Amphiphilic core-cross-linked micelles functionalized with bis(4-methoxyphenyl)phenylphosphine as catalytic nanoreactors for biphasic hydroformylation - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Polymer Année : 2015

Amphiphilic core-cross-linked micelles functionalized with bis(4-methoxyphenyl)phenylphosphine as catalytic nanoreactors for biphasic hydroformylation

Résumé

Core-cross-linked micelles (CCM) functionalized at the core with covalently linked bis(p-methoxyphenyl) phenylphosphine (BMOPPP) ligands have been synthesized by a three-step one-pot radical polymerization in emulsion, using the polymerization-induced self-assembly (PISA) strategy and reversible addition-fragmentation chain transfer (RAFT) as the controlling method. The CCM are obtained by chain extending in water poly(methacrylic acid-co-poly(ethylene oxide) methyl ether methacrylate) (P(MAA-co-PEOMA), degree of polymerization of 30, MAA/PEOMA units molar ratio of 50:50) synthesized in a first step by RAFT with a 95:5 M mixture of styrene and 4-[bis(p-methoxyphenyl)phosphino]styrene (BMOPPS) units. The resulting micelles exhibiting a core composed of P(S-co-BMOPPS) segments with a degree of polymerization of 300 are then crosslinked in a third step with a mixture of di(ethylene glycol) dimethacrylate (DEGDMA) and styrene. The resulting BMOPPP@CCM exhibit a narrow size distribution (PDI = 0.16) with an average diameter of 81 nm in water and swell in THF or by addition of toluene to the latex. The addition of [Rh(acac) (CO)2] to the toluene-swollen latex results in metal coordination to the phosphine ligands. 31P{1H} NMR spectroscopy shows that the Rh centers undergo rapid intraparticle phosphine ligand exchange. Application of these nanoreactors to the aqueous biphasic hydroformylation of 1-octene shows excellent activity and moderate catalyst leaching.

Domaines

Chimie
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Dates et versions

hal-01877399 , version 1 (03-03-2021)

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Si Chen, Andrés Fernando Cardozo Perez, Carine Julcour-Lebigue, Jean-François Blanco, Laurie Barthe, et al.. Amphiphilic core-cross-linked micelles functionalized with bis(4-methoxyphenyl)phenylphosphine as catalytic nanoreactors for biphasic hydroformylation. Polymer, 2015, 72, pp.327-335. ⟨10.1016/j.polymer.2015.02.024⟩. ⟨hal-01877399⟩
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