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Bisphenol oxygen-imine ligand zirconium compound, as well as preparation method and application thereof

A technology of bisphenoloxyimine and zirconium compound, applied in the field of olefin polymerization, can solve the problems of limited application scope, high price, and many catalyst synthesis steps, and achieves the effects of overcoming low molecular weight, high catalytic activity and stable properties

Inactive Publication Date: 2018-08-14
SHANGHAI RES INST OF CHEM IND
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In summary, although great breakthroughs have been made in the research of olefin polymerization catalysts, there are still many difficulties to be overcome, such as the high molecular weight and narrow molecular weight distribution of polymers cannot be realized at the same time, and it is difficult to control the comonomer in The distribution in the polymer chain, the many steps of catalyst synthesis, and the high price limit its application range in industry.

Method used

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  • Bisphenol oxygen-imine ligand zirconium compound, as well as preparation method and application thereof
  • Bisphenol oxygen-imine ligand zirconium compound, as well as preparation method and application thereof
  • Bisphenol oxygen-imine ligand zirconium compound, as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0034] Synthesis of Ligand L1

[0035] Add 3,5-di-tert-butyl salicylaldehyde (4.68g, 20mmol), absolute ethanol (50mL) and 1.0g molecular sieves to the 100mL reaction flask successively Stir at room temperature for 5 minutes, add 1,3-propanediamine (0.74 g, 10 mmol), and react under reflux for 16 hours. The reaction liquid was filtered, and the solvent was removed from the filtrate under reduced pressure, and the product (4.11 g, yield: 81.1%) was obtained by recrystallization from petroleum ether.

[0036]

[0037] 1 H NMR (CDCl 3 ,400MHz):δ10.93(s,2H,OH),8.56(s,2H,CH=N),7.20(d,2H, 4 J=2.2Hz, ArH), 6.80(d, 2H, 4 J=2.2Hz, ArH), 3.71(t, 4H, 3 J=7.5Hz, NCH 2 ),2.01(m,2H,CH 2 CH 2 CH 2 ),1.43(s,18H,C(CH 3 ) 3 ),1.28(s,18H,C(CH 3 ) 3 ). 13 C NMR (CDCl 3 ,100MHz): δ161.4,154.3,140.4,135.4,123.2,122.7,121.5,59.4,34.5,32.2,31.6,25.0.Anal.Calcd.forC 33 h 50 N 2 o 2 : C, 78.21; H, 9.95; N, 5.53. Found: C, 78.47; H, 10.02; N, 5.77%.

Embodiment 2

[0039] Synthesis of Ligand L2

[0040] Add 3-tert-butyl-5-methyl salicylaldehyde (3.84g, 20mmol), absolute ethanol (50mL) and 1.0g molecular sieves to the 100mL reaction flask successively Stir at room temperature for 5 minutes, add 1,3-propanediamine (0.74 g, 10 mmol), and react under reflux for 16 hours. The reaction liquid was filtered, and the solvent was removed from the filtrate under reduced pressure, and the product (2.87 g, yield: 70.2%) was obtained by recrystallization from petroleum ether.

[0041]

[0042] 1 H NMR (CDCl 3 ,400MHz):δ10.79(s,2H,OH),8.44(s,2H,CH=N),7.37(d,2H, 4 J=2.4Hz, ArH), 7.08(d, 2H, 4 J=2.4Hz, ArH), 3.95(t, 4H, 3 J=7.2Hz, NCH 2 ),2.36(s,6H,ArCH 3 ),1.40(s,18H,C(CH 3 ) 3 ). 13 C NMR (CDCl 3 ,100MHz): δ161.4,157.3,140.4,135.4,123.2,122.7,121.5,61.9,34.5,31.6,21.6.Anal.Calcd.for C 26 h 36 N 2 o 2 : C, 76.43; H, 8.88; N, 6.86. Found: C, 76.47; H, 9.02; N, 6.77%.

Embodiment 3

[0044] Synthesis of Ligand L3

[0045] Add 2-hydroxy-3-cumyl-5-methoxybenzophenone (5.69g, 20mmol), absolute ethanol (50mL), 1 drop of formic acid and 1.0g molecular sieves to the 100mL reaction flask successively Stir at room temperature for 5 minutes, add 1,3-propanediamine (0.74 g, 10 mmol), and react under reflux for 16 hours. The reaction liquid was filtered, and the solvent was removed from the filtrate under reduced pressure, and the product was obtained by recrystallization from petroleum ether (3.25 g, yield: 53.6%).

[0046]

[0047] 1 H NMR (CDCl 3 ,400MHz):δ10.12(s,2H,OH),7.35-7.13(m,12H,ArH),6.85(d,2H, 4 J=2.4Hz, ArH), 3.81(s, 6H, OCH 3 ),3.67(t, 3 J=7.2Hz, 4H, NCH 2 ),2.11(m,2H,CH 2 CH 2 CH 2 ),1.81(s,6H,NCCH 3 ),1.69(s,12H,CPh(CH 3 ) 2 ). 13 CNMR (CDCl 3 for C 39 h 46 N 2 o 4 : C, 77.20; H, 7.64; N, 4.62. Found: C, 77.41; H, 7.75; N, 4.56%.

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Abstract

The invention relates to a bisphenol oxygen-imine ligand zirconium compound, as well as a preparation method and application thereof. The method comprises the steps of after reacting a bisphenol imineligand compound and alkyl lithium, reacting with a zirconium halide compound in an organic medium according to the molar ratio being 1:(1.0 to 1.5), controlling the reaction temperature to be -78 to110 DEG C, reacting for 2 to 96 hours, filtering, concentrating, and recrystallizing to obtain the bisphenol oxygen-imine ligand zirconium compound; the bisphenol oxygen-imine ligand zirconium compound is applied to olefin homopolymerization and copolymerization in the presence of alkylaluminoxane. Compared with the prior art, according to the bisphenol oxygen-imine ligand zirconium compound, as well as the preparation method and the application thereof provided by the invention, the raw materials are easy to get, a synthetic route is simple, the product yield is high, the bisphenol oxygen-imine ligand zirconium compound has a stable property and higher catalytic activity at the same time, polyethylene, polypropylene, a copolymer of ethylene and propylene, a copolymer of ethylene and 1-hexene, and a copolymer of ethylene and 1-octylene with high molecular weight and narrow molecular weight distribution can be obtained, and the demands of an industrial department can be met.

Description

technical field [0001] The invention relates to the field of olefin polymerization, in particular to a bisphenoloxyimine ligand zirconium compound, a preparation method thereof and an application in olefin polymerization. Background technique [0002] Polyolefin materials such as polyethylene (PE) and polypropylene (PP) have the advantages of high strength, low density, strong chemical corrosion resistance and low manufacturing cost, and can replace paper, wood, glass, metal and concrete to a certain extent Ordinary materials have a wide range of uses and have become the most widely used polymer materials in the world today. Among them, polyethylene is the variety with the largest output among general-purpose synthetic resins. As the most widely used thermoplastic, it is mainly used to make films, containers, pipes, monofilaments, wires and cables, daily necessities, etc. It can also be used to make TVs, Radar and other high-frequency insulating materials. LLDPE is a copol...

Claims

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Application Information

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IPC IPC(8): C07F7/00C08F110/02C08F110/06C08F210/02C08F210/06C08F210/16C08F210/14
CPCC08F110/02C08F110/06C08F210/02C08F210/06C08F210/16C08F4/64175C08F210/14C08F2500/03
Inventor 王原郑浩罗勇叶晓峰刘婷婷
Owner SHANGHAI RES INST OF CHEM IND
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