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Pyridine imine compound and preparation method thereof, pyridine imine nickel catalyst and preparation method thereof and polyolefin

A pyridine imine nickel and pyridine imine technology, applied in the field of catalysts, can solve the problems of reducing the molecular weight, unable to increase the molecular weight of polyethylene, unable to effectively increase the molecular weight of polyethylene and the like

Inactive Publication Date: 2016-07-06
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But for the nickel pyridinium catalyst, the results are very interesting. Increasing the steric hindrance does not increase the molecular weight of polyethylene, but reduces the molecular weight. Many adjustments cannot effectively increase the molecular weight of polyethylene.

Method used

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  • Pyridine imine compound and preparation method thereof, pyridine imine nickel catalyst and preparation method thereof and polyolefin
  • Pyridine imine compound and preparation method thereof, pyridine imine nickel catalyst and preparation method thereof and polyolefin
  • Pyridine imine compound and preparation method thereof, pyridine imine nickel catalyst and preparation method thereof and polyolefin

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preparation example Construction

[0054] The present invention also provides a preparation method of the above-mentioned pyridine imine compounds, comprising:

[0055] The substituted naphthylamine derivative represented by formula (I-1) is reacted with the pyridine carbonyl compound represented by formula (I-2) to obtain the pyridine imine compound represented by formula (I).

[0056]

[0057] where the R 1 , R 2 with R 3 Each is independently hydrogen, aryl or arylalkyl; the number of carbon atoms of the alkyl in the arylalkyl is 1-6;

[0058] The R 4 , R 5 with R 6 each independently hydrogen, C1-C6 alkyl, nitro, C1-C6 alkoxy, N,N-dialkylamino or trifluoromethyl; in the N,N-dialkylamino The number of carbon atoms in the alkyl group is 1-6.

[0059] where the R 1 , R 2 , R 3 , R 4 , R 5 with R 6 All are the same as above, and will not be repeated here.

[0060] In the present invention, the substituted naphthylamine derivatives represented by the formula (I-1) are preferably prepared accordi...

Embodiment 1

[0116] Example 1: 2,4-bis(benzhydryl)-8-phenyl-1-naphthylamine

[0117]

[0118] Add 20 millimoles of 8-phenyl-1-naphthylamine and 40 millimoles of diphenylmethanol to a 150-ml pressure-resistant flask, heat to 120 degrees, and then add 10 millimoles of concentrated hydrochloric acid solution of anhydrous zinc chloride. Mole, the reaction bubbles, heated to 160 degrees; after half an hour of reaction at 160 degrees, stop the reaction, cool to room temperature, dissolve in 200 ml of dichloromethane solution, wash with 3 times 100 ml of water, dry over anhydrous magnesium sulfate . Filter, concentrate to 20 mL, add 200 mL of methanol to the product, wash with 3 times 100 mL of methanol to give a white powder solid as 2,4-bis(benzhydryl)-8-phenyl-1-naphthalene The amine was vacuum-dried to obtain 10.49 g of a solid with a yield of 95% and a purity greater than 99%.

[0119] Utilize nuclear magnetic resonance to analyze the 2,4-bis(benzhydryl)-8-phenyl-1-naphthylamine obtaine...

Embodiment 2

[0121] Example 2: 2,4-bis(benzhydryl)-8-p-methylphenyl-1-naphthylamine

[0122]

[0123] Add 20 mmoles of 8-p-methylphenyl-1-naphthylamine and 40 mmoles of diphenylmethanol in a 150 ml pressure-resistant flask, heat to 120 degrees, then add concentrated hydrochloric acid of anhydrous zinc chloride The solution was 10 millimoles, the reaction bubbled, heated to 160 degrees, and after half an hour of reaction at 160 degrees, the reaction was stopped, cooled to room temperature, and dissolved in 200 milliliters of dichloromethane solution. Wash with 3 times 100 ml of water and dry over anhydrous magnesium sulfate. Filter, concentrate to 20 mL, add 200 mL of methanol to the product, wash with 3 times 100 mL of methanol to give a white powder solid as 2,4-bis(benzhydryl)-8-p-methylphenyl- 1-Naphthylamine was vacuum-dried to obtain 10.75 g of solid with a yield of 95% and a purity of more than 99%.

[0124] The 2,4-bis(benzhydryl)-8-p-methylphenyl-1-naphthylamine obtained in Ex...

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Abstract

The invention provides a pyridine imine compound and a preparation method thereof, a pyridine imine nickel catalyst and a preparation method thereof and polyolefin. The pyridine imine compound is shown in the formula (I), wherein R1, R2 and R3 are hydrogen or aryl or aryl alkyl respectively and independently; the number of carbon atoms of alkyl in aryl alkyl ranges from 1 to 6; R4, R5 and R6 are hydrogen or C1-C6 alkyl or nitryl or C1-C6 nitryl alkoxy or N,N'-dialkyl amino or trifluoromethyl respectively and independently; the number of carbon atoms of alkyl in N,N'-dialkyl amino ranges from 1 to 6. Compared with the prior art, the pyridine imine compound shown in the formula (I) has a large-steric-hindrance sandwich structure, the pyridine imine nickel catalyst of the structure shown in the formula (II) is formed with the pyridine imine compound as a ligand and also has a large-steric-hindrance sandwich structure, the catalyst has high thermal stability and activity on olefin polymerization, and therefore polyolefin with a controllable degree of branching and a high molecular weight can be generated. (Please see the description for the formula (I) and the formula (II).).

Description

technical field [0001] The invention belongs to the field of catalysts and the technical field of polymer material preparation, and particularly relates to pyridinimine compounds and their preparation methods, pyridinimine nickel catalysts and their preparation methods, and polyolefins. Background technique [0002] Due to its excellent properties and relatively low price, polyolefin has become an indispensable material in modern social life. At present, the output of synthetic polyolefin is very huge, and because of the particularity of its synthesis method, the research on its core catalyst occupies the most important position. [0003] Looking at the history of the development of the olefin polymerization industry, we can find that technological progress is closely related to the discovery of new catalysts and the successful development of process technology. In the process of olefin polymerization, catalysts often determine the polymerization behavior of the entire olef...

Claims

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Application Information

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IPC IPC(8): C07D213/53B01J31/22C07F15/04C08F4/70C08F110/02
CPCC07D213/53B01J31/1815B01J2531/0213B01J2531/847C07F15/045C08F4/7034C08F110/02
Inventor 陈昶乐代胜瑜隋学林
Owner UNIV OF SCI & TECH OF CHINA
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