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Improved process for 2,3,5-trimethylhydroquinone manufacture: highly efficient catalytic hydrogenation of 2,3,5-trimethylbenzoquinone

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Abstract

An efficient and green process of catalytic hydrogenation of 2,3,5-trimethylbenzoquinone (TMBQ) to 2,3,5-trimethylhydroquinone (TMHQ) on Pd/C catalyst using the LBA (a commercial mixed solvent) as solvent is described. The important reaction parameters (e.g. temperature, catalyst loading, initial concentration of TMBQ, hydrogen pressure, and agitation speed) have been investigated to acquire the optimal process conditions. The hydrogenation molar yield of TMHQ by HPLC analysis is 99.4 %. The solvent could be recovered by steam distillation, while the isolated TMHQ overall molar yield reaches up to 96.7 %. The deactivation of Pd/C during the reuse of catalysts was ascribed to the depositions of TMHQ and TMBQ based on various characterizations and regeneration study of catalyst. The possible catalytic hydrogenation mechanism is also discussed.

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Acknowledgments

This study was supported by National Natural Science Foundation of China (Grant Nos. 21103121 and 21276187) and the Research Fund for the Doctoral Program of Higher Education of China (Grant No. 20110032120011), and the open foundation supported by the State Key Laboratory of Fine Chemicals (KF1101) was also appreciated.

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Authors and Affiliations

  1. School of Chemical Engineering and Technology, Tianjin University, Tianjin, 300072, People’s Republic of China

    Tianyong Zhang, Guan Yin, Bin Li, Xiao Wang & Shuang Jiang

  2. Nantong Baisheng Chemical Industry Co., Ltd, Nantong, 226000, People’s Republic of China

    Zhongfei Yuan

  3. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116024, People’s Republic of China

    Bin Li

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  1. Tianyong Zhang
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  2. Guan Yin
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  3. Bin Li
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  4. Xiao Wang
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Correspondence to Bin Li.

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Zhang, T., Yin, G., Li, B. et al. Improved process for 2,3,5-trimethylhydroquinone manufacture: highly efficient catalytic hydrogenation of 2,3,5-trimethylbenzoquinone. Res Chem Intermed 41, 663–677 (2015). https://doi.org/10.1007/s11164-013-1219-8

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