Two-phase catalytic hydrogenation of olefins by Ru(II) and Co(II) complexes dissolved in 1-n-butyl-3-methylimidazolium tetrafluoroborate ionic liquid

Suarez, Paulo A. Z.; Dullius, Jeane E.L.; Einloft, Sandra; Souza, Roberto Fernando de; Dupont, Jaı̈rton

doi:10.1016/s0020-1693(96)05363-7

Cited by 103 publications

(61 citation statements)

References 8 publications

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“…A key advantage of ionic liquids is that homogeneous transition-metal catalysts can be used and the products of the reaction can be easily separated from the ionic liquid and catalyst [2]. Examples of this include the hydrogenation of cyclohexene [29], and the complete hydrogenation of benzene rings [30]. Recently, asymmetric hydrogenation reactions have appeared.…”

Section: Reactions In Neutral Ionic Liquidsmentioning

confidence: 99%

Ionic liquids. Green solvents for the future

Earle

Seddon

2000

Pure and Applied Chemistry

2,615

1,325

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Section: Reactions In Neutral Ionic Liquidsmentioning

confidence: 99%

Ionic liquids. Green solvents for the future

Earle

Seddon

2000

Pure and Applied Chemistry

2,615

1,325

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“…8 In these reactions, the catalysts maintain their molecular properties and achieve catalytic activities and selectivities similar to those obtained from the same catalyst precursors in homogeneous media. Indeed, oligomerization, 9-12 hydroformylation, 13 hydrogenation [13][14][15][16] , immobilized in 1-butyl-3-methyl imidazolium based molten salts are able to hydrogenate 1,3-butadiene into butenes in typical two-phase catalytic reactions under mild reaction conditions. Moreover, we present here kinetic and thermodynamic studies which evidence that, for the first time in this area, the reaction occurs preferentially in the ionic liquid catalyst solution.…”

Section: Introductionmentioning

confidence: 99%

Selective hydrogenation of 1,3-butadiene by transition metal compounds immobilized in 1-butyl-3-methyl imidazolium room temperature ionic liquids

Consorti¹,

Umpierre²,

Souza³

et al. 2003

J. Braz. Chem. Soc.

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Os complexos [Co(acac) 2 ], [Co(acac) 3 ], [Fe(acac) 3 ] e [Ni(acac) 2 ] (acac = acetilacetonato) dissolvidos em tetrafluoroborato de 1-butil-3-metilimidazônio (1), trifluorometanosulfonato de 1-butil-3-metilimidazólio (2) ou hexafluorofosfato de 1-butil-3-metilimidazólio (3), catalisam a hidrogenação de 1,3-butadieno em butenos em sistema catalítico tipicamente bifásico. A conversão do 1,3-butadieno, a seletividade e a freqüência de rotação (TOF) são fortemente dependentes do metal de transição e do líquido iônico. Para [Co(acac) 2 ] dissolvido em 1, estudos cinéticos sugerem que a reação ocorre no meio líquido iônico, com uma energia aparente de ativação de of 33.8 kJ mol -1 . A solução iônica do catalisador pode ser recuperada e reutilizada várias vezes sem mudanças perceptíveis na atividade e seletividade da reação.The compounds [Co(acac) 2 ], [Co(acac) 3 ], [Fe(acac) 3 ] and [Ni(acac) 2 ] (acac = acetylacetonate) dissolved in 1-butyl-3-methyl imidazolium tetrafluoroborate (1), trifluoromethanesulphonate (2) or hexafluorophosphate (3) catalyze the reduction of 1,3-butadiene into butenes in a typical two-phase catalytic reaction. The 1,3-butadiene conversion, the selectivity and turnover frequencies (TOF) are strongly dependent on the nature of the transition metal catalyst precursor and the ionic liquid. For [Co(acac) 2 ] dissolved in 1, kinetic studies strongly suggest that the reaction takes place in the ionic solution bulk, having an apparent activation energy for the overall process of 33.8 kJ mol -1 . The recovered ionic catalyst solution can be reused several times without any significant changes on activity and selectivity. Keywords: biphasic hydrogenation, ionic liquids, dienes, cobalt catalysts IntroductionThe hydrogenation of dienes to mono-olefins has several potentially useful applications in industry. In applications where only moderate selectivity is required heterogeneous catalysts excel due to their easy separability from reaction products by decantation or filtration, and the catalyst can be recycled. 1-5 Transition metal catalyst precursors are known to hydrogenate dienes to olefins under homogeneous conditions. 1,2 In these cases, however, C=C bond isomerization reactions are also operative decreasing the selectivity to hydrogenation products. 6 Moreover, the separation of the products from the reaction mixture and recovery of the catalyst represent disadvantages of these homogeneous catalytic reactions. [3][4][5] The catalytic system formed by dissolving cobalt cyanide in water is highly specific and active (compared with the homogeneous systems) for the hydrogenation of conjugated dienes. 7 Given the restriction that the cobalt catalyst is rapidly deactivated, this aqueous system remains the best catalyst for the hydrogenation of dienes as far as selectivity is concerned.Room temperature molten salts (or ionic liquids) have been demonstrated to be the immobilizing agents of choice for various organometallic catalyst precursors. 8 In these reactions, the catalysts maintain their m...

