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Alpha-sulfonic acid-beta-diimine nickel complex, preparation method and application of alpha-sulfonic acid-beta-diimine nickel complex in catalyzing olefin polymerization

A technology of diimine compound and diimine nickel, which is applied in the direction of nickel organic compounds, organic chemical methods, chemical instruments and methods, etc., can solve the problem of low polymerization activity of phosphonic acid nickel palladium catalyst, low molecular weight of copolymerized products, thermal stability Poor resistance and other problems, to achieve good tolerance characteristics, good broad-spectrum, temperature resistance to improve the effect

Active Publication Date: 2021-03-23
链行走新材料科技(广州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to overcome the poor thermal stability of the existing bidentate [N,N]diimine nickel-palladium catalyst, the serious attenuation of the copolymerization activity, and the low molecular weight branched polymer obtained, and the polar monomers are mainly limited to esters. The monomers of other polar monomers are generally difficult to copolymerize; and bidentate [N, O] salicylaldimine nickel catalyst has poor thermal stability, low polymerization activity, and the molecular weight of the copolymerization product is very low; and bidentate [P, O] phosphine sulfonate Niacid nickel palladium catalyst polymerization activity is too low, the defects or deficiencies of the obtained copolymer molecular weight are all very low, provide a kind of tridentate [N,N,O]α-sulfonic acid-β-diimine nickel complex

Method used

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  • Alpha-sulfonic acid-beta-diimine nickel complex, preparation method and application of alpha-sulfonic acid-beta-diimine nickel complex in catalyzing olefin polymerization
  • Alpha-sulfonic acid-beta-diimine nickel complex, preparation method and application of alpha-sulfonic acid-beta-diimine nickel complex in catalyzing olefin polymerization
  • Alpha-sulfonic acid-beta-diimine nickel complex, preparation method and application of alpha-sulfonic acid-beta-diimine nickel complex in catalyzing olefin polymerization

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Experimental program
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Effect test

Embodiment 1

[0059] This embodiment provides a 2,6-diisopropylphenyl-substituted β-diimine A1, the synthesis method of which is as follows.

[0060] Acetylacetone (4.1 g, 41 mmol), 2,6-diisopropylaniline (15.1 g, 85.2 mmol), ethanol (500 mL) and hydrochloric acid (12 M, 6 mL) were sequentially added to the round-bottomed flask. The system was heated to 100°C in an oil bath and reacted for 72h. The solution was then cooled to room temperature and the solvent was removed by rotary evaporation to give a brown solid. The resulting solid was dissolved in dichloromethane (300 mL), saturated NaHCO 3 The solution was washed and extracted twice, and the organic phase was collected. The organic phase was dried with anhydrous magnesium sulfate, filtered, and the filtrate was collected; then the filtrate was rotary evaporated to obtain a crude product, which was recrystallized from methanol to obtain a white solid. Yield 87.3%. The NMR spectrum is as follows: 1 H NMR (CDCl 3, 400MHz)δ(ppm): 12....

Embodiment 2

[0062] This embodiment provides a 2,6-dimethylphenyl-substituted β-diimine A2, the synthesis method of which is as follows.

[0063] According to the synthetic method of Example 1, 2,6-dimethylaniline was replaced by 2,6-dimethylaniline to obtain a white solid. The yield was 82.7%. The NMR spectrum is as follows: 1 H NMR (CDCl 3 ,400MHz)δ(ppm):12.17(s,1H,NH),7.05-6.92(m,6H,Ar-H),4.87(s,1H,H β ),2.16(s, 12H,CH 3 ),1.68(s,6H,α-CH 3 ).

Embodiment 3

[0065] This embodiment provides an α-sulfonic acid-β-diimide lithium salt compound L1, the synthesis method of which is as follows.

[0066] Under nitrogen atmosphere, β-diimine A1 (3.86 g, 9.24 mmol) was dissolved in dry tetrahydrofuran, n-BuLi (4.3 mL, 10.75 mmol) was slowly added dropwise at -78 °C, and stirring was continued for 1 h at -78 °C. , the obtained system was slowly warmed to room temperature, and stirring was continued for 30 min. -78℃, add SO 3 .NMe 3 (0.84 g, 6.04 mmol), slowly warmed to room temperature, and continued stirring for 24 h. The filtrate obtained after the solution was filtered was concentrated, and frozen at -30°C to obtain a white precipitate. The white solid obtained by filtration was washed twice with n-hexane and dried in vacuo to obtain a white solid with a yield of 82.3%. The NMR spectrum is as follows: 1 H NMR (MeOD, 400MHz) δ (ppm): 7.13-7.02 (m, 6H, Ar-H), 5.04 (s, 1H, H β ),3.72(m,8H,THF),3.09(m,4H,CHMe 2 ),2.09(s,6H,CH 3 ),1.86(...

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Abstract

The invention discloses an alpha-sulfonic acid-beta-diimine nickel complex, a preparation method and application of the alpha-sulfonic acid-beta-diimine nickel complex in catalyzing olefin polymerization. The invention provides the alpha-sulfonic acid-beta-diimine nickel complex. The invention also provides a preparation method of the alpha-sulfonic acid-beta-diimine nickel complex and applicationof the alpha-sulfonic acid-beta-diimine nickel complex in catalyzing olefin polymerization. The alpha-sulfonic acid-beta-diimine nickel complex provided by the invention can be used as a main catalyst to catalyze olefin polymerization in a catalyst system formed by the alpha-sulfonic acid-beta-diimine nickel complex. The catalyst shows excellent temperature resistance, can be used for preparing apolymer with high molecular weight and narrow distribution, has excellent polar monomer tolerance, and can be used for preparing a high molecular weight olefin copolymer with relatively high polar group content, so that a polyolefin material with high performance is prepared.

Description

technical field [0001] The present invention relates to the technical field of olefin catalysis. More specifically, it relates to a nickel compound and its preparation method and its application in the field of catalytic olefin polymerization. Background technique [0002] Polyolefin is a widely used material, with more than 100 million tons of polyolefin produced globally each year, but the non-polar nature of polyolefin limits its wider application. By introducing polar groups into the polyolefin chain, the adhesion, dyeability, and compatibility of polyolefin materials will be greatly improved. Compared with post-functionalization, the preparation of functionalized polyolefins by the direct copolymerization of olefins and polar monomers through catalysts is the most simple, direct and effective method. [0003] Olefin polymerization catalysts are at the heart of polyolefin production and R&D. From traditional Ziegler-Natta catalysts to metallocene catalysts to late tra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/04C08F10/00C08F4/70C08F110/02C08F110/06C08F110/08C08F110/14C08F210/02C08F220/14C08F220/06C08F214/16C08F216/04C08F218/08C08F218/12C08F220/44C08F216/36C08F214/20C08F216/18C08F220/56C08F226/10C08F228/02C08F220/04C08F216/10
CPCC07B2200/13C07F15/045C08F10/00C08F110/02C08F110/06C08F110/08C08F110/14C08F210/02C08F2500/01C08F4/7055C08F220/14C08F220/06C08F214/16C08F216/04C08F218/08C08F218/12C08F220/44C08F216/36C08F214/205C08F216/18C08F220/56C08F226/10C08F228/02C08F220/04C08F216/10
Inventor 高海洋杜文博钟柳
Owner 链行走新材料科技(广州)有限公司
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