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Bimetal complexes of phenoxy imine ligand framework, preparation method and application

A technology of phenoxyimine and complexes, which is applied in the field of bimetallic complexes, can solve the problems of catalyst thermal stability that needs to be improved, polymer molecular weight is low, and it is difficult to meet application requirements, so as to achieve good catalytic activity and thermal stability , The effect of broadening the scope of application

Pending Publication Date: 2020-11-17
WANHUA CHEM GRP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although existing FI catalysts (as reported in journal literature Journal of the American Chemical Society, 2001,123 (28): 6847-6856) have higher catalytic activity and tunability, the polymer molecular weight prepared is usually lower , and the thermal stability of the catalyst needs to be improved, which is difficult to meet the application requirements

Method used

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  • Bimetal complexes of phenoxy imine ligand framework, preparation method and application
  • Bimetal complexes of phenoxy imine ligand framework, preparation method and application
  • Bimetal complexes of phenoxy imine ligand framework, preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089] Under a nitrogen atmosphere, 6.81g of 2-hydroxy-5-methylbenzaldehyde (50mmol, 1.0eq.) and 9.21g of diphenylmethanol (50mmol, 1.0eq.) were dissolved in 150mL of dichloromethane, and slowly added 1.10g of Tin bromide (2.5mmol, 0.05eq.), stirred at room temperature for 8h. Add 10 mL of saturated aqueous sodium bicarbonate solution to quench the reaction, extract with dichloromethane, wash with saturated brine, combine the organic phases, dry over anhydrous sodium sulfate, concentrate the filtrate and purify by silica gel column chromatography (petroleum ether: ethyl acetate = 100: 1 (v / v)), to obtain 14.15 g of white solid, which was denoted as compound 1, and the yield was 93.6%.

[0090] The NMR structure confirmation data of compound 1 are as follows:

[0091] 1 H NMR (CDCl 3 ,400MHz,TMS):δ12.03(s,1H),10.18(s,1H),7.39(s,1H),7.29(t,J=8.0Hz,4H),7.20–7.18(m,3H), 7.13(d, J=8.0Hz, 4H), 5.46(s, 1H), 2.35(s, 3H). 13 C NMR (CDCl 3 ,100MHz,TMS):δ190.0,156.7,142.4,136.3,131...

Embodiment 2

[0093] Under a nitrogen atmosphere, 2.84g of 1,2,4,5-benzenetetramine tetrahydrochloride (10mmol, 1.0eq.) and 13.30g of compound 1 (44mmol, 4.4eq.) were dissolved in 100mL of toluene, and 0.38g p-toluenesulfonic acid (2mmol, 0.2eq.), heated under reflux for 12h. The reaction solution was concentrated and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 200:1 (v / v)) to obtain 9.99 g of a white solid, which was designated as compound 2, with a yield of 78.3%.

[0094] The NMR structure confirmation data of compound 2 are as follows:

[0095] 1 H NMR (CDCl 3 ,400MHz,TMS):δ11.93(s,4H),8.94(s,4H),7.47(s,4H),7.29(t,J=8.0Hz,16H),7.20(t,J=8.0Hz, 8H), 7.13(d, J=8.0Hz, 16H), 6.95(s, 4H), 6.75(s, 2H), 5.46(s, 4H), 2.35(s, 12H). 13 C NMR (CDCl 3 ,100MHz,TMS):δ159.0,156.0,143.5,142.4,132.8,130.6,129.2,128.2,127.2,125.2,118.4,117.9,49.3,21.6.

Embodiment 3

[0097] In the glove box, dissolve 6.38g of compound 2 (5mmol, 1.0eq.) in 50mL of dry toluene, slowly add 11mL, 2mol / L n-butyllithium (22mmol, 4.4eq.) dropwise, react at room temperature for 1h, and drain Toluene, add 20mL of dry n-hexane, stir for 15min and let stand, filter and wash with dry n-hexane, add 50mL of dry toluene to the filter residue to dissolve, and add 4.98g of TiCl 4 (THF) 2 (15mmol, 3.0eq.), heated to reflux for 8h, drained the toluene after the reaction, added 20mL of dry n-hexane, stirred for 15min and allowed to stand, filtered and washed with dry n-hexane, the filtrate was drained, then added 30mL of dry toluene, filtered The filtrate was collected, and the solvent was drained to obtain 3.95 g of a dark red solid, which was recorded as compound 3, and the yield was 52.4%.

[0098] The NMR structure confirmation data of compound 3 are as follows:

[0099] 1 H NMR (CDCl 3 ,400MHz,TMS):δ8.39(s,4H),7.46(s,4H),7.29(t,J=8.0Hz,16H),7.20(t,J=8.0Hz,8H),7.13(d,...

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Abstract

The invention provides a bimetallic complex of a phenoxy imine ligand skeleton, and a preparation method and application thereof. The bimetallic complex has a structural expression shown in the specification. The phenoxy imine bimetal complex provided by the invention shows very good catalytic activity and thermal stability when being used for catalyzing olefin polymerization and ethylene / alpha-olefin copolymerization reaction. The olefin homopolymer has the characteristics of high linearity and high melting point, the copolymerization product contains a certain amount of alkyl branched chains, the melting point is low, the olefin homopolymer has the performance of a polyolefin elastomer, and the potential application range of the olefin homopolymer is widened.

Description

technical field [0001] The invention relates to a class of bimetallic complexes, in particular to a class of bimetallic complexes with phenoxyimine ligand skeletons, a preparation method and applications. Background technique [0002] Polyolefin is an extremely important class of polymer materials, and is widely used in many fields such as military, industry, agriculture, and medical care. Among polyolefin products, polyethylene has the largest output and consumption, and the development and research of polyethylene synthesis technology has always been one of the topics of concern to the business community and academia. In addition, polyolefin elastomers based on the copolymerization of ethylene / α-olefins (propylene, 1-butene, 1-hexene, 1-octene, etc.) have both the plasticity of plastics and the high elasticity of rubber, and are more flexible than traditional polyolefins. The higher added value of vinyl resin is also one of the main directions for the development of high-...

Claims

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Application Information

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IPC IPC(8): C07F7/00C08F110/02C08F110/06C08F210/16C08F4/642C08F4/646
CPCC07F7/003C07F7/00C08F110/02C08F110/06C08F210/16C08F4/64189Y02P20/52
Inventor 黄传兵张彦雨郭华刘万弼郗朕捷王金强焦栋林小杰
Owner WANHUA CHEM GRP CO LTD
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