Nitryl asymmetric alpha-diimine nickel complex for preparation of ultrahigh-molecular-weight polyethylene and preparation method and application of nitryl asymmetric alpha-diimine nickel complex

A technology of nickel complexes and nickel diimides, applied to nickel organic compounds, compounds containing elements of group 8/9/10/18 of the periodic table, chemical instruments and methods, etc.

Active Publication Date: 2018-11-13
INST OF CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] However, the catalytic performance of the above catalysts, as well as the cond

Method used

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  • Nitryl asymmetric alpha-diimine nickel complex for preparation of ultrahigh-molecular-weight polyethylene and preparation method and application of nitryl asymmetric alpha-diimine nickel complex
  • Nitryl asymmetric alpha-diimine nickel complex for preparation of ultrahigh-molecular-weight polyethylene and preparation method and application of nitryl asymmetric alpha-diimine nickel complex
  • Nitryl asymmetric alpha-diimine nickel complex for preparation of ultrahigh-molecular-weight polyethylene and preparation method and application of nitryl asymmetric alpha-diimine nickel complex

Examples

Experimental program
Comparison scheme
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Example Embodiment

[0126] Example 1

[0127] Preparation of 2-(2,6-bis(diphenylmethyl)-4-nitroaniline)acenaphthenone represented by formula (V).

[0128] Add the amount of catalyst (1.25g) to the solution of 2,6-bis(diphenylmethyl)-4-nitroaniline (9.40g, 20mmol) and acenaphthylene dione (4.00g, 22mmol) in toluene (150mL) Toluenesulfonic acid, reflux for 5h. The solvent is removed, and the residue is subjected to silica gel column chromatography with a mixed solvent of ethyl acetate and petroleum ether in a volume ratio of 1:50, and the elution fraction is detected through a thin-layer silica gel plate. The developing solvent is the volume of petroleum ether and ethyl acetate. The third fraction is collected for the mixed solvent with a ratio of 10:1 and the solvent is removed to obtain an orange solid. Yield: 70%.

[0129] The structure confirmation data is as follows:

[0130] 1 H NMR (400MHz, DMSO, TMS): δ8.32 (d, J = 8.8Hz, 1H), 8.18 (d, J = 6.8Hz, 1H), 7.86-7.82 (m, 2H), 7.69-7.52 (m ,3H),7.32(t...

Example Embodiment

[0132] Example 2

[0133] Preparation of 1-(2,6-dimethylaniline)-2-(2,6-bis(diphenylmethyl)-4-nitroaniline)acenaphthene [L1] represented by formula (II), wherein R 1 Is methyl, R 2 Is hydrogen.

[0134] 2-(2,6-bis(diphenylmethyl)-4-nitroaniline)acenaphthene (0.98g, 1.55mmol) and 2,6-dimethylaniline (0.2g, 1.65mmol) in toluene (100mL ) Add a catalyst amount of p-toluenesulfonic acid to the solution, and heat to reflux for 10 hours. The solvent toluene was removed, and the residue was subjected to basic alumina column chromatography with a mixed solvent of ethyl acetate and petroleum ether in a volume ratio of 1:50. The eluted fraction was detected by a thin-layer silica gel plate, the second fraction was collected, and the solvent was removed to obtain an orange solid. Yield: 23%. Melting point: 162-164°C.

[0135] The structure confirmation data is as follows:

[0136] FT-IR(KBr,cm -1 ): 3057(w), 1661(ν(C=N),w), 1589(w), 1494(m), 1467(s), 1408(w), 1294(vs), 1182(m), 1071 (m), 102...

Example Embodiment

[0140] Example 3

[0141] Preparation of 1-(2,6-diethylaniline)-2-(2,6-bis(diphenylmethyl)-4-nitroaniline)acenaphthene [L2] represented by formula (II), wherein R 1 Is ethyl, R 2 Is hydrogen.

[0142] 2-(2,6-bis(diphenylmethyl)-4-nitroaniline)acenaphthene (0.98g, 1.55mmol) and 2,6-diethylaniline (0.21g, 1.65mmol) in toluene (100mL ) Add a catalyst amount of p-toluenesulfonic acid to the solution, and heat to reflux for 10 hours. The solvent toluene was removed, and the residue was subjected to basic alumina column chromatography with a mixed solvent of ethyl acetate and petroleum ether in a volume ratio of 1:50. The eluted fraction was detected by a thin-layer silica gel plate, the second fraction was collected, and the solvent was removed to obtain an orange solid. Yield: 41%. Melting point: 170-172°C.

[0143] The structure confirmation data is as follows:

[0144] FT-IR(KBr,cm -1 ): 3058(w), 2960(w), 1656(ν(C=N),w), 1587(w), 1498(m), 1470(m), 1447(s), 1340(m), 1290 (vs), 1184(...

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Abstract

The invention provides a nitryl asymmetric alpha-diimine nickel complex for preparation of ultrahigh-molecular-weight polyethylene and an intermediate, a preparation method and application of the nitryl asymmetric alpha-diimine nickel complex. The nickel complex has a single catalytic active center, regulation of polymer molecular weight and branching degrees can be realized through changing of aligand structure and polymerization conditions, and high catalytic activity, low cost, performance stability and the like are achieved. The preparation method is mild in condition, short in period andsimple in operation condition. The nickel complex can be applied to catalytic vinyl polymerization, the catalytic activity is up to 4.61*10<6>g mol<-1>(Ni) h<-1>, the weight-average molecular weightMw of prepared polyethylene fluctuates in a range of 8.2-32.8*10<5>g mol<-1>, molecular weight distribution is in a range of 1.8-2.8, the remarkable performance of polyethylene molecular weight control is achieved, and the nickel complex can be used for preparation of ultrahigh-molecular-weight polyethylene; obtained polyethylene is high in branching degree, the melt temperature Tm is in a range of 76.9-117.2 DEG C, and accordingly the polyethylene can be used as engineering plastic at a high environment temperature, and a promising industrial application potential is achieved.

Description

technical field [0001] The invention relates to the technical field of polyolefin catalysts, in particular to a nitro-containing asymmetric α-diimine nickel complex for preparing ultra-high molecular weight polyethylene, its intermediate, preparation method and application. Background technique [0002] As the fastest-growing, largest-yield, and most-used synthetic resin-polyethylene, it is widely used in many fields such as industry, agriculture, military, medical and health care, and daily life. The extensive development and application of polyethylene products is inseparable from the development of olefin polymerization catalysts. At present, industrialized polyethylene catalysts mainly include Ziegler-Natta type catalysts (DEPat 889229 (1953); IT Pat 536899 (1955) and IT Pat 545332 (1956); Chem.Rev., 2000, 100, 1169 and relevant Literature), Phillips type catalyst (Belg.Pat.530617 (1955); Chem.Rev.1996,96,3327) and metallocene type catalyst (W.Kaminsky, Metalorganic Cat...

Claims

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Application Information

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IPC IPC(8): C07F15/04C07C251/20C08F10/02C08F110/02C08F4/70
CPCC07C251/20C07F15/045C08F10/02C08F110/02C08F4/7006C08F2500/01C08F2500/03Y02P20/52
Inventor 马艳平凯萨马穆德王新鑫孙文华
Owner INST OF CHEM CHINESE ACAD OF SCI
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