NMR spectroscopic studies of cellobiose solvation in EmimAc aimed to understand the dissolution mechanism of cellulose in ionic liquids

Phys Chem Chem Phys. 2010 Feb 28;12(8):1941-7. doi: 10.1039/b920446f. Epub 2010 Jan 19.

Abstract

The dissolution mechanism of cellulose in ionic liquids has been investigated by using cellobiose and 1-ethyl-3-methylimidazolium acetate (EmimAc) as a model system under various conditions with conventional and variable-temperature NMR spectroscopy. In DMSO-d(6) solution, NMR data of the model system clearly suggest that hydrogen bonding is formed between hydroxyls of cellobiose and both anion and cation of EmimAc. The CH(3)COO(-) anion favors the formation of hydrogen bonds with hydrogen atoms of hydroxyls, and the aromatic protons in bulky cation [Emim](+), especially the most acidic H2, prefer to associate with the oxygen atoms of hydroxyls with less steric hindrance, while after acetylation of all hydroxyls in cellobiose the interactions between cellobiose octaacetate and EmimAc become very weak, implying that hydrogen bonding is the major reason of cellobiose solvation in EmimAc. Meanwhile the stoichiometric ratio of EmimAc/hydroxyl is estimated to be between 3:4 and 1:1 in the primary solvation shell, suggesting that there should be one anion or cation to form hydrogen bonds with two hydroxyl groups simultaneously. In situ and variable-temperature NMR spectra suggest the above mechanism also works in the real system.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cellobiose / analogs & derivatives*
  • Cellobiose / chemistry
  • Hydrogen Bonding
  • Imidazoles / chemistry
  • Ionic Liquids / chemistry*
  • Magnetic Resonance Spectroscopy
  • Solvents / chemistry*
  • Temperature

Substances

  • Imidazoles
  • Ionic Liquids
  • Solvents
  • Cellobiose
  • cellobiose octaacetate
  • 1-ethyl-3-methylimidazolium