Novel Cellulose Ethers: Synthesis and Structure Characterization of 3-Mono-O-(3'-hydroxypropyl) Cellulose

The synthesis of 3-mono-O-(3'-hydroxypropyl) cellulose via 3-mono-O-allyl-2,6-di-O-thexyldimethylsilyl cellulose was studied. Conversion of the double bond with 9-borabicyclo[3.3.1]nonane and subsequent alkaline oxidation lead to the 3'-hydroxypropyl group. Finally, the treatment with tetr...

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Bibliographic Details
Published in:Macromolecular symposia. 2009-06, Vol.280 (1), p.86-94
Main Authors: Schumann, Kristin, Pfeifer, Annett, Heinze, Thomas
Format: Article
Language:English
Subjects:
Bonding
Cellulose
Cellulose ethers
Cleavage
Conversion
etherification
Fluorides
hydroboration
NMR
protecting group
Spectroscopy
Synthesis
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Summary:The synthesis of 3-mono-O-(3'-hydroxypropyl) cellulose via 3-mono-O-allyl-2,6-di-O-thexyldimethylsilyl cellulose was studied. Conversion of the double bond with 9-borabicyclo[3.3.1]nonane and subsequent alkaline oxidation lead to the 3'-hydroxypropyl group. Finally, the treatment with tetrabutylammonium fluoride trihydrate yields the complete cleavage of the protecting groups. The structure of the polymer was confirmed by one- and two dimensional NMR spectroscopic techniques. 3-mono-O-(3'-hydroxypropyl) cellulose is soluble in water and aprotic-dipolar organic media.
ISSN:1022-1360
1521-3900
DOI:10.1002/masy.200950610