Study on Synthesis and NMR Characterization of 2,3-O-Hydroxyethyl Cellulose Depending on Synthesis Conditions

The synthesis of hydroxyethyl celluloses with regioselective functionalization in position 2 and 3 starting from triphenylmethyl (trityl) cellulose is described. The effects of reaction conditions upon both the degree of substitution and the distribution of the hydroxyethyl moieties were investigate...

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Bibliographic Details
Published in:Macromolecular symposia. 2010-08, Vol.294 (2), p.133-140
Main Authors: Petzold-Welcke, Katrin, Kötteritzsch, Manuela, Fenn, Dominik, Koschella, Andreas, Heinze, Thomas
Format: Article
Language:English
Subjects:
Cellulose
Hydrolysis
Hydroxyethyl celluloses
hydroxyethylation
NMR
NMR spectroscopy
Nuclear magnetic resonance
protecting group
regioselective functionalization
Synthesis
Two dimensional
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Summary:The synthesis of hydroxyethyl celluloses with regioselective functionalization in position 2 and 3 starting from triphenylmethyl (trityl) cellulose is described. The effects of reaction conditions upon both the degree of substitution and the distribution of the hydroxyethyl moieties were investigated in detail. The interest was not only focused on regioselective functionalization within the anhydroglucose unit but also on the formation of oxyethylene side chains. To avoid the formation of oxyethylene side chains, 2-(2-bromoethoxy)tetrahydropyran was used as etherifying agent in comparison with 2-bromoethanol. By acidic hydrolysis, both protecting groups - trityl at 6 position and tetrahydropyran at the hydroxyethyl substituent - can be simultaneously cleaved off. The hydroxyethyl celluloses were characterized by one- and two-dimensional NMR spectroscopy in order to determine the substitution pattern.
ISSN:1022-1360
1521-3900
1521-3900
DOI:10.1002/masy.201000003