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Preparation of higher aliphatic acid esters of wood in an N 2 O 4 –DMF cellulose solvent medium
Author(s) -
Shiraishi Nobuo,
Matsunaga Tadayo,
Yokota Tokuo,
Hayashi Yoshiyuki
Publication year - 1979
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.1979.070241203
Subject(s) - cellulose , reactivity (psychology) , solvent , organic chemistry , pyridine , chemistry , chloride , acyl chloride , acylation , polymer chemistry , catalysis , medicine , alternative medicine , pathology
Esterification of wood meal with a series of aliphatic acid anhydrides and acid chlorides in a nonaqueous cellulose solvent, an N 2 O 4 –DMF solvent, has been studied. The N 2 O 4 –DMF–pyridine solution used as the reaction medium plays a role in destroying the molecular order of the cellulose within the wood, enabling the cellulose to be uniformly substituted by acyl groups along its chain. These uniformly distributed blocking groups result in the permanent decrystallization of the wood. The acyl blocking groups are best achieved by esterification using acid chlorides in the nonaqueous solvent. Acid chlorides, from caproyl to stearoyl chloride, were found to be much more effective as acylating agents than acid anhydrides, from propionic to caproic anhydride. Although no difference in reactivity can be recognized among the acid chlorides, the reactivity decreases with increase in the number of carbon atoms in the acyl group among the acid anhydrides.