Homogenous esterification of cellulose pulp in [DBNH][OAc]

Tia Kakko, Alistair W.T. King, Ilkka Kilpeläinen

Research output: Contribution to journalArticleScientificpeer-review

24 Citations (Scopus)

Abstract

Cellulose acetate is widely used in films, filters, textiles, lacquer and cosmetic products. Herein we demonstrate the production of cellulose esters under homogeneous conditions using 1,5-diazabicyclo[4.3.0]non-5-ene acetate ([DBNH][OAc]) as solvent. The reagents have been chosen such that the system is recyclable, i.e. by-products are low boiling and easy to remove. It is demonstrated that cellulose acetate can be synthesized with different degree of substitution (DS) values, and that some commonly used acylation regents, like vinyl carboxylates react well without additional base catalyst. Low to high DS values are possible with good recovery of high purity ionic liquid (IL). A linear correlation method of two separate methods, IR and 31P NMR, is proposed to reliably assess the DS of the products. The recyclability of the solvent is demonstrated by acetylating cellulose with isopropenyl acetate to high degree and regeneration into water. After regeneration of cellulose acetate from the IL with addition of water, the residual water was entrained using n-butanol to minimize hydrolysis of [DBNH][OAc], to allow for high recovery and high purity of the ionic liquid. Thus, an overall scheme for batch cellulose acetylation and recovery of [DBNH][OAc] from aqueous solutions is proposed.

Original languageEnglish
Pages (from-to)5341-5354
Number of pages14
JournalCellulose
Volume24
Issue number12
DOIs
Publication statusPublished - 1 Dec 2017
MoE publication typeA1 Journal article-refereed

Keywords

  • Acetate
  • Acetylation
  • Cellulose
  • Cellulose acetate
  • Cellulose propionate
  • Distillable
  • Ester
  • IONCELL
  • Ionic liquid
  • Organic superbase
  • Recyclable
  • Recycling
  • [DBNH][OAc]

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