Ionic liquids in regioselective platinum-catalysed hydroformylation

Wasserscheid, Peter; Waffenschmidt, Horst

doi:10.1016/s1381-1169(00)00259-4

Cited by 100 publications

(37 citation statements)

References 22 publications

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“…Various organic reactions are successfully carried out in ionic liquids. Additionally, they are used as reaction media in reactions with transition metals such as oxidation [4,5], hydrogenation [6,7], hydroformylation [8,9], oligomerization [10,11], and so on [12,13]. Chauvin 2 ]PF 6 (nbd = norbornadiene) complex and reported a higher activity than that in acetone media [14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Catalytic Hydrogenation Activity of New N-Acyl-Benzotriazole Rh(I) and Ru(III) Complexes in [bmim][BF4]

Ünver

Yılmaz

2016

Catalysts

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Abstract:The hydrogenation activity of new N-acyl-benzotriazole Rh(I) and Ru(III) complexes in ionic liquid media is reported in this study. Both complexes were completely soluble in 1-butyl-3-methylimidazolium tetrafluoroborate, [bmim][BF 4 ], and they were able to catalyze the hydrogenation of styrene and 1-octene. While ethylbenzene conversion in styrene hydrogenation reached 84% when the Ru complex was used, 100% conversion was obtained with the Rh complex at 393 K in 6 h. Additionally, total conversion in 1-octene hydrogenation reached 100% with the Rh complex in [bmim] [BF 4 ] media. The hydrogenation of styrene and 1-octene in dimethyl sulfoxide (DMSO) and toluene was also studied to compare the solvent effect on catalytic system. The effect of some catalytic parameters such as temperature, H 2 (g) pressure, and catalyst amount on the conversion was examined, and it was found that the conversion increased parallel to the increasing temperature and H 2 pressure. The recyclability of catalysts was also investigated, and it was revealed that the Rh complex in particular maintained the activity for at least 10 cycles.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Catalytic Hydrogenation Activity of New N-Acyl-Benzotriazole Rh(I) and Ru(III) Complexes in [bmim][BF4]

Ünver

Yılmaz

2016

Catalysts

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“…1-Butyl-3-methyl-imidazolium tetrafluoroborate [bmim]BF 4 and 1-butyl-3-methyl-imidazolium hexafluorophospate [bmim]PF 6 were synthesized using the procedures reported in the previous literature [15][16][17][18][19][20] and were vacuum-treated before each use. Dimethyl itaconate and (R)-BINAP were purchased from Aldrich and used as-received without further purification.…”

Section: Methodsmentioning

confidence: 99%

Catalytic performance of chiral rhodium complex with water-soluble sulfonated (R)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl for enantioseletive hydrogenation in ionic liquid biphasic system

She

Zhu

et al. 2007

Catal Lett

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Asymmetric hydrogenation of dimethyl itaconate by the chiral rhodium complex ligated with water-soluble sulfonated (R)-2,2¢-bis(diphenylphosphino)-1,1¢-binaphthyl (labeled as (R)-BINAPS) was performed in ionic liquid-isopropanol biphasic catalytic system. A moderate enantiomeric excess (ee) of 64% and initial turnover frequency (TOF max ) as high as 1234 h )1 could be obtained at 303 K and 2.0 MPa when the molar ration of substrate to rhodium was set at 1000. Application of imidazolium ionic liquid [bmim]BF 4 (bmim = 1-butyl-3-methyl imidazolium cation) made it possible to reuse the catalyst several times, showing rather good stability in the catalyst performance. According to the ICP-OES analyses, the total extraction of rhodium species by the reactants from the ionic liquid phase was about 3.24 wt% after the catalyst for four runs, which was about three times lower than that of total loss of phosphorous species. The slight decreases in the ee value and TOF max during the catalyst reuse could be recovered essentially to the pristine levels by replenishing certain amount of the fresh ligand into the used catalyst.

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“…[27] All Pt(II) catalysts reported were monomeric chloro derivatives bearing a diphosphine or two monophosphines or other ligands [28] activated with SnCl 2 always tested in organic media or in ionic liquids. [29] The role of tin chloride is still incompletely understood, [30] although it is assumed that the À SnCl 3 moiety formed by interaction with Pt À Cl is more labile compared to À Cl itself and can be easily displaced giving access to substrate interaction with Pt.…”

Section: Introductionmentioning

confidence: 99%

Efficient Platinum(II) Catalyzed Hydroformylation Reaction in Water: Unusual Product Distribution in Micellar Media

et al. 2010

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The hydroformylation of a variety of terminal and internal alkenes is efficiently performed by cationic platinum triflate complexes of the type With styrene derivatives also the corresponding benzaldehydes are formed. The catalyst can be separated by extraction of the organic products with hexane and recycled for at least four times with only a modest loss of activity and no effect on selectivity.

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Ionic liquids in regioselective platinum-catalysed hydroformylation

Cited by 100 publications

References 22 publications

Synthesis, Characterization, and Catalytic Hydrogenation Activity of New N-Acyl-Benzotriazole Rh(I) and Ru(III) Complexes in [bmim][BF4]

Synthesis, Characterization, and Catalytic Hydrogenation Activity of New N-Acyl-Benzotriazole Rh(I) and Ru(III) Complexes in [bmim][BF4]

Catalytic performance of chiral rhodium complex with water-soluble sulfonated (R)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl for enantioseletive hydrogenation in ionic liquid biphasic system

Efficient Platinum(II) Catalyzed Hydroformylation Reaction in Water: Unusual Product Distribution in Micellar Media

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