Alpha-diimine nickel (II) olefin polymerization catalyst as well as preparation method and application thereof

A technology for the polymerization of nickel diimide and olefin, which is applied in the polymer field and can solve problems such as affecting the development of ethylene polymerization catalysis.

Inactive Publication Date: 2011-05-18
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the development of ethylene polymerization catalysis has been hampered by the fact that late transition metals are prone to β-hydrogen elimination reactions.

Method used

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  • Alpha-diimine nickel (II) olefin polymerization catalyst as well as preparation method and application thereof
  • Alpha-diimine nickel (II) olefin polymerization catalyst as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Synthesis of 2-methyl-4-phenylaniline: Palladium acetate (0.06mmol, 0.0135g), phenylboronic acid (4.5mmol, 0.5487g), 4-bromo-2-methylaniline (3mmol, 0.5582g) and potassium carbonate (6mmol, 0.8293g) were added to 5mL of polyethylene glycol-400 solvent, reacted at room temperature for 24 hours, extracted with ether after the reaction, the extract was dried with anhydrous magnesium sulfate, filtered and concentrated Afterwards, 0.5122 g of 2-methyl-4-phenylaniline was obtained by silica gel column chromatography, and the yield was 93.16%. 1 H NMR (400MHz, CDCl 3 ): δ=2.28(s, 3H), 3.69(s, 2H), 6.79(d, J = 8.0Hz, 1H), 7.34(m, 3H), 7.46(m, 2H), 7.61(m, 2H); 13 C NMR (400 MHz, CDCl 3 ): δ=17.47, 115.18, 122.48, 125.58, 126.09, 126.38, 128.56, 129.15, 131.57, 141.27, 144.03.

[0026] (2) Ligand (4-Ph-2-MePh) 2 Synthesis of DABAn: 0.4581g (2.5mmol) of 2-methyl-4-phenylaniline and 0.2277g (1.25mmol) of acenaphthenequinone were dissolved in 20mL of anhydrous methanol, a...

Embodiment 2

[0031] (1) Synthesis of 2-ethyl-4-phenylaniline: palladium acetate (0.06mmol, 0.0135g), phenylboronic acid (4.5mmol, 0.5487g), 4-bromo-2-ethylaniline (3mmol, 0.6002g) and potassium carbonate (6mmol, 0.8293g) were added to 5mL polyethylene glycol-400 solvent, reacted at room temperature for 24 hours, extracted with ether after the reaction, the extract was dried with anhydrous magnesium sulfate, filtered and concentrated Afterwards, 0.5364 g of 2-ethyl-4-phenylaniline was obtained by silica gel column chromatography, and the yield was 90.64%. 1 H NMR (400MHz, CDCl 3 ): δ = 1.34(t, 3H), 2.62(q, J =7.6Hz, 2H), 3.68(s, 2H), 6.78(d, J = 8.0Hz, 1H), 7.34(m, 3H), 7.44(m, 2H), 7.58(m, 2H); 13 C NMR (400 MHz, CDCl 3 ): δ=13.03, 24.14, 115.65, 125.46, 126.11, 126.44, 127.18, 128.24, 128.57, 131.77, 141.45, 143.45.

[0032] (2) Ligand (4-Ph-2-EtPh) 2 Synthesis of DABAn: 0.4931g (2.5mmol) of 2-ethyl-4-phenylaniline and 0.2277g (1.25mmol) of acenaphthenequinone were dissolved in 20...

Embodiment 3

[0037] (1) Synthesis of 2,6-dimethyl-4-phenylaniline: palladium acetate (0.06mmol, 0.0135g), phenylboronic acid (4.5mmol, 0.5487g), 2,6-dimethyl-4- Bromo-aniline (3mmol, 0.6002g) and potassium carbonate (6mmol, 0.8293g) were added to 5mL of polyethylene glycol-400 solvent, reacted at room temperature for 24 hours, extracted with ether after the reaction, and the extract was washed with anhydrous sulfuric acid Dried over magnesium, filtered, concentrated and separated by silica gel column chromatography to obtain 0.5386 g of 2,6-dimethyl-4-phenylaniline. The yield was 91.01%. 1 H NMR (400MHz, CDCl 3 ): δ=2.15(s, 6H), 3.54(s, 2H), 7.13(m, 3H), 7.30(m, 2H), 7.47(m, 2H); 13 C NMR (400 MHz, CDCl 3 ): δ=17.37, 121.91, 125.99, 126.43, 126.95, 128.52, 130.92, 141.43, 142.24.

[0038] (2) Ligand (4-Ph-2,6-MePh) 2 Synthesis of DABAn: 0.4933g (2.5mmol) of 2,6-dimethyl-4-phenylaniline and 0.2277g (1.25mmol) of acenaphthoquinone were dissolved in 20mL of anhydrous methanol, and 0.2mL ...

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Abstract

The invention discloses a novel late transition metal alpha-diimine nickel (II) olefin polymerization catalyst with a symmetrical structure. The catalyst is a didentate coordination compound formed by an alpha-diimine ligand with a symmetrical Schiff base structure and a halogenide of later transition metal nickel (II). In the presence of diethyl aluminium chloride (DEAC) used as a cocatalyst, the coordination compound catalyst of nickel has higher activity for catalyzing ethylene to polymerize, which can reach 107gPE/(mol Ni h Bar), and obtained polyethylene has higher degree of branching, which can reach 114 branched chains per 1,000C.

Description

technical field [0001] The invention belongs to the technical field of macromolecules, and relates to a class of olefin polymerization catalysts, in particular to a class of α-diimine nickel (II) olefin polymerization catalysts; the invention also relates to the preparation method of the catalyst and its application in ethylene polymerization . Background technique [0002] Polyolefin is the polymer material with the largest output and widest application among synthetic resins. Catalysts are at the heart of polyolefin production and R&D. From traditional Ziegler-Natta (Ziegler-Natta) catalysts, to metallocene catalysts, and then to late transition metal catalysts, the progress of polyolefin catalytic technology and the continuous development of new polyolefin materials are always high Frontier topics in molecular chemistry and materials science. Therefore, the research and development of new and efficient olefin polymerization catalysts is of great significance to the dev...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F10/00C08F4/70C08F10/02C07F15/04
Inventor 袁建超刘玉凤王学虎梅铜简
Owner NORTHWEST NORMAL UNIVERSITY
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