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Dynamic Spinning Disc Reactor Technology to Enable In Situ Solid Product Formation in a Diazotization and Azo Coupling Sequence
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    Dynamic Spinning Disc Reactor Technology to Enable In Situ Solid Product Formation in a Diazotization and Azo Coupling Sequence
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    • Dominik Polterauer
      Dominik Polterauer
      Center for Continuous Flow Synthesis and Processing, Research Center Pharmaceutical Engineering GmbH, Inffeldgasse 13, A-8010 Graz, Austria
      Institute of Chemistry, NAWI Graz, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria
    • Kevin M. P. van Eeten
      Kevin M. P. van Eeten
      Flowid B.V., Valeton 2A, 5301 LW Zaltbommel, The Netherlands
    • Wouter Stam
      Wouter Stam
      Flowid B.V., Valeton 2A, 5301 LW Zaltbommel, The Netherlands
      More by Wouter Stam
    • Christopher A. Hone*
      Christopher A. Hone
      Center for Continuous Flow Synthesis and Processing, Research Center Pharmaceutical Engineering GmbH, Inffeldgasse 13, A-8010 Graz, Austria
      Institute of Chemistry, NAWI Graz, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria
      *Email: [email protected]
    • C. Oliver Kappe*
      C. Oliver Kappe
      Center for Continuous Flow Synthesis and Processing, Research Center Pharmaceutical Engineering GmbH, Inffeldgasse 13, A-8010 Graz, Austria
      Institute of Chemistry, NAWI Graz, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria
      *Email: [email protected]
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    Organic Process Research & Development

    Cite this: Org. Process Res. Dev. 2024, 28, 5, 1903–1909
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    https://doi.org/10.1021/acs.oprd.3c00448
    Published February 21, 2024
    Copyright © 2024 American Chemical Society

    Abstract

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    Solid-forming reactions are notoriously challenging to process in standard flow processes. Even though the formation of a solid product within a reaction can facilitate simple purification, homogeneous reactions are often utilized to enable flow processing. We report the application of dynamic spinning disc reactor (SDR) technology as a strategy to handle in situ solid product formation while handling exothermic chemistry. The system is exemplified by using a diazotization and azo coupling reaction system. Advantages of the approach include the use of water as the sole reaction solvent, mild operating conditions (20 °C), and a simple isolation procedure by filtration and drying. We demonstrate that stable operation of the system is possible for 120 min, affording 55.9 g of Sudan II.

    Copyright © 2024 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.oprd.3c00448.

    • Detailed description of the flow configuration, synthetic procedures, reaction optimization data, compound characterization data, and copies of NMR spectra (PDF)

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    Cited By

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    This article is cited by 3 publications.

    1. Arnab Chaudhuri, Wouter F.C. de Groot, Jasper H.A. Schuurmans, Stefan D.A. Zondag, Alessia Bianchi, Koen P.L. Kuijpers, Rémy Broersma, Amin Delparish, Matthieu Dorbec, John van der Schaaf, Timothy Noël. Scaling Up Gas–Liquid Photo-Oxidations in Flow Using Rotor-Stator Spinning Disc Reactors and a High-Intensity Light Source. Organic Process Research & Development 2025, Article ASAP.
    2. Arnab Chaudhuri, John van der Schaaf. Intensified reactors for a paradigm shift in chemical processing: the case for spinning disc reactors. Current Opinion in Chemical Engineering 2024, 46 , 101052. https://doi.org/10.1016/j.coche.2024.101052
    3. Jihong Ouyang, Wenbo Yang, Zhaoyan Guo, Fujun Li, Wendong Liu, Pengfei Guo, Yumeng Zhou, Dali Gao, Lijing Zhang, Shengyang Tao. Modular Cascade of Flow Reactors: Continuous Flow Synthesis of Water‐Insoluble Diazo Dyes in Aqueous System. ChemSusChem 2024, 23 https://doi.org/10.1002/cssc.202400413

    Organic Process Research & Development

    Cite this: Org. Process Res. Dev. 2024, 28, 5, 1903–1909
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.oprd.3c00448
    Published February 21, 2024
    Copyright © 2024 American Chemical Society

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