Amino imine ligand, and amino imine coordination compound and applications thereof

An aminoimine and complex technology, which is applied in the field of aminoimine ligands, can solve the problems of low catalytic activity of aminoimine complexes, difficulty in designing and synthesizing ligand sterically hindered catalysts, etc., and achieves the effect of high activity

Active Publication Date: 2020-05-08
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, too low temperature is not suitable for existing industrial reaction devices, and the excessive ligand steric hindrance makes the design and synthesis of catalysts more difficult.
Some people apply aminoimine complexes to ethylene polymerization, but the catalytic activity of aminoimine complexes is low

Method used

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  • Amino imine ligand, and amino imine coordination compound and applications thereof
  • Amino imine ligand, and amino imine coordination compound and applications thereof
  • Amino imine ligand, and amino imine coordination compound and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] 1) Preparation of ligand:

[0068] ɑ-diimine compound A1 3.88g (8mmol), add 30ml of toluene, 1M trimethylaluminum (16ml, 16mmol) in sequence, reflux for 8 hours, stop the reaction with sodium hydroxide / ice water, extract with ethyl acetate, and combine The organic phase was dried with anhydrous magnesium sulfate, and the product was separated by petroleum ether / ethyl acetate column chromatography to obtain colorless crystal ligand L1 with a yield of 84.2%. 1 HNMRδ(ppm) 7.19-7.06(m,6H,Ar-H),3.42(s,1H,NH), 2.98(m,2H,CH(CH 3 ) 2 ),2.88(m,2H,CH(CH 3 ) 2 ),2.32(m,1H,),1.81(m,4H,CH 2 ),1.50(s,3H,CH 3 ),1.21(m,24H,CH 3 ),0.92(s,3H,CH 3 ),0.75(s,3H,CH 3 ),0.72(s,3H,CH 3 ).

[0069] 2) Preparation of complex 1: add 10ml (DME) NiBr 2 (277mg, 0.9mmol) of dichloromethane solution was added dropwise to 10ml of ligand 1 (425mg, 0.9mmol) of dichloromethane solution, stirred at room temperature for 6 hours, precipitated out, filtered, washed with ether and dried to obtain a red powder solid....

Embodiment 2

[0072] 10atm ethylene polymerization: A 1L stainless steel polymerizer equipped with mechanical stirring was continuously dried at 130°C for 6hrs, vacuumed while hot, and N 2 Gas replacement 3 times. Add 7.2 mg (10 μmol) of complex 1 and then vacuum and replace with ethylene 3 times. Inject 500 ml of hexane, and then add 6.5 ml of methylaluminoxane (MAO) (1.53 mol / l toluene solution) to make Al / Ni=1000. At 60°C, maintaining an ethylene pressure of 10 atm, the reaction was stirred vigorously for 30 minutes. It is neutralized with an ethanol solution acidified with 5% hydrochloric acid to obtain polyethylene.

Embodiment 3

[0074] 10atm ethylene polymerization: A 1L stainless steel polymerizer equipped with mechanical stirring was continuously dried at 130°C for 6hrs, vacuumed while hot, and N 2 Gas replacement 3 times. Add 7.2 mg (10 μmol) of complex 1 and then vacuum and replace with ethylene 3 times. Inject 500 ml of hexane, and then add 6.5 ml of methylaluminoxane (MAO) (1.53 mol / l toluene solution) to make Al / Ni=1000. At 60° C., maintaining an ethylene pressure of 10 atm, vigorously stir the reaction for 10 min. It is neutralized with an ethanol solution acidified with 5% hydrochloric acid to obtain polyethylene.

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Abstract

The invention discloses an amino imine ligand, which has a structure represented by a formula I, wherein R5 is selected from H and C1-C20 saturated or unsaturated alkyl, R1-R10 are respectively and independently selected from H, halogen, C1-C24 saturated or unsaturated hydrocarbyl and C1-C24 saturated or unsaturated alkoxy, R1-R3, R9 and R10 are optionally cyclized with each other, and R4-R8 are optionally cyclized with each other. The coordination compound formed by the amino imine ligand has high catalytic activity when applied to olefin polymerization, and a polymer with narrow molecular weight distribution is obtained.

Description

Technical field [0001] The invention relates to an aminoimine ligand, an aminoimine complex and applications thereof. Background technique [0002] my country is the country with the fastest growing consumption of synthetic resins and the largest importer of synthetic resins. At present, the proportion of polyolefin production is nearly 60%. Compared with other resin materials, olefin resin has excellent environmental compatibility. It is used as a key promotion material in the automobile industry in developed countries. In 2003, the world production volume reached 83.3 million tons, of which polyethylene is the fastest growing , The largest output and extremely versatile synthetic resin reached 51.1 million tons that year. Industrialized polyethylene catalysts include Ziegler-Natta type catalysts, Phillips type catalysts, metallocene type catalysts, and late transition metal complex type high-efficiency ethylene oligomerization and polymerization catalysts developed in recent y...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/20C07C249/02C07F15/04C08F110/02C08F210/16C08F4/70
CPCC07C251/20C07C249/02C07F15/045C08F110/02C08F210/16C07C2602/42C08F2500/03C08F4/7021Y02P20/52
Inventor 高榕郭子芳周俊领宋文波张晓帆李岩傅捷赖菁菁黄廷杰
Owner CHINA PETROLEUM & CHEM CORP
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