Simultaneous hypercrosslinking and functionalization of polyHIPEs for use as coarse powder catalyst supports

[Display omitted] •Identification of suitable synthetic routes for simultaneous hypercrosslinking and organophosphorus functionalisation of macroporous polyHIPEs.•Demonstration that oxidised phenylphosphines moieties can still function as efficient Pd ligands, which has previously been overlooked in...

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Veröffentlicht in:Chemical engineering science 2022-12, Vol.264, p.118151, Article 118151
Hauptverfasser: Barkan-Öztürk, Hande, Menner, Angelika, Bismarck, Alexander, Woodward, Robert T.
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Sprache:eng
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Zusammenfassung:[Display omitted] •Identification of suitable synthetic routes for simultaneous hypercrosslinking and organophosphorus functionalisation of macroporous polyHIPEs.•Demonstration that oxidised phenylphosphines moieties can still function as efficient Pd ligands, which has previously been overlooked in the literature.•The complexing of Pd at organophosphorus sites to produce coarse powder catalysts for Suzuki-Miyaura coupling reactions (turnover frequencies of up to 5722 h−1).•Simple catalyst recovery from the reaction mixture without filtration for quick reuse and product isolation. Porous polymers offer desirable properties for heterogeneous catalysis, such as excellent stability, high active site density, and reusability. However, their synthesis is often complicated, requiring expensive reagents and laborious synthetic processes. We produce organophosphorus functionalized polyHIPEs by the polymerization of particle and surfactant stabilized water-in-styrene/divinylbenzene high internal phase emulsion templates, followed by post-functionalization using low-cost hypercrosslinking strategies. Three hypercrosslinking approaches were investigated, including knitting with an external crosslinker, solvent stitching and Scholl coupling reaction. Each approach’s ability to simultaneously create micro/mesoporosity and incorporate organophosphorus moieties into the polyHIPE structure as catalyst anchor sites were assessed, introducing surface areas of up to 410 m2/g and phosphorus concentrations of up to 7.4 wt%. After Pd-loading, the polyHIPEs displayed outstanding catalytic performance in a Suzuki-Miyaura coupling reaction, reaching turnover frequencies of 5722 h−1. The coarse powder form of the polyHIPEs allowed for simple catalyst recovery from the reaction mixture for reuse.
ISSN:0009-2509
1873-4405
DOI:10.1016/j.ces.2022.118151