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

Synthesis of 2,3,5-trimethylbenzoquinone from 2,3,6-trimethylphenol and tert-butyl hydroperoxide... 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.Graphical Abstract[graphic not available: see fulltext] http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Flow Chemistry Springer Journals

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

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Publisher
Springer Journals
Copyright
Copyright © Akadémiai Kiadó 2022. Springer Nature or its licensor holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
ISSN
2062-249X
eISSN
2063-0212
DOI
10.1007/s41981-022-00218-0
Publisher site
See Article on Publisher Site

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.Graphical Abstract[graphic not available: see fulltext]

Journal

Journal of Flow ChemistrySpringer Journals

Published: Jun 1, 2022

Keywords: Oxidation; 2,3,5-trimethylbenzoquinone; Multi-injection; Microreactor; Process intensification

References