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Oxidative cleavage of C-C bonds in lignin.

Elena SubbotinaThanya RukkijakanM Dolores Marquez-MedinaXiaowen YuMats JohnssonJoseph S M Samec
Published in: Nature chemistry (2021)
Lignin is an aromatic polymer that constitutes up to 30 wt% of woody biomass and is considered the largest source of renewable aromatics. Valorization of the lignin stream is pivotal for making biorefining sustainable. Monomeric units in lignin are bound via C-O and C-C bonds. The majority of existing methods for the production of valuable compounds from lignin are based on the depolymerization of lignin via cleavage of relatively labile C-O bonds within lignin structure, which leads to yields of only 36-40 wt%. The remaining fraction (60 wt%) is a complex mixture of high-molecular-weight lignin, generally left unvalorized. Here we present a method to produce additional valuable monomers from the high-molecular-weight lignin fraction through oxidative C-C bond cleavage. This oxidation reaction proceeds with a high selectivity to give 2,6-dimethoxybenzoquinone (DMBQ) from high-molecular-weight lignin in 18 wt% yield, thus increasing the yield of monomers by 32%. This is an important step to make biorefining competitive with petroleum-based refineries.
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