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Asymmetric pyridine imine coordination compounds containing large steric hindrance substituent groups, preparation method and application thereof

A technology of complexes and metal complexes, which is applied to compounds containing Group 8/9/10/18 elements of the periodic table, iron-group organic compounds without C-metal bonds, and iron-organic compounds, which can solve post-transition problems Problems such as poor thermal stability of metal complexes, limited molecular weight range of polyethylene materials, and reduced catalyst activity

Active Publication Date: 2020-11-20
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, as a new catalyst system, late transition metal catalysts still have some difficulties in basic research and constraints to promote industrialization.
For example, the thermal stability of the late transition metal complex itself is poor, which easily causes the activity of the catalyst to decrease with the increase of the reaction temperature, and the molecular weight range of the obtained polyethylene material is also very limited. The catalyst with higher activity and high thermal stability is One of the core contents of the research is also the key to advancing industrialization as soon as possible

Method used

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  • Asymmetric pyridine imine coordination compounds containing large steric hindrance substituent groups, preparation method and application thereof
  • Asymmetric pyridine imine coordination compounds containing large steric hindrance substituent groups, preparation method and application thereof
  • Asymmetric pyridine imine coordination compounds containing large steric hindrance substituent groups, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0129] Preparation of 2-acetyl-6(1-(2,4-bis(dibenzocycloheptyl)-6-methyl-anilino)ethyl)pyridine (A) shown in the following formula

[0130]Weigh 2.13g (13.10mmol) of 2,6-diacetylpyridine and 6.42g (13.10mmol) of 2,4-bis(dibenzocycloheptyl)-6-methyl-aniline into a 15% In 100 mL of toluene solution of p-toluenesulfonic acid, after stirring at reflux temperature for 10 h, the reaction mixture was filtered under heating conditions, and all volatiles were evaporated under reduced pressure conditions. Next, the unprocessed product obtained was dissolved in dichloromethane, loaded with basic alumina, and subjected to column chromatography through a silica-based alumina column, using a mixed solvent of petroleum ether and ethyl acetate as an eluent (25 / 2) carries out elution, detects elution fraction by thin-layer chromatography, developing agent is the mixed solvent that the volume ratio of sherwood oil and ethyl acetate is 10:1, collects the 3rd fraction, removes solvent, obtains 3....

Embodiment 2

[0136] Example 2. Preparation of 2-(1-(2,4-bis(dibenzocycloheptyl)-6-methyl-anilino) ethyl)-6(1-(2, 6-Dimethyl-anilino)ethyl)pyridine (ligand L1)

[0137] Weigh 1.10g (1.70mmol) 2-acetyl-6(1-(2,4-bis(dibenzocycloheptyl)-6-methyl-anilino)ethyl)pyridine (compound A), Add it into the reaction flask, then add catalytic equivalent of p-toluenesulfonic acid (15%) into the reaction flask, and add it into 100mL of toluene solvent to form a solution containing A. 0.21 g (1.70 mmol) of 2,6-dimethylaniline was dropped into the reactor solution containing A. The reaction mixture was heated to reflux for 8h. After the completion of the reaction was detected by TLC, it was cooled to room temperature, and the volatiles were evaporated under reduced pressure. Then, the obtained unprocessed residual solid was dissolved in dichloromethane, loaded with basic alumina, and carried out column chromatography through a silica basic alumina column (using a mixed solvent of petroleum ether and ethyl...

Embodiment 3

[0144] Example 3. Preparation of 2-(1-(2,4-bis(dibenzocycloheptyl)-6-methyl-anilino) ethyl)-6(1-(2, 6-Diethyl-anilino)ethyl)pyridine (ligand L2)

[0145] Basically the same as the method in Example 2, the difference is: in the case of maintaining the same molar number of reactants, the aniline compound reacted with solution A is 2,6-diethylaniline, and after drying, 0.34g of yellow powder is obtained, which is Ligand L2, 2-(1-(2,4-bis(dibenzocycloheptyl)-6-methyl-anilino)ethyl)-6(1-(2,6-diethyl- Anilino)ethyl)pyridine, yield: 26%. Melting point: 215–217°C.

[0146]

[0147] The structural confirmation data are as follows:

[0148] FTIR (KBr, cm-1): 3059(w), 3015(w), 2935(w), 2876(w), 2824(w), 1643(υ(C=N),s), 1569(υ( C=N),w),1489(w),1448(m),1363(m),1302(w),1242(w),1219(w),1197(w),1119(m),1100( w), 1076(w), 1050(w), 1014(w), 963(w), 910(w), 871(w), 849(w), 802(w), 787(w), 759( s), 704(w).

[0149] 1H NMR (400MHz, CDCl 3 .TMS): δ8.45(d, J=8.02Hz, 2H, Py–H), 7.94(t, J=7...

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Abstract

The invention provides a class of asymmetric pyridineimine transition metal coordination compounds containing a large steric hindrance substituent, a preparation method and application thereof. According to the invention, the preparation method of the coordination compound is mild in condition, short in period and simple to operate; the coordination compound can be applied to a catalyst for ethylene polymerization, has a single catalytic active center, can regulate and control the molecular weight of a polymer by changing a ligand structure and polymerization conditions, and has the advantagesof low cost, high catalytic activity, good thermal stability and the like; And especially, compared with reported diphenylmethyl, the iron coordination compound provided by the invention has the advantages that the molecular weight of highly linear polyethylene obtained by catalyzing ethylene polymerization is high while high catalytic reaction activity and high thermal stability are maintained,wherein the molecular weight can reach 913.36 kg / mol, so that the coordination compound can be used as engineering plastic at a high environment temperature, is used for synthesizing high-molecular-weight linear polyethylene, 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 class of asymmetric pyridine imine complexes containing large steric hindrance substituents, a preparation method and application thereof. Background technique [0002] As a pillar product of modern science and technology and social development, polyolefin materials not only meet the needs of people's daily life in society, but also become indispensable and important materials in various fields such as cutting-edge technology and national defense construction. Among them, polyethylene (PE) is the most produced variety of general-purpose synthetic resins in the world. It has the characteristics of good chemical resistance, low density, good mechanical strength, recyclability, and low cost. It occupies a pivotal position in the field of synthetic olefin materials. The design and development of olefin polymerization catalysts is the key to the development ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/02C07F15/06C07D213/53C08F110/02C08F4/70
CPCC07D213/53C07F15/025C07F15/065C08F110/02C08F4/7042
Inventor 孙文华穆罕默德·扎达马艳平
Owner INST OF CHEM CHINESE ACAD OF SCI
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