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Unsymmetrical diimine palladium catalyst and its ligand, preparation method and use

A technology of catalysts and complexes, applied in the preparation of imino compounds, chemical instruments and methods, palladium organic compounds, etc., can solve the problems of low insertion, low degree of branching, inconvenient processing, etc.

Active Publication Date: 2018-05-01
合肥中科科乐新材料有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this application, due to the symmetrical large steric hindrance structure of the ligand compound, the obtained catalyst has a low degree of branching and a narrow molecular weight distribution for the obtained polyolefin compound or copolymer, which is not convenient for processing, and for polar monomers body insertion, the insertion is relatively low

Method used

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  • Unsymmetrical diimine palladium catalyst and its ligand, preparation method and use
  • Unsymmetrical diimine palladium catalyst and its ligand, preparation method and use
  • Unsymmetrical diimine palladium catalyst and its ligand, preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Example 1: Synthesis of N,N-bis(2-benzyl-4-methoxy-6-methylphenyl)butane-2,3-diimine

[0073]

[0074] At room temperature, add 8.41 g of 2-benzyl-4-methoxy-6-methylaniline into an eggplant-shaped flask (equipped with a thermometer, reflux condenser and stirrer) containing 200 ml of toluene. 0.86 g of diketone and 20 mg of p-toluenesulfonic acid were heated to 80°C in an oil bath to react for 24 hours. Then, use a water separator (Xinville 14-port water separator) to divide the water and reflux for three days. Use petroleum ether and dichloromethane 1:1 to point the board, and you will find that there is mainly one point, indicating that the reaction has ended. Finally, part of the solvent was removed by rotary evaporation, and then 300 ml of methanol was added to the remaining reaction solution to precipitate a large amount of yellow solid. The solid was obtained by filtration under reduced pressure, washed three times with 20 ml of methanol, and dried under vacuum to ob...

Embodiment 2

[0076] Example 2: Synthesis of N,N-bis(2-benzyl-4-chloro-6-methylphenyl)butane-2,3-diimine

[0077]

[0078] Similar to Example 1, at room temperature, 8.61 g of 2-benzyl-4-chloro-6-methylaniline, 0.86 g of butanedione, and p-methyl were added to an eggplant-shaped flask containing 200 ml of toluene. 20 mg of benzene sulfonic acid, heated to 80°C in an oil bath for 24 hours, and then used a water separator (Xinville 14) to divide the water and reflux for seven days. Use petroleum ether and dichloromethane 1:1 to find the main A point indicates that the reaction has ended. Part of the solvent was removed by rotary evaporation, and then 300 ml of methanol was added to the remaining reaction solution, and a large amount of yellow solid was precipitated. The solid was obtained by filtration under reduced pressure with a water pump, washed three times with 20 ml of methanol, and dried under vacuum to obtain 8.22 g of solid with a yield of 81%.

[0079] 1 H NMR(400MHz, CDCl 3 )δ7.27(d,...

Embodiment 3

[0080] Example 3: Synthesis of N,N-bis(2-diphenylmethyl-4-trifluoromethyl-6-methylphenyl)butane-2,3-diimine

[0081]

[0082] Similar to Example 1, at room temperature, add 9.01 g of 2,6-benzyl-4-trifluoromethylaniline, 0.86 g of butanedione and p-methyl to an eggplant-shaped flask containing 200 ml of toluene 20 mg of benzene sulfonic acid, heated to 80°C in an oil bath for 24 hours, and then used a water separator (Xinweier 14) to reflux and divide the water for seven days. Use petroleum ether and methylene chloride 1:1 to point the board and you will find that it is mainly one Click to indicate that the reaction has ended. Part of the solvent was removed by rotary evaporation, and then 300 ml of methanol was added to the remaining reaction solution, and a large amount of yellow solid was precipitated. The solid was obtained by filtration under reduced pressure, washed three times with 20 ml of methanol, and dried under vacuum to obtain 4.03 g of solid with a yield of 50%.

[0...

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Abstract

The invention relates to an asymmetric diimine palladium catalyst as shown in the following formula and a ligand, preparation method and application thereof, wherein R1-R6 and X are defined according to the description. The palladium catalyst has high heat stability and activity on ethylene polymerization, and polyethylene which has an appropriate branching degree and high molecular weight is generated; in addition, the catalyst can be used for copolymerization of ethylene and methyl acrylate. Please see the formula in the description.

Description

Technical field [0001] The invention relates to the field of catalysis and synthetic polymer polyolefin materials, in particular to asymmetric diimine palladium catalysts and their ligands, preparation methods and applications. Background technique [0002] Polyolefin has become an indispensable material in modern social life due to its low price and excellent performance. At present, the demand for polyolefins is very alarming, and because of its unique synthesis method, the research on the core catalysts in its synthesis occupies a very important position. [0003] Throughout the history of the development of the olefin polymerization industry, it can be found that the technological progress in the industry is closely related to the discovery of new catalysts and the progress of process technology. In the process of olefin polymerization, the catalyst often determines the polymerization behavior of the entire polymerization process, the particle state of the produced polymer, an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/08C07C249/02C07F15/00C08F110/02C08F210/02C08F220/14C08F4/80
CPCC09B55/005C07F15/006C08F110/02C08F4/80C08F210/02C08F220/14
Inventor 陈昶乐隋学林代胜瑜
Owner 合肥中科科乐新材料有限责任公司
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