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Studies on regioselective acylation of cellulose with bulky acid chlorides

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Abstract

The regioselective esterification of cellulose by reaction with bulky acyl halides including pivaloyl chloride, adamantoyl chloride and 2,4,6-trimethylbenzoyl chloride was studied. Functionalization conditions to achieve a given degree of substitution (DS) and the resulting ester substitution pattern were described in detail. One- and two-dimensional NMR spectroscopy techniques were used to confirm the structure of the esters obtained. We compared the effects on substitution of using different esterifying reagents and solvent systems including DMAc/LiCl, DMSO/TBAF, and ionic liquids (ILs).

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Acknowledgments

We thank ICTAS and MII at Virginia Tech for their financial, facilities, and educational support, Mr. Mark Flynn for performing SEC measurements and Dr. Hugo Azurmendi for performing HMBC measurements.

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Authors and Affiliations

  1. Department of Wood Science and Forest Products, Macromolecules and Interfaces Institute, Virginia Tech, Blacksburg, VA, 24061, USA

    Daiqiang Xu, Bin Li, Courtney Tate & Kevin J. Edgar

  2. Institute for Critical Technology and Applied Science, Virginia Tech, Blacksburg, VA, 24061, USA

    Daiqiang Xu, Bin Li, Courtney Tate & Kevin J. Edgar

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  1. Daiqiang Xu
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  2. Bin Li
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  3. Courtney Tate
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  4. Kevin J. Edgar
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Correspondence to Kevin J. Edgar.

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Xu, D., Li, B., Tate, C. et al. Studies on regioselective acylation of cellulose with bulky acid chlorides. Cellulose 18, 405–419 (2011). https://doi.org/10.1007/s10570-010-9476-9

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