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Ethylidene acenaphthene (alpha-diimine) nickel olefin catalyst, and preparation method and application thereof

An olefin catalyst, the technology of ethylene acenaphthene, which is applied in the field of ethylene acenaphthene (α-diimine) nickel olefin catalyst and its preparation, can solve the problem of high aluminum-nickel ratio, which is not conducive to industrialization and commercialization, and catalyst ligands Complex process and other issues, to achieve the effect of high activity, low cost and high yield

Active Publication Date: 2012-12-19
HANGZHOU XINGLU TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Then, the process of synthesizing this kind of catalyst ligand is relatively complicated, and it is activated by methyl aluminoxane, and the aluminum-nickel ratio is high (600) during the polymerization process, which is not conducive to industrialization and commercialization.

Method used

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  • Ethylidene acenaphthene (alpha-diimine) nickel olefin catalyst, and preparation method and application thereof
  • Ethylidene acenaphthene (alpha-diimine) nickel olefin catalyst, and preparation method and application thereof
  • Ethylidene acenaphthene (alpha-diimine) nickel olefin catalyst, and preparation method and application thereof

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Experimental program
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preparation example Construction

[0025] The preparation method of the described ethylene acenaphthylene (α-diimine) nickel olefin catalyst is characterized in that: its steps are as follows:

[0026] 1) Compound C1 is obtained by diacylation of acenaphthoquinone: using acenaphthoquinone as raw material and carbon disulfide as solvent. Adding anhydrous aluminum bromide, under the condition of oxalyl bromide as the oxidizing agent, the yellow solid acenaphthyldione (C1) was obtained.

[0027]

[0028] 2) Compound C1 undergoes ketoamine condensation reaction with symmetrical aniline to obtain α-diimine ligand C2 or C3. The acenaphthedione (C1) raw material obtained in step 1) is reacted, acetonitrile is used as a solvent, acetic acid is used as a catalyst, and α-diimine ligand (C2 or C3) is obtained through ketone-amine condensation reaction.

[0029]

[0030] 3) Under anhydrous and oxygen-free conditions, the α-diimine ligand C2 or C3 and (DME)NiBr 2 Complexation, the olefin polymerization catalyst (C4,...

Embodiment 1

[0038] Add 0.305g (1.47mmol) of C1 into a 100mL three-neck flask, add 30mL of acetonitrile, reflux at 88°C for one hour, add 7mL of acetic acid, and reflux for another four hours. Then, 0.68 mL (3.23 mmol) of 2,6-diisopropylaniline was added and reacted for 24.5 hours. After the reaction, the solvent was drained, and the crude product was separated by column chromatography (petroleum ether / dichloromethane: 1 / 1, 0.75% triethylamine, silica gel) to obtain 0.301 g of the product with a yield of 38.9%. 1 H-NMR (300MHz, CDCl 3 ,δin ppm):7.50(s,6H,Ar-H),6.45-7.15(dd,4H,Py-H),2.98-3.14(sept,4H,CH(CH 3 ) 2 ),0.86-1.36(dd,24H,CH(CH 3 ) 2 ).

[0039] Elem.Anal.Calcd.For C 38 h 42 N 2 :C,86.65%;H,8.04%;N,5.32%.Found:C,86.09%;H,8.04%;N,5.31%.

[0040] ESI-MS: m / z 527.10 ([M+H] + .

Embodiment 2

[0042] 0.290g (1.40mmol) of C1 was added to a 100mL three-neck flask, 30mL of acetonitrile was added, refluxed at 88°C for one hour, 7mL of acetic acid was added, and refluxed for another four hours. Then, 0.65 mL (3.07 mmol) of 2,6-dimethylaniline was added and reacted for 24 hours. After the reaction, the solvent was drained, and the crude product was separated by column chromatography (petroleum ether / dichloromethane: 1 / 1, 0.75% triethylamine, silica gel) to obtain 0.249 g of the product, with a yield of 42.9%.

[0043] Elem.Anal.Calcd.For C 30 h 26 N 2 :C,86.09%;H,8.04%;N,5.31%.Found:C,86.82%;H,6.36%;N,6.56%.

[0044] ESI-MS: m / z 415.3 ([M+H] + .

[0045] 2. Preparation of ethylene acenaphthylene α-diimine nickel complex

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Abstract

The invention discloses an ethylidene acenaphthene (alpha-diimine) nickel olefin catalyst, and a preparation method and application thereof. The structural formula of the ethylidene acenaphthene (alpha-diimine) nickel olefin catalyst is disclosed as Formula (I). The ethylidene acenaphthene (alpha-diimine) nickel olefin polymerization catalyst disclosed as Formula (I) has the advantages of high activity and high stability, and can catalyze the preparation of high-molecular-weight hyperbranched polyethylene from ethylene at high activity at the temperature of higher than or equal to 60 DEG C. When being used for ethylene polymerization as a catalyst, the thylidene acenaphthene (alpha-diimine) nickel olefin polymerization catalyst has high activity only when the aluminum-nickel ratio is 100. In addition, the preparation method of the olefin polymerization catalyst disclosed by the invention has the advantages of simple technique, short synthetic route, low cost and high yield, and can easily implement industrialization.

Description

technical field [0001] The invention relates to the field of catalytic polymerization of olefins, in particular to an ethylene acenaphthylene (α-diimine) nickel olefin catalyst and a preparation method and application thereof. Background technique [0002] Polyolefin is a basic material related to the national economy and people's livelihood, and because of its excellent performance, variety of varieties, easy availability of raw materials and low price, it is widely used in various fields such as industry, agriculture and national defense. The development and application of new catalysts is one of the core driving forces to promote the progress and development of the polyolefin industry, and is the key to controlling the structure and performance of polyolefin materials. [0003] In recent decades, the study of functionalized and differentiated polyolefin materials obtained by coordination polymerization has received extensive attention. In 1995, the Brookhart research gro...

Claims

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Application Information

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IPC IPC(8): C08F10/00C08F10/02C08F10/06C08F4/70
CPCY02P20/52
Inventor 傅智盛朱良范志强韦真博程绍明
Owner HANGZHOU XINGLU TECH CO LTD
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