Hydroformylation of alkenes in supercritical carbon dioxide catalysed by rhodium trialkylphosphine complexes

Sellin, Murielle; Bach, Ingrid; Webster, Jeremy M.; Montilla, Francisco; Rosa, Vítor; Avilés, Teresa; Poliakoff, Martyn; Cole‐Hamilton, David J.

doi:10.1039/b207747g

Cited by 77 publications

(44 citation statements)

References 85 publications

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“…These aldehydes can be easily converted into many industrially important secondary products, such as solvents, biodegradable detergents, soaps, fragrance, flavors, perfumes, pharmaceuticals, surfactants, lubricants, and plasticizers [1][2][3][4][5][6][7]. The hydroformylation reaction has been carried out in different reaction media such as organic solvents [8], aqueous-biphasic [9], supercritical CO 2 [10], or ionic liquids [5,11].…”

Section: Introductionmentioning

confidence: 99%

Advantages of the solventless hydroformylation of olefins

Alsalahi

Trzeciak

2015

Journal of Molecular Catalysis A: Chemical

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Section: Introductionmentioning

confidence: 99%

Advantages of the solventless hydroformylation of olefins

Alsalahi

Trzeciak

2015

Journal of Molecular Catalysis A: Chemical

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“…Sellins and co-workers have used III for the hydroformylation of 1a in scCO 2 at 100 8C using Rh 2 A C H T U N G T R E N N U N G (OAc) 4 as the metal precursor with L:Rh = 3.3. [27] They obtained a low activity, (TOF = 104 mol aldehyde mol Rh À1 h À1 ) but a comparable n:iso ratio of 3.4 and a slightly lower selectivity towards aldehydes at a conversion of 39.6 %. The observed differences in activity and selectivity are probably a result of the higher temperature and the lower initial pressure used than in our experiments.…”

mentioning

confidence: 97%

Hydroformylation of 1‐Octene in Supercritical Carbon Dioxide and Organic Solvents using Trifluoromethyl‐Substituted Triphenylphosphine Ligands

Koeken

Vliet²,

Broeke

et al. 2006

Adv Synth Catal

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Two different in situ prepared catalysts generated from Rh(CO) 2 acac and trifluoromethylsubstituted triphenylphosphine ligands have been evaluated for their activity and selectivity in the hydroformylation of 1-octene. The solvents used were supercritical carbon dioxide, hexane, toluene, and perfluoromethylcyclohexane. The highest value for the turnover frequency, 9820 mol 1-octene mol Rh À1 h À1

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“…Table 1 also shows that substrate isomerization can be reduced by increasing the catalyst loading. A similar effect of catalyst loading on the isomerization has been reported for the hydroformylation of 1-hexene in scCO 2 by Sellin et al [17] The effect of CO 2 pressure has been examined using the catalyst with ligand VII at a syngas pressure of 4 MPa. The results are given in Figure 3 and indicate that the conversion passes through a minimum at 9 MPa of CO 2 pressure.…”

Section: Effect Of the Reaction Conditions On The Reaction In Sccomentioning

confidence: 55%

Hydroformylation of 1,5‐Hexadiene Catalyzed by Rhodium Complexes in Supercritical Carbon Dioxide and in Toluene: Effects of Fluorinated Phosphane Ligands and Reaction Conditions

et al. 2004

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Shin-ichiroKeywords: Hydroformylation / Rhodium / Dialdehyde / Fluorinated ligand / Supercritical carbon dioxideRhodium-catalyzed hydroformylation of 1,5-hexadiene to dialdehydes was investigated in compressed CO 2 and in toluene using different fluorinated phosphane compounds as ligands at a temperature of 60°C. Product yields depend greatly on the ligand used and, of the ligands examined, tris[3,5-bis(trifluoromethyl)phenyl]phosphane is the most effective for the production of dialdehydes both in supercritical CO 2 (scCO 2 ) and in toluene. The total yield of the dialde- IntroductionSupercritical carbon dioxide (scCO 2 ) is gaining considerable interest as an ecologically benign and economically feasible new generation reaction medium that could replace conventional toxic, flammable organic solvents. [1,2] Various chemical substances are soluble in scCO 2 and they can be easily separated by depressurization; scCO 2 is also nonflammable, nontoxic and has no gas/liquid phase boundary. The physicochemical properties of scCO 2 can be tuned within a certain range by adjusting the pressure and temperature, these also being the parameters for optimization of reactions in this solvent.Organometallic complexes are effective catalysts for various chemical transformations in conventional solvents. [3] Although homogeneous organometallic catalysis in scCO 2 is attractive, the organometallic complexes must be soluble in scCO 2 . Phosphane ligands, such as triphenylphosphane (TPP), that are often used in these complexes are less sol- [a]

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Hydroformylation of alkenes in supercritical carbon dioxide catalysed by rhodium trialkylphosphine complexes

Cited by 77 publications

References 85 publications

Advantages of the solventless hydroformylation of olefins

Advantages of the solventless hydroformylation of olefins

Hydroformylation of 1‐Octene in Supercritical Carbon Dioxide and Organic Solvents using Trifluoromethyl‐Substituted Triphenylphosphine Ligands

Hydroformylation of 1,5‐Hexadiene Catalyzed by Rhodium Complexes in Supercritical Carbon Dioxide and in Toluene: Effects of Fluorinated Phosphane Ligands and Reaction Conditions

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