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Naphthyl-substituted asymmetric acenaphthenediimine nickel complexes, and preparing method and applications thereof

A technology of metal complexes and ligand compounds, applied in the preparation of imino compounds, nickel organic compounds, organic chemistry, etc., can solve the problems of structural shortage and structural excess.

Active Publication Date: 2016-06-08
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are still some contradictions and shortcomings in my country's polyethylene industry. Polyethylene products show structural excess and structural shortage.

Method used

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  • Naphthyl-substituted asymmetric acenaphthenediimine nickel complexes, and preparing method and applications thereof
  • Naphthyl-substituted asymmetric acenaphthenediimine nickel complexes, and preparing method and applications thereof
  • Naphthyl-substituted asymmetric acenaphthenediimine nickel complexes, and preparing method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] Embodiment 1, preparation 2-two (phenyl) methylnaphthylamines

[0092] 1-naphthylamine (10g, 63.84mmol), di(phenyl)methanol (8.84g, 34.92mmol), anhydrous ZnCl 2 (5g, 36.68mmol) were added to round bottom flasks respectively, heated in an oil bath, and the temperature was controlled at about 150°C. Reaction 8h. After stopping the heating and cooling, DCM was added to dissolve, filtered through diatomaceous earth, and the solvent was removed, and the residue was subjected to silica gel column chromatography with a mixed solvent of petroleum ether and ethyl acetate at a volume ratio of 100:1. The eluted fraction was detected by a thin-layer silica gel plate, and the solvent was removed to obtain 2.66 g of a purple powder, with a yield of 18.6%.

[0093] The structural confirmation data are as follows: 1 HNMR (400MHz, CDCl 3 ,TMS):δ7.80-7.89(m,2H),7.47-7.49(m,2H),7.29-7.39(m,8H),7.23(d,J=7.2Hz,5H),6.96(d,J =8.4Hz, 1H), 5.79(s, 1H), 3.98(s, 2H).

[0094] 13 CNMR (100M...

Embodiment 2

[0095] Embodiment 2, preparation 1-[2-two (phenyl) methyl naphthylimino] acenaphthylenone

[0096] Acenaphthenequinone (0.73g, 4mmol) and 2-di(phenyl)methylnaphthylamine (1.24g, 4mmol) were dissolved in a mixed solvent of an appropriate amount of ethanol and dichloromethane (the volume ratio of the two was 20:1), and added p-toluenesulfonic acid (0.015g, 0.08mmol), stirred at room temperature for 24h. The solvent was removed, and the residue was subjected to silica gel column chromatography with a mixed solvent of petroleum ether and ethyl acetate at a volume ratio of 80:1. The eluted fraction was detected by a thin-layer silica gel plate, and the solvent was removed to obtain 1.5 g of red powder with a yield of 53%.

[0097] The structural confirmation data are as follows: 1 HNMR (400MHz, CDCl 3 ,TMS): δ7.90(d,J=8.0Hz,1H),7.82–7.76(m,2H),7.71(d,J=8.4Hz,1H),7.63(d,J=8.0Hz,1H) ,7.47(t,J=8.0Hz,2H),7.35–7.04(m,9H),6.99(d,J=8.0Hz,1H),6.85(t,J=8.0Hz,1H),6.47(t, J=7.6Hz, 2H), 5...

Embodiment 3

[0099] Example 3, Preparation of 1-[2-bis(phenyl)methylnaphthalene imino]-2-(2,6-dimethylphenylimino)acenaphthylenene [L1]

[0100] 1-[2-di(phenyl)methylnaphthylimino]acenaphthylenone (3.06g, 6.46mmol) and 2,6-dimethylaniline (0.86g, 7.10mmol) were dissolved in 100mL toluene solution, added P-toluenesulfonic acid (0.03g, 0.13mmol), heated to reflux, reacted for 8h. The solvent toluene was removed, and the residue was subjected to silica gel column chromatography with a mixed solvent of petroleum ether and ethyl acetate at a volume ratio of 200:1. The eluted fraction was detected by a thin-layer silica gel plate, and the solvent was removed to obtain 0.17 g of a red solid, yield: 4.7%. Melting point: 160°C.

[0101] The structure confirmation data are as follows: FT-IR(KBr,cm -1 ):3054(w), 2968(w), 1663(w), 1637(m), 1592(s), 1493(s), 1372(s), 1274(m), 1152(w), 1032(m ), 918(w), 829(m), 778(vs), 745(vs), 696(vs). 1 HNMR (400MHz, CDCl 3 ,TMS): δ7.89(d,J=8.0Hz,1H),7.77–7.74(...

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Abstract

The invention relates to a catalyst containing naphthyl-substituted asymmetric acenaphthenediimine nickel complexes, a preparing method of the complexes and applications of the complexes. The general structure of the nickel complexes is shown as a formula I, wherein R<1> is bis(phenyl)methyl or bis(fluorophenyl)methyl, R<2> is hydrogen and bis(phenyl)methyl or bis(fluorophenyl)methyl, R<3> is C1-C3 alkyl, R<4> is hydrogen or methyl, and X is selected from bromine or chlorine. The preparing method includes reacting ligands shown as a formula V and (DME)NiBr2 or NiCl2.6H2O under oxygen-free conditions to obtain the nickel complexes shown as the formula I. Under the existence of a cocatalyst that is diethylaluminium chloride or / and methylaluminoxane, and the like, the nickel complexes can catalyze ethylene polymerization well to obtain polymer with a high molecular weight and a low degree of branching. The highest catalyzing activity of the nickel complexes can be 7.71*10<6> g.mol<-1>(Ni).h<-1>. The nickel complexes have a wide industrial application prospect.

Description

technical field [0001] The invention belongs to the field of complex catalysis, and specifically relates to a complex containing naphthyl-substituted asymmetric nickel acenaphthylenediimide, a preparation method and application thereof. Background technique [0002] Polyolefins mainly include polyethylene, polypropylene and poly-1-butene, etc. Among them, polyethylene resin (PE) is the variety with the largest output among general-purpose synthetic resins, and is widely used in industry and agriculture due to its excellent material properties. , military, medical and health, daily life and many other fields. Due to the huge economic and social benefits of the polyethylene industry and the coverage of many international patents, my country is in a very passive situation in the production of high-performance polyethylene new materials. There are still some contradictions and shortcomings in my country's polyethylene industry. Polyethylene products show structural excess and s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/04C07C251/20C07C249/02C08F10/02C08F4/70
Inventor 袁世芳温春艳孙文华岳二林
Owner INST OF CHEM CHINESE ACAD OF SCI
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