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Symmetrical alpha-diimine nickel complex catalyst as well as preparation method and application thereof

A nickel diimide catalyst technology, applied in the field of polyolefins, can solve the problems of limited metal catalysts, achieve high catalytic activity and wide industrial application prospects

Inactive Publication Date: 2015-05-20
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These all limit the practical application of metal catalysts to a certain extent.

Method used

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  • Symmetrical alpha-diimine nickel complex catalyst as well as preparation method and application thereof
  • Symmetrical alpha-diimine nickel complex catalyst as well as preparation method and application thereof
  • Symmetrical alpha-diimine nickel complex catalyst as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1. Preparation of N,N'-bis(4-benzhydryl-2,6-dimethylphenyl)butan-2,3-diimine [L1]

[0044]

[0045] Add catalyst amount ( 0.03g, 1mmol) of formic acid and anhydrous magnesium sulfate (0.5g, 4.1mmol), heated to reflux for 72h. The solvent dichloromethane was removed, and the residue was subjected to basic alumina column chromatography with a mixed solvent of petroleum ether and ethyl acetate at a volume ratio of 5:1. The eluted fractions were detected by a thin-layer silica gel plate, the first fraction was collected, and the solvent was removed to obtain a yellow solid, which was N,N'-bis(4-benzhydryl-2,6-dimethylphenyl)butane- 2,3-diimine. Yield: 13%, melting point: 230°C.

[0046] The structure confirmation data are as follows: FT-IR(KBr,cm -1 ):3057(w), 2946(w), 2361(m), 1647(s), 1599(w), 1491(m), 1447(s), 1377(w), 1355(m), 1203(m ), 1119(s), 889(w), 792(w), 739(s), 696(vs). 1 H NMR (CDCl 3 ,400MHz): δ7.29(t,J=7.2Hz,8H,Ph-H),7.20(t,J=7.2Hz,4H,Ph-H),...

Embodiment 2

[0048] Example 2. Preparation of N,N'-bis(4-benzhydryl-2,6-diethylphenyl)butan-2,3-diimine [L2]

[0049]

[0050] Add catalyst amount ( 0.03g, 1mmol) of formic acid and anhydrous magnesium sulfate (0.5g, 4.1mmol), heated to reflux for 72h. The solvent dichloromethane was removed, and the residue was subjected to basic alumina column chromatography with a mixed solvent of petroleum ether and ethyl acetate at a volume ratio of 5:1. The eluted fractions were detected by a thin-layer silica gel plate, the first fraction was collected, and the solvent was removed to obtain a yellow solid, which was N,N'-bis(4-benzhydryl-2,6-diethylphenyl)butane- 2,3-diimine. Yield: 9.1%, melting point: 214°C.

[0051] The structure confirmation data are as follows: FT-IR(KBr,cm -1 ):3023(w),2970(w),2930(w),2874(w),1648(m),1598(w),1491(m),1447(s),1362(w),1251(s ), 1075(w), 1030(w), 892(w), 779(w), 745(s), 696(vs). 1 H NMR (CDCl 3 ,400MHz): δ7.29(t,J=7.2Hz,8H,Ph-H),7.21(t,J=7.2Hz,4H,Ph-H),7...

Embodiment 3

[0053] Example 3. Preparation of N,N'-bis(4-benzhydryl-2,6-diisopropylphenyl)butan-2,3-diimine [L3]

[0054]

[0055] 4-benzhydryl-2,6-diisopropylaniline (3.6g, 10.5mmol) and 2,3-butanedione (0.43g, 5.0mmol) in dichloromethane (50mL) solution, add catalyst amount (0.03g, 1mmol) of formic acid and anhydrous magnesium sulfate (0.5g, 4.1mmol), heated to reflux for 72h. The solvent dichloromethane was removed, and the residue was subjected to basic alumina column chromatography with a mixed solvent of petroleum ether and ethyl acetate at a volume ratio of 5:1. The eluted fraction was detected by a thin-layer silica gel plate, the first fraction was collected, and the solvent was removed to obtain a yellow solid, which was N,N'-bis(4-benzhydryl-2,6-diisopropylphenyl)butyl -2,3-diimine. Yield: 12%, melting point: 236°C.

[0056] The structure confirmation data are as follows: FT-IR(KBr,cm -1 ):3058(w), 2961(w), 2929(w), 2865(w), 1641(m), 1597(w), 1490(m), 1447(s), 1358(w), 13...

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Abstract

The invention discloses a symmetrical alpha-diimine nickel complex catalyst as well as a preparation method and an application thereof. The complex shown in formula I is chosen from at least one of the methyl, ethyl, isopropyl and benzhydryl; R2 is at least one of the methyl, ethyl and isopropyl; R3 is benzhydryl. The invention also discloses a preparation method of a catalyst containing symmetrical alpha-diimine ligand and nickel metal. The catalyst is cooperated with a cocatalyst diethylaluminium chloride for vinyl polymerization, and the catalyst has a high polymerization reaction activity with the highest activity of 106g.mol<-1>(Ni).h<-1>, thus an olefin polymerization product with a high molecular weight can be obtained. The formula I is as shown in the specification.

Description

technical field [0001] The invention belongs to the field of polyolefins, and relates to a catalyst for olefin polymerization, in particular to a metal catalyst for ethylene polymerization and a preparation method thereof. Background technique [0002] Polyethylene is widely used in many fields such as industry, agriculture, military, medical and health care, and daily life. It is the fastest growing synthetic resin with the largest output and extremely wide uses in the world. The present industrialized polyethylene catalyst has Ziegler-Natta type catalyst (DE Pat 889229 (1953); IT Pat 536899 (1955) and IT Pat 545332 (1956); Phillips type catalyst (Belg.Pat.530617 (1955); Chem.Rev.1996,96,3327) and metallocene type catalyst (W.Kaminsky, Metalorganic Catalysts for Synthesis and Polymerization, Berlin: Springer, 1999), and in recent years Development of highly efficient ethylene oligomerization and polymerization catalysts of the late transition metal complex type. [0003] ...

Claims

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Application Information

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IPC IPC(8): C07C249/02C07C251/12C07F15/04C08F10/02C08F4/70
Inventor 高梦龙班青
Owner QILU UNIV OF TECH
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