Catalytic carbon–carbon bond cleavage in lignin via manganese–zirconium-mediated autoxidation
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Published:2024-01-29
Issue:1
Volume:15
Page:
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ISSN:2041-1723
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Container-title:Nature Communications
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language:en
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Short-container-title:Nat Commun
Author:
Palumbo Chad T., Gu Nina X., Bleem Alissa C., Sullivan Kevin P., Katahira Rui, Stanley Lisa M., Kenny Jacob K., Ingraham Morgan A.ORCID, Ramirez Kelsey J.ORCID, Haugen Stefan J., Amendola Caroline R., Stahl Shannon S.ORCID, Beckham Gregg T.ORCID
Abstract
AbstractEfforts 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.
Funder
DOE | Office of Energy Efficiency & Renewable Energy | Bioenergy Technologies Office DOE | SC | Biological and Environmental Research DOE | SC | Basic Energy Sciences
Publisher
Springer Science and Business Media LLC
Subject
General Physics and Astronomy,General Biochemistry, Genetics and Molecular Biology,General Chemistry,Multidisciplinary
Reference102 articles.
1. Zakzeski, J., Bruijnincx, P. C., Jongerius, A. L. & Weckhuysen, B. M. The catalytic valorization of lignin for the production of renewable chemicals. Chem. Rev. 110, 3552–3599 (2010). 2. Chundawat, S. P., Beckham, G. T., Himmel, M. E. & Dale, B. E. Deconstruction of lignocellulosic biomass to fuels and chemicals. Annu. Rev. Chem. Biomol. Eng. 2, 121–145 (2011). 3. Li, C., Zhao, X., Wang, A., Huber, G. W. & Zhang, T. Catalytic transformation of lignin for the production of chemicals and fuels. Chem. Rev. 115, 11559–11624 (2015). 4. Rinaldi, R. et al. Paving the way for lignin valorisation: recent advances in bioengineering, biorefining and catalysis. Angew. Chem. Int. Ed. 55, 8164–8215 (2016). 5. Sun, Z., Fridrich, B., de Santi, A., Elangovan, S. & Barta, K. Bright side of lignin depolymerization: toward new platform chemicals. Chem. Rev. 118, 614–678 (2018).
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