthalic anhydride/lignins from 10 to 50 mmol/g. The phthalation degree ranged from 41.1% to 68.8% for the phthalated lignins. The aliphatic hydroxyls of lignins were more easily phthalated than the phenolic hydroxyls as revealed by 31 P nuclear magnetic resonance (NMR) analysis. Fourier transform infrared spectroscopy (FT-IR) and two dimensional (2D) heteronuclear single quantum correlation (HSQC) confirmed the attachment of phthaloyl group onto lignins. Severe degradation of lignin macromolecules was found at high ratios of phthalic anhydride/lignins (30 to 50 mmol/g) by gel permeation chromatography (GPC) analysis. These results provide a detailed understanding of reaction behaviors of lignins during bagasse phthalation, which are beneficial to prepare composites based on phthalated lignocellulose with better properties.

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Homogeneous modification of sugarcane bagasse with maleic anhydride in 1-butyl-3-methylimidazolium chloride without any catalysts

Cited by 36 publications

References 47 publications

Butyration of Lignosulfonate with Butyric Anhydride in the Presence of Choline Chloride

Butyration of Lignosulfonate with Butyric Anhydride in the Presence of Choline Chloride

Thermal Stability of Sugarcane Bagasse Derivatives bearing Carboxyl Groups Synthesized in Ionic Liquid

Homogeneous Esterification Mechanism of Bagasse Modified with Phthalic Anhydride in Ionic Liquid, Part 3: Structural Transformation of Lignins

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