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Surprising Insensitivity of Homogeneous Acetylation of Cellulose Dissolved in Triethyl( n ‐octyl)ammonium Chloride/Molecular Solvent on the Solvent Polarity
Author(s) -
Achtel Christian,
Jedvert Kerstin,
Kostag Marc,
El Seoud Omar A.,
Heinze Thomas
Publication year - 2018
Publication title -
macromolecular materials and engineering
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.913
H-Index - 96
eISSN - 1439-2054
pISSN - 1438-7492
DOI - 10.1002/mame.201800032
Subject(s) - microcrystalline cellulose , acetic anhydride , solvent , cellulose , chloride , ammonium chloride , ionic liquid , polarity (international relations) , polymer chemistry , chemistry , ammonium , electrolyte , inorganic chemistry , solvatochromism , organic chemistry , catalysis , biochemistry , electrode , cell
The homogeneous acetylation of microcrystalline cellulose (MCC) by acetyl chloride and acetic anhydride in triethyl( n ‐octyl)ammonium chloride (N 2228 Cl)/molecular solvents (MSs) is investigated. The reaction with both acylating agents shows the expected increase of the degree of substitution (DS) on reaction temperature and time. Under comparable reaction conditions, however, DS is surprisingly little dependent on the MS employed, although the MSs differ in empirical polarity by 7 kcal mol −1 as calculated by use of solvatochromic probes. The empirical polarities of (MCC + N 2228 Cl + MS) differ only by 0.8 kcal mol −1 . The formation a polar electrolyte sheath around cellulose chains presumably contributes to this “leveling‐off” of the dependence DS on the polarity of the parent MS employed. N 2228 Cl recovery and recycling is feasible.