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Aromatic amine based on rigid terphenyl structure, alpha-diimine ligand, nickel catalyst and preparation method and application thereof

A technology of diimine ligand and terphenyl, which is applied in the preparation of imino compounds, chemical instruments and methods, preparation of amino compounds from amines, etc., can solve the problem of hindering the insertion of polar monomers and unfavorable for the synthesis of functionalized polyolefin materials , can not significantly improve the polymerization effect and other problems, to achieve the effect of excellent catalytic performance, excellent thermal stability, molecular weight and thermal stability improvement

Active Publication Date: 2021-07-20
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the prior art, there are two mainstream methods of regulating the electronic effect and steric effect of the catalyst. Because the axial steric hindrance of the catalyst is too large, the insertion of polar monomers will be hindered, which will be unfavorable for the synthesis of functionalized polyolefin materials. ; In addition, using a series of electron-absorbing (donating) substituents (such as methyl, methoxy, trifluoromethyl, nitro) to adjust the electron cloud density of the central metal can not significantly improve the polymerization effect

Method used

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  • Aromatic amine based on rigid terphenyl structure, alpha-diimine ligand, nickel catalyst and preparation method and application thereof
  • Aromatic amine based on rigid terphenyl structure, alpha-diimine ligand, nickel catalyst and preparation method and application thereof
  • Aromatic amine based on rigid terphenyl structure, alpha-diimine ligand, nickel catalyst and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Step 1, the preparation of 4-methyl-2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) aniline

[0074]

[0075] Under an inert atmosphere (nitrogen), 2,6-dibromo-4-methylaniline (0.50g, 1.9mmol), bis(pinacol)diborane (1.44g, 5.7mmol), potassium acetate (0.55g , 5.6mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.028g) were dissolved in dimethyl sulfoxide (20mL), then stirred at 80°C for 24 hours or more. After the reaction was completed, the black-red liquid mixture was poured into ice water (50 mL) and the precipitate was filtered. The precipitate was redissolved in dichloromethane, the organic layer was washed with water, separated and dried over anhydrous sodium sulfate. After the solid was filtered, the organic phase was concentrated by rotary evaporation in vacuo. By flash column chromatography (silica gel; PE / CH 2 Cl 2 = 3:1) to purify the resulting residue and then use CH 2 Cl 2 / CH 3 Recrystallization from OH afforded 0.40 g (60%...

Embodiment 2

[0090] Step 1-Step 5 are the same as in Example 1, except for the variables in Tables 1-4, other conditions are unchanged. In the table, the substitute for 4-methyl-2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)aniline of Example 1 is designated A , the substitute of 4-anthracenyl bromobenzene is recorded as B, the substitute of 4-methyl-2,6-bis[(4-anthracenyl)phenyl]aniline is recorded as C,2,3-butanedione The substitute is denoted as D, the substitute of bis-[2,6-bis(4-anthracenyl)phenyl-4-methylphenyl)butanedione-1,2-diimine is denoted as E, [( MeN^N)NiBr 2 and [(MeN^N)Ni(acac)][B(C 6 f 5 ) 4 ] The substitute is denoted as F.

[0091] Table 1 Reactants of Step 2 Synthesis C (reaction temperature: 90°C, reaction time: 24h)

[0092]

[0093]

[0094]

[0095] Table 2 Reactants of step 3 synthesis E (reaction temperature: 130°C, reaction time: 48h)

[0096]

[0097]

[0098]

[0099]

[0100] Table 3 Step 4 Synthesis of F reactants (reaction time:...

Embodiment 3

[0110] A 350 mL glass pressure reactor connected to a high pressure gas line was first vacuum dried at 90 °C for at least 1 h. Then adjust the reactor to 30°C, add 98 mL of toluene and 500 μmol of MMAO into the reactor under an inert atmosphere, and then dissolve 1 μmol of Ni catalyst in 2 mL of dichloromethane (or chloroform) and inject it into the polymerization system through a syringe middle. Under rapid stirring (over 750 rpm), ethylene was introduced and kept at 8 atm. After 10 minutes, the pressure reactor was emptied, and a large amount of ethanol (or methanol) solution with a concentration of 5 wt% hydrochloric acid was added to quench the polymerization reaction, filtered, and dried in a vacuum oven to constant weight.

[0111] Wherein, the structural general formula of nickel catalyst is shown in formula (Ⅲ), R 2 =CH 3 , R 3 = R 4 =H,R 5 = Anthracene, R 1 , R 10 , R 11 See Table 5.

[0112] Different nickel catalysts under table 5 high pressure (change sub...

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Abstract

The invention relates to aromatic amine based on a rigid terphenyl structure, an alpha-diimine ligand, a nickel catalyst and a preparation method and application of the aromatic amine, the alpha-diimine ligand and the nickel catalyst, and belongs to the technical field of catalysts. The structural formula of the nickel catalyst is shown as a formula (III) or a formula (IV), and the nickel catalyst has excellent performance in preparation of polyethylene by catalyzing ethylene polymerization: under the ethylene pressure condition of 8bar, the polymerization time is 10 minutes, and ultrahigh molecular weight polyethylene can be obtained; under the ethylene pressure condition of 1 bar, the ultra-high molecular weight polyethylene can still be obtained after the polymerization time is 30 minutes; and the catalyst has the advantage of high activity, can still maintain the high activity of 2.1 * 10 < 6 > g mol <-1 > h <-1 > even at 150 DEG C, and shows extremely excellent thermal stability.

Description

technical field [0001] The invention belongs to the technical field of catalysts, in particular to a class of aromatic amines based on a rigid terphenyl structure, an α-diimine ligand, a nickel catalyst and a preparation method and application thereof, especially to the use of the nickel catalyst in the preparation of polyethylene by catalyzing ethylene polymerization Applications. Background technique [0002] Ultra-high molecular weight polyethylene, this type of polyolefin material has very broad industrial application prospects, for example, it can be used as ultra-high molecular weight polyethylene fiber, and it is currently one of the booming high-tech materials in the 21st century. The ultra-high molecular weight polyethylene material has the advantages of high strength, good toughness, high rigidity, heat resistance, and cold resistance. It also has good environmental stress cracking resistance, impact resistance, tear resistance, etc. , alkali, organic solvents, et...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/45C07C251/08C07F15/04C07C209/68C07C249/02C08F10/02C08F4/70
CPCC07C211/45C07C251/08C07F15/045C08F10/02C08F4/7006C08F4/7083Y02P20/52
Inventor 简忠保胡小强
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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