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Diaryl imine pyridyl complexes containing flexible eight-membered rings and their preparation methods and applications

A kind of compound and composition technology, applied in the field of diarylimine pyridyl complex and preparation thereof

Active Publication Date: 2020-10-27
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the catalytic performance of these catalysts, as well as the conditions and efficiency of their preparation methods, still need to be further improved
As a new catalyst system, there are still some difficulties in basic research and constraints to promote industrialization

Method used

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  • Diaryl imine pyridyl complexes containing flexible eight-membered rings and their preparation methods and applications
  • Diaryl imine pyridyl complexes containing flexible eight-membered rings and their preparation methods and applications
  • Diaryl imine pyridyl complexes containing flexible eight-membered rings and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0099] Example 1 Preparation of intermediate α,α'-dioxo-2,3:5,6-bis(hexamethylene)pyridine compound shown in formula II-1

[0100]

[0101] 24.30g (0.10mol) 2,3:5,6-two (hexamethylene) pyridine compound shown in IV-1 formula, 106.00g (1.00mol) benzaldehyde and 81.60g (0.80mol) acetic anhydride in Under nitrogen atmosphere, react at 180°C for 72h. After the reaction was detected by TLC, it was cooled to room temperature, and a vacuum distillation device was set up, and the reaction solution was subjected to vacuum distillation (100° C., 10 mm Hg) to remove unreacted benzaldehyde, acetic anhydride, and by-products. The crude product obtained after distillation under reduced pressure was dissolved in 500 mL of dichloromethane. The reaction solution was cooled to below -40°C and passed through dry O 3 / O2 , carry out ozonation reaction until the solution turns light yellow, react for about 3 hours, TLC detects that the reaction is complete, stop passing O 3 / O 2 , N 2 Bubb...

Embodiment 2

[0106] Example 2 Preparation of α,α'-bis(2,6-dimethylphenylimino)-2,3:5,6-bis(hexamethylene)pyridylferric chloride represented by the following formula [Fe-1](R 1 is methyl, R 2 for hydrogen)

[0107]

[0108] 0.27g (1.0mmol) α,α'-dioxo-2,3:5,6-bis(hexamethylene)pyridine compound represented by formula II-1, 0.48g (4.0mmol) 2,6- Dimethylaniline and 0.19g (0.9mol) FeCl 2 4H 2 O was dissolved in 15 mL of acetic acid, stirred and refluxed at 130°C for 12 hours under nitrogen atmosphere, the reaction liquid was concentrated, a large amount of ether was added to precipitate, the precipitate was collected by filtration, and then the precipitated substrate was dissolved in methanol, the solution was concentrated, and a large amount of Diethyl ether precipitated and the precipitate was collected by filtration and washed with copious amounts of diethyl ether. A light blue powder (0.49 g, 89%) was obtained.

[0109] The structural confirmation data are as follows:

[0110] FT-...

Embodiment 3

[0112] Example 3 Preparation of α,α'-bis(2,6-diethylphenylimino)-2,3:5,6-bis(hexamethylene)pyridylferric chloride represented by the following formula [Fe-2](R 1 is ethyl, R 2 for hydrogen)

[0113]

[0114] 0.27g (1.0mmol) α,α'-dioxo-2,3:5,6-bis(hexamethylene)pyridine compound represented by formula II-1, 0.59g (4.0mmol) 2,6- Diethylaniline and 0.19g (0.9mol) FeCl 2 4H 2 O was dissolved in 15 mL of acetic acid, stirred and refluxed at 130°C for 12 hours under nitrogen atmosphere, the reaction liquid was concentrated, a large amount of ether was added to precipitate, the precipitate was collected by filtration, and then the precipitated substrate was dissolved in methanol, the solution was concentrated, and a large amount of Diethyl ether precipitated and the precipitate was collected by filtration and washed with copious amounts of diethyl ether. A light blue powder (0.45 g, 75%) was obtained.

[0115] The structural confirmation data are as follows:

[0116] FT-IR ...

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Abstract

The invention provides a preparation method and application of a diaryliminopyridyl complex containing flexible eight-membered ring and an intermediate thereof. The complex has multiple catalytic active centers, can achieve regulation of the polymer molecular weight by changing the ligand structure and polymerization conditions, and has the advantages of high catalytic activity, low cost, stable performance and the like. The preparation method of the intermediate alpha, alpha'-dioxo-2, 3:5, 6-bis(hexamethylene)pyridine compound and the complex has the advantages of mild conditions, short cycle, simple operation conditions, etc. The complex can be applied in catalysts for ethylene polymerization, especially the provided iron complex has high thermal stability, and under the action of a cocatalyst, the catalytic activity can reach 12.23*10<6>g.mol<-1>(Fe)h<-1>, and highly linear polyethylene with high molecular weight (188kg.mol<-1>) can be obtained, even at a high temperature of 90DEG C, the catalytic activity can still be maintained at 6.75*10<6>g.mol<-1>(Fe)h<-1>, meeting the operating temperature of industrial production, the complex has very good industrial application prospects.

Description

technical field [0001] The invention relates to the technical field of polyolefin catalysts, in particular to a class of diarylimine pyridyl complexes containing a flexible eight-membered ring, a preparation method and application thereof. Background technique [0002] Polyethylene (PE) is the variety with the largest output among the general-purpose synthetic resins in the world, and occupies a pivotal position in the field of synthetic olefin materials. my country's polyethylene industry has gradually developed since the 1960s, and the production and consumption of polyethylene have increased year by year. At present, my country has become the world's largest importer of PE and the second largest consumer. By 2019, China's polyethylene demand will reach 22 million tons, and imports will be about 10 million tons (Source: parpinelli TECNON / Basell Polyolefins). PE is not only cheap, but also has good mechanical properties, processing properties and chemical stability, and i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C07D221/06C08F110/02C08F4/70
Inventor 王征马艳平孙文华
Owner INST OF CHEM CHINESE ACAD OF SCI
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