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Please use this identifier to cite or link to this item: http://hdl.handle.net/1942/24240

Title: High-throughput polymer screening in microreactors: boosting the Passerini three component reaction
Authors: Haven, Joris J.
Baeten, Evelien
Claes, Jonathan
Vandenbergh, Joke
Junkers, Tanja
Issue Date: 2017
Publisher: ROYAL SOC CHEMISTRY
Citation: POLYMER CHEMISTRY, 8(19), p. 2972-2978
Abstract: The Passerini three-component reaction (Passerini-3CR) has been studied via on-line microreactor/electrospray ionisation mass spectrometry (MRT/ESI-MS) reaction monitoring to demonstrate the high-throughput screening potential of continuous microreactors for macromolecular design. The Passerini-3CR is an efficient reaction, but generally requires some reagents in excess and comparatively long reaction times to complete. Herein, a reaction protocol is proposed for high yields within minutes of reaction time at equimolar reactant concentrations. The Passerini-3CR allows for the synthesis of a-acyloxy carboxamides by combining an aldehyde (or ketone), an isocyanide and a carboxylic acid moiety. A carboxylic acid (i, 1300 g mol(-1)) and aldehyde (ii, 1150 g mol(-1)) endgroup functionalized low molecular weight poly(n-butyl acrylate) were separately screened with their corresponding components as follows: (i) with dodecylaldehyde and ethylisocyano acetate and (ii) with acetic acid and ethylisocyano acetate. Screened parameters were molarity ratios, residence times, absolute reagent concentrations and reactor temperatures. Equimolar carboxylic acid/aldehyde concentrations give excellent Passerini product yields (> 95%) within 10 minutes of reaction time. The established reaction protocol is then transferred to a conventional batch process for the synthesis of diblock copolymers P(nBA)-b-P(nBA), P(nBA)-b-P(MMA) and P(nBA)-b-P(EGMEA) with variable block lengths. All diblock copolymers are synthesized by using equimolar carboxylic acid/aldehyde polymer mixtures, showing excellent coupling efficiencies in size exclusion chromatography analysis. The isocyanide component, being ethylisocyano acetate, is consistently utilized in excess in agreement with the literature.
Notes: [Haven, Joris J.; Baeten, Evelien; Claes, Jonathan; Vandenbergh, Joke; Junkers, Tanja] Hasselt Univ, Polymer React Design Grp, Inst Mat Res Imo Imomec, Campus Diepenbeek,Bldg D, B-3590 Diepenbeek, Belgium. [Junkers, Tanja] IMEC Div IMOMEC, Wetenschapspk 1, B-3590 Diepenbeek, Belgium.
URI: http://hdl.handle.net/1942/24240
DOI: 10.1039/c7py00360a
ISI #: 000401553200010
ISSN: 1759-9954
Category: A1
Type: Journal Contribution
Appears in Collections: Research publications

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