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A kind of α-sulfonic acid-β-diimine nickel complex, its preparation method and its application in catalytic olefin polymerization

A nickel diimide, catalyzing olefin technology, applied in nickel organic compounds, organic chemical methods, chemical instruments and methods, etc., can solve the problems of poor thermal stability, low polymerization activity of phosphine sulfonate nickel palladium catalyst, low polymerization activity and the like , to achieve the effect of improved temperature resistance, good broad spectrum and high insertion rate

Active Publication Date: 2021-11-26
链行走新材料科技(广州)有限公司
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  • 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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  • A kind of α-sulfonic acid-β-diimine nickel complex, its preparation method and its application in catalytic olefin polymerization
  • A kind of α-sulfonic acid-β-diimine nickel complex, its preparation method and its application in catalytic olefin polymerization
  • A kind of α-sulfonic acid-β-diimine nickel complex, its preparation method and its application in catalytic olefin polymerization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] This example provides a β-diimine A1 substituted with 2,6-diisopropylphenyl, and its synthesis method is as follows.

[0060] Acetylacetone (4.1g, 41mmol), 2,6-diisopropylaniline (15.1g, 85.2mmol), ethanol (500mL) and hydrochloric acid (12M, 6mL) were successively added into the round bottom flask. The system was heated to 100°C in an oil bath and reacted for 72 hours. Then the solution was cooled to room temperature, and the solvent was removed by rotary evaporation to obtain 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 with methanol to obtain a white solid. Yield 87.3%. The H NMR spectrum is as follows: 1 H NMR (CDCl 3, 400MHz) δ(ppm): 12...

Embodiment 2

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

[0063] According to the synthesis method of Example 1, 2,6-dimethylaniline was replaced by 2,6-dimethylaniline to obtain a white solid. The yield was 82.7%. The H 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 example 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 (3.86g, 9.24mmol) was dissolved in dry tetrahydrofuran, and n-BuLi (4.3mL, 10.75mmol) was slowly added dropwise at -78°C, and then stirred at -78°C for 1h , the resulting system was slowly warmed up to room temperature, and continued to stir for 30 min. -78°C, add SO 3 .NMe 3 (0.84g, 6.04 mmol), slowly rose to room temperature, and continued to stir for 24h. After the solution was filtered, the filtrate obtained was concentrated, frozen at -30°C to obtain a white precipitate, filtered to obtain a white solid, washed twice with n-hexane, and vacuum-dried to obtain a white solid with a yield of 82.3%. The H 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(m,8H,THF),1.15(m,24H,CH(CH 3 ) 2 ).

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Abstract

The invention discloses an α-sulfonic acid-β-diimine nickel complex, a preparation method and its application in catalyzing olefin polymerization. The invention provides an α-sulfonic acid-β-diimine nickel complex. The invention also provides a preparation method of α-sulfonic acid-β-diimine nickel complex and its application in catalyzing olefin polymerization. In the catalyst system formed by the α-sulfonic acid-β-diimine nickel complex provided by the invention, it can be used as a main catalyst to catalyze olefin polymerization. The catalyst not only shows excellent temperature resistance, can prepare polymers with high molecular weight and narrow distribution, but also has excellent tolerance to polar monomers, and can prepare high molecular weight olefin copolymers with high polar group content, Thus, a high-performance polyolefin material is prepared.

Description

technical field [0001] The invention relates to the technical field of olefin catalysis. More specifically, it relates to a nickel compound, its preparation method and its application in the field of catalytic olefin polymerization. Background technique [0002] Polyolefin is a widely used material, and more than 100 million tons of polyolefin are produced globally every year, but the non-polar nature of polyolefin limits its wider application. By introducing polar groups into polyolefin chains, the adhesion, dyeability, and compatibility of polyolefin materials will be greatly improved. Compared with the post-functionalization, the direct copolymerization of olefins and polar monomers by catalysts to prepare functionalized polyolefins 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 transition metal cataly...

Claims

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Application Information

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Patent Type & Authority Patents(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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