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Acylation of Cellulose with N , N′ ‐Carbonyldiimidazole‐Activated Acids in the Novel Solvent Dimethyl Sulfoxide/Tetrabutylammonium Fluoride
Author(s) -
Hussain Muhammad Ajaz,
Liebert Tim,
Heinze Thomas
Publication year - 2004
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.200300308
Subject(s) - cellulose , dimethyl sulfoxide , chemistry , dimethylformamide , solvent , acylation , organic chemistry , alicyclic compound , cellulose acetate , acetone , carboxylic acid , polymer chemistry , catalysis
Summary: Carboxylic acids were efficiently activated with N , N′ ‐carbonyldiimidazole (CDI) and applied for the acylation of cellulose under homogeneous conditions using dimethyl sulfoxide (DMSO)/tetrabutylammonium fluoride trihydrate (TBAF) as solvent. The simple and elegant method is a very mild and easily applicable tool for the synthesis of pure aliphatic, alicyclic, bulky, and unsaturated cellulose esters with degrees of substitution of up to 1.9. Products are soluble in organic solvents, e.g., DMSO or N , N ‐dimethylformamide (DMF). The cellulose esters were characterized by elemental analysis, FT‐IR, 1 H and 13 C NMR spectroscopy and show no impurities or substructures resulting from side reactions.The esterification of cellulose using carboxylic acids activated in situ with N , N′ ‐carbonyldiimidazole.