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Ligand compound and preparation thereof, and complex containing ligand compound

A technology of ligand compounds and complexes, applied in the preparation of imino compounds, nickel organic compounds, organic chemistry, etc., can solve the problems that late transition metal catalysts cannot meet the requirements

Active Publication Date: 2017-02-15
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing ethylene gas-phase polymerization process requires a polymerization temperature of above 85°C, and the ethylene solution polymerization process requires a polymerization temperature of 150-250°C. The original post-transition metal catalyst cannot meet the requirements of the existing gas-phase and solution ethylene polymerization devices

Method used

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  • Ligand compound and preparation thereof, and complex containing ligand compound
  • Ligand compound and preparation thereof, and complex containing ligand compound
  • Ligand compound and preparation thereof, and complex containing ligand compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] 1) preparation of ligand (R in structural formula (I) 1 , R 3 , R 4 and R 6 is methyl, R 2 , R 5 and R 7 -R 10 are hydrogen):

[0063] Compound A (4.07g, 4.8mmol) and 2,6-methylaniline (1.3ml, 10.4mmol), p-toluenesulfonic acid as a catalyst, refluxed in 100mL toluene for 1 day, removed the solvent after filtration, and the residue was treated with dichloro Methane was dissolved, and the column of perbasic alumina was rinsed with petroleum ether / ethyl acetate (20:1). The second fraction was divided into the product, and the solvent was removed to obtain a yellow solid with a yield of 81%. 1 H NMR (CDCl 3 ,δ,ppm): 1.16(s,36H), 1.86(s,12H), 5.20(s,2H), 7.08(m,22H), 7.68(m,8H).

[0064] 2) Preparation of complex 1:

[0065] 10ml (DME)NiBr 2 (277mg, 0.9mmol) in dichloromethane solution was added dropwise to 10ml of the above ligand (962mg, 0.9mmol) in dichloromethane solution, stirred at room temperature for 6 hours, a precipitate precipitated, filtered, washed wi...

Embodiment 2

[0069]10atm ethylene polymerization: Dry the 1L stainless steel polymerization kettle equipped with mechanical stirring at 130°C for 6hrs continuously, vacuumize while it is hot and use N 2 Air replacement 3 times. Add 12.9 mg (10 μmol) of the complex 1 prepared in Example 1 and then evacuate and replace with ethylene three times. 500 ml of hexane was injected, and 6.5 ml of methylaluminoxane (MAO) (1.53 mol / l toluene solution) was added to make Al / Ni=1000. At 100°C, the ethylene pressure was maintained at 10 atm, and the reaction was stirred for 30 min. Neutralize with ethanol solution acidified with 5% hydrochloric acid to obtain polyethylene with a polymerization activity of 4.86×10 6 g·mol -1 (Ni)·h -1 , and the results are shown in Table 1.

Embodiment 3

[0071] 1) preparation of ligand (R in structural formula (I) 1 , R 3 , R 4 and R 6 is ethyl, R 2 , R 5 and R 7 -R 10 are hydrogen):

[0072] Compound A (6.62g, 7.8mmol) and 2,6-diethylaniline (3.0ml, 17.4mmol), p-toluenesulfonic acid as a catalyst, refluxed in 100mL toluene for 1 day, removed the solvent after filtration, and the residue was washed with di Methane chloride was dissolved, and the column of perbasic alumina was rinsed with petroleum ether / ethyl acetate (20:1). The second fraction was divided into the product, and the solvent was removed to obtain a yellow solid with a yield of 88%. 1 H NMR (CDCl 3 ,δ,ppm):1.08(t,12H,J=7.5Hz),1.16(s,36H),2.24(dd,8H,J=7.5Hz),5.20(s,2H),7.07(22H),7.68 (m,8H).

[0073] 2) Preparation of complex 2: 10ml (DME) NiBr 2 (155mg, 0.5mmol) in dichloromethane solution was added dropwise to 10ml of the above ligand (563mg, 0.5mmol) in dichloromethane solution, stirred at room temperature for 6 hours, a precipitate precipitated, fil...

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Abstract

The invention provides a ligand compound with a structural formula I as shown in the specification. In the structural formula I, R1 to R10 are same or different and are independently selected from a group consisting of hydrogen, saturated or unsaturated alkyl groups, oxyl groups and halogen. The invention also relates to the preparation method for the ligand compound, a complex containinging the ligand compound, and a preparation method and application of the complex. When the complex is used as a main catalyst, higher polymerization activity is obtained under a high-temperature polymerization condition, and an obtained polymer has high molecular weight.

Description

technical field [0001] The invention relates to the field of catalysts, in particular to a ligand compound with a novel structure and a nickel complex formed therefrom. The invention also relates to the preparation method of the ligand compound and the complex, and the application of the complex as an olefin polymerization catalyst in olefin polymerization. Background technique [0002] my country is the country with the fastest growing consumption of synthetic resin and the largest importer of synthetic resin. At present, the proportion of polyolefin production is nearly 60%. Compared with other resin materials, olefin resin has excellent environmental coordination. In 2003, the world production of the materials used for key promotion in the industry reached 83.3 million tons; among them, polyethylene is the synthetic resin with the fastest development, the largest output and a wide range of uses, reaching 51.1 million tons that year. Industrialized polyethylene catalysts i...

Claims

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Application Information

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IPC IPC(8): C07C251/20C07C249/02C07F15/04C08F10/02C08F4/70
Inventor 高榕刘东兵周俊领李岩廖浩瀚傅捷
Owner CHINA PETROLEUM & CHEM CORP
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