Telescoped continuous flow synthesis of phenyl acrylamide
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Telescoped continuous flow synthesis of phenyl acrylamide Jatuporn Salaklang 1 & Erika Mertens 1 & Veronique Maes 1 & Rudy Dams 2 & Wim Dermaut 3 & Tanja Junkers 1,4 Received: 28 June 2020 / Accepted: 18 August 2020 # Akadémiai Kiadó 2020
Abstract Functional acrylamides are valuable intermediates for organic synthesis and building blocks in many industrial areas, like polymer synthesis, fine chemicals and pharmaceutics. The conventional batch reaction copes with some safety issues, due to the intrinsic reactivity and careful handling of the reagents. Moreover, the hazardous solvents used and the energy consumed have an enormous environmental impact. The development of an efficient and robust continuous flow process, allowing a safe and ondemand synthesis of acrylamides with high yield leads the way to a more sustainable chemistry. Two alternative synthesis routes for the preparation of N-phenyl acrylamide, but applicable as a continuous production process, are presented: both based on the Schotten-Baumann reaction, one starting from 3-chloropropanoyl chloride and the other starting from acrylic acid. The latter reaction, with a laboratory throughput of 16.5 g·h−1, low operation temperatures and the use of less hazardous chemicals, provides an efficient and sustainable alternative synthesis route of the desired acrylamides, minimizing side-products and enabling a safe and convenient scale-up. Keywords Flow chemistry . Acrylamide . Acid chloride . Microreactor
Introduction Functional polyacrylamides are widely used in various applications in fine-chemical and pharmaceutical industry, mostly as additives such as coagulators, (soil) conditioners in paper and textile industry [1–3]. Cross-linking of acrylamides opens doors to valuable and interesting applications in coatings, hydrogels, adhesives or ion exchange membranes [4–6]. Due to their good biocompatibility and water-solubility, Electronic supplementary material The online version of this article (https://doi.org/10.1007/s41981-020-00113-6) contains supplementary material, which is available to authorized users. * Tanja Junkers [email protected] 1
Institute for Materials Research, Polymer Reaction Design Group, Universiteit Hasselt, Agoralaan, Gebouw D, BE-3590 Diepenbeek, Belgium
2
Materials Resource Division, 3 M Belgium BVBA, Haven 1005, Canadastraat 11, BE-2070 Zwijndrecht, Belgium
3
Agfa Materials, Agfa-Gevaert NV, Septestraat 27, 2640 Mortsel, Belgium
4
School of Chemistry, Monash University, 19 Rainforest Walk, Clayton, VIC 3800, Australia
polyacrylamides are also used extensively in biomedical research and applications. An elegant way to produce functional acrylamide monomers is through enzymatic processes [7, 8]. Although promising, the full process involves many tedious steps to screen cultures, in conjunction with expensive unit operations for purification [9, 10]. Chemical routes to synthesize acrylamides involve the hydration of acrylonitrile in the presence of a copper catalyst through the Ritter reaction. Yet the yield o
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