Tert-butyl asymmetric alpha-diimine nickel complex for preparation of ultrahigh-molecular-weight polyethylene elastomers and preparation method and application of tert-butyl asymmetric alpha-diimine nickel complex

A nickel complex, nickel diimide technology, applied in 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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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] However, the catalytic performance of the above catalysts, as well as the conditions and efficiency of their preparation methods, still need to be further improved

Method used

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  • Tert-butyl asymmetric alpha-diimine nickel complex for preparation of ultrahigh-molecular-weight polyethylene elastomers and preparation method and application of tert-butyl asymmetric alpha-diimine nickel complex
  • Tert-butyl asymmetric alpha-diimine nickel complex for preparation of ultrahigh-molecular-weight polyethylene elastomers and preparation method and application of tert-butyl asymmetric alpha-diimine nickel complex
  • Tert-butyl asymmetric alpha-diimine nickel complex for preparation of ultrahigh-molecular-weight polyethylene elastomers and preparation method and application of tert-butyl asymmetric alpha-diimine nickel complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0125] Preparation of 2-(2,6-bis(diphenylmethyl)-4-tert-butylaniline)acenaphthenone represented by formula (V).

[0126] Add the amount of catalyst (1.25g) to a solution of 2,6-bis(diphenylmethyl)-4-tert-butylaniline (9.63g, 20mmol) and acenaphthenedione (4.00g, 22mmol) in toluene (150mL) P-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. 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%. Melting point: 186-188°C.

[0127] The structure confirmation data is as follows:

[0128] FT-IR(KBr,cm -1 ): 3059(w), 2958(w), 1727(ν(C=O)m), 1657(ν(C=N)m), 1598(s), 1582(s), 1492(s), 1456 (m), 1332(s)...

Embodiment 2

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

[0134] Toluene (2,6-bis(diphenylmethyl)-4-tert-butylaniline)acenaphthene (1.00g, 1.55mmol) and 2,6-dimethylaniline (0.2g, 1.65mmol) 100mL) Add a catalytic amount of p-toluenesulfonic acid to the solution, and heat to reflux for 10h. 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: 32%. Melting point: 146-148°C.

[0135] The structure confirmation data is as follows:

[0136] FT-IR(KBr,cm -1 ): 3026(w), 2953(w), 1659(ν(C=N)m), 1631(ν(C=N)m), 1593(s), 1446(s), 1361(w), 1255 (w), 1110(w), 1031(m), 924(s), 8...

Embodiment 3

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

[0142] Toluene (2,6-bis(diphenylmethyl)-4-tert-butylaniline)acenaphthene (1.00g, 1.55mmol) and 2,6-diethylaniline (0.21g, 1.65mmol) 100mL) Add a catalytic amount of p-toluenesulfonic acid to the solution, and heat to reflux for 10h. 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: 35%. Melting point: 197-199°C.

[0143] The structure confirmation data is as follows:

[0144] FT-IR(KBr,cm -1 ): 3026(w), 2959(w), 1659(ν(C=N)m), 1632(ν(C=N)m), 1593(m), 1447(s), 1361(w), 1257 (m), 1111(m), 1073(m), 923(s), 777...

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Abstract

The invention provides a tert-butyl asymmetric alpha-diimine nickel complex and an intermediate, a preparation method and application thereof. The prepared nickel complex has a single catalytic activecenter, regulation of polymer molecular weight and branching degrees can be realized through changing of a ligand 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 and simple in operation condition. The nickel complex can be applied to catalysts for vinyl polymerization, the catalytic activity is up to 1.26*10<7>g mol<-1>(Ni) h<-1>, the weight-average molecular weight Mw of prepared polyethylene fluctuates in a range of 1.0-30.8*10<5>g mol<-1>, molecularweight distribution is in a range of 1.9-5.0, the remarkable performance of polyethylene molecular weight control is achieved, the nickel complex can be used for preparation of ultrahigh-molecular-weight polyethylene, and obtained polyethylene is high in branching degree and is potential polyolefin elastomer.

Description

Technical field [0001] The invention relates to the field of polyolefin catalysts, in particular to a kind of asymmetric α-diimine nickel complexes containing tert-butyl groups for preparing ultra-high molecular weight polyethylene elastomers, intermediates, preparation methods and uses thereof. Background technique [0002] As the fastest growing, largest output, and most versatile synthetic resin-polyethylene, it is widely used in many fields such as industry, agriculture, military, medical and health, and daily life. The extensive development and application of polyethylene products are inseparable from the development of olefin polymerization catalysts. At present, the industrialized polyethylene catalysts mainly include Ziegler-Natta type catalysts (DEPat 889229 (1953); IT Pat 536899 (1955) and IT Pat545332 (1956); Chem. Rev., 2000, 100, 1169 and related documents of this special issue ), Phillips-type catalysts (Belg. Pat. 530617 (1955); Chem. Rev. 1996, 96, 3327) and meta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
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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