Investigations on esterification reactions of starches in 1-N-butyl-3-methylimidazolium chloride and resulting substituent distribution

The ionic liquid (IL) 1-N-butyl-3-methylimidazolium chloride ([C₄mim]⁺Cl⁻) was used as solvent for different esterification reactions of the biopolymer starch. Therefore, maize starches with varying content of amylose were used. Different carboxylic acid anhydrides were applied to esterify starch wi...

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Bibliographic Details
Published in:Journal of applied polymer science 2009-10, Vol.114 (1), p.369-376
Main Authors: Lehmann, André, Volkert, Bert
Format: Article
Language:English
Subjects:
13C-NMR
Acetates
Anhydrides
Applied sciences
Chlorides
ester
Esterification
Esters
Exact sciences and technology
ionic liquid
Mass distribution
Natural polymers
Physicochemistry of polymers
polysaccharides
Reproduction
Solvents
Starch and polysaccharides
Starches
substituent distribution
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Summary:The ionic liquid (IL) 1-N-butyl-3-methylimidazolium chloride ([C₄mim]⁺Cl⁻) was used as solvent for different esterification reactions of the biopolymer starch. Therefore, maize starches with varying content of amylose were used. Different carboxylic acid anhydrides were applied to esterify starch with a degree of substitution (DS) in the range of 0.7-3.0. For example, starch acetates with the mentioned DS are accessible within 30 min at a 105°C-reaction temperature. The DS distribution of starch acetates synthesized in IL was compared with the common starch acetate synthesis of Mark and Mehltretter. Also, a consideration of starch acetates and cellulose acetates synthesized in [C₄mim]⁺Cl⁻ is given. The starch esters were characterized by means of Raman spectroscopy for qualitative- and nuclear magnetic resonance spectroscopy for quantitative determination of the functionalization pattern. Moreover, the molecular mass distribution was determined after saponification by means of GPC-MALLS.
ISSN:0021-8995
1097-4628
1097-4628
DOI:10.1002/app.29883