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Synthesis of 2,3,5-trimethylbenzoquinone from 2,3,6-trimethylphenol and tert-butyl hydroperoxide in microreactors

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A Correction to this article was published on 10 October 2022

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Abstract

The synthesis of 2,3,5-trimethylbenzoquinone (TMBQ) from 2,3,6-trimethylphenol (TMP) and tert-butyl hydroperoxide (TBHP) was carried out in microreactors. The yield of TMBQ increased first and then decreased with raising the reaction temperature. The reaction temperature and the residence time were optimized to be 40 °C and 12 min, respectively. The effects of the inner diameter of microreactor and the total volumetric flow rate on the reaction performance were found to be negligible under involved operational conditions. In order to reduce the overoxidation in the initial stage, the influence of the molar ratio of TBHP to TMP and the injection strategy of TBHP were investigated. The results showed that the optimal yield of TMBQ could reach 73% at 12 min residence time and 40 °C with the molar ratio of TBHP to TMP being 3 and the two-injection strategy for TBHP. The space-time yield in the microreactor was significantly improved compared to the batch reactor, indicating the effectiveness of this continuous-flow protocol for the process intensification in the TMBQ synthesis.

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Acknowledgements

We would like to acknowledge financial support from the National Natural Science Foundation of China (Nos. 221782152 and 1676164) and China Postdoctoral Science Foundation (2017M611565).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai, 200240, People’s Republic of China

    Junguo Li, Weifeng Lin, Yingjie Shao, Yuanhai Su & Minjing Shang

  2. Jiangsu Rotam Chemistry Co., Ltd, Kunshan, Jiangsu, 215301, People’s Republic of China

    Junguo Li, Tianren Tang, Wei Qiang & Zhaohui Pan

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  1. Junguo Li
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  7. Yuanhai Su
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Correspondence to Zhaohui Pan or Minjing Shang.

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Li, J., Lin, W., Shao, Y. et al. Synthesis of 2,3,5-trimethylbenzoquinone from 2,3,6-trimethylphenol and tert-butyl hydroperoxide in microreactors. J Flow Chem 12, 219–226 (2022). https://doi.org/10.1007/s41981-022-00218-0

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  • DOI: https://doi.org/10.1007/s41981-022-00218-0

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