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Continuous-flow synthesis of (E)-2-Hexenal intermediates using a two-stage microreactor system

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Abstract

A flow synthesis method of (E)-2-hexenal intermediates by employing a two-stage microreactor system was reported as an example of autothermal Prins-type reaction. The continuous flow technology not only overcame the low efficiency of batch reactions, it also met the demand for high selectivity and required less consumption of reactants. Temperature monitors of a micro-mixer and a reaction tube covered by thick thermal insulation materials provided an apparent reaction enthalpy of −112 kJ·mol−1 for the generations of hexenal intermediates and by-products. A two-stage reaction platform was therefore developed to enable efficient control of the reaction temperature, which was from 20 °C and 110 °C. Under optimized operating conditions, the yield of (E)-2-hexenal intermediates reached 72%, with a space time yield of 273 kg·h−1 L−1, which was over 1200 times that of a traditional batch reactor with dripping fed reactants. The final yield of (E)-2-hexenal was maintained at 72% after hydrolysis of the intermediates.

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Acknowledgements

We gratefully acknowledge the support from National Natural Science Foundation of China (21991104).

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Authors and Affiliations

  1. The State Key Lab of Chemical Engineering, Department of Chemical Engineering, Tsinghua University, Beijing, 100084, China

    Jian Deng, Pengcheng Zou, Kai Wang & Guangsheng Luo

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  1. Jian Deng
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  2. Pengcheng Zou
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  3. Kai Wang
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Correspondence to Kai Wang.

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Highlights

1. An autothermal Prins-type synthesis was realized for (E)-2-hexenal intermediates.

2. A two-stage microreactor system with high reaction yield of (E)-2-hexenal intermediates was developed.

3. Space time yield of (E)-2-hexenal intermediates was over 1000 times that of a traditional batch reactor.

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Deng, J., Zou, P., Wang, K. et al. Continuous-flow synthesis of (E)-2-Hexenal intermediates using a two-stage microreactor system. J Flow Chem 10, 661–672 (2020). https://doi.org/10.1007/s41981-020-00112-7

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  • DOI: https://doi.org/10.1007/s41981-020-00112-7

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