The chemistry and catalytic properties of ruthenium and osmium compounds. Part 7. Regioselective hydrogenation of cinnamaldehyde (3-phenyl-2-propenal) catalyzed by Ru and Os triphenylphosphine complexes in homogeneous solution and by meta-sulfonatophenyl-diphenyldiphosphine (TPPMS) and tris-meta-sulfonato-phenylphosphine (TPPTS) derivatives in an aqueous biphasic system

Sánchez‐Delgado, Roberto A.; Medina, Miriam Desireé Dávila; López-Linares, Francisco; Fuentes, Alberto

doi:10.1016/s1381-1169(96)00191-4

Cited by 70 publications

(26 citation statements)

References 43 publications

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“…As pointed out by Sanchez-Delgado [12], the polar C=O bond points towards the catalyst-containing water phase but the less hydrophilic C=C bond points away from the water phase. As a result, the former is selectively hydrogenated, yielding COL; the COL formed remains its amphiphilic nature and its C=C bond is difficult to hydrogenate at the water -organic liquid interface.…”

Section: Activity Of Used Catalyst For Aqueous Homogeneous Hydrogenationmentioning

confidence: 79%

“…2 and 4. Sánchez-Delgado et al studied selective hydrogenation of CAL in a water -toluene multiphase system at 100 using Os and Ru complex catalysts [12].…”

Section: Activity Change On Recyclingmentioning

confidence: 99%

“…Important factors for this fact are the interfacial catalysis that the hydrogenation occurs mainly at interface between the catalyst-containing aqueous phase and the CAL-containing phase (toluene, CAL, or dense CO 2 ) and the amphiphilic nature of CAL substrate [12,20]. As pointed out by Sanchez-Delgado [12], the polar C=O bond points towards the catalyst-containing water phase but the less hydrophilic C=C bond points away from the water phase.…”

Section: Activity Of Used Catalyst For Aqueous Homogeneous Hydrogenationmentioning

confidence: 99%

“…Such a selective hydrogenation is one of important reactions for the production of perfume and fine chemicals [5][6][7]. The selectivity for the corresponding unsaturated alcohol, cinnamyl alcohol (COL), can be improved by multiphase reactions using water -organic liquid systems [8][9][10][11][12][13][14][15][16][17][18], water -dense CO 2 systems [19], and supported liquid phase catalysts [20,21]. The present authors have recently indicated that COL is selectively produced with a water-soluble complex of ruthenium -TPPTS (trisodium tris(m-sulfonatophenyl)phosphine), which exists in an aqueous phase being in contact with a bulk CAL phase in toluene, pure CAL, or dense CO 2 ( Fig.…”

Section: Introductionmentioning

confidence: 99%

“…Although the recycling is an important aspect from practical point of view, it has little been studied so far for multiphase hydrogenation of CAL and other α, β-unsaturated aldehydes. Sánchez-Delgado et al studied selective hydrogenation of CAL in a water -toluene multiphase system using Os and Ru complex catalysts [12]. They examined the recycling with OsCl 3 3H 2 O/TPPTS and found that this catalyst was recyclable with no appreciable loss of activity and selectivity for three repeated runs, indicating a stable COL selectivity of 85%.…”

Section: Introductionmentioning

confidence: 99%

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Recyclability of water-soluble ruthenium–phosphine complex catalysts in multiphase selective hydrogenation of cinnamaldehyde using toluene and pressurized carbon dioxide

Fujita

Akihara

Arai

2006

Journal of Molecular Catalysis A: Chemical

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The recyclability of water-soluble ruthenium -phosphine complex catalysts was investigated in water -toluene and in water -pressurized carbon dioxide systems for selective hydrogenation of trans-cinnamaldehyde (CAL). For the first hydrogenation run, the selectivity for cinnamyl alcohol (COL) is high for both toluene and dense CO 2 , because of interfacial catalysis in which the reaction mainly occurs at the interface between the aqueous phase and the other toluene or dense CO 2 phase. The total CAL conversion and the COL selectivity decrease on the second run, more significantly with dense CO 2 than toluene. On the subsequent runs, however, less significant changes were observed. During the first run, the active metal complexes should change to much less active ones such as Ru(H) 2 L n (TPPTS) m (L=COL) by accumulation of the main product of COL. This structural change may occur more easily in multiphase hydrogenation with dense CO 2 than that with toluene, probably because the solubility in the dense CO 2 gas phase is even smaller than that in toluene. For homogeneous reaction of COL in aqueous phase, Ru(H) 2 L n (TPPTS) m catalyzes the isomerization to HCAL compared with the hydrogenation to hydrocinnamyl alcohol. With those complexes, however, the selectivity for COL is still comparable to that for HCAL for multiphase hydrogenation reactions because the hydrogenation of an ampholytic substrate of CAL occurs mainly at interface between water and toluene or dense CO 2 gas phase. Interactions of CO 2 molecules with CAL would also increase the reactivity of carbonyl group of the substrate.

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Section: Activity Of Used Catalyst For Aqueous Homogeneous Hydrogenationmentioning

confidence: 79%

“…2 and 4. Sánchez-Delgado et al studied selective hydrogenation of CAL in a water -toluene multiphase system at 100 using Os and Ru complex catalysts [12].…”

Section: Activity Change On Recyclingmentioning

confidence: 99%