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Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2019, 21, 13, 5326-5330
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HCN on Tap: On-Demand Continuous Production of Anhydrous HCN for Organic Synthesis

  • Manuel Köckinger
    Manuel Köckinger
    Center for Continuous Flow Synthesis and Processing (CCFLOW), Research Center Pharmaceutical Engineering GmbH (RCPE), Inffeldgasse 13, 8010 Graz, Austria
    Institute of Chemistry, University of Graz, Heinrichstraße 28, A-8010 Graz, Austria
    More by Manuel Köckinger
  • , 
  • Christopher A. Hone*
    Christopher A. Hone
    Center for Continuous Flow Synthesis and Processing (CCFLOW), Research Center Pharmaceutical Engineering GmbH (RCPE), Inffeldgasse 13, 8010 Graz, Austria
    Institute of Chemistry, University of Graz, Heinrichstraße 28, A-8010 Graz, Austria
    *E-mail: [email protected]
    More by Christopher A. Hone
    Orcidhttp://orcid.org/0000-0002-5939-920X
  • , and 
  • C. Oliver Kappe*
    C. Oliver Kappe
    Center for Continuous Flow Synthesis and Processing (CCFLOW), Research Center Pharmaceutical Engineering GmbH (RCPE), Inffeldgasse 13, 8010 Graz, Austria
    Institute of Chemistry, University of Graz, Heinrichstraße 28, A-8010 Graz, Austria
    *E-mail: [email protected]
    More by C. Oliver Kappe
    Orcidhttp://orcid.org/0000-0003-2983-6007
Cite this: Org. Lett. 2019, 21, 13, 5326–5330
Publication Date (Web):June 19, 2019
https://doi.org/10.1021/acs.orglett.9b01941
Copyright © 2019 American Chemical Society
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    Abstract

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    A continuous process for the on-demand generation, separation, and reaction of hydrogen cyanide (HCN) using membrane separation technology was developed. The inner tube of the reactor is manufactured from a gas-permeable, hydrophobic fluoropolymer (Teflon AF-2400) membrane. HCN is formed from aqueous reagents within the inner tube and then diffuses through the membrane into an outer tubing containing organic solvent. This technique enabled the safe handling of HCN for three different organic transformations without the need for distillation.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.9b01941.

    • Description and images of the experimental setups, optimization data, and 1H NMR, 13C NMR, and 19F NMR spectra of all isolated products (PDF)

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    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

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