Gas/Liquid Reactions in Flow

    Flow chemistry systems are particularly suitable for hazardous gas handling for the following reasons:

    • Pressure can be safely applied in the flow system.  The addition of pressure means that a far greater proportion of the gas will be in solution during the reaction than is the case in traditional batch reactors.
    • Comparatively small amounts of gas are continually exhausted by the system, eliminating the need for many of the special precautions normally required for handling toxic and/or flammable gases
    • Systems allow the use of a fixed bed catalyst. Combined with low solution concentrations, this allows all the starting material to be adsorbed to catalyst in the presence of gas
    • The greatly enhanced mixing of the solid, liquid and gaseous phases allows the researcher to exploit the kinetic benefits of elevated temperatures without being concerned about the gas being displaced from solution
    • They open the opportunity for a hazardous gas to be synthesized and immediately consumed in a continuous process eliminating the need for isolation and storage of the hazardous gas as is required when traditional batch reactors are used.

    Examples of published literature for Gas/Liquid Reactions in Flow

    Singlet oxygen oxidations in homogeneous continuous flow using a gas–liquid membrane reactor

    Antonia Kouridaki, Kevin Huvaere

    • EcoSynth NV, Industrielaan 12, 9800 Deinze, Belgium
    View abstract

    Hydrogen sulfide chemistry in continuous flow: Efficient synthesis of 2-oxopropanethioamide

    David Cantillo1,2, Phillip A. Inglesby3, Alistair Boyd3, Oliver Kappe1,2

    • 1 Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, 8010 Graz, Austria
    • 2 Research Center Pharmaceutical Engineering (RCPE), Inffeldgasse 13, 8010 Graz, Austria
    • 3 AstraZeneca, Silk Road Business Park, Macclesfield, SK10 2NA, United Kingdom
    View abstract

    Catalytic Chan–Lam coupling using a ‘tube-in-tube’ reactor to deliver molecular oxygen as an oxidant

    Carl J. Mallia1, Paul M. Burton2, Alexander M. R. Smith2, Gary C. Walter2, Ian R. Baxendale1

    • 1 Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, United Kingdom
    • 2 Syngenta CP R&D Chemistry, Jealott’s Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, United Kingdom
    View abstract

    Flow carbonylation of sterically hindered ortho-subsituted iodoarenes

    Carl J. Mallia1, Gary C. Walter2, Ian R. Baxendale1

    • 1 Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, United Kingdom
    • 2 Syngenta CP R&D Chemistry, Jealott’s Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, United Kingdom
    View abstract

    Controlled generation and use of CO in flow†‡

    Steffen V. F. Hansen a,b, Zoe E. Wilson a, Trond Ulven *b, Steven V. Ley *a

    • a Department of Chemistry, University of Cambridge Lensfield Road, Cambridge, CB2 1EW, UK
    • b Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej 55, 5230 Odense M, Denmark
    View abstract

    A General Continuous Flow Method for Palladium Catalysed Carbonylation Reactions Using Single and Multiple Tube-in-Tube Gas-Liquid Microreactors

    Ulrike Gross1, Peter Koos1, Matthew O'Brien1,2,*, Anastasios Polyzos1,3, Steven V. Ley1

    • 1Whiffen Laboratory, Department of Chemistry, University of Cambridge, Cambridge, UK
    • 2School of Physical and Geographical Sciences, Keele University, Staffordshire, UK
    • 3CSIRO, Materials Science and Engineering, Clayton South, Australia
    View abstract

    Microwave heating and conventionally-heated continuous-flow processing as tools for performing cleaner palladium-catalyzed decarboxylative couplings using oxygen as the oxidant – a proof of principle study

    Nicholas E. Leadbeater1, DiAndra M. Rudzinski1

    • 1 Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269, USA
    View abstract

    The Continuous-Flow Synthesis of Carboxylic Acids using CO2 in a Tube-In-Tube Gas Permeable Membrane Reactor

    Anastasios Polyzos, Matthew O’Brien, Trine P. Petersen, Ian R. Baxendale, Steven V. Ley

    • Innovative Technology Centre, Department of Chemistry, University of Cambridge
    View abstract

    The Oxygen-Mediated Synthesis of 1,3-Butadiynes in Continuous Flow: Using Teflon AF-2400 to Effect Gas/Liquid Contact

    Trine P. Petersen1,2,3, Anastasios Polyzos1,4, Matthew O’Brien1, Trond Ulven2, Ian R. Baxendale1, Steven V. Ley1

    • 1Whiffen Laboratory, University of Cambridge, UK
    • 2Department of Physics and Chemistry, University of Southern Denmark
    • 3Discovery Chemistry and DMPK, H. Lundbeck A/S,Denmark
    • 4CSIRO, Materials Science and Engineering, Australia
    View abstract

    Continuous-flow, palladium-catalysed alkoxycarbonylation reactions using a prototype reactor in which it is possible to load gas and heat simultaneously

    Michael A. Mercadante, Nicholas E. Leadbeater

    • Department of Chemistry, University of Connecticut, USA
    View abstract

    Teflon AF-2400 mediated gas–liquid contact in continuous flow methoxycarbonylations and in-line FTIR measurement of CO concentration

    Peter Koos, Ulrike Gross, Anastasios Polyzos, Matthew O'Brien, Ian Baxendale, Steven V. Ley

    • Innovative Technology Centre, University of Cambridge, UK
    View abstract

    Application Notes regarding Gas/Liquid Reactions in Flow

    Application Note 32: High Pressure and Temperature Process Scale S N Ar Reaction under Solvent Free Conditions using Liquefied Dimethylamine.

    app_note32

    This application note illustrates the use of the Vapourtec R-Series system to run reactions under solvent free (neat) conditions and it’s ability to pump liquefied gases at high temperatures and pressures. This expands on work carried out in Application note 29 (where a game changing throughput of material from a bench top system was demonstrated).

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    Application Note 30: Oxidation using a Gas/Liquid Membrane Reactor

    app_note30

    This application note illustrates the use of the Vapourtec R-Series system with gas-liquid “tube-in-tube” reactor to perform in flow an oxidation previously shown in batch in the publication
    “Transition-Metal free approach to efficient aerobic oxidation of alcohols to aldehydes and ketones under mild conditions”

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    Application Note 23 –  SNAr with dimethylamine

    app_note23

    This example illustrates the use of the Vapourtec R-Series system to react
    dissolved gases under pressure without the use of scale limiting pressure
    reactors (e.g. Parr ‘bombs’). The SnAr displacement of an aryl fluoride with
    dimethylamine is described.

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    Application Note 20 – Ethoxycarbonylation of Unprotected Iodoindole with CO Gas

    app_note20

    This example illustrates the use of the new Vapourtec tube in tube gas reactor combined with the Vapourtec R-Series system to react reagent gases under pressure without the use of scale limiting pressure reactors (e.g. Parr ‘bombs’). Here we describe the catalytic ethoxycarbonylation of unprotected iodoindole with CO gas.

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    Application Note 19 – Ethoxycarbonylation of Iodotoluene with CO Gas

    app_note19

    This example illustrates the use of the new Vapourtec tube in tube gas reactor combined with the Vapourtec R-Series system to react reagent gases under pressure without the use of scale limiting pressure reactors (e.g. Parr ‘bombs’). Here we describe the catalytic ethoxycarbonylation of iodotoluene with CO gas.

    Read more

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