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Pyridino six-membered ring binuclear-metal complex, preparation method thereof, and application of complex in ethylene polymerization

A metal complex, complex technology, applied to iron group organic compounds without C-metal bond, 2/12 group organic compounds without C-metal bond, containing elements of group 8/9/10/18 of the periodic table It can solve the problems of high cost, limited application development, unstable properties, etc., and achieve the effect of low cost, large industrial application prospects, and good catalytic activity.

Active Publication Date: 2021-01-01
BEIJING INSTITUTE OF CLOTHING TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, Phillips catalysts, Ziegler-Natta catalysts and metallocene catalysts that have been industrially produced have limited their application development to a certain extent due to their high cost and unstable properties.

Method used

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  • Pyridino six-membered ring binuclear-metal complex, preparation method thereof, and application of complex in ethylene polymerization
  • Pyridino six-membered ring binuclear-metal complex, preparation method thereof, and application of complex in ethylene polymerization
  • Pyridino six-membered ring binuclear-metal complex, preparation method thereof, and application of complex in ethylene polymerization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] Embodiment 1: Preparation of bis (methyl, methyl substituted pyrido six-membered ring imine) (L1, R in the formula (II)) bridged by phenol-4-methylene 1 = Me; R 2 = OH compound)

[0106]

[0107] (1.47g, 10mmol) shown in formula (Ⅲ) and 4-(bis(4-amino-3,5-dimethylphenyl)methyl)phenol (1.38g, 4.00 mmol) in toluene (150mL) solution, add 0.14g of p-toluenesulfonic acid catalyst, reflux and stir for 12h, concentrate under reduced pressure, separate on silica gel column, and use ratio of ethyl acetate:petroleum ether=1:1 eluent to elute out Target product, obtains 0.42g yellow solid, is the bispyrido six-membered ring ligand compound L1 and its isomer (L1') belonging to formula (II) (wherein, R 1 is methyl, R 2 For hydroxyl), the yield is 35%, wherein the molar ratio L1:L1'=80:20.

[0108] The structural confirmation data are as follows:

[0109] L1: 1 H NMR (300MHz, CDCl 3 ): δ8.69(d, J=3.6Hz, 2H, Py-H); 7.56(d, J=7.5Hz, 2H, Py-H); 7.29(d, J=7.2Hz, 2H, Py-H ); 6....

Embodiment 2

[0115] Embodiment 2: Preparation of bis (ethyl, ethyl substituted pyrido six-membered ring imine) (L2, R in the formula (II)) bridged by phenol-4-methylene 1 = Et; R 2 = OH compound)

[0116]

[0117] Use the same method as Example 1 (only the steps described in Example 1) to replace 4-(bis(4-amino-3,5-dimethylphenyl)methyl)phenol with 4-(bis( 4-amino-3,5-diethylphenyl) ethyl) phenol, obtains 0.74g yellow solid, is the bispyridine ligand compound L2 and its isomer (L2') ( Among them, R 1 is ethyl, R 2 Hydroxyl hydrogen), yield 56%, wherein the molar ratio L2:L2'=70:30.

[0118] The structural confirmation data are as follows:

[0119] L2: 1 H NMR (300MHz, CDCl 3 ): δ8.70(d, J=3.0Hz, 2H, Py-H); 7.55(d, J=8.4Hz, 2H, Py-H); 7.28(t, J=3.6Hz, 2H, Py-H ); 7.04-6.96 (m, 2H, Ph-H); 6.90 (d, J=7.2Hz, 2H, Ph-H); 6.82-6.74 (m, 4H, Ar-H); 5.38 (s, 1H, -CH); 2.93(t, J=5.4Hz, 4H, -CH 2 ); 2.43-2.34 (m,8H,-CH 2 ); 2.30-2.24(m,4H,-CH 2 ); 1.92(t,J=5.1Hz,4H,-CH 2 ); 1.11-1.10 (...

Embodiment 3

[0125] Embodiment 3: Preparation of benzene-4-methylene bridged bis(methyl, methyl substituted pyrido six-membered ring imine) (L3, R in the formula (II) 1 = Me; R 2 = Compound of H)

[0126]

[0127] Use the same method as in Example 1 (only the steps described in Example 1) to replace 4-(bis(4-amino-3,5-dimethylphenyl)methyl)phenol with 4,4'- (Phenylmethyl) two (2,6-dimethylaniline) obtains 0.57g yellow solid, namely belongs to the pyridine ligand compound L3 of formula (II) (wherein, R 1 is methyl, R 2 For hydrogen), the yield is 49%, wherein the molar ratio L3:L3'=62:38.

[0128] The structural confirmation data are as follows:

[0129] 1 H NMR (400MHz, CDCl 3 ): δ8.48(d, J=7.6Hz, 4H, Py-H); 7.91(t, J=8.0Hz, 2H, Py-H); 7.12(d, J=7.6Hz, 4H, Ar-H ); 7.06-6.98 (m, 4H, Ar-H and Ph-H); 6.87 (d, J = 5.6Hz, 4H, Ar-H); 6.62 (d, J = 7.6Hz, 2H, Ph-H) ;5.37(s,1H,(Ar) 2 -CH-Ph); 2.48-2.31(m,8H,-CH 2 CH 3 ); 2.27(d,J=10.4Hz,12H,-CH 3 ); 2.03(s,12H,-CH 3 ); 1.15(t,J=7.6H...

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Abstract

The invention discloses a pyridino six-membered ring binuclear-metal complex represented by formula (I) shown in the description, and a preparation method and application thereof. The binuclear metalcomplex has the advantages of novel structure, high catalytic activity, low cost, stable performance and the like. The binuclear metal complex provided by the invention can catalyze ethylene polymerization with high activity under mild conditions, regulates and controls the types of cocatalysts to obtain different types of high molecular weight branched polyethylene, can regulate and control the microstructure of the obtained polymer to enable the obtained polymer to have the characteristics of double melting points or single melting point, and meets the application requirements of different types of polyolefin. The binuclear metal complex disclosed by the invention shows very good catalytic activity when catalyzing olefin polymerization reaction, and has a great industrial application prospect.

Description

technical field [0001] The invention belongs to the technical field of polyolefin catalysts, and specifically relates to a pyrido six-membered ring dinuclear-metal complex, a preparation method thereof and an application in ethylene polymerization. Background technique [0002] Polyolefin materials have received widespread attention because of their low price and wide range of applications. Especially since the discovery of the Ziegler-Natta catalytic system in the 1950s, the polyolefin industry has developed rapidly. In the development process of polyolefin industry, catalyst plays a vital role. So far, olefin polymerization catalysts mainly include Ziegler-Natta catalysts, Phillips catalysts, metallocene catalysts and late transition metal complex catalysts. Among these types of catalysts, late-transition metal catalysts have attracted widespread attention from researchers because of their advantages such as simple preparation and the ability to adjust the performance of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/02C07F15/04C07F15/06C07F15/00C07F3/06C08F110/02C08F4/70C08F4/50
CPCC07F15/025C07F15/045C07F15/065C07F15/0066C07F3/003C08F110/02C08F4/7006C08F2500/01C08F2500/03C08F4/50Y02P20/52
Inventor 张文娟陈强索泓一孙文华赵巧美
Owner BEIJING INSTITUTE OF CLOTHING TECHNOLOGY
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