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01-12-2009

Syntheses of 2,6-O-alkyl celluloses: influence of methyl and ethyl groups regioselectively introduced at O-2 and O-6 positions on their solubility

Authors: Hiroshi Kamitakahara, Toshihiro Funakoshi, Toshiyuki Takano, Fumiaki Nakatsubo

Published in: Cellulose | Issue 6/2009

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Abstract

2,6-Di-O-ethyl (2E6E) (1), 2-O-ethyl-6-O-methyl (2E6M) (2), and 6-O-ethyl-2-O-methyl (6E2M) (3) celluloses were synthesized via ring-opening polymerization of glucose orthopivalate derivatives. 2,6-Di-O-methyl cellulose (2M6M) was insoluble in any common solvents, though it was not expected. On the other hand, cellulose derivative 1 (2E6E) was soluble in chloroform. Introduced positions of alkyl groups on cellulose affected solubilities of cellulose derivatives. Their solubility in chloroform decreased in the order: polymer 1 (2E6E) > polymer 2 (2E6M) > polymer 3 (6E2M) ≫ 2M6M.

previous article Solid-state NMR studies of methyl celluloses. Part 2: Determination of degree of substitution and O-6 vs. O-2/O-3 substituent distribution in commercial methyl cellulose samples

next article Syntheses of 6-O-ethyl/methyl-celluloses via ring-opening copolymerization of 3-O-benzyl-6-O-ethyl/methyl-α-d-glucopyranose 1,2,4-orthopivalates and their structure–property relationships

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Title: Syntheses of 2,6-O-alkyl celluloses: influence of methyl and ethyl groups regioselectively introduced at O-2 and O-6 positions on their solubility
Authors: Hiroshi Kamitakahara
Toshihiro Funakoshi
Toshiyuki Takano
Fumiaki Nakatsubo
Publication date: 01-12-2009
Publisher: Springer Netherlands
Published in: Cellulose / Issue 6/2009
Print ISSN: 0969-0239
Electronic ISSN: 1572-882X
DOI: https://doi.org/10.1007/s10570-009-9332-y

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