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β-ketimine-coordinated binuclear copper complex, preparation method and use

A technology of copper complexes and ketimines, which is applied in the direction of copper organic compounds, can solve the problems of inability to catalyze the polymerization of styrene and butadiene, and the low catalytic activity of ethylene polymerization, and achieve simple synthesis methods, high activity and low reaction conditions. mild effect

Inactive Publication Date: 2016-04-06
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the catalytic activity for ethylene polymerization is relatively low
Subsequently, Stibrany et al. of ExxonMobil also reported the synthesis of benzimidazole-based copper dichloride 2 in the patent. In the role of cocatalyst MAO, this type of complex can not only catalyze the homopolymerization of ethylene and acrylate, but also can Catalyze the copolymerization reaction between them [StibranyR.T., SchulzD.N., KackerS., PatilA.O.Group11transisitionmetalaminecatalystsforolefinpolymerization.WO:9930822,1999]; but this catalytic system can not catalyze the polymerization of styrene and butadiene

Method used

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  • β-ketimine-coordinated binuclear copper complex, preparation method and use
  • β-ketimine-coordinated binuclear copper complex, preparation method and use
  • β-ketimine-coordinated binuclear copper complex, preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of Binuclear Copper Complex 1 Coordinated by β-Ketimine (hereinafter referred to as Cu1)

[0033] Take the copper complex of 0.412g (1mmol) of ligand L1 and 0.52g (2mmol) of diacetylacetone in a round bottom flask, add 30ml of methanol, and heat to reflux for 5 hours. The reaction was stopped, and after the solution was cooled, the solvent methanol was distilled off under reduced pressure to obtain a crude product, which was then recrystallized with toluene to obtain 0.61 g of a black solid product with a yield of 82%. Elemental analysis (C 34 h 44 Cu 2 f 2 N 2 o 6 ): Theoretical value (%): C, 55.05; H, 5.98; N, 3.78. Test value (%): C, 55.70; H, 5.29; N, 4.20.

[0034]

[0035] L1Cu1

Embodiment 2

[0037] Synthesis of Binuclear Copper Complex 2 Coordinated by β-Ketimine (hereinafter referred to as Cu2)

[0038]

[0039] L2Cu2

[0040] Take 1mmol of ligand L2 and 2mmol of [Cu(NH 3 ) 4 ]Cl 2 Place in a round bottom flask, add 50ml of methanol, and heat to reflux for 6 hours. The reaction was stopped, and after the solution was cooled, the solvent methanol was distilled off under reduced pressure to obtain a crude product, which was then recrystallized with toluene to obtain a black solid with a yield of 76%. Elemental analysis (C 34 h 56 Cl 2 Cu 2 N 8 o 2 ): Theoretical value (%): C, 50.61; H, 7.00; N, 13.89. Test value (%): C, 50.52; H, 7.30; N, 13.67.

Embodiment 3

[0042] Synthesis of Binuclear Copper Complex 3 Coordinated by β-Ketimine (hereinafter referred to as Cu3)

[0043] Take 1 mmol of ligand L3 and 2 mmol of benzylcopper complex and put them in a round bottom flask, add 30 ml of dichloromethane, and heat to reflux for 3 hours. The reaction was stopped, and after the solution was cooled, the solvent dichloromethane was distilled off under reduced pressure to obtain a crude product, which was then recrystallized with toluene to obtain a black solid product with a yield of 62%. Elemental analysis (C 39 h 37 Cu 2 f 3 N 2 o 2 ): Theoretical value (%): C, 62.47; H, 4.97; N, 3.74. Test value (%): C, 62.70; H, 4.79; N, 3.50.

[0044]

[0045] L3Cu3

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Abstract

The invention discloses a beta-ketimine coordinated binuclear copper complex, a preparation method thereof and an application of the binuclear copper complex to catalyzing the homopolymerization of acrylate monomers, methacrylate monomers and norbornene monomers and the copolymerization of the acrylate monomers and alpha-olefins. The beta-ketimine coordinated binuclear copper complex disclosed by the invention is simple in synthesis method, mild in reaction condition, lower in catalyst cost and high in catalytic activity; and particularly, the product obtained when the beta-ketimine coordinated binuclear copper complex is used for catalyzing the coordination polymerization of the methacrylate monomers has better steric regularity, so that the selective controllable polymerization of the product is realized.

Description

technical field [0001] The invention belongs to the technical field of metal organic chemistry, and specifically relates to a dinuclear copper complex coordinated by β-ketimine, a preparation method and an application. Background technique [0002] Copper complexes have attracted widespread attention in recent years, with numerous documents and applications. For example, in the field of life sciences, it has been discovered that some copper complexes have biological activities such as anticancer, antibacterial, antitumor, and oxygen carrying; in the field of catalysis, copper complexes can be used to catalyze many organic reactions, such as hydrocarbons, alcohols and phenols. Selective oxidation of species, olefin cyclopropanation reaction, etc., can also be used to simulate biological enzyme catalysis. [0003] Copper complexes can also be used in the coordination polymerization of olefins or polar monomers. There are few catalysts related to the transition metal copper, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F1/08C08F4/50C08F220/14C08F220/18
Inventor 谢光勇徐晓航李龙刘公毅张爱清
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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