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[n,o] bidentate nickel and palladium complexes of ketone-imidazoline-2-imine ligands and their preparation methods and applications

A technology of palladium complexes and imine ligands is applied in the directions of palladium organic compounds, nickel organic compounds, compounds containing elements of Group 8/9/10/18 of the periodic table, etc. High cost, poor tolerance of polar monomers, etc., to achieve the effect of improving thermal stability, strong electronegativity, and improving catalytic activity

Active Publication Date: 2020-07-28
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The purpose of the present invention is to solve the problems of high application cost, poor tolerance to polar monomers and difficulty in obtaining both high polymer and oligomer in the prior art, and to provide a ketone- [N,O] bidentate nickel and palladium complexes of imidazoline-2-imine ligands and their preparation methods and applications, especially providing a method for catalyzing the homopolymerization of ethylene and / or cycloolefins, polar / functional monomers Or [N, O] bidentate nickel and palladium complexes of ketone-imidazoline-2-imine ligands used in copolymerization and their preparation methods and applications

Method used

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  • [n,o] bidentate nickel and palladium complexes of ketone-imidazoline-2-imine ligands and their preparation methods and applications
  • [n,o] bidentate nickel and palladium complexes of ketone-imidazoline-2-imine ligands and their preparation methods and applications
  • [n,o] bidentate nickel and palladium complexes of ketone-imidazoline-2-imine ligands and their preparation methods and applications

Examples

Experimental program
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Effect test

Embodiment 1

[0083] The preparation method of ketone-imidazoline-2-imine [N, O] bidentate nickel complex, concrete steps are as follows:

[0084] (1) preparation of ketone-imidazoline-2-imine ligand;

[0085] (1.1) Dissolve aminoacetaldehyde dimethyl acetal and O-methylisourea sulfate in water at a molar ratio of 1.5:1, react at 60°C with catalyst hydrochloric acid for 6 hours, and obtain a colorless solution, wherein hydrochloric acid and The mol ratio of O-methylisourea sulfate is 3:1; Be 2-amino-1H-imidazole hemisulfate, the productive rate is 75%, 1 H NMR (D 2 O, δ, ppm): 7.80 (s, 2H, = CH);

[0086] (1.2) React 2-amino-1H-imidazole hemisulfate in aqueous solution with sodium carbonate whose molar weight is 2 times its molar weight at room temperature for 3 hours to obtain 2-amino-1H-imidazole, an insoluble yellow-brown oil ;

[0087] (1.3) Dissolve 2-amino-1H-imidazole and iodobenzene in absolute ethanol, react for 16 hours at 80°C under the action of a catalytic system, cool to 5...

Embodiment 2

[0095] The preparation method of ketone-imidazoline-2-imine [N, O] bidentate nickel complex, concrete steps are as follows:

[0096] (1) preparation of ketone-imidazoline-2-imine ligand;

[0097] (1.1) Dissolve aminoacetaldehyde dimethyl acetal and O-methylisourea sulfate in water at a molar ratio of 1.5:1, and react for 6 hours at 60°C under the action of catalyst sulfuric acid to obtain a colorless solution, wherein sulfuric acid and The molar ratio of O-methylisourea sulfate is 3:2; that is, 2-amino-1H-imidazole hemisulfate, and the yield is 75%. 1 H NMR (D 2 O, δ, ppm): 7.80 (s, 2H, = CH);

[0098] (1.2) react 2-amino-1H-imidazole hemisulfate in an aqueous solution with sodium carbonate whose molar weight is 2.5 times its molar weight at room temperature for 3 hours to obtain 2-amino-1H-imidazole;

[0099] (1.3) Dissolve 2-amino-1H-imidazole and iodobenzene in anhydrous isopropanol, react for 16 hours at 80°C under the action of a catalytic system, cool to 50°C, drain t...

Embodiment 3

[0107] The preparation method of ketone-imidazoline-2-imine [N, O] bidentate palladium complex, the specific steps are as follows:

[0108] (1) preparation of ketone-imidazoline-2-imine ligand;

[0109] (1.1) Dissolve aminoacetaldehyde dimethyl acetal and O-methylisourea sulfate in water with a molar ratio of 1.5:1, and react for 6 hours at 60°C with catalyst nitric acid to obtain a colorless solution, wherein nitric acid and The molar ratio of O-methylisourea sulfate is 3:2; that is, 2-amino-1H-imidazole hemisulfate, and the yield is 75%. 1 H NMR (D 2 O, δ, ppm): 7.80 (s, 2H, = CH);

[0110] (1.2) react 2-amino-1H-imidazole hemisulfate in an aqueous solution with sodium carbonate whose molar weight is 3 times its molarity at room temperature for 3 hours to obtain 2-amino-1H-imidazole;

[0111] (1.3) Dissolve 2-amino-1H-imidazole and iodobenzene in anhydrous isopropanol, react for 16 hours at 80°C under the action of a catalytic system, cool to 50°C, drain the reaction solv...

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Abstract

The invention relates to a keto-imidazoline-2-imine [N,O] bidentate nickel and palladium complex as well as a preparation method and application thereof. The preparation method comprises the followingsteps: reacting a keto-imidazoline-2-imine ligand with a hydrogen withdrawing reagent and a metal precursor in sequence to prepare a keto-imidazoline-2-imine [N,O] bidentate nickel and palladium complex; and the structural formula of the prepared complex is one of formulas shown in the specification. The complex and a cocatalyst form a catalyst composition, the complex or the catalyst compositionis used for catalyzing homopolymerization or copolymerization of olefin monomers, and the specific process is as follows: under the protection of nitrogen, firstly dissolving the complex or the catalyst composition in a solvent, then adding an olefin monomer, and conducting reacting for a period of time at a certain temperature and under a certain pressure to prepare the olefin polymer. The complex and the catalyst composition provided by the invention have relatively high catalytic activity, high tolerance to polar monomers and relatively low application cost.

Description

technical field [0001] The invention belongs to the technical field of olefin catalysis, and relates to a [N,O] bidentate nickel and palladium complex with a ketone-imidazoline-2-imine ligand and a preparation method and application thereof, in particular to a method for catalyzing ethylene and [N,O] bidentate nickel and palladium complexes of ketone-imidazoline-2-imine ligands used in homopolymerization or copolymerization of cycloolefins and polar / functional monomers, and their preparation methods and applications. Background technique [0002] Polyolefin catalyst is the core and key of olefin polymerization industrial production process, and its kind is numerous, and the catalyst of industrialization mainly contains Ziegler-Natta catalyst system (DE Pat889229 (1953); IT Pat545332 (1956); IT Pat536899 (1956); Chem. Rev., 2000,100,1169.), Phillips catalyst system (Belg.Pat.530617 (1955); Chem.Rev., 1996,96,3327.) and metallocene catalyst system (Kaminsky.W., Berlin: Springe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C07F15/04C08F10/00C08F4/70C08F110/02C08F210/16C08F132/08C08F232/08C08F210/14C08F212/08
CPCC07F15/006C07F15/0066C07F15/04C07F15/045C08F10/00C08F110/02C08F132/08C08F210/16C08F232/08C08F4/7022C08F2500/03C08F210/14C08F212/08
Inventor 蔡正国李彦青肖茹
Owner DONGHUA UNIV