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Ligand, oligomerization catalyst comprising same, and method for producing ethylene oligomer by using oligomerization catalyst

一种乙烯低聚物、乙烯低聚的技术,应用在催化剂、有机化合物/氢化物/配位配合物催化剂、碳化合物催化剂等方向,能够解决产量和选择性降低、堵塞和结垢、催化活性降低等问题,达到催化活性和选择性优异、节省成本、催化活性优异的效果

Active Publication Date: 2020-05-01
SK INNOVATION CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Specifically, in the case of tetramerization catalyst systems, the catalytic activity decreases at high temperatures, which leads to a decrease in the yield and selectivity of olefins, especially 1-octene
In addition, clogging and fouling occur due to increased generation of by-products, which inevitably lead to downtime
As a result, serious problems arose during the polymerization of olefins

Method used

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  • Ligand, oligomerization catalyst comprising same, and method for producing ethylene oligomer by using oligomerization catalyst
  • Ligand, oligomerization catalyst comprising same, and method for producing ethylene oligomer by using oligomerization catalyst
  • Ligand, oligomerization catalyst comprising same, and method for producing ethylene oligomer by using oligomerization catalyst

Examples

Experimental program
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Embodiment approach

[0114] According to an exemplary embodiment of the present invention, organoaluminoxanes suitable for use as activators in ethylene oligomerization catalyst compositions are oligomeric aluminoxanes which can be prepared by adding water to an aluminum alkyl compound such as trimethylaluminum. compound. The resulting aluminoxane oligomeric compounds may be linear, cyclic or cage compounds, or mixtures thereof.

[0115] The organoaluminoxane may be selected from alkylaluminoxanes such as methylaluminoxane (MAO), ethylaluminoxane (EAO), tetraisobutylaluminoxane (TIBAO) and isobutylaluminoxane ( IBAO), may also be selected from modified alkylaluminoxanes, such as modified methylaluminoxane (MMAO). Modified methylalumoxanes (manufactured by Akzo Nobel N.V.) contain mixed alkyl groups such as isobutyl or n-octyl groups in addition to methyl groups. As a specific example, the organoaluminoxane may be selected from methylalumoxane (MAO), modified methylalumoxane (MMAO), ethylalumoxan...

preparation example A

[0133] [Preparation Example A] Preparation of chloro(2-fluorophenyl)phenylphosphine

[0134]

[0135] Preparation of N,N-Diethylaminochloro(phenyl)phosphine

[0136] N,N-Diethylaminochloro(phenyl)phosphine was prepared by referring to known literature (M.Oliana et.al., J.Org.Chem., 2006, p.2472-2479).

[0137] In a dry flask under nitrogen atmosphere, dichloro(phenyl)phosphine (8.949 g, 50 mmol) was dissolved in n-hexane (400 mL), then diethylamine (7.314 g, 100 mmol) was added slowly at room temperature. The mixture was reacted for more than 1 hour, and then filtered through celite under reduced pressure to remove volatile materials, thereby obtaining the title compound (10.2 g, 94.6%) as a clear colorless liquid.

[0138] 1 H NMR (500MHz, C 6 D. 6 )δ7.74 (m, 2H, aromatic compounds), 7.10 (m, 2H, aromatic compounds), 7.03 (m, 1H, aromatic compounds), 2.85 (m, 4H, -CH 2 -),0.79(m,6H,-CH 3 ).

[0139] Preparation of N,N-diethyl-1-(2-fluorophenyl)-1-phenylphosphinea...

preparation example B

[0145] [Preparation Example B] Preparation of (2-fluorophenyl) (phenyl) phosphine

[0146]

[0147] In a dry flask under a nitrogen atmosphere, the chloro(2-fluorophenyl)phenylphosphine (2.3863 g, 10 mmol) obtained in Preparation A was dissolved in n-hexane (20 mL), and then trimethyltin hydride was slowly added (4.0163 g, 11 mmol). The mixture was reacted for 30 minutes, and then filtered through celite under reduced pressure to remove volatile materials to obtain the title compound (2.0418 g, 100%) as a liquid.

[0148] 1 H NMR (500MHz, C 6 D. 6 )δ7.37 (m, 2H, aromatic compounds), 7.11 (m, 1H, aromatic compounds), 6.97 (m, 3H, aromatic compounds), 6.80 (m, 1H, aromatic compounds), 6.68 (m , 1H, aromatic compounds), 5.51-5.07 (d, 1H, -P).

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Abstract

The present invention relates to a ligand, an ethylene oligomerization catalyst comprising same, and a method for selectively producing 1-hexene or 1-octene from ethylene by using the catalyst. The ligand according to the present invention is a bis (diphenylphosphino) ethane with a phosphorus atom substituted with a fluoro-substituted phenyl, and when the ligand is used for ethylene oligomerization, the high temperature activity of the catalyst can be increased.

Description

technical field [0001] The present invention relates to ligands for the preparation of highly active and highly selective ethylene oligomerization catalysts for use in oligomerization reactions of ethylene such as trimerization or tetramerization, oligomerization catalysts comprising the ligands and by using the oligomerization Catalyst for the preparation of 1-hexene or 1-octene. Background technique [0002] Oligomers, specifically 1-hexene or 1-octene, are important commercial raw materials that are widely used as monomers or comonomers in polymerization processes to produce linear low-density polyethylene, which are purified by Obtained as a product of the oligomerization of ethylene. However, conventional ethylene oligomerization has the disadvantage of producing large amounts of butenes, higher oligomers and polyethylene together with 1-hexene or 1-octene. In such conventional ethylene oligomerization techniques, generally, various α-olefins are produced according to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/50B01J31/24B01J31/14C07C2/32C07C11/02C07C11/04
CPCY02P20/52B01J31/14C07F9/5027C07F11/005C07C2531/14C07C2531/24C07C2/36B01J2231/20B01J2531/62B01J2540/22B01J31/2409C07C11/02C07C11/107C07F9/5022C07F9/5045B01J31/2404B01J31/143C07C2/32B01J2531/64C07C11/04B01J31/12B01J31/24C07F9/50
Inventor 李豪晟赵镛男
Owner SK INNOVATION CO LTD
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