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Fast and highly efficient acetylation of xylans in ionic liquid systems

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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.

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Acknowledgments

The authors would like to acknowledge the Knut and Alice Wallenberg foundation for financing this research, carried out in the Wallenberg Wood Science Center. Linda Härdelin is acknowledged for helping with the rheology measurements of the xylan solutions in ILs, Susanne Svensson and Kerstin Jedvert with the GPC measurements and Pirkko Karhunen for her assistance with NMR analysis.

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Authors and Affiliations

  1. WWSC, Wallenberg Wood Science Center, Chalmers University of Technology, Kemivägen 10, 412 96, Göteborg, Sweden

    Agnes M. Stepan, Guillermo Toriz & Paul Gatenholm

  2. Biopolymer Technology, Department of Chemical and Biological Engineering, Chalmers University of Technology, Kemivägen 10, 412 96, Göteborg, Sweden

    Agnes M. Stepan & Paul Gatenholm

  3. Department of Chemistry, University of Helsinki, PL 55, 00014, Helsinki, Finland

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

  4. Department of Wood, Cellulose and Paper Research, University of Guadalajara, Guadalajara, Mexico

    Guillermo Toriz

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  1. Agnes M. Stepan
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  2. Alistair W. T. King
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  3. Tia Kakko
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  5. Ilkka Kilpeläinen
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Correspondence to Paul Gatenholm.

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Stepan, A.M., King, A.W.T., Kakko, T. et al. Fast and highly efficient acetylation of xylans in ionic liquid systems. Cellulose 20, 2813–2824 (2013). https://doi.org/10.1007/s10570-013-0028-y

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  • DOI: https://doi.org/10.1007/s10570-013-0028-y

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