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Asymmetric diimine palladium catalyst and ligand, preparation method and application thereof

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

Active Publication Date: 2016-09-28
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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  • Asymmetric diimine palladium catalyst and ligand, preparation method and application thereof
  • Asymmetric diimine palladium catalyst and ligand, preparation method and application thereof
  • Asymmetric diimine palladium catalyst and ligand, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1: N, the synthesis of N-two (2-benzhydryl-4-methoxy-6-methylphenyl) butane-2,3-diimine

[0073]

[0074] At room temperature, add 8.41 grams of 2-benzhydryl-4-methoxy-6-methylaniline, butyl 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, divide the water and reflux for three days with a water separator (Sinwell 14-port water separator), and use petroleum ether and dichloromethane 1: 1 to spot the plate, 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, 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 in vacuo to obtain 8.23 ​​g of solid with a yield of 85%.

[0075] 1 H NMR (400MHz, CDCl 3...

Embodiment 2

[0076] Embodiment 2: N, the synthesis of N-two (2-benzhydryl-4-chloro-6-methylphenyl) butane-2,3-diimine

[0077]

[0078] Similar to Example 1, at room temperature, 8.61 grams of 2-benzhydryl-4-chloro-6-methylaniline, 0.86 grams of diacetyl and p-methyl 20 milligrams of benzenesulfonic acid, and heated to 80 ℃ by oil bath for 24 hours to react, then use a water separator (Xinweier 14 port) to divert water and reflux for seven days, and use petroleum ether and dichloromethane 1: 1 point board to find that mainly A dot, indicating 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 filtering under reduced pressure with a water pump, washed three times with 20 ml of methanol, and dried in vacuo to obtain 8.22 g of a solid with a yield of 81%.

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

Embodiment 3

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

[0081]

[0082] Similar to Example 1, at room temperature, 9.01 grams of 2,6-benzhydryl-4-trifluoromethylaniline, 0.86 grams of diacetyl and p-methyl 20 mg of benzenesulfonic acid was heated to 80°C in an oil bath to react for 24 hours, and then refluxed and separated for seven days with a water separator (Xinwell 14 port). With petroleum ether and dichloromethane 1: 1, it was found that mainly a dot, indicating 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 in vacuo to obtain 4.03 g of solid with a yield of 50%.

[0083] 1 H NMR (400MHz, CDCl 3 )δ8.06, 8.04 (d, J=2.1Hz, 2H, aryl-H), 7.75, 7.6...

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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 the field of synthetic polymer polyolefin materials, in particular to an asymmetric diimine palladium catalyst and its ligand, preparation method and application. Background technique [0002] Due to its low price and excellent performance, polyolefin has become an indispensable class of materials in modern social life. At present, the demand for polyolefins is very astonishing, and because of its unique synthesis method, the research on the core catalyst 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, catalysts often determine the polymerization behavior of the entire polymerization process, the particle state o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/08C07C249/02C07F15/00C08F110/02C08F210/02C08F220/14C08F4/80
CPCC07C251/08C07F15/006C08F110/02C08F210/02C08F220/14C08F4/80C09B55/005
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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