Highly efficient propionylation and butyralation of cellulose in an ionic liquid catalyzed by 4-dimethylminopyridine

Carbohydr Polym. 2013 Jan 30;92(1):307-11. doi: 10.1016/j.carbpol.2012.08.111. Epub 2012 Sep 19.

Abstract

Using 4-dimethylaminopyridine (DMAP) as the catalyst, highly efficient propionylation and butyralation of cellulose were successfully carried out in an ionic liquid 1-allyl-3-methylimidazolium chloride (AmimCl) under mild conditions. Cellulose propionate (CP) and cellulose butyrate (CB) with a degree of substitution (DS) in the range from 0.89 to 2.89 were synthesized within only 30 min at 30 °C. The DS values of the products could be well controlled just by molar ratio of acid anhydride/anhydroglucose unit (AGU). More interestingly, the conversions of acid anhydrides in both propionylation and butyralation were as high as above 90%, even 96%. Therefore, this work provides a facile and highly efficient way for the synthesis of cellulose esters CP and CB.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Aminopyridine / analogs & derivatives*
  • 4-Aminopyridine / chemistry
  • Allyl Compounds / chemistry
  • Butyrates / chemistry*
  • Catalysis
  • Cellulose / chemistry*
  • Imidazoles / chemistry
  • Ionic Liquids / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Propionates / chemistry*
  • Temperature

Substances

  • 1-allyl-3-methylimidazolium
  • Allyl Compounds
  • Butyrates
  • Imidazoles
  • Ionic Liquids
  • Propionates
  • Cellulose
  • 4-Aminopyridine
  • 4-dimethylaminopyridine