Imidazolium-Based Ionic Liquids as Efficient Reagents for the C-O Bond Cleavage of Lignin

ChemSusChem. 2018 Jan 23;11(2):439-448. doi: 10.1002/cssc.201701668. Epub 2017 Dec 13.

Abstract

The demethylation of lignin in ionic liquids (ILs) was investigated by using pure lignin model monomers and dimers together with dioxane-isolated lignins from poplar, miscanthus, and maize. Different methylimidazolium ILs were compared and the samples were treated with two different heating processes: microwave irradiation and conventional heating in a sealed tube. The conversion yield and influence of the treatment on the lignin structure were assessed by 31 P NMR spectroscopy, size-exclusion chromatography, and thioacidolysis. The acidic methylimidazolium IL [HMIM]Br was shown to be an effective combination of solvent and reagent for the demethylation and depolymerization of lignin. The relatively mild reaction conditions, the clean work-up, and the ability to reuse the IL makes the described procedure an attractive and new green method for the conversion of lignin to produce phenol-rich lignin oligomers.

Keywords: biomass; dealkylation; green chemistry; ionic liquids; lignin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, Gel
  • Demethylation
  • Green Chemistry Technology / methods*
  • Hydrolysis
  • Imidazoles / chemistry*
  • Indicators and Reagents / chemistry*
  • Ionic Liquids / chemistry*
  • Lignin / chemistry*
  • Magnetic Resonance Spectroscopy / methods
  • Microwaves
  • Poaceae / chemistry
  • Polymerization
  • Populus / chemistry
  • Zea mays / chemistry

Substances

  • Imidazoles
  • Indicators and Reagents
  • Ionic Liquids
  • Lignin