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Materials 2017, 10(8), 966; https://doi.org/10.3390/ma10080966

Esterification Mechanism of Bagasse Modified with Glutaric Anhydride in 1-Allyl-3-methylimidazolium Chloride

1
State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou 510640, China
2
Beijing Key Laboratory of Lignocellulosic Chemistry, Beijing Forestry University, Beijing 100083, China
*
Author to whom correspondence should be addressed.
Received: 28 June 2017 / Revised: 13 August 2017 / Accepted: 14 August 2017 / Published: 18 August 2017
(This article belongs to the Section Structure Analysis and Characterization)
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Abstract

The esterification of bagasse with glutaric anhydride could increase surface adhesion compatibility and the surface of derived polymers has the potential of immobilizing peptides or proteins for biomedical application. Due to its complicated components, the esterification mechanism of bagasse esterified with glutaric anhydride in ionic liquids has not been studied. In this paper, the homogenous esterification of bagasse with glutaric anhydride was comparatively investigated with the isolated cellulose, hemicelluloses, and lignin in 1-allyl-3-methylimidazolium chloride (AmimCl) to reveal the reaction mechanism. Fourier transform infrared (FT-IR) indicated that the three components (cellulose, hemicelluloses, and lignin) were all involved in the esterification. The percentage of substitution (PS) of bagasse was gradually improved with the increased dosage of glutaric anhydride (10–40 mmol/g), which was primarily attributed to the increased esterification of cellulose and hemicelluloses. However, the PS fluctuation of lignin led to a decrease in the PS of bagasse at high glutaric anhydride dosage (50 mmol/g). The esterification reactivity of bagasse components followed the order of lignin > hemicelluloses > cellulose. The esterification mechanism was proposed as a nucleophilic substitution reaction. Nuclear magnetic resonance (NMR) analysis indicated that lignin aliphatic hydroxyls were prior to be esterified, and primary hydroxyls were more reactive than secondary hydroxyls in cellulose and hemicelluloses. View Full-Text
Keywords: bagasse; ionic liquid; glutaric anhydride; esterification mechanism bagasse; ionic liquid; glutaric anhydride; esterification mechanism
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Wang, H.; Chen, W.; Zhang, X.; Liu, C.; Sun, R. Esterification Mechanism of Bagasse Modified with Glutaric Anhydride in 1-Allyl-3-methylimidazolium Chloride. Materials 2017, 10, 966.

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