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Asymmetric (α-diimine) nickel olefin catalyst and preparation method and application thereof
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A nickel catalyst, diimine technology, applied in the preparation of imino compounds, chemical instruments and methods, nickel organic compounds, etc., can solve the problems of large steric hindrance, low ligand yield, hindering the rapid insertion of ethylene, etc. The effect of good thermal stability and good polymerization activity
Active Publication Date: 2022-03-08
HANGZHOU XINGLU TECH CO LTD +1
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However, the catalyst with a symmetrical structure in which the aniline substituents on both sides are large-volume substituents, when preparing the ligand of the catalyst, due to the large steric hindrance, the yield of the ligand is very low, resulting in the synthesis cost of the catalyst. At the same time, the R' of the bulky substituent group hinders the rapid insertion of ethylene, resulting in low polymerization activity of the catalyst when catalyzing ethylene polymerization, which limits its industrial application
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Embodiment 1
[0041] Preparation A1: To a solution of 2,6-bis(benzhydryl)-4-methylaniline (8.8 g, 20 mmol) and 1,2-benzoacenaphthoquinone (4.2 g, 18 mmol) in toluene (150 mL) was added P-toluenesulfonic acid (0.34g, 2mmol) was refluxed for 6h. The solvent was removed, and the residue was subjected to silica gel column chromatography with a mixed solvent of dichloromethane and petroleum ether at a volume ratio of 2:1 to obtain A1 with a mass of 4.1 g and a yield of 35%.
Embodiment 2
[0043] Preparation A2: To a solution of 2,4-bis(benzhydryl)-6-methylaniline (8.8 g, 20 mmol) and 1,2-benzoacenaphthoquinone (4.2 g, 18 mmol) in toluene (150 mL) was added P-toluenesulfonic acid (0.34g, 2mmol) was refluxed for 6h. The solvent was removed, and the residue was subjected to silica gel column chromatography with a mixed solvent of dichloromethane and petroleum ether at a volume ratio of 2:1 to obtain A2 with a mass of 5.0 g and a yield of 42%.
Embodiment 3
[0045] Preparation A3: 2,4-bis(bis(4-fluorophenyl)methyl)-6-methylaniline (10.2 g, 20 mmol) and 1,2-benzoacenaphthenequinone (4.2 g, 18 mmol) in toluene (150mL) was added p-toluenesulfonic acid (0.34g, 2mmol) into the solution, and the reaction was refluxed for 10h. The solvent was removed, and the residue was subjected to silica gel column chromatography with a mixed solvent of dichloromethane and petroleum ether at a volume ratio of 2:1 to obtain A3 with a mass of 6.3 g and a yield of 48%.
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Abstract
The invention discloses a large sterically hindered asymmetric (α-diimine) nickel olefin catalyst based on 1,2-acenaphthylenquinone as a skeleton, a preparation method and an application thereof. Based on 1,2-benzonaphthylenquinone of the present invention as the structural formula of the large sterically hindered asymmetric (α-diimine) nickel olefin catalyst as shown in formula (I), wherein R 1 is benzhydryl or bis(4-fluorophenyl)methyl, R 2 is benzhydryl, bis(4-fluorophenyl)methyl or methyl, R 3 is methyl, ethyl, isopropyl, benzhydryl, bis(4-fluorophenyl)methyl, halogen, trifluoromethyl or methoxy, R 4 is methyl, ethyl or isopropyl, R 5 is methyl, ethyl or isopropyl, R 6 is hydrogen, methyl, ethyl or isopropyl, and X is chlorine or bromine. The catalyst has a simple preparation process, can catalyze ethylene polymerization under the action of a co-catalyst, exhibits good thermal stability and polymerization activity, and has good industrial application prospects.
Description
technical field [0001] The invention relates to an asymmetric (α-diimine) nickel olefin catalyst and its preparation method and application, in particular to a large sterically hindered asymmetric (α-diimine) based on 1,2-benzonaphthylquinone as a skeleton. ) nickel olefin catalyst and its preparation method, and the application of using the catalyst to catalyze ethylene or propylene to obtain polyethylene or polypropylene. 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. [0...
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