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Two-alkoxyl-silicon-containing alpha-diimine compound and application of load type metal complex thereof in olefin polymerization

A technology of diimine compound and bisalkoxy silicon is applied in the application field of α-diimine compound and its supported metal complex in olefin polymerization, which can solve the problem of not very firm ligand loading, and achieves the The effect of strong chemical bond force, reduced influence and large adjustable range

Inactive Publication Date: 2018-09-14
TIANJIN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since there is only one alkoxy silicon group in this type of ligand, there will also be a problem that the ligand is not very firmly loaded on the carrier.

Method used

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  • Two-alkoxyl-silicon-containing alpha-diimine compound and application of load type metal complex thereof in olefin polymerization
  • Two-alkoxyl-silicon-containing alpha-diimine compound and application of load type metal complex thereof in olefin polymerization
  • Two-alkoxyl-silicon-containing alpha-diimine compound and application of load type metal complex thereof in olefin polymerization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of load f1

[0033] Its preparation route is as follows:

[0034]

[0035] Synthesis of 5,6-dibromoacenaphthenequinone bis(2,4-dimethyl-6-benzhydryl)phenylimine a1:

[0036] Add compound 5,6-dibromoacenaphthenequinone (2.72g, 8mmol), 2,4-dimethyl-6-benzhydrylaniline (5.46g, 19mmol) and p-toluene to the reaction flask of 250mL Sulfonic acid (3.27g, 19mmol) and 150mL of anhydrous toluene, the mixture was heated to reflux, and the water formed during the reaction was removed. The reaction was tracked by chromatography until the reaction of the raw materials was complete, and a clear wine red solution was obtained. After the reaction solution was concentrated, the reaction mixture was separated by column chromatography to obtain 6.05g red solid a1 (i.e. the structure of compound A, wherein R 1 =[2-Benzhydryl-4,6-dimethyl]phenyl), the yield was 86%. 1 H NMR (400MHz, CDCl 3 ): δ7.69(d, J=7.8Hz, 2H), 7.28(d, J=8.1Hz, 2H), 7.25-7.17(m, 8H), 7.11(s, 2H), 6.91(d...

Embodiment 2

[0044] Synthesis of load g1

[0045] Its preparation route is as follows:

[0046]

[0047] SiO 2 / MgCl 2 Preparation of composite carrier:

[0048] Add the solvent n-heptane 50mL and 1g of anhydrous MgCl in sequence in a five-neck flask with mechanical stirring under the protection of argon 2 , and a certain amount of n-butanol was added at 35°C (the molar ratio of n-butanol to magnesium chloride was 4.0:1), and then the temperature was programmed to rise to 90°C for 3h to obtain a colorless transparent solution. Then the solution was cooled to 60°C, and a certain amount of SiO was added 2 (MgCl 2 and SiO 2 Mass ratio is equal to 0.05), and after stirring at this temperature for 2h, stop, and obtain SiO through suction filtration and drying 2 / MgCl 2 Composite carrier.

[0049] 5,6-bis[4-(3-(monoethyldipropoxysilyl)propylcarbamatemethyl)phenyl]acenaphthenequinonebis(2,4-dimethyl-6-benzhydryl) Benzene imine d1 (i.e. the structure of D compound, where R 1 =[2-benz...

Embodiment 3

[0051] Synthesis of cargo h1

[0052] Its preparation route is as follows:

[0053]

[0054] 5,6-bis[4-(3-dimethyldimethoxysilyl)propylcarbamatemethyl)phenyl]acenaphthenequinonebis(2,4-dimethyl-6-benzhydryl)benzene Imine e1 (that is, the structure of the E compound, where R 1 =[2-benzhydryl-4,6-dimethyl]phenyl, Ar=benzyl, X=O, R 2 = methyl, R 3 =methyl) was synthesized in the same steps as that of c1 in Example 1. The specific preparation process of the load h1 is the same as that of the load f1 in Example 1, wherein diatomaceous earth is used instead of SiO in Example 1 2 . Elemental analysis of load h1: C, 19.8%; N, 1.1%.

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Abstract

The invention discloses a two-alkoxyl-silicon-containing alpha-diimine compound and the application of a load type metal complex thereof in olefin polymerization. The alpha-diimine compound structurecontains two active groups, namely alkoxyl silicon, so that the alpha-diimine compound can be loaded on the surface of a carrier in a covalent grafting manner; moreover, the two active groups greatlyincrease the firmness of the alpha-diimine compound loaded on the carrier. The loaded alpha-diimine compound is matched with the metal complex to obtain an alpha-diimine compound-loaded metal complexwhich is applied to the olefin polymerization. During the olefin polymerization, the loaded metal complex used as a catalyst is high in thermal stability and can still keep relatively high activity ata reaction temperature of 100 DEG C; the catalyst is hard to fall off, and the phenomenon of kettle sticking during the polymerization is obviously improved.

Description

technical field [0001] The invention relates to the field of olefin catalytic polymerization, in particular to the application of an α-diimine compound with bisalkoxy silicon and its supported metal complex in olefin polymerization. Background technique [0002] In 1995, after Brookhart et al. reported that this α-diimine nickel and palladium could catalyze ethylene polymerization (JAm ChemSoc, 1995, 117: 6414), this type of post-transition metal catalyst has attracted much attention of researchers (WO96 / 23010; US6103658; CN201010177711.8; CN201210051457.6; CN201210276331.9; CN201010572741.9). In 2014, Long et al. reported α-diimine nickel with large steric hindrance groups (ACSCatal. 2014, 4, 2501-2504). The catalyst still had good catalytic activity for ethylene polymerization at 90°C. This discovery makes this type of catalyst show great prospects for its industrial application. [0003] Although the homogeneous α-diimine post-transition metal catalyst has many advantag...

Claims

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Application Information

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IPC IPC(8): C08F4/02C08F4/70C08F10/02C08F10/06C08F110/02C08F110/06C08F210/02C08F210/06C08F110/14C08F132/06C08F132/08C08F232/08C08F212/08C07F7/18
CPCC07F7/1892C08F10/02C08F10/06C08F110/02C08F110/06C08F110/14C08F132/06C08F132/08C08F210/02C08F210/06C08F212/08C08F232/08C08F4/02C08F4/7006C08F4/7098C08F4/70C08F210/08
Inventor 侯彦辉郭海洋杨敏任合刚韦德帅路小敏姜湃
Owner TIANJIN POLYTECHNIC UNIV
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