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Fluorine-containing alpha-diimine nickel coordination compounds for preparing polyolefin elastomer, intermediate, preparation method and application thereof

A technology of polyolefin elastomer and diimine ligand, which is applied in the preparation of nickel organic compounds, compounds containing elements of group 8/9/10/18 of the periodic table, amino compounds, etc.

Active Publication Date: 2020-06-19
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, the catalytic performance of the above catalysts, as well as the conditions and efficiency of their preparation methods, still need to be further improved

Method used

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  • Fluorine-containing alpha-diimine nickel coordination compounds for preparing polyolefin elastomer, intermediate, preparation method and application thereof
  • Fluorine-containing alpha-diimine nickel coordination compounds for preparing polyolefin elastomer, intermediate, preparation method and application thereof
  • Fluorine-containing alpha-diimine nickel coordination compounds for preparing polyolefin elastomer, intermediate, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0098] In this example, 2-(2,6-bis(benzhydryl)-3,4-difluoroanilino)acenaphthylenone represented by formula (V) was prepared.

[0099] In 2,6-bis(benzhydryl)-3,4-difluoroaniline (4.61g, 10.0mmol) and acenaphthylenedione (1.82g, 10.0mmol) in dichloromethane (150mL) and ethanol (30mL) A catalytic amount (0.57 g) of p-toluenesulfonic acid was added to the mixed solution, and the mixture was reacted at room temperature for 12 h. The solvent was removed, and the residue was subjected to basic alumina column chromatography with a mixed solvent of petroleum ether and ethyl acetate at a volume ratio of 5:1, and the eluted fraction was detected through a thin-layer silica gel plate, and the developing solvent was petroleum ether and ethyl acetate. The volume ratio of the ester was 5:1 mixed solvent, the third fraction was collected, and a yellow solid was obtained after removing the solvent. Yield: 49%.

[0100] The structural confirmation data are as follows:

[0101] 1 H NMR (400M...

Embodiment 2

[0107] In this example, the α-diimine intermediate represented by formula (II): 1-(2,6-dimethylaniline)-2-(2,6-bis(benzhydryl)-3 , 4-difluoroaniline) acenaphthene [L1], where R 1 is methyl, R 2 for hydrogen.

[0108] Get 2-(2,6-bis(benzhydryl)-3,4-difluoroaniline) acenaphthenone (0.625g, 1.0mmol) and 2,6-dimethylaniline (0.111 g, 1.0mmol) in toluene solution (50mL) was added a catalytic amount of p-toluenesulfonic acid, heated to reflux for 12h. The solvent toluene was removed, and the residue was subjected to basic alumina column chromatography with a mixed solvent of petroleum ether and ethyl acetate at a volume ratio of 5:1. The eluted fractions were examined through a thin-layer silica gel plate, the third fraction was collected, and the solvent was removed to obtain a red solid. Yield: 17%.

[0109] The structural confirmation data are as follows:

[0110] 1 H NMR (400MHz, CDCl 3 ,TMS): δ7.69(d,J=11.2Hz,1H),7.49(d,J=10.8Hz,1H),7.28(s,1H),7.20(d,J=10.0Hz,3H),7.17 ...

Embodiment 3

[0116] In this example, the α-diimine intermediate represented by formula (II) was prepared: 1-(2,6-diethylaniline)-2-(2,6-bis(benzhydryl)-3 , 4-difluoroaniline) acenaphthene [L2], where R 1 is ethyl, R 2 for hydrogen.

[0117] Get 2-(2,6-bis(benzhydryl)-4-methylaniline) acenaphthylenone (0.625g, 1.0mmol) and 2,6-diethylaniline (0.149g, 1.0 mmol) of toluene (50 mL) was added a catalytic amount of p-toluenesulfonic acid, and heated to reflux for 12 h. The solvent toluene was removed, and the residue was subjected to basic alumina column chromatography with a mixed solvent of petroleum ether and ethyl acetate at a volume ratio of 5:1. The eluted fractions were examined through a thin-layer silica gel plate, the third fraction was collected, and the solvent was removed to give a yellow solid. Yield: 13%.

[0118] The structural confirmation data are as follows:

[0119] 1 H NMR (400MHz, CDCl 3 ,TMS): δ7.65(d,J=11.2Hz,1H),7.45(d,J=11.2Hz,1H),7.27(s,2H),7.20(d,J=6.0Hz,8H),7...

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Abstract

The invention discloses a class of fluorine-containing alpha-diimine nickel coordination compounds for preparing a polyolefin elastomer, and an intermediate thereof, wherein the coordination compoundhas a single catalytic activity center, the molecular weight of a polymer can be regulated and controlled by changing a ligand structure and polymerization conditions, and the coordination compound has the advantages of high catalytic activity, low cost, stable performance and the like. The invention further provides preparation methods of an asymmetric alpha-diimine nickel coordination compound containing a difluoro group, and an intermediate thereof, wherein the two preparation methods have the advantages of mild reaction conditions, short period, simple operation conditions and the like. The invention also provides uses of a metal nickel coordination compound and a catalyst system thereof, wherein the metal nickel coordination compound is used for catalyzing ethylene polymerization, shows good catalytic activity and obtains a polyethylene elastomer material with narrow molecular weight distribution. The obtained polyethylene elastomer material is high in branching degree, has good tensile strength, elongation at break and elastic resilience, is a thermoplastic elastomer material and has great industrial application potential.

Description

technical field [0001] The invention belongs to the technical field of polyolefin catalysts, and in particular relates to a kind of fluorine-containing α-diimine nickel complexes, intermediates, preparation methods and uses for preparing polyolefin elastomers. Background technique [0002] Among many late transition metal catalysts, nickel complexes have been widely studied due to their high catalytic activity, low cost, and low toxicity. α-diimine nickel complex is a highly active polyethylene (PE) and polypropylene (PP) catalyst, and the catalyzed products are used in food packaging, medical equipment, auto parts, etc. in our daily life field, and the ensuing huge economic achievements are mainly based on novel catalyst design, reaction engineering and polyolefin processing. [0003] Thermoplastic elastomers (TPEs) have become important industrial materials due to their low cost and ease of fabrication enabled by rapid and reversible thermoplastic processing. Examples of...

Claims

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Application Information

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IPC IPC(8): C07F15/04C07C251/20C07C249/02C07C211/52C07C209/74C08F10/00C08F110/02C08F4/70
CPCC07C211/52C07C251/20C07F15/045C08F10/00C08F110/02C07C2603/20C08F4/7006C08F2500/03Y02P20/52
Inventor 孙文华阿鲁穆加姆·维格涅什张秋月马艳平
Owner INST OF CHEM CHINESE ACAD OF SCI
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