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Surprising Insensitivity of Homogeneous Acetylation of Cellulose Dissolved in Triethyl(n‐octyl)ammonium Chloride/Molecular Solvent on the Solvent Polarity

Macromolecular materials and engineering, 2018-05, Vol.303 (5), p.n/a [Peer Reviewed Journal]

2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim ;ISSN: 1438-7492 ;ISSN: 1439-2054 ;EISSN: 1439-2054 ;DOI: 10.1002/mame.201800032

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  • Title:
    Surprising Insensitivity of Homogeneous Acetylation of Cellulose Dissolved in Triethyl(n‐octyl)ammonium Chloride/Molecular Solvent on the Solvent Polarity
  • Author: Achtel, Christian ; Jedvert, Kerstin ; Kostag, Marc ; El Seoud, Omar A. ; Heinze, Thomas
  • Subjects: Acetyl chloride ; Acetylation ; Ammonium chloride ; Anhydrides ; Cellulose ; cellulose acetate ; Crystalline cellulose ; homogeneous acetylation ; Molecular chains ; Polarity ; Recovering ; recycling ; solvent polarity ; Solvents ; Substitution reactions ; triethyl(n‐octyl)ammonium chloride
  • Is Part Of: Macromolecular materials and engineering, 2018-05, Vol.303 (5), p.n/a
  • Description: The homogeneous acetylation of microcrystalline cellulose (MCC) by acetyl chloride and acetic anhydride in triethyl(n‐octyl)ammonium chloride (N2228Cl)/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 + N2228Cl + 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. N2228Cl recovery and recycling is feasible. Homogeneous acetylation of cellulose is investigated in different mixtures of triethyl(n‐octyl)ammonium chloride (N2228Cl)/molecular solvents. To determine a dependency of polarity of solvents on degree of substitution achieved, the E T(WB) value of the solvent mixtures is examined. The results lead to the assumption that cellulose is covered by a sheath of N2228Cl isolating the biopolymer due to high N2228Cl concentration.
  • Publisher: Weinheim: John Wiley & Sons, Inc
  • Language: English
  • Identifier: ISSN: 1438-7492
    ISSN: 1439-2054
    EISSN: 1439-2054
    DOI: 10.1002/mame.201800032
  • Source: SWEPUB Freely available online
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