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Diimine palladium catalyst with great steric hindrance, and ligand, preparation method and application thereof

A compound and complex technology, applied in the field of large sterically hindered diimide palladium catalysts and their ligands, can solve the problems of low molecular weight, limited application, low activity, etc., and achieve the effect of high thermal stability and activity

Active Publication Date: 2015-12-16
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, these palladium catalysts have corresponding defects: first, at low temperature, their activity is very low relative to classical catalysts (such as butanedione diisopropylimine palladium catalyst), even an order of magnitude lower; secondly, using The molecular weight of the olefin homopolymers and copolymers they produce is also lower than the classical molecular weight (usually 10000-100000g / mol); third, they have the same chain walking properties as the classical catalysts, and obtain highly branched polyethylene and copolymers , the obtained polymer is usually oily liquid or waxy solid, which limits its application in some aspects

Method used

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  • Diimine palladium catalyst with great steric hindrance, and ligand, preparation method and application thereof
  • Diimine palladium catalyst with great steric hindrance, and ligand, preparation method and application thereof
  • Diimine palladium catalyst with great steric hindrance, and ligand, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Example 1: Synthesis of N,N-bis(2,6-diphenylmethyl-4-methoxyphenyl)butane-2,3-diimine

[0071]

[0072] At room temperature, add 9.11 g of 2,6-benzyl-4-methoxyaniline and 0.86 of diacetyl into an eggplant-shaped bottle (equipped with a thermometer, reflux condenser and stirrer) containing 200 ml of toluene. Gram 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 spot 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 o...

Embodiment 2

[0074] Example 2: Synthesis of N,N-bis(2,6-diphenylmethyl-4-chlorophenyl)butane-2,3-diimine

[0075]

[0076] Similar to Example 1, at room temperature, add 9.20 g of 2,6-benzyl-4-chloroaniline, 0.86 g of butanedione and p-toluenesulfonic acid into an eggplant-shaped bottle containing 200 ml of toluene 20 mg, and heated to 80°C in an oil bath to react for 24 hours, and then use a water separator (Xinville 14 ports) to divide the water and reflux for seven days. Use petroleum ether and dichloromethane 1:1 to point the board, you will find that it is mainly 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 8.82 g of solid with a yield of 91%.

[0077] 1...

Embodiment 3

[0078] Example 3: Synthesis of N,N-bis(2,6-diphenylmethyl-4-trifluoromethylphenyl)butane-2,3-diimine

[0079]

[0080] Similar to Example 1, at room temperature, add 9.87 g of 2,6-benzyl-4-trifluoromethylaniline, 0.86 g of butanedione and p-methyl to an eggplant-shaped bottle 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 reflux the water for seven days. Use petroleum ether and dichloromethane 1:1 to spot 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 9.03 g of solid with a yield of 90%.

[0081] 1 HNMR(CDCl 3 , ...

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Abstract

The invention relates to a diimine palladium catalyst with great steric hindrance, and ligand, preparation method and application thereof. The diimine palladium catalyst has a formula as described in the specification, and R1 to R7 and X are as defined in the specification. The catalyst provided by the invention has high thermal stability and activity to vinyl polymerization and enables polyethylene with low branching degree and high molecular weight to be produced. Moreover, the catalyst can be applied to copolymerization of ethylene and methyl acrylate. Polyethylene and ethylene-methyl acrylate copolymer prepared in the aid of the catalyst are hypocrystalline solids.

Description

Technical field [0001] The invention relates to the field of catalysis and synthetic polymer polyolefin materials, in particular to a large hindered diimine palladium catalyst and its ligands, preparation methods and applications. Background technique [0002] Polyolefin has become an indispensable material in modern social life due to its excellent properties and relatively low price. At present, the demand for polyolefins is very huge, and due to the particularity of their synthesis methods, the research on the core catalysts in their synthesis occupies the most important position. [0003] Looking at the history of the development of the olefin polymerization industry, it can be found that technological progress is all closely related to the discovery of new catalysts and the successful development of process technologies. In the process of olefin polymerization, the catalyst often determines the polymerization behavior of the entire olefin, the particle morphology of the produ...

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
Inventor 陈昶乐代胜瑜隋学林
Owner 合肥中科科乐新材料有限责任公司
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