Pieter J. Nieuwland

Radboud University Nijmegen

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Floris P. J. T. Rutjes

Radboud University Nijmegen

Kaspar Koch

Radboud University Nijmegen

René Becker

Avantium (Netherlands)

Jan C. M. van Hest

Eindhoven University of Technology

Sebastiaan A. M. W. van den Broek

Radboud University Nijmegen

F.P.J.T. Rutjes

Radboud University Nijmegen

K. H. Koch

Klinikum rechts der Isar

Daniel Blanco‐Ania

Radboud University Nijmegen

Mariëlle M. E. Delville

Radboud University Nijmegen

Roel Wijtmans

Radboud University Nijmegen

Cooperative Institutions

Radboud University Nijmegen

Radboud University Medical Center

Radboud Institute for Molecular Life Sciences

University of Twente

University of Amsterdam

Universitat de Barcelona

DSM (Netherlands)

Vrije Universiteit Amsterdam

Netherlands Leprosy Relief

ETH Zurich

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Cu-catalysed pyrazole synthesis in continuous flow

Catalysis Science & Technology (2016)

Júlia Comas‐Barceló Daniel Blanco‐Ania Sebastiaan A. M. W. van den Broek Pieter J. Nieuwland Joseph P. A. Harrity

By using supported Cu(ii) catalysts for the regioselective synthesis of 1,4-disubstituted pyrazoles, we significantly reduced the Cu loading to 30 mol% and the alkyne required. Also, continuous flow allowed a dramatic reduction of reaction times going from 16 h to residence times of 5–15 min, being able to easily scale up this methodology.

Alkyne

Pyrazole

Flow chemistry

10.1039/c5cy02247a

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Citations (24)

Flow chemistry today: Practical approaches for optimisation and scale-up

Chimica oggi (2011)

René Becker K. H. Koch Pieter J. Nieuwland F.P.J.T. Rutjes

Flow chemistry

Source

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Citations (18)

Highly Controlled Gas/Liquid Processes in a Continuous Lab‐Scale Device

Chemical Engineering & Technology (2013)

Jasper J. F. van Gool Sebastiaan A. M. W. van den Broek Renée M. Ripken Pieter J. Nieuwland K. H. Koch

Abstract The use of reactive gases for syntheses on small laboratory scale is often avoided due to safety concerns so that expensive alternatives are required. The recent development of gas‐permeable membrane‐based reactors offers new options for safe handling of these gases in a continuous‐flow system. A prototype of a gas/liquid system was built to introduce gas in the microreactor. An integrated gas flow controller and inline FTIR analysis were used to safely handle the gas. With the system, the carboxylation of a Grignard reagent with carbon dioxide was chosen as a nonhazardous model reaction to validate the prototype reactor.

Microreactor

Carbon dioxide removal

Flow chemistry

Liquid gas

Carboxylation

10.1002/ceat.201200553

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Citations (20)

6. Experimental procedures for conducting organic reactions in continuous flow

De Gruyter eBooks (2014)

Pieter J. Nieuwland Kaspar Koch René Becker Sándor B. Ötvös István M. Mándity

10.1515/9783110289169.157

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Inline Reaction Monitoring of Amine-Catalyzed Acetylation of Benzyl Alcohol Using a Microfluidic Stripline Nuclear Magnetic Resonance Setup

Journal of the American Chemical Society (2019)

Anna Jo Oosthoek-de Vries Pieter J. Nieuwland Jacob Bart Kaspar Koch Johannes W.G. Janssen

We present an in-depth study of the acetylation of benzyl alcohol in the presence of N,N-diisopropylethylamine (DIPEA) by nuclear magnetic resonance (NMR) monitoring of the reaction from 1.5 s to several minutes. We have adapted the NMR setup to be compatible to microreactor technology, scaling down the typical sample volume of commercial NMR probes (500 μL) to a microfluidic stripline setup with 150 nL detection volume. Inline spectra are obtained to monitor the kinetics and unravel the reaction mechanism of this industrially relevant reaction. The experiments are combined with conventional 2D NMR measurements to identify the reaction products. In addition, we replace DIPEA with triethylamine and pyridine to validate the reaction mechanism for different amine catalysts. In all three acetylation reactions, we find that the acetyl ammonium ion is a key intermediate. The formation of ketene is observed during the first minutes of the reaction when tertiary amines were present. The pyridine-catalyzed reaction proceeds via a different mechanism.

