Pyrene-4,5,9,10-tetra-imine nickel-palladium complex catalyst and preparation method and application thereof

A catalyst and compound technology, which is applied in the direction of preparation of imino compounds, compounds containing elements of Group 8/9/10/18 of the periodic table, nickel organic compounds, etc., can solve the problems of limited metal catalysts, achieve high catalytic activity, Broad industrial application prospects and the effect of increasing catalytic life

Active Publication Date: 2014-04-30
INST OF CHEM CHINESE ACAD OF SCI
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  • Pyrene-4,5,9,10-tetra-imine nickel-palladium complex catalyst and preparation method and application thereof
  • Pyrene-4,5,9,10-tetra-imine nickel-palladium complex catalyst and preparation method and application thereof
  • Pyrene-4,5,9,10-tetra-imine nickel-palladium complex catalyst and preparation method and application thereof

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Example Embodiment

[0074] Example 1. Preparation of pyrene-4,5,9,10-tetraimine-(2,6-dimethylanilino) [L1](R 1 Is methyl, R 2 Is hydrogen)

[0075]

[0076] 3.60g (30mmol) belongs to the compound of formula III 2,6-dimethylaniline (R 1 Is methyl, R 2 Is hydrogen) and 9.08g (90mmol) triethylamine dissolved in 100ml solvent toluene and heated to 90℃, then add 3.2ml (30mmol) TiCl 4 , White smoke appears, then add 1.33g (5mmol) of the compound pyrene-4,5,9,19-tetraketone represented by formula II. The condensation reaction was carried out for 30 minutes, and the mixture was subjected to column chromatography, eluting with a mixed solvent of petroleum ether and dichloromethane as the eluent, and the eluted fraction was detected by thin layer chromatography to obtain 1.94g of a red solid with a yield of 57%.

[0077] 1 H NMR(400MHz, CDCl 3 ,ppm): 8.37(d,J=8.0Hz,2H,Ph-H),7.13(t,J=7.6,2H,Ph-H),7.02(d,J=7.6Hz,4H,Ph-H) ,6.92(t,J=7.6,2H,Ph-H),6.82-6.86(m,8H,Ph-H),2.09(s,12H,4×CH 3 ),1.44(s,12H,4×CH 3 ). 13 C NMR...

Example Embodiment

[0078] Example 2. Preparation of pyrene-4,5,9,10-tetraimine-(2,6-diethylanilino) [L2](R 1 Is ethyl, R 2 Is hydrogen)

[0079]

[0080] 4.47g (30mmol) 2,6-dimethylaniline and 9.08g (90mmol) triethylamine were dissolved in 100ml toluene and heated to 90℃, then 3.2ml TiCl was added 4 , White smoke appears, then add 1.33g (5mmol) of pyrene-4,5,9,19-tetraketone. The condensation reaction was carried out for 30 minutes, and the mixture was subjected to column chromatography, eluted with a mixed solvent of petroleum ether and ethyl acetate as the eluent, and the eluted fraction was detected by thin layer chromatography to obtain 0.86 g of a red solid with a yield of 32.0%.

[0081] The structure confirmation data is as follows: 1 H NMR(400MHz, CDCl 3 ,ppm): 8.36(d,J=8.0Hz,2H,Ph-H),7.11-7.04(m,10H,Ph-H),6.96-6.83(m,6H,Ph-H),2.52-2.46( m,4H,2×CH 2 ),2.39-2.34(m,4H,2×CH 2 ),1.69-1.62(m,8H,4×CH 2 ),0.87(t,J=7.6Hz,12H,4×CH 3 ),0.73(t,J=7.6Hz,12H,4×CH 3 ). 13 C NMR(100MHz, CDCl 3 ,ppm): 157.2, ...

Example Embodiment

[0082] Example 3. Preparation of pyrene-4,5,9,10-tetraimine-(2,4,6-trimethylanilino) [L4](R 1 Is methyl, R 2 For methyl)

[0083]

[0084] 4.05g (30mmol) 2,6-dimethylaniline and 9.08g (90mmol) triethylamine were dissolved in 100ml toluene and heated to 90℃, then 3.2ml TiCl was added 4 , White smoke appears, then add 1.33g (5mmol) of pyrene-4,5,9,19-tetraketone. The condensation reaction was carried out for 30 minutes, and the mixture was subjected to column chromatography, eluted with a mixed solvent of petroleum ether and dichloromethane as the eluent, and the eluted fraction was detected by thin layer chromatography to obtain 1.69 g of a red solid with a yield of 45.6%.

[0085] The structure confirmation data is as follows: 1 H NMR(400MHz, CDCl 3 ,ppm): 8.29(d,J=7.6Hz,2H,Ph-H),7.12(t,J=7.6Hz,2H,Ph-H),6.88(t,J=7.6Hz,2H,Ph-H ), 6.84(s, 4H, Ph-H), 6.63(s, 4H, Ph-H), 2.34(s, 6H, 2×CH 3 ), 2.27(s, 6H, 2×CH 3 ), 2.18(s, 12H, 4×CH 3 ),1.31(s,12H,4×CH 3 ). 13 C NMR(100MHz, CDCl 3 ,ppm):...

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Abstract

The invention discloses a pyrene-4,5,9,10-tetra-imine nickel-palladium complex catalyst and a preparation method and application thereof. The pyrene-4,5,9,10-tetra-imine nickel-palladium complex catalyst has the structural general formula represented by a formula I shown in the specification. According to the pyrene-4,5,9,10-tetra-imine nickel-palladium complex catalyst and the preparation method and application thereof, the pyrene-4,5,9,10-tetra-imine nickel (palladium) complex is designed and synthesized, the complex can better catalyze ethylene polymerization in the presence of cocatalysts, namely methylaluminoxane and dimethyl aluminum chloride, so as to obtain a polymer with high molecular weight, meanwhile, the activity of the complex is very high, and the highest activity can reach 10<6>g.mol<-1>(M).h<-1>; nickel series complexes show long catalytic activity, thereby having broad industrial application prospects.

Description

technical field [0001] The invention relates to a pyrene-4,5,9,10-tetraimine nickel-palladium complex catalyst and a preparation method and application thereof. Background technique [0002] Polyethylene is the world's fastest growing synthetic resin with the largest output and a wide range of uses. It is widely used in many fields such as industry, agriculture, military, medical and health care, and daily life. At present, industrialized polyethylene catalysts have Ziegler-Natta type catalysts (DE Pat 889229 (1953); IT Pat 536899 (1955) and IT Pat 545332 (1956); Chem.Rev., 2000,100,1169 and the related literature , Phillips-type catalysts (Belg.Pat.530617 (1955); Chem.Rev.1996, 96, 3327) and metallocene catalysts (W.Kaminsky, Metalorganic Catalysts for Synthesis and Polymerization, Berlin: Springer, 1999), and in recent years To develop high-efficiency ethylene oligomerization and polymerization catalysts of late transition metal complex type. [0003] In 1995, Brookhart ...

Claims

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Application Information

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IPC IPC(8): C07F15/04C07F15/00C07C251/20C07C249/02C08F4/70C08F110/02
Inventor 邢其锋宋奎峰杜世振孙文华
Owner INST OF CHEM CHINESE ACAD OF SCI
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