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Pincerlike bi-N-heterocyclic carbene biphenyl amine rare earth metal catalyst, preparation method and application thereof

A technology of heterocyclic carbene and bisphenylamine, which is applied in the field of catalysts and can solve the problems that the preparation method of pincer bis-N-heterocyclic carbene bisphenylamine rare earth metal catalyst has not yet been reported.

Inactive Publication Date: 2015-04-29
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The pincer double N-heterocyclic carbene bisphenylamine rare earth metal catalyst involved in the present invention, its preparation method and its application in polymerization have not yet been reported

Method used

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  • Pincerlike bi-N-heterocyclic carbene biphenyl amine rare earth metal catalyst, preparation method and application thereof
  • Pincerlike bi-N-heterocyclic carbene biphenyl amine rare earth metal catalyst, preparation method and application thereof
  • Pincerlike bi-N-heterocyclic carbene biphenyl amine rare earth metal catalyst, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] (1) Preparation of clamp-shaped bis-N-heterocyclic carbene bisphenylamine ligand

[0065]

[0066] First, under a nitrogen atmosphere, 8.65 g (30.58 mmol) of o-iodobromobenzene, 5.26 g (30.58 mmol) of 2-bromoaniline, 4.11 g (42.81 mmol) of sodium n-butoxide, 0.03 g (0.15 mmol) of palladium acetate, bis Add 0.12 g (0.23 mmol) of (2-diphenylphosphine) phenyl ether into 100 ml Schlenk bottles, dissolve in 20 ml toluene to obtain mixture a; heat to 110°C in the dark, take it out after 12 hours of reaction, cool to 25°C, Add saturated brine to the mixture to obtain an organic phase, add anhydrous magnesium sulfate (5g), filter, take the filtrate and carry out rotary evaporation to obtain a mixture b containing the first step product; column chromatography obtains the first step product c, the yield 94%; secondly, the first step product c 2.97g (9.10mmol), imidazole 1.24g (18.2mmol), cesium carbonate 11.86g (36.40mmol), cuprous iodide 0.35g (1.82mmol) were added to 100ml ...

Embodiment 2

[0071] (1) Preparation of clamp-shaped bis-N-heterocyclic carbene bisphenylamine ligand

[0072]

[0073] First, under a nitrogen atmosphere, 8.65 g (30.58 mmol) of o-iodobromobenzene, 5.26 g (30.58 mmol) of 2-bromoaniline, 4.11 g (42.81 mmol) of sodium n-butoxide, 0.03 g (0.15 mmol) of palladium acetate, bis Add 0.12 g (0.23 mmol) of (2-diphenylphosphine) phenyl ether into 100 ml Schlenk bottles and dissolve in 20 ml toluene to obtain mixture a; heat to 120°C in the dark, take it out after 16 hours of reaction, and cool to 25°C. Add saturated brine to the mixture to obtain an organic phase, add anhydrous magnesium sulfate (10g), filter, take the filtrate and carry out rotary evaporation to obtain a mixture b containing the product of the first step; column chromatography obtains the product c of the first step, and the yield 94%; secondly, the first step product c 2.97g (9.10mmol), imidazole 1.24g (18.2mmol), cesium carbonate 11.86g (36.40mmol), cuprous iodide 0.35g (1.82m...

Embodiment 3

[0078] (1) Preparation of clamp-shaped bis-N-heterocyclic carbene bisphenylamine ligand

[0079]

[0080] First, under a nitrogen atmosphere, 8.65 g (30.58 mmol) of o-iodobromobenzene, 5.26 g (30.58 mmol) of 2-bromoaniline, 4.11 g (42.81 mmol) of sodium n-butoxide, 0.03 g (0.15 mmol) of palladium acetate, bis Add 0.12g (0.23mmol) of (2-diphenylphosphine)phenyl ether into 100ml Schlenk bottles, dissolve in 20ml toluene to obtain mixture a; heat to 115°C in the dark, take it out after 14h of reaction, cool to 25°C, Add saturated brine to the mixture to obtain an organic phase, add anhydrous magnesium sulfate (8g), filter, take the filtrate and carry out rotary evaporation to obtain a mixture b containing the first step product; column chromatography obtains the first step product c, the yield 94%; secondly, the first step product c 2.97g (9.10mmol), imidazole 1.24g (18.2mmol), cesium carbonate 11.86g (36.40mmol), cuprous iodide 0.35g (1.82mmol) were added to 100ml In a round...

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Abstract

The invention discloses a pincerlike bi-N-heterocyclic carbene biphenyl amine rare earth metal catalyst, a preparation method and an application thereof and belongs to the field of catalysts. The catalyst has one structural formula. The preparation method comprises the following steps: firstly heating bromoiodobenzene, 2-bromobenzenamine and the like to react in a dark place in a nitrogen or an argon atmosphere, so as to obtain a first-step product by column chromatography, heating with imidazole to react, so as to obtain a second-step product by virtue recrystallization; reacting with alkyl iodides while heating, filtering, washing and drying to obtain a pincerlike bi-N-heterocyclic carbene biphenyl amine ligand; and dropwise adding a hydrogen-pulling reagent into a ligand liquid to react in a low-temperature, nitrogen or argon atmosphere, then dropwise adding a liquid with a metal source dissolved to react, and filtering and recrystallizing to obtain the pincerlike bi-N-heterocyclic carbene biphenyl amine rare earth metal catalyst. The raw materials are easily available and the catalyst can be used for homopolymerization or copolymerization of olefins, alkynes and polar monomers or copolymerization with CO2, respectively. The preparation method is simple in process, economic and environment-friendly and suitable for industrial production.

Description

technical field [0001] The invention relates to a pincer bis-N-heterocyclic carbene bisphenylamine rare earth metal catalyst, a preparation method and an application, and belongs to the technical field of catalysts. Background technique [0002] At present, olefin polymerization catalysts can be mainly divided into three categories, namely Ziegler-Natta catalysts, metallocene catalysts and non-metallocene catalysts. Compared with traditional Ziegler-Natta catalysts and metallocene catalysts, non-metallocene catalysts are homogeneous, single-site catalytic systems, which are conducive to the study of polymerization mechanisms, have high catalytic activity, high selectivity, and are not subject to patent restrictions. Ligand selection Wide range, simple synthesis, easy modification and other advantages are the mainstream development direction of polymerization reaction at present and in the future. [0003] Due to their good reactivity, stability and stereoselectivity, pincer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F136/08C08F210/02C08F232/08C08G63/08C08G63/84C08F138/00C08G64/34C07F5/00
Inventor 李晓芳王航航毕娇娇杜改霞贺剑云
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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