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CELLULOSE CHEMISTRY AND TECHNOLOGY

PREPARATION OF HIGH REGIOSELECTIVELY MONO-SUBSTITUTED CARBOXYMETHYLCELLULOSES


NAOTAKA NISHIO, TOSHIYUKI TAKANO, HIROSHU KAMITAKAHARA and FUMIAKI NAKATSUBO Division of Forest and Biomaterial Science, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto, 606-8502, Japan

This paper is dedicated to Prof. Cr. I. Simionescu on the occasion of his 85th birth anniversary.

Received March 14, 2005

High

regioselectively

mono-substituted

carboxymethylcelluloses

(that

is,

6-O-Carboxy-methylcellulose (6-O-CMC), 3-O-Carboxymethylcellulose (3-O-CMC), 2-O-Carboxy-methylcellulose (2-O-CMC)) were prepared by ring-opening

polymerization of glucose orthoester derivatives. In the synthesis of 6-O-CMC or 3-O-CMC, tert-butyloxycarbonylmethyl (t-BCM) group, which can be converted to carboxymethyl group, was introduced to the orthoester at O-3 or O-6 position, respectively, before polymerization. On the other hand, 2-O-CMC was prepared by tert-butyloxy-carbonylmethylation of the cellulose derivative, which had a free

Cellulose Chem. Technol., 39, 56, 377387 (2005)

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