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http://hdl.handle.net/1942/24240
Title: | High-throughput polymer screening in microreactors: boosting the Passerini three component reaction | Authors: | HAVEN, Joris BAETEN, Evelien Claes, Jonathan VANDENBERGH, Joke JUNKERS, Tanja |
Issue Date: | 2017 | Publisher: | ROYAL SOC CHEMISTRY | Source: | 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. | Document URI: | http://hdl.handle.net/1942/24240 | ISSN: | 1759-9954 | e-ISSN: | 1759-9962 | DOI: | 10.1039/c7py00360a | ISI #: | 000401553200010 | Rights: | This journal is © The Royal Society of Chemistry 2017 | Category: | A1 | Type: | Journal Contribution | Validations: | ecoom 2018 |
Appears in Collections: | Research publications |
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c7py00360a.pdf Restricted Access | Published version | 1.47 MB | Adobe PDF | View/Open Request a copy |
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