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A bridged asymmetric binuclear metallocene compound and its preparation and application

A metallocene compound, asymmetric technology, applied in the direction of metallocene, catalytic reaction, organic compound/hydride/coordination complex catalyst, etc., can solve the problem of molecular weight reduction, achieve stable steric configuration, and facilitate the selection of propylene Sexual polymerization, high activity effect

Active Publication Date: 2019-11-08
PETROCHINA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Moreover, contrary to mononuclear catalytic systems, the molecular weight decreases with increasing Al / Zr ratio

Method used

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  • A bridged asymmetric binuclear metallocene compound and its preparation and application
  • A bridged asymmetric binuclear metallocene compound and its preparation and application
  • A bridged asymmetric binuclear metallocene compound and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0099] Ligand L1[(CH 3 ) 2 C(C 5 h 4 )(C 13 h 9 )](CH 2 C 6 h 4 CH 2 )[(C 6 h 5 ) 2 C(C 5 h 4 )(C 13 h 9 )]Synthesis

[0100]

[0101]Under argon protection, with carbon tetrachloride as a solvent, p-xylene (5.04g, 47.53mmol), NBS (30g) and BPO (dibenzoyl peroxide) (2g) were added to the bottle for reaction, heated , when heated to 70°C, the solid and liquid in the bottle began to melt, after stabilization, continue heating to 80°C, reflux reaction for 20 hours, cooling down, white solid in the upper layer, light yellow clear liquid in the lower layer, cooled to 40°C, Filter, take the filtrate, and put it in the refrigerator. After 24 hours, white crystals, about 5 g, are precipitated, which is p-dibromobenzyl, and the yield is 40%.

[0102] Add fluorene (10g, 60.24mmol), 100mL of n-hexane, and 20mL of diethyl ether into a 200mL Schlenk bottle, and slowly add n BuLi (36.7mL, 1.64mol / L), a precipitate formed immediately. Naturally rise to room temperature,...

Embodiment 2

[0113] Ligand L2[(CH 3 ) 2 C(C 5 h 4 )(C 13 h 9 )](CH 2 C 6 h 4 CH 2 )[(CH 2 ) 5 C(C 5 h 4 )(C 13 h 9 )]Synthesis

[0114]

[0115] 0°C, a solution of 6,6-dimethylfulvene (5.11g, 48.18mmol) in ether (40mL) was added dropwise to a solution of fluorenelithium (FluLi) (8g, 48.18mmol) in ether (80mL), after 8h Precipitation appeared, and the reaction was continued for 20 hours, a large amount of precipitates formed, press-filtered, the solid was washed twice with ether, once with hexane, and dried to obtain 9.18 g of solid, ie, the yield was 70%.

[0116] At 0°C, a solution of 6,6-pentamethylenefulvene (8.89g, 48.18mmol) in ether (40mL) was added dropwise to a solution of FluLi (8g, 48.18mmol) in ether (80mL). No precipitate was formed, but after about 4 hours, a precipitate appeared, and after 20 hours of reaction, a large amount of precipitate formed, and the solid was washed twice with ether and once with hexane, and dried to obtain 11.49 g of solid, with a y...

Embodiment 3

[0125] Ligand L3[(C 6 h 5 ) 2 C(C 5 h 4 )(C 13 h 9 )](CH 2 C 6 h 4 CH 2 )[(CH 2 ) 5 C(C 5 h 4 )(C 13 h 9 )]Synthesis

[0126]

[0127] At 0°C, a solution of 6,6-pentamethylenefulvene (8.89g, 48.18mmol) in ether (40mL) was added dropwise to a solution of FluLi (8g, 48.18mmol) in ether (80mL). No precipitate was formed, but after about 4 hours, a precipitate appeared, and after 20 hours of reaction, a large amount of precipitate formed, and the solid was washed twice with ether and once with hexane, and dried to obtain 11.49 g of solid, with a yield of 68%.

[0128] At 0°C, a solution of 6,6-diphenylfulvene (11.08g, 48.18mmol) in ether (40mL) was added dropwise to a solution of FluLi (8g, 48.18mmol) in ether (80mL). After 6 hours, Precipitation appeared, and a large amount of precipitates formed after 20 hours of reaction. The solvent was removed by pressure filtration, and the solid was washed twice with ether and once with hexane, and dried to obtain 12.41 ...

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Abstract

The invention provides bridged asymmetric dinuclear metallocene compounds, and preparation and application thereof. The compounds have the structure disclosed as Formula I, wherein R1s and R2s are selected from C1-C5 alkyl or phenyl, and are different; optionally, the two R1s or two R2s can independently form a naphthene base with the carbon atom connected with the R1 or R2; and R3 and R4 are selected from hydrogen, C1-C8 alkyl, bromine or chlorine. The bridged asymmetric dinuclear metallocene compounds for sPP have the advantages of simple synthesis route, high product yield and easy separation and purification; and when being used for catalyzing propylene polymerization, the bridged asymmetric dinuclear metallocene compounds have the advantages of low cocatalyst consumption, high catalytic activity and high polymer syndiotacticity.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a bridging asymmetric dinuclear metallocene compound and its preparation and application. Background technique [0002] Since Fina produced sPP in a liquid-phase loop reactor in 1993, foreign companies such as Basell, Huntsman, Dow, ExxonMobil, Mitsui Topress, and Idemitsu Petrochemical have devoted themselves to the development of sPP. At present, Fina, Basell, ExxonMobil, and Japan's Idemitsu Petrochemical Company have realized the industrial production of sPP. [0003] This kind of mononuclear metallocene catalyst has become the focus of research by scientists from all over the world. The mononuclear catalyst that has been patented covers almost all aspects of this research field, and it is difficult to have great original innovation. It is a new field of research to connect bridging mononuclear metallocene compounds with certain bridging groups to obtain double bridge metall...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F17/00B01J31/22C08F110/06C08F4/6592
CPCB01J31/2295B01J2231/12B01J2531/48C07F17/00C08F110/06C08F4/65927C08F2500/16
Inventor 米普科许胜刘敏
Owner PETROCHINA CO LTD
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