Nucleophilic Thiols Reductively Cleave Ether Linkages in Lignin Model Polymers and Lignin

ChemSusChem
Grace E KlingerEric L Hegg

Abstract

Lignin may serve as a renewable feedstock for the production of chemicals and fuels if mild, scalable processes for its depolymerization can be devised. The use of small organic thiols represents a bioinspired strategy to cleave the β-O-4 bond, the most common linkage in lignin. In the present study, synthetic β-O-4 linked polymers were treated with organic thiols, yielding up to 90 % cleaved monomer products. Lignin extracted from poplar was also treated with organic thiols resulting in molecular weight reductions as high as 65 % (Mn ) in oxidized lignin. Thiol-based cleavage of other lignin linkages was also explored in small-molecule model systems to uncover additional potential pathways by which thiols might depolymerize lignin. The success of thiol-mediated cleavage on model dimers, polymers, and biomass-derived lignin illustrates the potential utility of small redox-active molecules to penetrate complex polymer matrices for depolymerization and subsequent valorization of lignin into fuels and chemicals.

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Aug 17, 2019·ChemSusChem·Grace E KlingerEric L Hegg

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Citations

Jun 13, 2021·Advanced Materials·Xuejiao WuYe Wang
Nov 11, 2021·Physical Chemistry Chemical Physics : PCCP·Qi QiaoQing Shao

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Methods Mentioned

BETA
NMR

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