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Issue 3, 2006
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Acylation and carbanilation of cellulose in ionic liquids

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Abstract

Ionic liquids (ILs) namely 1-N-butyl-3-methylimidazolium chloride ([C4mim]+Cl), 1-N-ethyl-3-methylimidazolium chloride ([C2mim]+Cl), 1-N-butyldimethylimidazolium chloride ([C4dmim]+Cl) and 1-N-allyl-2,3-dimethylimidazolium bromide ([Admim]+Br) were investigated as solvent for the homogeneous acylation and carbanilation of the biopolymer cellulose. Cellulose acetates with a degree of substitution (DS) in the range from 2.5 to 3.0 are accessible within 2 h at 80 °C in a complete homogeneous procedure. The acylation of cellulose with the fatty acid chloride lauroyl chloride leads to cellulose laurates with DS from 0.34 to 1.54. The reaction starts homogeneously and continues heterogeneously. The synthesis of cellulose carbanilates succeeds in the ionic liquid [C4mim]+Cl without any catalyst. The new homogeneous path gives pure cellulose carbanilates. All reactions are carried out under mild conditions, low excess of reagent and a short reaction time. The reaction media applied can be easily recycled and reused.

Graphical abstract: Acylation and carbanilation of cellulose in ionic liquids

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Publication details

The article was received on 16 Sep 2005, accepted on 06 Dec 2005 and first published on 22 Dec 2005


Article type: Paper
DOI: 10.1039/B513157J
Green Chem., 2006,8, 301-306

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    Acylation and carbanilation of cellulose in ionic liquids

    S. Barthel and T. Heinze, Green Chem., 2006, 8, 301
    DOI: 10.1039/B513157J

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