Pd(II)-dissolved in ionic liquids: a recyclable catalytic system for the selective biphasic hydrogenation of dienes to monoenes

Dupont, Jaı̈rton; Suarez, Paulo A. Z.; Umpierre, Alexandre P.; Souza, Roberto Fernando de

doi:10.1590/s0103-50532000000300016

Cited by 62 publications

(38 citation statements)

References 8 publications

(12 reference statements)

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“…Work by Dupont and co-workers [11] using Pd(acac) 2 dissolved in the ionic liquid 1-n-butyl-3-methylimidazolium tetrafluoroborate (BMIM.BF 4 ) resulted in the hydrogenation of simple and functionalized dienes to their corresponding monoolefins at 50 8C and 5 -20 atm in selectivities ranging from 93 to 100%. Kaneda and co-workers demonstrated that the dendrimer-bound palladium complex of phosphonated poly(propyleneimine) can selectively hydrogenate conjugated cyclic dienes to monoolefins.…”

Section: Introductionmentioning

confidence: 99%

Silica-Supported Dendrimer-Palladium Complex-Catalyzed Selective Hydrogenation of Dienes to Monoolefins

Zweni

Alper

2006

Adv. Synth. Catal.

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Section: Introductionmentioning

confidence: 99%

Silica-Supported Dendrimer-Palladium Complex-Catalyzed Selective Hydrogenation of Dienes to Monoolefins

Zweni

Alper

2006

Adv. Synth. Catal.

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“…These results contrast with those obtained using [Pd(acac) 2 ] as catalyst precursor, where no changes on selectivity was observed by changing the ionic liquid. 18 As shown in Table 3 other transition metal acetylacetonates complexes are also able to hydrogenate 1,3-butadiene under relatively mild reaction conditions. As observed in the hydrogenation reactions with [Co(acac) 2 ], the separation of the products from the reaction mixture can be performed by simple decantation and the recovered ionic catalyst solution can be reused without any significant changes in activity or selectivity.…”

mentioning

confidence: 97%

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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“…The Pd-catalyzed hydrogenation of dienes to mono-hydrogenated olefins was effectively obtained in ILs. 178 The 6 ] was derived from a common phase transfer catalyst Aliquat 336. It was observed that the selectivity profiles of citral hydrogenation can be efficiently influenced not only by varying the transition metal species in line with classical catalysis and the experimental conditions (temperature, pressure), but also by the choice of the ionic liquid in which the transition metal species is dissolved.…”

Section: Hydrogenationmentioning

confidence: 99%

Ionic liquids: a versatile medium for palladium-catalyzed reactions

Singh¹,

Sharma²,

Mamgain³

et al. 2008

J. Braz. Chem. Soc.

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Um grande número de reações de formação de ligações carbono-carbono (tais como: acoplamentos de Heck, Suzuki, Stille, Negishi e Sonogashira, entre outros) é facilitado pela catálise com compostos de paládio. Neste artigo de revisão, apresentamos uma visão detalhada e compreensiva da literatura sobre a versatilidade do uso de líquidos iônicos em conjunto com paládio em vários tipos de reações.A number of carbon-carbon bond forming reactions in organic chemistry (such as the Heck, Suzuki, Stille, Negishi, Sonogashira coupling etc) are facilitated by catalysis with palladium compounds. An attempt has been made to present a detailed and comprehensive literature collection about the versatility of ionic liquid in conjunction with palladium for various types of reactions.

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Pd(II)-dissolved in ionic liquids: a recyclable catalytic system for the selective biphasic hydrogenation of dienes to monoenes

Cited by 62 publications

References 8 publications

Silica-Supported Dendrimer-Palladium Complex-Catalyzed Selective Hydrogenation of Dienes to Monoolefins

Silica-Supported Dendrimer-Palladium Complex-Catalyzed Selective Hydrogenation of Dienes to Monoolefins

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

Ionic liquids: a versatile medium for palladium-catalyzed reactions

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