Benzyl alcohol

Stripline

10.1021/jacs.9b00039

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Citations (39)

Flash Chemistry Extensively Optimized: High‐Temperature Swern–Moffatt Oxidation in an Automated Microreactor Platform

Chemistry - An Asian Journal (2010)

Pieter J. Nieuwland Kaspar Koch Noud van Harskamp Ron Wehrens Jan C. M. van Hest

Abstract The generally accepted benefits of small lateral dimensions of microreactors (1 μm to 1 mm) enable a different way of performing synthetic chemistry: Extremely short contact times in the millisecond range can circumvent the need for performing highly exothermic and fast reactions at very low temperatures. In order to fully exploit this technology, such fast processes need to be redesigned and investigated for optimal reaction conditions, which can differ drastically from the ones traditionally applied. In a comprehensive study, we optimized the selective Swern–Moffatt oxidation of benzyl alcohol to benzaldehyde by varying five experimental parameters, including reaction time and temperature. Employing an ultrashort mixing and reaction time of only 32 ms, the optimal temperature was determined to be 70 °C, approximately 150 °C higher than in the conventional batch conditions. This remarkable difference shows both the potency of continuous‐flow chemistry as well as the urgency of a paradigm shift in reaction design for continuous‐flow conditions.

Swern oxidation

Microreactor

Millisecond

Exothermic reaction

Flow chemistry

Benzaldehyde

10.1002/asia.200900705

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Citations (88)

A Microfluidic High-Resolution NMR Flow Probe

Journal of the American Chemical Society (2009)

Jacob Bart A.J. Kolkman Anna Jo Oosthoek-de Vries Kaspar Koch Pieter J. Nieuwland

A microfluidic high-resolution NMR flow probe based on a novel stripline detector chip is demonstrated. This tool is invaluable for the in situ monitoring of reactions performed in microreactors. As an example, the acetylation of benzyl alcohol with acetyl chloride was monitored. Because of the uncompromised (sub-Hz) resolution, this probe holds great promise for metabolomics studies, as shown by an analysis of 600 nL of human cerebrospinal fluid.

Microreactor

10.1021/ja900389x

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Citations (150)

Microreactortechnology: Real-Time Flow Measurements in Organic Synthesis

Micromachines (2012)

Sebastiaan A. M. W. van den Broek René Becker Kaspar Koch Pieter J. Nieuwland

With the commercial availability of integrated microreactor systems, the numbers of chemical processes that are performed nowadays in a continuous flow is growing rapidly. The control over mixing efficiency and homogeneous heating in these reactors allows industrial scale production that was often hampered by the use of large amounts of hazardous chemicals. Accurate actuation and in line measurements of the flows, to have a better control over the chemical reaction, is of added value for increasing reproducibility and a safe production.

Microreactor

Scale-up

Chemical reactor

Static mixer

10.3390/mi3020244

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Citations (11)

Fast Scale-Up Using Microreactors: Pyrrole Synthesis from Micro to Production Scale

Organic Process Research & Development (2011)

Pieter J. Nieuwland R. P. A. M. Segers Kaspar Koch Jan C. M. van Hest Floris P. J. T. Rutjes

A flow chemistry method for the synthesis of pyrroles was developed. The method was optimized in 0.13 to 7 μL microreactors in continuous flow, reaching yields of nearly 100%. Subsequently, the method was scaled up in continuous flow using a 9.6-mL internal volume, glass, microstructured flow reactor, leading to production of a pyrrole derivative at a rate of 55.8 g per hour .

Microreactor

Scale-up

Pyrrole

10.1021/op100338z

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Citations (52)

Enzymatic synthesis of optically pure cyanohydrins in microchannels using a crude cell lysate

Chemical Engineering Journal (2007)

Karoline Koch R VANDENBERG Pieter J. Nieuwland Roel Wijtmans M. Wubbolts

Microreactor

Biocatalysis

Microchannel

Cyanohydrin

Enzyme Catalysis

10.1016/j.cej.2007.07.013

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Citations (41)