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Bridged metallocene complex and its application

A technology of metallocene complexes and metallocene catalysts, applied in metallocene, organic chemistry, chemical instruments and methods, etc., can solve problems such as the inability to control the performance of ethylene-propylene rubber, and achieve the effect of strong copolymerization catalytic ability

Inactive Publication Date: 2014-03-19
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although the above-mentioned patents can efficiently synthesize ethylene-propylene rubber, it is impossible to obtain ethylene-propylene rubber with a certain structure through the control of raw material ratio and reaction conditions, and it is impossible to control the performance of ethylene-propylene rubber.

Method used

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  • Bridged metallocene complex and its application
  • Bridged metallocene complex and its application
  • Bridged metallocene complex and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Synthesis of bridged metallocene complex A1:

[0045] (1) Synthesis of 1-(2,5-dimethylphenyl)-2-methylpropan-1-one: 78.6 g (0.74 mol) p-xylene, 61 g (0.45 mol) anhydrous AlCl 3 The mixture of the powder and 500mL of carbon disulfide was cooled to 0°C, and 79.4g (0.74mol) of methacryloyl chloride was slowly added dropwise to the mixture while stirring. After the temperature of the mixture was raised to room temperature, stirring was continued for 12 hours. Then add 61 g (0.45 mol) of anhydrous AlCl 3 powder and 250mL carbon disulfide. The mixture was refluxed at 45°C for 3 hours, cooled to room temperature and poured into an ice / hydrochloric acid mixture. The organic phase is separated and the carbon disulfide is removed by gas flow. The remaining liquid was extracted with ether and washed with anhydrous Na 2 SO 4 After drying, 93.0 g of 1-(2,5-dimethylphenyl)-2-methylpropan-1-one were obtained, with a yield of 71%. 1 H-NMR (300MHz, CDCl 3 ,δin ppm):7.57(s,1H,Ar-...

Embodiment 2

[0053] Synthesis of bridged metallocene complex A2:

[0054] (1) Synthesis of 1-(2,5-diethylphenyl)-2-methylpropan-1-one: the reaction conditions are the same as those of 1-(2,5-dimethylphenyl)-2 in Example 1 -Synthesis of methylpropan-1-one, only by replacing p-xylene with p-diethylbenzene, to obtain 91.3 g of 1-(2,5-dimethylphenyl)-2-methylpropan-1-one, Yield 59%. 1 H-NMR (300MHz, CDCl 3 ,δin ppm):7.70(s,1H,Ar-H),7.25(s,1H,Ar-H),7.15(s,1H,Ar-H),3.34(sept,1H,CH(CH 3 ) 2 ),2.59(s,4H,Ar-CH 2 ),1.23(d,6H,CHCH 3 ). Elem.Anal.Calcd.For C 14 h 20 O: C, 82.35%; H, 9.80%; O, 7.84%. Found: C, 82.30%; H, 9.84%; O, 7.86%. ESI-MS: m / z205.10 ([M+H] + ).

[0055] (2) Synthesis of α-bromo-2,5-diethylisobutyrophenone: the reaction conditions are the same as the synthesis of α-bromo-2,5-dimethylisobutyrophenone in Example 1, only 1-( 2,5-Dimethylphenyl)-2-methylpropan-1-one was replaced by 1-(2,5-diethylphenyl)-2-methylpropan-1-one to give 69.9 g of α -Bromo-2,5-dimethylisobutyr...

Embodiment 3

[0062] Synthesis of bridged metallocene complex A3:

[0063] (1) Synthesis of 1-(2-methoxy-5-methylphenyl)-2-methylpropan-1-one: the reaction conditions are the same as those of 1-(2,5-dimethylphenyl) in Example 1 )-2-methylpropan-1-one, only p-xylene was replaced by p-methylanisole, and 72.8 g of 1-(2-methoxy-5-methylphenyl)-2- Methylpropan-1-one, 51% yield. 1 H-NMR (300MHz, CDCl 3 ,δin ppm):7.58(s,1H,Ar-H),7.13(s,1H,Ar-H),6.73(s,1H,Ar-H),3.73(s,3H,OCH 3 ),3.34(sept,1H,CH(CH 3 ) 2 ),2.35(s,3H,Ar-CH 3 ),1.23(d,6H,CHCH 3 ). Elem.Anal.Calcd.For C 12 h 16 o 2 : C, 75.0%; H, 8.33%; O, 16.67%. Found: C, 74.95%; H, 8.31%; O, 16.74%. ESI-MS: m / z193.10 ([M+H] + ).

[0064] (2) Synthesis of α-bromo-2-methoxy-5-methylisobutyrophenone: the reaction conditions are the same as the synthesis of α-bromo-2,5-dimethylisobutyrophenone in Example 1, only 1-(2,5-Dimethylphenyl)-2-methylpropan-1-one was replaced by 1-(2-methoxy-5-methylphenyl)-2-methylpropane-1- ketone to obtain 64...

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Abstract

The invention discloses a bridged metallocene complex, which is characterized by having a structural formula shown as the following A1, A2, A3 or A4. The invention also discloses a preparation method of ethylene propylene rubber. The ethylene propylene rubber is formed by copolymerization of ethylene, propylene and a third monomer in the presence of a metallocene catalyst, which takes the bridged metallocene complex as a main catalyst, and adopts methoxy aluminoxane or isobutyl modified methoxy aluminoxane as an assistant catalyst. In the structure of the ternary ethylene propylene rubber prepared from the metallocene catalyst involved in the invention, the content of the ethylene and propylene structural units is very close to the charging ratio of ethylene and propylene monomers, so that ternary ethylene propylene rubber of specific composition can be obtained directly by controlling the charging ratio, thereby realizing regulation of the ethylene propylene rubber's performance. The method involved in the invention is efficient and simple, and is suitable for industrial production of ethylene propylene rubber.

Description

technical field [0001] The invention relates to a metallocene catalyst, in particular to a bridged metallocene complex and its application. Background technique [0002] Ethylene-propylene-diene rubber (EPDM) is a synthetic rubber obtained by copolymerizing ethylene, propylene and a small amount of non-conjugated diene monomers. The current global annual production capacity exceeds 1.3 million tons, second only to styrene-butadiene rubber (SBR) Butadiene rubber (BR) ranks third among the seven synthetic rubber varieties, accounting for about 11% of the total global synthetic rubber production capacity. The molecular main chain of EPDM rubber is composed of chemically stable saturated hydrocarbons, which has a high degree of saturation, making it have excellent aging resistance, chemical corrosion resistance, low temperature resistance and excellent electrical insulation properties, a small amount of side chains It contains unsaturated double bonds, which can be cross-linked...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/00C08F210/18C08F4/659
Inventor 傅智盛范志强黄耀顾雪萍冯连芳
Owner ZHEJIANG UNIV
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