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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

Accelerating gas–liquid chemical reactions in flow

Suyong Han^a, Marjan Alsadat Kashfipour^a, Mahdi Ramezani^a, Milad Abolhasani^*a

^aDepartment of Chemical and Biomolecular Engineering, North Carolina State University, 911 Partners Way, Raleigh, NC, USA

View abstract

Studies toward the scaling of gas‐liquid photocycloadditions

Dr. Emily B. Corcoran, Dr. François Lévesque, Dr. Jonathan P. McMullen, Dr. John R. Naber

Department of Process Research and Development, Merck Sharp & Dohme Corp., Rahway, USA

View abstract

Photooxygenation in an advanced led-driven flow reactor module: Experimental investigations and modelling

Robbie Radjagobalou^ab, Jean-François Blanco^a, Odile Dechy-Cabaret^b, Michael Oelgemöller^c, Karine Loubière^a

^a Laboratoire de Génie Chimique LGC, Université de Toulouse, CNRS, Toulouse, France

^b Laboratoire de Chimie de Coordination LCC, CNRS, Toulouse, France

^c James Cook University, College of Science and Engineering, Townsville, Queensland 4811, Australia

View abstract

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 Cantillo^1,2, Phillip A. Inglesby³, Alistair Boyd³, Oliver Kappe^1,2

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'Brien^1,2,*, Anastasios Polyzos^1,3, 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

Continuous Flow Hydrogenation Using an On-Demand Gas Delivery Reactor

Michael A. Mercadante, Christopher B. Kelly, Christopher (Xiang) Lee, Nicholas E. Leadbeater^*

Department of Chemistry, University of Connecticut, USA

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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. Petersen^1,2,3, Anastasios Polyzos^1,4, 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).

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

app-note-30-scheme

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”

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.

Application Note 20 – Ethoxycarbonylation of Unprotected Iodoindole with CO Gas

app-note-20-scheme

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.

Application Note 19 – Ethoxycarbonylation of Iodotoluene with CO Gas

app-note-19-scheme

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.

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