Journal
CARBOHYDRATE RESEARCH
Volume 346, Issue 13, Pages 1985-1990Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2011.05.022
Keywords
Acetate ionic liquid; Cellulose; Carbene; Mechanism
Funding
- National Science Foundation [CBET 0844882]
- Div Of Chem, Bioeng, Env, & Transp Sys
- Directorate For Engineering [1137795] Funding Source: National Science Foundation
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Quantum mechanical calculations were carried out to determine the mechanisms for the superiority of the imidazoliumacetate-based ionic liquids to the corresponding chloride-based ionic liquids. Our results indicate that the imidazolium cation can react with the acetate anion to generate a carbene, a highly reactive intermediate. The carbene produced then reacts with cellulose to facilitate its dissolution in the ionic liquid solvents in addition to the stronger hydrogen bonds formed between the acetate anion and the hydroxyl groups on cellulose. The mechanisms for the imidazolium cation and acetate anion reactions involve the initial ion pairing of the cation and anion via hydrogen bonding and electrostatic interactions. The hydrogen bond formed between the C2-H on the imidazolium cation and COO of the anion facilitates the transfer of the H+ to the anion to form a carbene intermediate. (C) 2011 Elsevier Ltd. All rights reserved.
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