Catalytic carbon–carbon bond cleavage in lignin via manganese–zirconium-mediated autoxidation

Palumbo, Chad T.; Gu, Nina X.; Bleem, Alissa C.; Sullivan, Kevin P.; Katahira, Rui; Stanley, Lisa M.; Kenny, Jacob K.; Ingraham, Morgan A.; Ramirez, Kelsey J.; Haugen, Stefan J.; Amendola, Caroline R.; Stahl, Shannon S.; Beckham, Gregg T.

doi:10.1038/s41467-024-45038-z

Title: Catalytic carbon–carbon bond cleavage in lignin via manganese–zirconium-mediated autoxidation

Journal Article · 28 January 2024 · Nature Communications

DOI: https://doi.org/10.1038/s41467-024-45038-z · OSTI ID:2283106

Palumbo, Chad T.; Gu, Nina X.; Bleem, Alissa C.; Sullivan, Kevin P.; Katahira, Rui; Stanley, Lisa M.; Kenny, Jacob K.;

;

; Haugen, Stefan J.; Amendola, Caroline R.;

;

Abstract Efforts to produce aromatic monomers through catalytic lignin depolymerization have historically focused on aryl–ether bond cleavage. A large fraction of aromatic monomers in lignin, however, are linked by various carbon–carbon (C–C) bonds that are more challenging to cleave and limit the yields of aromatic monomers from lignin depolymerization. Here, we report a catalytic autoxidation method to cleave C–C bonds in lignin-derived dimers and oligomers from pine and poplar. The method uses manganese and zirconium salts as catalysts in acetic acid and produces aromatic carboxylic acids as primary products. The mixtures of the oxygenated monomers are efficiently converted to cis,cis -muconic acid in an engineered strain of Pseudomonas putida KT2440 that conducts aromatic O -demethylation reactions at the 4-position. This work demonstrates that autoxidation of lignin with Mn and Zr offers a catalytic strategy to increase the yield of valuable aromatic monomers from lignin.

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Research Organization:: National Renewable Energy Laboratory (NREL), Golden, CO (United States); Univ. of Wisconsin, Madison, WI (United States)

Sponsoring Organization:: USDOE; USDOE Office of Energy Efficiency and Renewable Energy (EERE); USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Biological and Environmental Research (BER)

Grant/Contract Number:: AC36-08GO28308; FG02-05ER15690

OSTI ID:: 2283106

Report Number(s):: NREL/JA-2A00-85269; 862; PII: 45038

Journal Information:: Nature Communications, Journal Name: Nature Communications Journal Issue: 1 Vol. 15; ISSN 2041-1723

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United Kingdom

Language:: English

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Title: Catalytic carbon–carbon bond cleavage in lignin via manganese–zirconium-mediated autoxidation

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