Fast and highly efficient acetylation of xylans in ionic liquid systems

Agnes M. Stepan, Alistair W.T. King, Tia Kakko, Guillermo Toriz, Ilkka Kilpeläinen, Paul Gatenholm

Research output: Contribution to journalArticleScientificpeer-review

28 Citations (Scopus)

Abstract

In this study high molecular weight pure rye arabinoxylan and spruce arabinoglucuronoxylan were acetylated in ionic liquid (IL) systems. Two different ILs were used in our study. In both IL, using optimized procedures, it was possible to achieve acetylation within 5 min. The first system involved direct dissolution into 1-ethyl-3-methylimidazolium dimethylphosphate ([emim][Me2PO4]), followed by addition of acetyl chloride/pyridine (AcCl/Pyr) and additional chloroform (CHCl3), as co-solvent. The other system involved direct dissolution into the novel protic IL 1,5-diazabicyclo[4.3.0]non-5-enium acetate ([DBNH][OAc]), followed by acetic anhydride/1,5-diazabicyclo[4.3.0]non-5-ene (Ac2O/DBN) and no co-solvent added. The full acetyl substitution of the xylans was confirmed by FT IR and 1H NMR. The acetylated xylans maintained a high molecular weight, which was confirmed by gel permeation chromatography. The products were soluble in CHCl3 and dimethyl carbonate, which is considered as a 'green' reagent or solvent. This allowed for the casting of the materials into clear transparent films, opening opportunity for further processing and evaluation of these materials.

Original languageEnglish
Pages (from-to)2813-2824
Number of pages12
JournalCellulose
Volume20
Issue number6
DOIs
Publication statusPublished - Dec 2013
MoE publication typeA1 Journal article-refereed

Keywords

  • Acetylation
  • Ionic liquid
  • Rye
  • Spruce
  • Xylan

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