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Pyridine amino hafnium compound as well as preparation method and application thereof

A technology for pyridylamino and hafnium compounds is applied in the field of pyridineamine-based hafnium compounds and their preparation, which can solve the problems of narrow application range of comonomers, and achieve the effects of simple and efficient ligand synthesis, improved solubility, and simple introduction.

Inactive Publication Date: 2021-10-22
PETROCHINA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, 2-isopropylbenzene-substituted catalysts are currently reported only for the homopolymerization and copolymerization of ethylene and α-olefins, and have not been used for the copolymerization of ethylene and other monomers. The scope of comonomer application is relatively narrow

Method used

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  • Pyridine amino hafnium compound as well as preparation method and application thereof
  • Pyridine amino hafnium compound as well as preparation method and application thereof
  • Pyridine amino hafnium compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Synthesis of Pyridine Aldehyde Compound A1

[0056] Under nitrogen atmosphere, add 1.86g (10mmol) of 6-bromopyridine-2 formaldehyde, 1.72g (10mmol) of naphthalene boronic acid, 15mg of tetrakis(triphenylphosphine)palladium, and 6g of potassium carbonate to the branch bottle successively, and pour into 30mL of ethanol , 20mL toluene, 10mL water, reflux overnight. Extract by liquid separation, wash with water, and dry to obtain 2.17 g of pyridine aldehyde compound A, with a yield of 93%. The H NMR spectrum is as follows: 1 H NMR (400MHz, CDCl 3 ):δ10.19(s,1H,CHO),8.00-8.07(m,3H,Py-H),7.92-7.99(m,2H,Ar-H),7.79-7.84(dd,1H,Ar-H ), 7.47-7.68 (m, 4H, Ar-H), 7.18-7.13 (m, 2H, ArH).

Embodiment 2

[0058] Synthesis of Pyridine Aldehyde Compound A2

[0059] According to the method in Example 1, naphthaleneboronic acid was replaced by phenylboronic acid.

[0060] The H NMR spectrum is as follows: 1 H NMR (400MHz, CDCl 3 ):δ10.17(s,1H,CHO),8.00-8.07(m,3H,Py-H),7.92-7.99(m,2H,Ar-H),7.79-7.84(dd,1H,Ar-H ), 7.47-7.13 (m, 2H, ArH).

Embodiment 3

[0062] Synthesis of Pyridinimine Compound B1

[0063] Under nitrogen atmosphere, 2.33g (10mmol) of pyridine aldehyde compound A1, 1.86g (10.5mmol) of 2,6-diisopropylaniline and 10mg of p-toluenesulfonic acid were dissolved in 50mL of toluene, and the water was refluxed for 48h. The solvent was spin-dried and dried to obtain the pyridine imine compound B with a yield of 94%. The H NMR spectrum is as follows: 1 H NMR (CDCl 3 ,400MHz):δ8.17(d,3H,Py-H),7.94(d,2H,Py-H),7.34-7.64(m,6H,Ar-H),6.76-6.94(m,4H,Ar -H),3.39(s,2H,CH(CH 3 ) 2 ),1.26(s,9H,C(CH 3 ) 3 ),1.15(d,6H,CH(CH 3 ) 2 ),0.86(d,6H,CH(CH 3 ) 2 ).

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Abstract

The invention discloses a pyridine amine hafnium compound as well as a preparation method and application thereof. A framework of the pyridine amine hafnium compound is a tert-butyl-substituted pyridine amine hafnium compound, wherein tert-butyl with large steric hindrance is introduced to a bridging framework of the pyridine amine hafnium compound, and the structural formula of the pyridine amine hafnium compound is as shown in formula I, in which, the Ar can be phenyl or naphthyl. The pyridine amine hafnium compound can be used as a main catalyst to catalyze olefin polymerization, not only shows a single active center, but also shows very strong copolymerization ability. The compound can catalyze copolymerization of ethylene, alpha-olefin and polar monomers with high activity, so that a high-performance polyolefin material is prepared.

Description

technical field [0001] The invention relates to the technical field of olefin catalytic polymerization. More specifically, it relates to a hafnium pyridylamine compound and its preparation method and application. Background technique [0002] Polyolefin is a material with a wide range of applications. Olefin polymerization catalysts have become the key to the polyolefin industry because of their ability to regulate the structure and properties of polyolefins. Therefore, designing and developing new polyolefin catalysts has become the core technology to promote the development of polyolefin industry. [0003] Pyridylamine-based hafnium catalysts were first developed by Symyx, showing good performance in catalytic olefin polymerization. The pyridylamine-based hafnium catalyst can catalyze ethylene polymerization with high activity to prepare linear polyethylene. It also exhibits high activity and high stereoselectivity, and can catalyze the polymerization of propylene and ...

Claims

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Application Information

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IPC IPC(8): C07F7/00C08F10/00C08F110/02C08F110/06C08F110/14C08F210/16C08F210/02C08F4/646
CPCC07F7/00C08F10/00C08F110/02C08F110/06C08F110/14C08F210/16C08F210/02C08F4/646
Inventor 王雄高海洋王申鸣王凌志钟柳龚光碧徐人威马艳萍康文倩李广全
Owner PETROCHINA CO LTD
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