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Behavior of oxygen-containing groups in grass lignin during dissolution in basic ionic liquids

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Abstract

Three basic ionic liquids(BILs), 1-amyl-3methylimidazolium acetate (C5mim][Ac]), 1-butyl-3methylimidazolium acetate ([Bmim][Ac]) and 1-ethyl-3-methylimidazolium acetate ([Emim][Ac]), have been applied for the dissolution of lignin from wheat grass under microwave conditions with the decreased alkalinity order of [Emim][Ac]>[Bmim][Ac]>[C5mim][Ac]. Also the behavior of oxygen-containing groups within lignin in the dissolution of ionic liquids was investigated by elemental analysis, analytical pyrolysis, 2D-HSQC spectra, GPC, TG and FTIR analysis. Results revealed that [Emim][Ac] showed a higher dissolution capacity (≥ 330 g/kg) at 80°C within 30 min under microwave condition with higher alkalinity. In the process of dissolution, ionic liquids mainly attack the oxygen-containing groups and the aryl ether bond in the lignin side chain. The methoxy content reduction, the cleavage of β-O-4’ linkages and the degradation of β–β linkages obviously happened in the dissolution process, resulting in the decrease of the molecular weights. Ionic liquids treatment selectively degraded the G-type lignin fragments with demethoxylation and dehydration reactions occurring during dissolution. The results also indicate that the shorter the alkyl chain of the ionic liquids, the stronger the alkalinity is, the more destructive the oxygen-containing groups in the lignin side chain.

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Acknowledgments

The authors are grateful for the support of the National key R & D project of China (Grant number 2017YFB0307901) and National Natural Science Foundation of China (Grant number 21476091). The authors also appreciate the financial support from the Science and Technology Planning Project of Guangdong Province (Grant number 2015A020215009) and the Science and Technology Planning Project of FoShan in Guangdong Province (Grant number 2015AG10011).

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Authors and Affiliations

  1. State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou, 510640, China

    Chao Liu, Youming Li & Yi Hou

  2. National Engineering Research Center of Papermaking and Pollution Control, South China University of Technology, Guangzhou, 510640, China

    Chao Liu, Youming Li & Yi Hou

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  1. Chao Liu
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  2. Youming Li
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  3. Yi Hou
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Correspondence to Yi Hou.

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Liu, C., Li, Y. & Hou, Y. Behavior of oxygen-containing groups in grass lignin during dissolution in basic ionic liquids. Cellulose 26, 737–749 (2019). https://doi.org/10.1007/s10570-018-2097-4

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