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2-ammonia methyl-pyridine nickel composition, preparation method and application thereof

A technology of aminomethylpyridine nickel and complexes, applied in nickel organic compounds, organic chemistry, etc., to achieve the effect of inhibiting chain transfer and chain termination

Inactive Publication Date: 2009-12-23
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Currently, there are few examples of living polymerization of ethylene catalyzed by late transition metal catalysts

Method used

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  • 2-ammonia methyl-pyridine nickel composition, preparation method and application thereof
  • 2-ammonia methyl-pyridine nickel composition, preparation method and application thereof
  • 2-ammonia methyl-pyridine nickel composition, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Synthesis of 2-pyridine imine compound A1:

[0045] Dissolve 10mL (0.048mol) of 2,6-diisopropylaniline in 60mL of ethanol, N 2 Protect. Then slowly add 4.8 mL (0.048 mol) of 2-formylpyridine and 5 drops of formic acid, and stir and reflux at 80°C for 3 hours. After cooling to room temperature, ethanol was removed under reduced pressure, and recrystallized with n-hexane. 11 g of yellow crystals were obtained, yield: 85.8%. The results of hydrogen spectroscopy are as follows: 1 H NMR (300MHz, CDCl 3 ): δ1.25-1.27 (12H, d, 4CH3), 3.34-3.43 (2H, m, 2CH), 7.50 (1H, S, CH), 7.05-7.14 (3H, m, benzyl), 7.18-7.22 (1H , t, Py-H), 7.30-7.32 (1H, d, Py-H), 7.62-7.68 (1H, t, Py-H), 8.61-8.63 (1H, d, Py-H). The product was determined to be 2-pyridine imine compound A1.

Embodiment 2

[0047] Synthesis of 2-pyridine imine compound A2

[0048] Under nitrogen protection, add 4.2503g (24mmol) 2,6-diisopropylaniline, and 20mL toluene to a branch bottle equipped with a condenser tube, inject 8mL of 3M trimethylaluminum toluene solution with a syringe, and heat to 120°C and stirred for 2 hours. After cooling, 3.6688 g (24 mmol) of phenyl(2-pyridyl)methanone was dissolved in 8 mL of toluene, and then the above solution was added. Heating was continued at 120°C for 6 hours, then the temperature was adjusted to 70°C and stirred overnight. Distilled water was added under stirring to terminate the reaction, extracted three times with ethyl acetate, and the organic phases were combined. The organic phase was washed once with distilled water, anhydrous Na 2 SO 4 Dry, filter, and spin dry in vacuo. Recrystallized from ethanol to obtain 6.8413 g of the product with a yield of 81%. The results of hydrogen spectroscopy are as follows: 1 HNMR (300MHz, CDCl 3 ): δ0.91-...

Embodiment 3

[0050] Synthesis of 2-pyridine imine compound A3

[0051] Dissolve 10mL (0.05mol) of 2,6-diisopropylaniline in 60mL of ethanol, N 2 Protect. Then 8.7 g (0.05 mol) of 2-formyl-6-phenylpyridine and 5 drops of formic acid were added slowly, and stirred and refluxed at 80° C. for 3 hours. After cooling to room temperature, ethanol was removed under reduced pressure, and recrystallized with n-hexane. 10 g of yellow crystals were obtained, yield: 62.5%. Mass spectrometry determined that the product was 2-pyridine imine compound A3.

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Abstract

The invention discloses a 2-ammonia methyl-pyridine nickel composition, a preparation method and the application thereof. The composition has a structure of a formula I, wherein R1 stands for hydrogen or alkyl, R2 stands for hydrogen or alkyl, R3 stands for hydrogen or alkyl, and X stands for halogen. The preparation method of the composition comprises the following steps: (1) generating 2-pyridine imine compound through the ketone-ammonia condensation reaction of an aromatic ketone compound and 2,6-diisopropyl aniline; then, reacting with trimethylbenzene magnesium bromide, trimethylaluminium or lithium aluminum hydride to obtain 2-ammonia methyl-pyridine ligand; and (2) under a waterless and anoxic condition, obtaining a 2-ammonia methyl-pyridine nickel composition I by the complexation reaction of the 2-ammonia methyl-pyridine ligand III and (DME) NiX2. The 2-ammonia methyl-pyridine nickel composition has a specific ligand substitute structure, can catalyze ethylene to actively polymerize so as to obtain polyethylene with high molecular weight, narrow distribution and a certain branching degree.

Description

technical field [0001] The invention belongs to the field of catalytic polymerization of olefins, and in particular relates to a 2-aminomethylpyridinium nickel complex, a preparation method thereof and an application for catalytic ethylene active polymerization. Background technique [0002] Living polymerization refers to the polymerization reaction without chain transfer and chain termination during the polymerization process, which can be used to prepare high polymers, block copolymers and end-functionalized polymer materials with controllable molecular weight and narrow molecular weight distribution Wait. Through the design of the catalyst structure, the active polymerization of olefins is catalyzed to obtain narrow-distribution polyolefins, or block, functionalized polyolefins, which greatly broadens the application range of olefin polymers. [0003] Ethylene is one of the most consumed olefins in the world. Although it has a simple structure, it can obtain many polyme...

Claims

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Application Information

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IPC IPC(8): C07D213/38C07F15/04C08F4/80C08F10/02
Inventor 伍青宰少波高海洋张玲
Owner SUN YAT SEN UNIV
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