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N-5,6,7-hydro-quinoline-8-aryl imine nickel complex catalyst and preparation method and application thereof

A technology of complexes and catalysts, applied in the direction of nickel organic compounds, organic chemistry, etc., to achieve the effect of large industrial application potential and high catalytic activity

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

The United States, Japan, and Germany are in the leading position in this technology. Japan’s Mitsui Oil and Chemical Company uses Ziegler-type catalysts to produce low-molecular polyethylene. The main catalyst used is a titanium-based catalyst. The company has also developed similar catalysts, but in summary, it is mainly based on the four metal compounds of chromium, vanadium, zirconium and titanium in transition metals, supplemented by the main catalyst and co-catalysts and carriers suitable for polymerization reactions to form a catalytic system , but there are few reports on the preparation of polyethylene wax by late transition metal catalysts

Method used

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  • N-5,6,7-hydro-quinoline-8-aryl imine nickel complex catalyst and preparation method and application thereof
  • N-5,6,7-hydro-quinoline-8-aryl imine nickel complex catalyst and preparation method and application thereof
  • N-5,6,7-hydro-quinoline-8-aryl imine nickel complex catalyst and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Example 1. Preparation of 8-(2,6-dicyclohexylaniline)-5,6,7-trihydroquinoline (L1) and 8-(2,6-dicyclohexylaniline)-5 shown in formula II ,Isomers of 6-dihydroquinoline (L1')

[0069] The hydroquinolinone compound represented by formula III was purchased from Shijiazhuang Likang Pharmaceutical Technology Co., Ltd., and the compound represented by formula IV was prepared according to the literature (Dokl. Phys. Chem., 2000, 374, 203-205). Add 43 mg of p-toluenesulfonic acid as a catalyst to compound hydroquinolinone (0.37 g, 2.5 mmol) shown in formula III and compound 2,6-dicyclohexylaniline (0.51 g, 2.0 mmol) shown in formula IV, and reflux in toluene After 4 hours, after concentration, the residue was separated by silica gel column chromatography, rinsed with petroleum ether / triethylamine (volume ratio 250:1), to obtain isomers of yellow oil (L1:L1'=36: 64) 0.25 g, yield 32%.

[0070] The NMR, IR and other structural confirmation data of the compound are as follows: ...

Embodiment 2

[0075] Example 2, preparation of 8-(2,6-dicyclopentylaniline)-5,6,7-trihydroquinoline (L2) and 8-(2,6-dicyclopentylaniline) shown in formula II Isomers of -5,6-dihydroquinoline (L2')

[0076] The compound hydroquinolinone (0.37g, 2.5mmol) shown in formula III and the compound 2,6-dicyclopentylaniline (0.46g, 2.0mmol) shown in formula IV were added into 43mg p-toluenesulfonic acid as catalyst, in toluene Reflux for 4 hours, after concentration, the residue was separated by silica gel column chromatography, rinsed with petroleum ether / triethylamine (volume ratio 250:1), to obtain isomers of yellow oil (L2:L2'=17 :83) 0.27g, the productive rate is 38%.

[0077] The NMR, IR and other structural confirmation data of the compound are as follows:

[0078] 1 HNMR (400MHz, CDCl 3 ,TMS): δ8.74(d,J=4.0Hz,1H,L2-PyH),8.41(d,J=4.8Hz,L2'-PyH),7.57(d,J=7.6Hz,1H,L2- PyH), 7.43 (d, J=7.6Hz, L2'-PyH), 7.44–7.28 (m, 1H, L2-PyHand L2'-PyH), 7.19 (s, L2'-ArH), 7.13 (d, J= 7.6Hz,2H,L2-ArH),7,0...

Embodiment 3

[0082] Example 3, preparation of 8-(2,4-dimethyl-6-cyclohexylaniline)-5,6,7-trihydroquinoline (L3) and 8-(2,4-dimethyl Isomers of -6-cyclohexylaniline)-5,6-dihydroquinoline (L3')

[0083] Compound hydroquinolinone (0.37g, 2.5mmol) shown in formula III and compound 2,4-dimethyl-6-cyclohexylaniline (0.41g, 2.0mmol) shown in formula IV were added to 43mg p-toluenesulfonic acid as Catalyst, refluxed 4 hours in toluene, after concentrating, the residue was separated by silica gel column chromatography, washed with sherwood oil / triethylamine (volume ratio 250:1), to obtain the isomers (L3: L3'=60:40) 0.20 g, yield 30%.

[0084] The NMR, IR and other structural confirmation data of the compound are as follows:

[0085] 1 HNMR (400MHz, CDCl 3 ,TMS): δ8.74(d,J=4.4Hz,1H,L3-PyH),8.42(d,J=4.8Hz,L3'-PyH),7.56(d,J=7.6Hz,1H,L3- PyH), 7.44(d, J=7.2Hz, L3'-PyH), 7.30–7.26(m,1H,L3-PyH), 7.11–7.08(m,L3'-PyH), 6.97(s,L3'- ArH), 6.92(s, 2H, L3-ArH), 6.84(s, L3'-ArH), 6.55(s, L3'-NH), 4.51(t,...

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Abstract

The present invention relates to a cycloalkyl-substituted N-5,6,7-hydro-quinoline-8-aryl imine nickel complex catalyst and a preparation method and application thereof. The N-5,6,7-hydro-quinoline-8-aryl imine nickel complex catalyst has a structural general formula as shown in a formula I. The catalyst complex can well catalyze vinyl polymerization under the effect of cocatalyst methylaluminoxane, diethylaluminium chloride and the like to obtain a low molecular weight high branching degree polymer, the catalyst complex also has high activity, the highest activity is up to 5.33*106g (PE) mol (Ni) <-1>h<-1>; the molecular weight of obtained polyethylene wax is 1430-3330g / mol, the molecular weight distribution is between 1.38-1.92, the branching degree is up to 422 / 1000C, and the catalyst complex has good prospects for industrial application.

Description

technical field [0001] The invention belongs to the field of complex catalysis, and specifically relates to a cycloalkyl-substituted N-5,6,7-hydroquinoline-8-arylimine nickel complex catalyst, a preparation method and application thereof. Background technique [0002] Polyethylene is the world's fastest growing synthetic resin with the largest output and a wide range of uses. It is widely used in many fields such as industry, agriculture, military, medical and health care, and daily life. Polyethylene wax (PE wax), also known as polymer wax or polyethylene wax for short, is a low molecular weight polyethylene homopolymer or copolymer, which is obtained because of its excellent cold resistance, heat resistance, chemical resistance and abrasion resistance. Wide range of applications. In normal production, this part of wax can be directly added to polyolefin processing as an additive, which can increase the gloss and processing performance of the product. As a lubricant, it h...

Claims

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Application Information

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IPC IPC(8): C07F15/04C07D215/40C08F10/02C08F4/70
Inventor 孙泽林岳二林张文娟孙文华
Owner INST OF CHEM CHINESE ACAD OF SCI
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