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Cellulose propionylpropionate as a side product in the reaction of cotton cellulose with propionyl chloride
Author(s) -
Sircar Anil K.,
Stais David J.,
Conrad Carl M.
Publication year - 1967
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.1967.070110908
Subject(s) - saponification , cellulose , pyridine , pyrolysis , moiety , chemistry , chloride , organic chemistry , polymer chemistry , side chain , polymer
In the reaction of cotton cellulose fiber with propionyl chloride in pyridine–DMF medium, the degree of substitution based on weight gain was much higher than that based on saponification. Gas–liquid chromatograms of the pyrolysis products of the samples showed an extra peak. This was identified as 3‐pentanone, which arises from the pyrolysis of α‐propionylpropionic acid, a substance which was proposed by Malm and co‐workers as a possible side product. This conclusion was further confirmed by the infrared and NMR spectra of the liquid, collected fractionally on pyrolysis of the sample. Quantitative GLC showed that one òut of every four hydroxyl groups is substituted with an α‐propionylpropionyl moiety, the rest with propionyl groups. A possible mechanism for the side reaction has been proposed.