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Acidic and basic amino acid-based novel deep eutectic solvents and their role in depolymerization of lignin

化学 解聚 共晶体系 氨基酸 木质素 深共晶溶剂 有机化学 生物化学 合金
作者
Md Sajjadur Rahman,Ranen Roy,Cynthia E. Montoya-Martínez,Mohammad A. Halim,Douglas E. Raynie
出处
期刊:Journal of Molecular Liquids [Elsevier]
卷期号:362: 119751-119751 被引量:23
标识
DOI:10.1016/j.molliq.2022.119751
摘要

• Amino acid-based deep eutectic solvents (AADESs) are newer and promising DESs with a wide range of applications. • Two novel AADESs were formulated using basic, L-(+) arginine (Arg), and acidic, L-glutamic acid (Glu) with glycerol (Gly). • Detailed interactions among the constituents were investigated using thermal, spectroscopic, and spectrometric methods. • Principal component analysis (PCA) also helped to visualize the spectroscopic outcomes. • A preliminary study was conducted to explore depolymerization of lignin using these newly obtained DESs. Amino acid-based deep eutectic solvents (AADESs) are emerging type of DESs with a wide range of applications. In this study, two novel AADESs were formulated using basic, L-(+) arginine (Arg), and acidic, L-glutamic acid (Glu), amino acids as hydrogen bond acceptors (HBA) and glycerol (Gly) as the hydrogen bond donor (HBD) at a 1:3 M ratio. The eutectic points of the formulated AADESs were found to be −0.14 °C for Glu-Gly and −1.36 °C for Arg-Gly. The successful interactions among the constituents were investigated using FT-IR, 1 H NMR spectroscopy, and mass spectrometry. These studies found that Glu-Gly could form ester impurities. However, the mass spectrometry showed that the impurities are negligible. The TGA revealed that both DESs could be applied up to 150–160 °C without losing weight, while Glu-Gly could be used up to 200 °C. Formation of Arg-Gly was strongly dominated by glycerol, while Glu-Gly DES was formed by an equal contribution of both components. Principal component analysis (PCA) helped to visualize the spectroscopic outcomes. Since AADESs are excellent pretreatment media for biomass, lignin was treated as a model biomass in this study with the formulated AADESs to determine their reaction products. It was found that Arg-Gly can isolate only one monomeric compound (4-methyl benzaldehyde), while Glu-Gly can isolate three monomeric compounds. Oxidative depolymerization of the lignin residues validated the outcomes obtained from the AADES-lignin reactions. Glu-Gly was more efficient for lignin depolymerization because of its smaller viscosity, higher stability, acidic environment, and stronger hydrogen bond formation between lignin and glycerol.
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