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Alkylation of Hydroquinone with tert-Butanol Catalyzed by Polymer-supported Sulfonimide

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Abstract

Polystyrene with pendant perfluorobutylsulfonylimide (PPFSI) was developed as a novel polymer-supported strong acid catalyst for alkylation of hydroquinone (HQ) with tert-butanol (TBA), and highly selective synthesis of 2-tert-butyl hydroquinone (2-TBHQ) was investigated over PPFSI under various experiment conditions. When the molar ratio of TBA to HQ was 1.2:1, using 3 mol% of PPFSI as catalyst in 1,2-dichloroethane at 130 °C for 5 h, the maximum of selectivity (85.9%) of 2-TBHQ was obtained while the conversion of HQ was 76.7%. Compared with other solid acid catalysts PPFSI was found to be a very effective and reusable catalyst for alkylation of hydroquinone with tert-butanol.

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Acknowledgments

The authors would like to thank DeFu Chem. Ltd. (Wuhan) for its generous supply of perfluoroalkanesulfonyl fluoride.

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Authors and Affiliations

  1. Department of Chemistry, Huazhong University of Science and Technology, Wuhan, 430074, P.R. China

    Zhengbo Zhang, Fei Zhou & Jin Nie

  2. Hubei Key Laboratory of Materials Chemistry & Service Failure, Wuhan, 430074, P.R. China

    Jin Nie

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  1. Zhengbo Zhang
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  2. Fei Zhou
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  3. Jin Nie
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Correspondence to Jin Nie.

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Zhang, Z., Zhou, F. & Nie, J. Alkylation of Hydroquinone with tert-Butanol Catalyzed by Polymer-supported Sulfonimide. Catal Lett 119, 271–276 (2007). https://doi.org/10.1007/s10562-007-9230-6

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  • DOI: https://doi.org/10.1007/s10562-007-9230-6

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