Reactions of Lignin Model Compounds in Ionic Liquids

Journal Article · Tue Sep 15 04:00:00 EDT 2009 · Biomass & Bioenergy, 33(9):1122-1130

DOI:https://doi.org/10.1016/j.biombioe.2009.03.006· OSTI ID:982572

Holladay, John E; Binder, Joseph B; Gray, Michel J; White, James F; Zhang, Z Conrad

Lignin, a readily available form of biomass, awaits novel chemistry for converting it to valuable aromatic chemicals. 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, we obtained up to 11.6% yield of the dealkylation product guaiacol from the model compound eugenol and cleaved phenethyl phenyl ether, a model for lignin ethers. Despite these successes, acid catalysis failed in dealkylation of the unsaturated model compound 4-ethylguaiacol and did not produce monomeric products from organosolv lignin, demonstrating that further work is required to understand the complex chemistry of lignin depolymerization.

• Research Organization: Pacific Northwest National Laboratory (PNNL), Richland, WA (US)
• Sponsoring Organization: USDOE
• DOE Contract Number: AC05-76RL01830
• OSTI ID: 982572
• Report Number(s): PNNL-SA-57524
• Journal Information: Biomass & Bioenergy, 33(9):1122-1130, Journal Name: Biomass & Bioenergy, 33(9):1122-1130 Journal Issue: 9 Vol. 33
• Country of Publication: United States
• Language: English

Related Subjects

09 BIOMASS FUELS
AROMATICS
Acid Catalysis
BIOMASS
CATALYSIS
CATALYSTS
CHEMISTRY
DEALKYLATION
DEPOLYMERIZATION
Dealkylation
ETHERS
Eugenol
Guaiacol
Ionic liquid
LIGNIN
Lignin
PHENYL ETHER
PROCESSING
Phenols
SOLVENTS