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Acetylation of β-cyclodextrin in ionic liquid green solvent

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Abstract

The ionic liquid (IL), 1-butyl-3-methylimidzolium bromide ([C4mim]Br), synthesized under supercritical CO2, was developed as a green solvent for the dissolution, regeneration and acetylation of β-cyclodextrin (β-CD). The dissolution of β-CD in [C4mim]Br of 25 wt% could be reached at 25 °C. The acetylation of β-CD was carried out under acetic anhydride in [C4mim]Br in the absence of catalyst. β-CD acetates with different degrees of substitution of 0.07–1.14 were obtained directly under the homogeneous reaction conditions. The reaction medium of IL applied can be easily recycled and reused after the synthesis of β-CD acetate. The effects of reaction time, temperature, and acetic anhydride/AGU on the acetylation of β-CD were investigated. The acetylated β-CD samples were characterized by NMR, FT-IR, and X-ray diffraction (XRD) spectroscopy. It is the first time that we have demonstrated that ILs can be used as an environmentally friendly solvent for the acetylation of β-CD, which will open a new route to acetylation of β-CD under green solvent without catalyst.

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Acknowledgements

The authors gratefully acknowledge the financial support from the Specialized Research Fund for the Doctoral Program of Higher Education (Grant No. 20070718003). We are also extremely grateful for the support provided by Natural Science Foundation of Shaanxi Province (2007B07).

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Authors and Affiliations

  1. Key Laboratory of Applied Surface and Colloid Chemistry (Shaanxi Normal University), Ministry of Education, Xi’an, 710062, People’s Republic of China

    Zhao-Tie Liu & Zhong-Wen Liu

  2. School of Chemistry & Materials Science, Shaanxi Normal University, Xi’an, 710062, People’s Republic of China

    Zhao-Tie Liu, Li-Hong Shen, Zhong-Wen Liu & Jian Lu

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  1. Zhao-Tie Liu
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  2. Li-Hong Shen
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  3. Zhong-Wen Liu
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Correspondence to Zhao-Tie Liu.

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Liu, ZT., Shen, LH., Liu, ZW. et al. Acetylation of β-cyclodextrin in ionic liquid green solvent. J Mater Sci 44, 1813–1820 (2009). https://doi.org/10.1007/s10853-008-3238-1

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  • DOI: https://doi.org/10.1007/s10853-008-3238-1

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