Reactions of lignin model compounds in ionic liquids

Lignin, a readily available form of biomass, is a potential source of renewable aromatic chemicals through catalytic conversion. Recent work has demonstrated that ionic liquids are excellent solvents for processing woody biomass and lignin. Seeking to exploit ionic liquids as media for depolymerizat...

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Bibliographic Details
Published in:Biomass & bioenergy 2009-09, Vol.33 (9), p.1122-1130
Main Authors: Binder, Joseph B., Gray, Michel J., White, James F., Zhang, Z. Conrad, Holladay, Johnathan E.
Format: Article
Language:English
Subjects:
2-Methoxyphenol
Acid catalysis
Alternative fuels. Production and utilization
Applied sciences
aromatic compounds
Biomass
catalysts
Dealkylation
depolymerization
Energy
eugenol
Exact sciences and technology
Fuels
guaiacol
Ionic liquid
ionic liquids
ionic strength
Lignin
liquids
Phenols
Renewable
simulation models
zeolites
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Summary:Lignin, a readily available form of biomass, is a potential source of renewable aromatic chemicals through catalytic conversion. Recent work has demonstrated that ionic liquids are excellent solvents for processing woody biomass and lignin. Seeking to exploit ionic liquids as media for depolymerization of lignin, we investigated reactions of lignin model compounds in these solvents. Using Brønsted acid catalysts in 1-ethyl-3-methylimidazolium triflate at moderate temperatures below 200 °C, we obtained up to 11.6% molar yield of the dealkylation product 2-methoxyphenol from the model compound 2-methoxy-4-(2-propenyl)phenol and cleaved 2-phenylethyl phenyl ether, a model for lignin ethers. Despite these successes, acid catalysis failed in dealkylation of the saturated-chain model compound 4-ethyl-2-methoxyphenol and did not produce monomeric products from organosolv lignin, demonstrating that further work is required to understand the complex chemistry of lignin depolymerization.
ISSN:0961-9534
1873-2909
DOI:10.1016/j.biombioe.2009.03.006