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

Authors
  • Zhang, Jinming
  • Zhang, Hao
  • Wu, Jin
  • Zhang, Jun
  • He, Jiasong
  • Xiang, Junfeng
Type
Published Article
Journal
Physical Chemistry Chemical Physics
Publisher
The Royal Society of Chemistry
Publication Date
Feb 28, 2010
Volume
12
Issue
8
Pages
1941–1947
Identifiers
DOI: 10.1039/b920446f
PMID: 20145862
Source
Medline
License
Unknown

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.

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