Oligomerization of olefins in a chloroaluminate ionic liquid

Stenzel, O.; Brüll, Robert; Wahner, Udo M.; Sanderson, Ronald D.; Raubenheimer, Helgard G.

doi:10.1016/s1381-1169(02)00450-8

Cited by 49 publications

(21 citation statements)

References 37 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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“…The buffer fully suppressed uncontrolled cationic oligomerization reactions, which are usually initiated by acidic chloroaluminate melts. [10] Due to mass transfer limitations, [13d] the term "activity" was replaced by "productivity". Thus, above a catalyst concentration of about 10 À6 mol/g ionic liquid , [14a] the product yield per hour is proportional to the amount of ionic liquid and independent from the catalyst concentration.…”

Section: Resultsmentioning

confidence: 99%

“…[9] Ethylaluminum groups were found to suppress uncontrolled cationic olefin oligomerization reactions, which occur in solely AlCl 3 -based ionic liquids. [10] The IFPEN …”

Section: Introductionmentioning

confidence: 99%

Nickel‐Catalyzed Propene Dimerization Reactions in Triphenylbismuth‐Buffered Chloroaluminate Ionic Liquids: High Performance with Unconventional Cations

Dötterl

Alt

2012

Adv Synth Catal

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The addition of triphenylbismuth (BiPh 3 ) efficiently buffers Lewis acidic chloroaluminate ionic liquids over a wide range of compositions. Since the melting points of these ternary mixtures are lower compared to unbuffered chloroaluminate systems, the scope of cations for the formation of buffered room temperature ionic liquids is greatly extended. The buffered ionic liquids were used to activate nickel complexes for selective biphasic propene dimerization reactions. Lifetimes, selectivities and productivities of such dimerization catalysts could be adjusted by the choice of the cation and the composition. At lower reaction temperatures, the selectivities to give dimers increased significantly. Propene dimers were obtained with selectivities of up to 98%. A cation screening with 100 ammonium and phosphonium halide salts was performed. N-Methylpyrrolidine hydrochloride gave the best results in terms of selectivity and lifetime. Propene dimerization reactions in BiPh 3 -buffered chloroaluminate melts were catalyzed by various soluble nickel compounds with similar performances. The introduction of basic, sterically demanding tricyclohexylphosphine ligands led to higher degrees of branching, however, at the expense of lower dimer selectivities.

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“…On the other hand, superacidic protons (Bronsted acid) also existed in [BMIm]Cl Á 2AlCl 3 due to the hydrolysis of a few AlCl 3 molecules [3,27]. Oligomerizing of olefins to dimmers, trimers and tetramers could be catalyzed by Lewis acidic chloroaluminate ionic liquid when the formation of superacidic protons was restrained [28]. That the superacidic proton in Lewis acidic ionic liquid was considered as the active species in the dimerization reaction has also been reported [3].…”

Section: Reusing Of [Hexmim]bf 4 -Hbfmentioning

confidence: 91%

Study on Selective Dimerization of α-Methylstyrenes Promoted by Ionic Liquids

Shen

et al. 2008

Catal Lett

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The catalytic systems composed of ionic liquids containing BF 4 -anion and HBF 4 showed high catalytic activity to produce 4-methyl-2,4-diphenyl-1-pentene (MDP-1) or 1,1,3-trimethyl-3-phenylindan (TPI) under different temperature conditions. Up to 90.8% selectivity to MDP-1 with a 98.7% conversion of a-methylstyrene was obtained at 60°C in the presence of [HexMIm]BF 4 -HBF 4 , while exclusive TPI was yielded when the reaction temperature increased to 120°C. Further studies showed that another ionic liquid, [BMIm]Cl Á 2AlCl 3 , could act as an excellent catalyst and solvent for the dimerization of a-methylstyrene to produce TPI. The dimerization of a-methylstyrene catalyzed by [HexMIm]BF 4 -HBF 4 and [BMIm]Cl Á 2AlCl 3 performed the same reaction mechanism and the proton was the active species.

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Oligomerization of olefins in a chloroaluminate ionic liquid

Cited by 49 publications

References 37 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]

Nickel‐Catalyzed Propene Dimerization Reactions in Triphenylbismuth‐Buffered Chloroaluminate Ionic Liquids: High Performance with Unconventional Cations

Study on Selective Dimerization of α-Methylstyrenes Promoted by Ionic Liquids

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