Catalysis of dimerization and oligomerization reactions of lower alkenes by systems based on Ni(PPh3)2(C2H4) and Ni(PPh3) n Cl (n = 2 or 3)

Titova, Yu. Yu.; Belykh, L. B.; Рохин, А. В.; Soroka, O. G.; Schmidt, Friedrich

doi:10.1134/s0023158414010169

“…Wilke et al 52 reported nickel complexes modified by monophosphine ligands (PR 3 , R=alkyl or phenyl) for selective propylene dimerization, while the Phillips company patented (Bu 3 P) 2 Ni(II) complexes which are highly selective for the dimerization of ethylene to 2-butenes. 26 Recently, Schmidt et al 66 described the reactivity of nickel (0) and nickel (I) pre-catalysts carrying monophosphine ligands (PPh 3 ) in the presence of a Brønsted acid or Lewis acid for the oligomerization of ethylene. The nickel (0) complex Ni(PPh 3 ) 2 (C 2 H 4 ) as a single component catalyst is slightly active in the dimerization of ethylene, whereas nickel(I) complexes Ni(PPh 3 ) 2 Cl and Ni(PPh 3 ) 3 Cl are inactive.…”

Section: Neutral Monophosphine Ligandsmentioning

confidence: 99%

“…427 Based on a 429 Increase of Brønsted acid content and its effect over time, from the reaction of BF 3 .Et 2 O with water (as a solvent impurity), was demonstrated in a more detailed study. 66 A complementary study carried out on phosphine-and diimine-based nickel complexes with various oxidation states (0, +1 and +2) associated with Lewis acid consolidated the role of Ni(II) hydride as an active catalyst, with the oxidation of Ni(0) species and disproportionation of Ni(I) being emphasized. 67 Active site identification in heterogeneous catalysis 6.3.2 Compared with homogeneous catalysis, the identification of Ni active sites responsible for ethylene oligomerization and the determination of which mechanism occurs with Ni-based heterogeneous catalysts has witnessed few comprehensive studies.…”

Section: Third Class Of Catalytic Systems : Single Site Organometallic Complexesmentioning

confidence: 99%

“…Recently, Schmidt et al66 described the reactivity of nickel(0) and nickel(I) precatalysts carrying monophosphine ligands (PPh 3 ) in the presence of a Brønsted acid or Lewis acid for the oligomerization of ethylene. The nickel(0) complex Ni-(PPh 3 ) 2 (C 2 H 4 ) as a single component catalyst is slightly active in the dimerization of ethylene, whereas nickel(I) complexes Ni(PPh 3 ) 2 Cl and Ni(PPh 3 ) 3 Cl are inactive.…”

mentioning

confidence: 99%

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Nickel Catalyzed Olefin Oligomerization and Dimerization

Olivier‐Bourbigou

¹

,

Breuil

²

,

Magna

³

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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“…The diethylaluminium chloride (Et2AlCl) easily alkylates nickel that results in the fast formation of active centers. At the same time it possesses lower Lewis acidity, compared to Et3Al2Cl3, that results in the better stabilization of nickel hydride complexes, which are considered to be the catalytically active species [85][86][87]. The maximum catalytic activity was achieved for catalytic systems based on complex 1 ( correspondingly.…”

Section: Ethylene Oligomerization and Friedel-crafts Alkylation Of Tomentioning

confidence: 99%

Trapping the Short-Chain Odd Carbon Number Olefins Using Nickel(II)-catalyzed Tandem Ethylene Oligomerization and Friedel-Crafts Alkylation of Toluene

