112-42-5Relevant articles and documents
Hydrogenation reactions using scCO2 as a solvent in microchannel reactors
Kobayashi, Juta,Mori, Yuichiro,Kobayashi, Shu
, p. 2567 - 2568 (2005)
We have developed an effective microfluidic system for hydrogenation reactions in ScCO2; the reactions proceeded very rapidly (within 1 second), by making the best use of ScCO2 and utilizing the large specific interfacial area of the microchannel reactor, and high reaction productivity was attained in each channel. The Royal Society of Chemistry 2005.
High-yielding tandem hydroformylation/hydrogenation of a terminal olefin to produce a linear alcohol using a Rh/Ru dual catalyst system
Takahashi, Kohei,Yamashita, Makoto,Ichihara, Takeo,Nakano, Koji,Nozaki, Kyoko
, p. 4488 - 4490 (2010)
(Chemical equation presented) A dual catalyst system has been developed for tandem hydroformylation/hydrogenation to produce n-undecanol from 1-decene in one pot. A combination of xantphos/[Rh(acac)(CO)2] and Shvo's catalyst (1) afforded the best results (see scheme; acac = acetylacetonate, DMA = N,N-dimethylacetamide). Polar solvents effectively suppressed the formation of undecyl formate.
Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis
Bricout, Herve,Leonard, Estelle,Len, Christophe,Landy, David,Hapiot, Frederic,Monflier, Eric
, p. 1479 - 1484 (2012)
In this study, we showed that the addition of randomly modified β-cyclodextrin (RAME-β-CD) in aqueous medium could have a beneficial impact on the catalytic performances of phosphane-based aggregates in the Pd-catalyzed cleavage of allyl carbonates (Tsuji-Trost reaction). The RAME-β-CD/phosphane supramolecular interactions helped explain the catalytic results. The presence of RAME-β-CD in the aqueous compartment improved the phosphane-based aggregate dynamics. The exchanges between the hydrophobic substrate-containing aggregate core and the catalyst-containing aqueous phase were then greatly favored, resulting in an increase in the catalytic performances.
Convenient synthesis of new amphiphilic triphenylphosphine analogues for aqueous biphasic catalysis
Caron, Laurent,Canipelle, Micha?l,Tilloy, Sébastien,Bricout, Hervé,Monflier, Eric
, p. 8837 - 8840 (2001)
The synthesis of three triphenylphosphine analogues with phenyl groups replaced by (4-tert-butyl)phenyl and (3-sulfonato)phenyl group is described. The surface-active properties of these new compounds are reported. The catalytic activities obtained with these phosphines in the palladium-catalyzed cleavage of undecyl allyl carbonate were up to 24000 times higher than those observed with trisulfonated triphenylphosphine, the ligand typically used in biphasic catalysis. One of these catalysts can be recovered six times without loss of catalytic activity.
Ruthenium catalyzed hydrogenation of aldehyde with synthesis gas
Takahashi, Kohei,Nozaki, Kyoko
, p. 5846 - 5849 (2014)
The hydrogenation of aldehyde utilizing synthesis gas as a dihydrogen source was examined with various ruthenium catalysts, among which Ru-cyclopentadienone complexes (Shvo-type catalysts) exhibited higher activity than others. DFT calculations proved that the exchange of coordinated carbon monoxide by dihydrogen is relatively preferable in Shvo-type catalysts compared to others, which is a pre-equilibrium for the generation of the hydrogenation-active species.
Ditopic cyclodextrin-based receptors: New perspectives in aqueous organometallic catalysis
Six, Natacha,Menuel, Stephane,Bricout, Herve,Hapiot, Frederic,Monflier, Eric
, p. 1467 - 1475 (2010)
The mass transfer properties of mono- and ditopic β-cyclodextrin-based receptors have been evaluated in a biphasic palladium-catalyzed Tsuji-Trost reaction and compared to one of the best mass-transfer promoters, namely the randomly methylated β-cyclodextrin. While monotopic receptors appeared to be poor mass-transfer promoters of long alkyl chain allyl carbonates or urethanes, cooperative effects have been evidenced with ditopic cyclodextrin-based receptors, opening new perspectives in aqueous organometallic catalysis.
Amphiphilic photo-isomerisable phosphanes for aqueous organometallic catalysis
Bricout, Herve,Banaszak, Estelle,Len, Christophe,Hapiot, Frederic,Monflier, Eric
, p. 7813 - 7815 (2010)
Water-soluble phosphanes were tagged with a light-responding diazo group. Upon UV exposure, the diazo-isomerisation led to phosphane morphology change, resulting in an increase in the reaction rate of an aqueous palladium-catalysed cleavage reaction. The Royal Society of Chemistry.
Scope and limitation of activated carbons in aqueous organometallic catalysis
Kania, Nicolas,Gokulakrishnan, Narasimhan,Leger, Bastien,Fourmentin, Sophie,Monflier, Eric,Ponchel, Anne
, p. 208 - 218 (2011)
The effect of activated carbons has been studied in the palladium-catalyzed cleavage reaction of allylalkylcarbonate under aqueous biphasic conditions. A number of parameters were investigated, such as the type of carbon, the structure of the water-soluble ligand, the water conditions, and the metal complex loading. It was found that the intrinsic properties of carbons had a strong influence on the reaction rates. The best performances were obtained with the AC-WV carbon possessing the largest part of mesopores and lowest content of oxygen-surface groups. The results were rationalized by considering that AC-WV acted as a mass-transfer promoter increasing the interfacial area and collisions between the reactive species in the pore volume. The hypothesis of a confinement effect of the catalyst and reactants within the pores via adsorption-desorption processes was supported by isothermal studies and 31P{1H} NMR investigations.
Chemically modified β-cyclodextrins: Efficient supramolecular carriers for the biphasic hydrogenation of water-insoluble aldehydes
Monflier, Eric,Tilloy, Sebastien,Castanet, Yves,Mortreux, Andre
, p. 2959 - 2960 (1998)
Hydrogenation of water-insoluble aldehydes can be achieved in high yields in a genuine two-phase system by using a recoverable catalytic system composed of a water-soluble ruthenium/triphenylphosphine trisulfonate complex and a suitable chemically modified β-cyclodextrin.
Molecular recognition between a water-soluble organometallic complex and a β-cyclodextrin: First example of second-sphere coordination adducts possessing a catalytic activity
Caron, Laurent,Bricout, Herve,Tilloy, Sebastien,Ponchel, Anne,Landy, David,Fourmentin, Sophie,Monflier, Eric
, p. 1449 - 1456 (2004)
Formation of stable second-sphere adducts between a water-soluble organometallic complex and a cyclodextrin (CD) is possible by finely designing the structure of the water-soluble phosphane. The key point to obtain such adducts was the synthesis of a water-soluble phosphane which possesses a tert-butylphenyl group recognized by the CD and separated from the phosphorus atom by a phenyl ring to avoid phosphane decoordination during the molecular recognition process between the organometallic complex and the CD. These adducts are able to catalyze the cleavage of water-insoluble carbonate in a biphasic system.
