Behaviour of water-soluble dinuclear rhodium complexes in the hydroformylation reaction of oct-1-ene

Monteil, Fanny; Quéau, R.; Kalck, Philippe

doi:10.1016/0022-328x(94)87115-9

Cited by 78 publications

(20 citation statements)

References 13 publications

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“…However, the same process cannot be applied to longer chain olefins (>C4), their poor solubility in water leading to poor reaction rates. Many strategies have been developed to overcome this issue, among which use of cosolvents [5][6][7] or phase transfer agents such as cyclodextrins [8,9] or activated carbons [10]. On the other hand, surfactants or amphiphilic ligands can also create organic substrate-rich nano-objects (micelles) within the aqueous catalyst phase.…”

Section: Introductionmentioning

confidence: 99%

Aqueous phase homogeneous catalysis using core–shell nanoreactors: Application to rhodium-catalyzed hydroformylation of 1-octene

Cardozo

Julcour-Lebigue

Barthe

et al. 2015

Journal of Catalysis

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High catalytic activity (turnover frequencies up to 700 h À1) was achieved using new triphenylphosphinefunctionalized core cross-linked micelles, TPP@CCM, as nanoreactors and [Rh(acac)(CO) 2 ] as catalyst precursor for the aqueous biphasic hydroformylation of 1-octene. While the hydrophobic core of the polymer offers an adequate environment for the catalytic reaction, its hydrophilic shell confines the catalyst into the aqueous phase and prevents extensive leaching toward the substrate/product phase. Selectivity is better than that of the homogeneous reaction catalyzed by the Rh/PPh 3 system, with minor isomerization and linear to branched aldehyde ratios (l/b) between 3 and 6. Various operating parameters, such as catalyst/ligand concentration, temperature, and P/Rh ratio, were varied and proved that these nanoreactors do not suffer from significant mass transfer limitations. The effect of the nanoreactor hydrophobic core size and degree of functionalization on activity and on l/b regioselectivity has also been investigated. The possible causes of catalyst leaching are discussed.

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Section: Introductionmentioning

confidence: 99%

Aqueous phase homogeneous catalysis using core–shell nanoreactors: Application to rhodium-catalyzed hydroformylation of 1-octene

Cardozo

Julcour-Lebigue

Barthe

et al. 2015

Journal of Catalysis

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“…Therefore, many methods have been developed over the past decades to overcome the mass transport limitations of the substrate to the catalyst-containing aqueous phase e.g. by addition of co-solvents, [13] surfactants, [14] amphiphilic phosphane ligands, [15] and amphiphilic polymers. [5,16] Especially the latter approach has been studied intensively in our group in the Ruthenium catalyzed hydroformylation of 1-octene with phosphane functionalized block copolymers.…”

Section: Introductionmentioning

confidence: 99%

Cascade Reactions in Polymeric Nanoreactors: Mono (Rh)‐ and Bimetallic (Rh/Ir) Micellar Catalysis in the Hydroaminomethylation of 1‐Octene

Gall

Bortenschlager

Nuyken

et al. 2008

Macro Chemistry & Physics

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The concept of micellar catalysis was transferred to the hydroaminomethylation of 1‐octene with N,N‐dimethylamine. In the first series of experiments a rhodium(I) complex with amphiphilic triphenylphosphane functionalized poly(2‐oxazoline)s as macroligand was applied as catalyst. Results obtained under standard hydroformylation conditions (T = 100 °C, p = 50 bar) were not satisfying with regard to activities and selectivities of the hydroaminomethylation reaction. Rising the temperature to 150 °C increased the yield of amine to 22% with a corresponding n/iso selectivity of 7.5 and a TOF number of 461 h−1. Best results were obtained by applying a dual Rh/Ir catalyst within the polymeric micelles leading at lower temperature of 130 °C to an amine yield of 24% with a corresponding n/iso selectivity of 11 and TOF numbers of about 600 h−1.magnified image

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“…The use of these reagents can improve the reaction rate to some extent, but often complicates the recovery of the homogeneous catalyst and decreases the catalytic selectivity. 5 As a result, there is a significant interest in developing soluble polymers with suitable hydrophilic/hydrophobic characteristics, which can be used in aqueous/organic biphasic systems to balance the desire for improved activity and selectivity with the need to constrain the catalyst in the aqueous phase. 6 Here, we chose bayberry tannin (BT) to synthesise a homogeneous Pd(0) catalyst for biphasic hydrogenation of a hydrophobic substrate, because BT is an environmentally friendly and water-soluble amphiphilic polymer that has a large number of hydrophilic phenolic hydroxyls in its hydrophobic macromolecular backbone (see ESI S1,wfor details).…”

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confidence: 99%

Soluble amphiphilic tannin-stabilized Pd(0) nanoparticles: a highly active and selective homogeneous catalyst used in a biphasic catalytic system

et al. 2009

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Behaviour of water-soluble dinuclear rhodium complexes in the hydroformylation reaction of oct-1-ene

Cited by 78 publications

References 13 publications

Aqueous phase homogeneous catalysis using core–shell nanoreactors: Application to rhodium-catalyzed hydroformylation of 1-octene

Aqueous phase homogeneous catalysis using core–shell nanoreactors: Application to rhodium-catalyzed hydroformylation of 1-octene

Cascade Reactions in Polymeric Nanoreactors: Mono (Rh)‐ and Bimetallic (Rh/Ir) Micellar Catalysis in the Hydroaminomethylation of 1‐Octene

Soluble amphiphilic tannin-stabilized Pd(0) nanoparticles: a highly active and selective homogeneous catalyst used in a biphasic catalytic system

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