Chemoselective Methylation of Phenolic Hydroxyl Group Prevents Quinone Methide Formation and Repolymerization During Lignin Depolymerization

Kim, Kwang Ho; Dutta, Tanmoy; Walter, Eric D.; Isern, Nancy G.; Cort, John R.; Simmons, Blake A.; Singh, Seema

doi:10.1021/acssuschemeng.6b03102

Chemoselective Methylation of Phenolic Hydroxyl Group Prevents Quinone Methide Formation and Repolymerization During Lignin Depolymerization

Journal Article · Thu Mar 30 00:00:00 EDT 2017 · ACS Sustainable Chemistry & Engineering

DOI:https://doi.org/10.1021/acssuschemeng.6b03102· OSTI ID:1356483

; ; Walter, Eric D.; Isern, Nancy G.; ; Simmons, Blake A.; Singh, Seema

Chemoselective blocking of the phenolic hydroxyl (Ar-OH) group by methylation was found to suppress secondary repolymerization and charring during lignin depolymerization. Methylation of Ar-OH prevents formation of reactive quinone methide intermediates, which are partly responsible for undesirable secondary repolymerization reactions. Instead, this structurally modified lignin produces more relatively low molecular weight products from lignin depolymerization compared to unmodified lignin. This result demonstrates that structural modification of lignin is desirable for production of low molecular weight phenolic products. This approach could be directed toward alteration of natural lignification processes to produce biomass more amenable to chemical depolymerization.

Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (US), Environmental Molecular Sciences Laboratory (EMSL)

Sponsoring Organization:: USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)

DOE Contract Number:: AC05-76RL01830

OSTI ID:: 1356483

Report Number(s):: PNNL-SA-122183; 48827; KP1704020

Journal Information:: ACS Sustainable Chemistry & Engineering, Journal Name: ACS Sustainable Chemistry & Engineering Journal Issue: 5 Vol. 5; ISSN 2168-0485

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

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Dimethyl carbonate: a versatile reagent for a sustainable valorization of renewables Fiorani, G.; Perosa, A.; Selva, M. Green Chemistry, Vol. 20, Issue 2 https://doi.org/10.1039/c7gc02118f	journal	January 2018
Lignin depolymerization to monophenolic compounds in a flow-through system Kumaniaev, Ivan; Subbotina, Elena; Sävmarker, Jonas Green Chemistry, Vol. 19, Issue 24 https://doi.org/10.1039/c7gc02731a	journal	January 2017
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