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“…Ionic liquids were synthezised according to published procedures [13]. Carbon dioxide (> 99.97 %) was supplied by Carbagas and used as received.…”

Section: Methodsmentioning

confidence: 99%

“…The concentration of dissolved CO 2 was determined after equilibration by 13 C NMR spectroscopy by integrating the 13 C NMR signal of the dissolved CO 2 against various 13 C NMR signals of the ionic liquid, as described previously for CO. NMR spectra were recorded on a Bruker DRX 400 MHz NMR spectrometer. TMS, phosphoric acid (50 %) and KF (1 M solution in D 2 O) were used as external references for 1 H, 13 C, 31 P, and 19 F NMR measurements, respectively. Spectra were fitted using the NMRICMA 2.8 software (non-linear least-squares iterative fitting application for the MatLab program).…”

Section: Methodsmentioning

confidence: 99%

Determination of the Viscosity of the Ionic Liquids [bmim][PF₆] and [bmim][TF₂N] Under High CO₂ Gas Pressure Using Sapphire NMR Tubes

Laurenczy

Dyson

2008

Zeitschrift Für Naturforschung B

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Two-phase catalytic hydrogenation of olefins by Ru(II) and Co(II) complexes dissolved in 1-n-butyl-3-methylimidazolium tetrafluoroborate ionic liquid

Cited by 103 publications

References 8 publications

Ionic liquids. Green solvents for the future

Ionic liquids. Green solvents for the future

Selective hydrogenation of 1,3-butadiene by transition metal compounds immobilized in 1-butyl-3-methyl imidazolium room temperature ionic liquids

Determination of the Viscosity of the Ionic Liquids [bmim][PF₆] and [bmim][TF₂N] Under High CO₂ Gas Pressure Using Sapphire NMR Tubes

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Two-phase catalytic hydrogenation of olefins by Ru(II) and Co(II) complexes dissolved in 1-n-butyl-3-methylimidazolium tetrafluoroborate ionic liquid

Cited by 103 publications

References 8 publications

Ionic liquids. Green solvents for the future

Ionic liquids. Green solvents for the future

Selective hydrogenation of 1,3-butadiene by transition metal compounds immobilized in 1-butyl-3-methyl imidazolium room temperature ionic liquids

Determination of the Viscosity of the Ionic Liquids [bmim][PF6] and [bmim][TF2N] Under High CO2 Gas Pressure Using Sapphire NMR Tubes

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Determination of the Viscosity of the Ionic Liquids [bmim][PF₆] and [bmim][TF₂N] Under High CO₂ Gas Pressure Using Sapphire NMR Tubes