Ionic Liquid-Supported Bis-(salicylaldimine) Nickel Complexes: Robust and Recyclable Catalysts for Ethylene Oligomerization in Biphasic Solvent System

Song, Keming; Gao, Haiyang; Liu, Feng-Shou; Jin, Pan; Guo, Lihua; Zai, Shaobo; Wu, Qing

doi:10.1007/s10562-009-9974-2

Cited by 19 publications

(10 citation statements)

References 36 publications

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“…Bis-(salicylaldimine)Ni(II) complexes were also evaluated for ethylene oligomerization in organochloraluminate ILs ([BMI][Cl]/AlCl 3 , 1/1 ratio with variable amounts of AlEt 2 Cl). 171 Imidazolium tags were attached to the bis-(salicylaldimine) scaffold for better solubility of the nickel complex in ILs (complexes 75-76, Figure 35). While these complexes appeared inactive in common organic solvents (toluene or heptane), they exhibited very high productivity in IL/toluene or IL/heptane biphasic mixtures with marked selectivity for C 4 -C 8 oligomers.…”

Section: Figure 33 Weakly-coordinating Ils For the Biphasic Ethylene Oligomerization Using Cationic Nicomplexesmentioning

confidence: 99%

Nickel Catalyzed Olefin Oligomerization and Dimerization

et al. 2020

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Brought to life more than half a century ago and successfully applied for high-value petrochemical intermediates production, nickel-catalyzed olefin oligomerization is still a very dynamic topic, with many fundamental questions to address and industrial challenges to overcome. The unique and versatile reactivity of nickel enables the oligomerization of ethylene, propylene and butenes into a wide range of oligomers that are highly sought-after in numerous fields to be controlled. Interestingly, both homogeneous and heterogeneous nickel catalysts have been scrutinized and employed to do this. This rare specificity encouraged us to interlink them in this review so as to open up opportunities for further catalyst development and innovation. An in-depth understanding of the reaction mechanisms in play is essential to being able to fine-tune the selectivity and achieve efficiency in the rational design of novel catalytic systems. This review thus provides a complete overview of the subject, compiling the main fundamental/industrial milestones and remaining challenges facing homogeneous/heterogeneous approaches as well as emerging catalytic concepts, with a focus on the last 10 years.

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Section: Figure 33 Weakly-coordinating Ils For the Biphasic Ethylene Oligomerization Using Cationic Nicomplexesmentioning

confidence: 99%

Nickel Catalyzed Olefin Oligomerization and Dimerization

et al. 2020

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“…[22] The stability of the catalyst could be enhanced by the use of ligands with imidazolium tags. [42] Recycling experiments showed that bis-(salicylaldimine) Ni(II) complexes bearing imidazolium moieties in the side chains (11, Figure 7) could be recycled more efficiently, retaining their catalytic activity (with TOF values of 49 h -1 -41 h -1 ) at least in three cycles of ethene oligomerization. In contrast, activity of complex 12 dropped considerably upon reuse with TOFs of 48 h -1 and 30 h -1 in the first and second batch, respectively.…”

Section: Oligomerization With Ni Catalystsmentioning

confidence: 99%

The Use of Ionic Liquids in the Oligomerization of Alkenes

Fehér¹,

Kriván²,

Eller³

et al. 2014

Oligomerization of Chemical and Biological Compounds

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“…Thus, the presence of bulky substituents in the backbone of the salicylamidinato ligand is a key requirement to generate highly active nickel catalysts for olefin polymerization . On the other hand, the use of less sterically encumbered phenoxy‐imine ligands afforded predominantly nickel catalysts for ethylene oligomerization . Selected examples are presented in Chart 1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of Ni (II) complexes supported by phenoxy/naphthoxy‐imine ligands with pendant N‐ and O‐donor groups and their use in ethylene oligomerization

Oliveira

Silva

Casagrande

et al. 2018

Applied Organom Chemis

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A series of new Ni(II) complexes of general formula Ni{ZNO} Br (2a‐i) (ZNO = phenoxy/naphthoxy‐imine with pendant N‐ and O‐donor groups) were prepared and characterized by elemental analysis, IR spectroscopy, ESI‐HRMS, and by X‐ray crystallography for 2e. In the solid state, 2e features a monomeric structure with κ3 coordination of the monoanionic naphthoxy‐imine‐quinoline ligand onto the nickel center. Upon activation with MAO, both classes of nickel catalysts were able to produce selectively 1‐butene (81.5–92.1 wt%) with turnover frequencies (TOFs) varying from 3,100 to 24,300 mol(C2H4) mol (Ni)−1 h−1. Nickel precatalysts bearing phenoxy‐imine ligands were much more active than its naphthoxy analogous under the same conditions. The use of a mixture of cocatalysts (MAO/TMA or MAO/TiBA) resulted in poor activities; however the presence of TiBA in the milieu led to a significant improvement on selectivity for 1‐hexene (25.5 wt%). Under optimized conditions ([Ni] = 10 μmol, 30 °C, oligomerization time = 5 min, 20 bar ethylene, [Al]/[Ni] = 600), precatalyst 2c led to TOF = 59,900 mol(C2H4) mol(Ni)−1 h−1 and selectivity for 1‐butene of 89.5 wt%.

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Ionic Liquid-Supported Bis-(salicylaldimine) Nickel Complexes: Robust and Recyclable Catalysts for Ethylene Oligomerization in Biphasic Solvent System

Cited by 19 publications

References 36 publications

Nickel Catalyzed Olefin Oligomerization and Dimerization

Nickel Catalyzed Olefin Oligomerization and Dimerization

The Use of Ionic Liquids in the Oligomerization of Alkenes

Synthesis and characterization of Ni (II) complexes supported by phenoxy/naphthoxy‐imine ligands with pendant N‐ and O‐donor groups and their use in ethylene oligomerization

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