Zubkevich¹,

Тuskaev²,

Гагиева³

et al. 2020

Preprint

0

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<div>Nickel(II) complexes with pyrazole-based ligands are widely employed in catalysis of ethylene</div><div>oligomerization and subsequent Friedel-Crafts alkylation of toluene. We have prepared ten new</div><div>nickel(II) dibromide complexes with various substituted bis(azolyl)methanes. They have been</div><div>characterized using <sup>1</sup>H NMR, IR, MALDI-TOF and elemental analysis. The structures of three</div><div>complexes have been unambiguously established using X-ray diffraction. It was found that these</div><div>complexes in the presence of Et<sub>2</sub>AlCl or Et<sub>3</sub>Al<sub>2</sub>Cl<sub>3</sub> are active both in ethylene oligomerization and</div><div>Friedel-Crafts alkylation processes (activity up to 3720 kgoligomer·mol[Ni]<sup>−1</sup>·h<sup>−1</sup>). The use of Et<sub>3</sub>Al<sub>2</sub>Cl<sub>3</sub></div><div>results in the higher share of alkylated products (up to 60%). Moreover, catalytic systems activated with</div><div>Et<sub>3</sub>Al<sub>2</sub>Cl<sub>3</sub> produced small amounts of odd carbon number olefins (up to 0.8%). The Friedel-Crafts</div><div>alkylation was used as a trap for previously undetected short-chain odd carbon number olefins (C<sub>3</sub> and</div><div>C<sub>5</sub>).</div>

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“…The diethylaluminium chloride (Et2AlCl) easily alkylates nickel that results in the fast formation of active centers. At the same time it possesses lower Lewis acidity, compared to Et3Al2Cl3, that results in the better stabilization of nickel hydride complexes, which are considered to be the catalytically active species [85][86][87]. The maximum catalytic activity was achieved for catalytic systems based on complex 1 (Table 2, runs 1-2) -3160 и 3720 kg•mol[Ni] -1 •h -1 after treatment with Et2AlCl or Et3Al2Cl3 correspondingly.…”

Section: Ethylene Oligomerization and Friedel-crafts Alkylation Of Toluenementioning

confidence: 99%

Trapping the Short-Chain Odd Carbon Number Olefins Using Nickel(II)-catalyzed Tandem Ethylene Oligomerization and Friedel-Crafts Alkylation of Toluene

Zubkevich

¹

,

Тuskaev²,

Гагиева³

et al. 2020

Preprint

1

0

View full text Add to dashboard Cite

<div>Nickel(II) complexes with pyrazole-based ligands are widely employed in catalysis of ethylene</div><div>oligomerization and subsequent Friedel-Crafts alkylation of toluene. We have prepared ten new</div><div>nickel(II) dibromide complexes with various substituted bis(azolyl)methanes. They have been</div><div>characterized using <sup>1</sup>H NMR, IR, MALDI-TOF and elemental analysis. The structures of three</div><div>complexes have been unambiguously established using X-ray diffraction. It was found that these</div><div>complexes in the presence of Et<sub>2</sub>AlCl or Et<sub>3</sub>Al<sub>2</sub>Cl<sub>3</sub> are active both in ethylene oligomerization and</div><div>Friedel-Crafts alkylation processes (activity up to 3720 kgoligomer·mol[Ni]<sup>−1</sup>·h<sup>−1</sup>). The use of Et<sub>3</sub>Al<sub>2</sub>Cl<sub>3</sub></div><div>results in the higher share of alkylated products (up to 60%). Moreover, catalytic systems activated with</div><div>Et<sub>3</sub>Al<sub>2</sub>Cl<sub>3</sub> produced small amounts of odd carbon number olefins (up to 0.8%). The Friedel-Crafts</div><div>alkylation was used as a trap for previously undetected short-chain odd carbon number olefins (C<sub>3</sub> and</div><div>C<sub>5</sub>).</div>

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Catalysis of dimerization and oligomerization reactions of lower alkenes by systems based on Ni(PPh3)2(C2H4) and Ni(PPh3) n Cl (n = 2 or 3)

Cited by 9 publications

References 28 publications

Nickel Catalyzed Olefin Oligomerization and Dimerization

Nickel Catalyzed Olefin Oligomerization and Dimerization

Trapping the Short-Chain Odd Carbon Number Olefins Using Nickel(II)-catalyzed Tandem Ethylene Oligomerization and Friedel-Crafts Alkylation of Toluene

Trapping the Short-Chain Odd Carbon Number Olefins Using Nickel(II)-catalyzed Tandem Ethylene Oligomerization and Friedel-Crafts Alkylation of Toluene

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