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Pyridine diimine iron complex and preparation method and application thereof

A pyridinediimide iron series, pyridinediimine technology, applied in the direction of iron organic compounds, iron group organic compounds without C-metal bonds, hydrocarbons, etc., can solve the problem of obtaining low molecular weight, highly branched oily The distribution of polymers and oligomerization products is not very ideal, and it is difficult to meet the requirements of ethylene oligomerization, so as to achieve the effect of increasing ethylene insertion rate, increasing instability, and accelerating insertion rate

Pending Publication Date: 2020-12-29
JIANGSU ZHONGSHENG GAOKE ENVIRONMENTAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the activity of the existing catalysts is still far from the requirements of the market, and it is difficult to meet the oligomerization requirements of ethylene. The distribution of the oligomerization products is not very ideal, and it is difficult to obtain low molecular weight, highly branched oily polymers, which leads to lubricating oil There is a bottleneck in performance improvement

Method used

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  • Pyridine diimine iron complex and preparation method and application thereof
  • Pyridine diimine iron complex and preparation method and application thereof
  • Pyridine diimine iron complex and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (1) Synthesis of pyridine diimine ligand L1:

[0039]

[0040] Dissolve 2-chloro-4-fluoro-6-benzhydrylaniline (1.25g, 4.0mmol) and 2,6-pyridinedicarbonyl chloride (0.41g, 2.0mmol) in 20ml of methanol, add formic acid under stirring 0.2ml, after reflux reaction at 55°C for 24 hours, the solvent was removed to obtain a crude product, which was then washed with C 2 h 5 OH / CH 2 Cl 2 (v / v=15:2) The mixed solvent was recrystallized to precipitate a solid precipitate, which was filtered and dried to obtain 1.36 g of the ligand with a yield of 86%.

[0041] 1 H NMR (400MHz, CDCl 3 ,ppm):δ8.20(d,J=8.4Hz,2H,Py-m-H),8.10(t,1H,Py-p-H),7.68(s,2H,Aryl-H),7.30(m,8H, Ph-H),7.21(m,4H,Ph-H),7.14(m,8H,Ph-H), 6.75(s,2H,Aryl-H),5.48(s,2H,-CHPh 2 ). 13 C NMR (100MHz, CDCl 3, ppm): δ163.3, 152.6, 150.5, 144.9 (C=N), 143.4, 139.5, 136.2, 129.9, 129.2, 128.2, 126.2, 116.6, 114.6, 56.1 (-CHPh 2 ).Anal.Calc.for C 45 h 29 Cl 4 f 2 N 3 (791.54): C, 68.28; H, 3.69; N, 5.31. Found: ...

Embodiment 2

[0051] (1) Synthesis of pyridinediimine ligand L2:

[0052]

[0053] Dissolve 2-bromo-4-fluoro-6-benzhydrylaniline (1.42g, 4.0mmol) and 2,6-pyridinedicarbonyl chloride (0.41g, 2.0mmol) in 20ml of methanol, add formic acid under stirring 0.2ml, after reflux reaction at 45°C for 12 hours, remove the solvent to obtain a crude product, and then use C 2 h 5 OH / CH 2 Cl 2 (v / v=15:2) The mixed solvent recrystallized to precipitate a solid precipitate, which was filtered and dried to obtain 1.44 g of the ligand with a yield of 82%.

[0054] 1 H NMR (400MHz, CDCl 3 ,ppm):δ8.17(d,J=8.1Hz,2H,Py-m-H),8.07(t,1H,Py-p-H),7.57(s,2H,Aryl-H),7.23-7.06(m, 20H,Ph-H),6.81(s,2H,Aryl-H),5.53(s,2H,-CHPh 2 ). 13 C NMR (100MHz, CDCl 3 , ppm): δ166.1, 155.7, 153.8, 148.2 (C=N), 146.2, 142.1, 139.7, 134.2, 132.1, 130.2, 129.2, 119.6, 117.3, 55.6 (-CHPh 2 ).Anal.Calc.forC 45 h 29 Br 2 Cl 2 f 2 N 3 (880.45): C, 61.39; H, 3.32; N, 4.77. Found: C, 61.37; H, 3.33; N, 4.78.

[0055] Its reac...

Embodiment 3

[0064] (1) Synthesis of pyridinediimine ligand L3:

[0065]

[0066] Dissolve 2-iodo-4-fluoro-6-benzhydrylaniline (1.61g, 4.0mmol) and 2,6-pyridinedicarbonyl chloride (0.41g, 2.0mmol) in 20ml of methanol, add formic acid under stirring 0.2ml, after reflux reaction at 50°C for 18 hours, the solvent was removed to obtain a crude product, which was then washed with C 2 h 5 OH / CH 2 Cl 2 (v / v=15:2) The mixed solvent recrystallized to precipitate a solid precipitate, which was filtered and dried to obtain 1.62 g of the ligand with a yield of 83%.

[0067] 1 H NMR (400MHz, CDCl 3 ,ppm):δ8.22(d,J=8.2Hz,2H,Py-m-H),8.14(t,1H,Py-p-H),7.71(s,2H,Aryl-H),7.35(m,8H, Ph-H),7.26(m,4H,Ph-H),7.17(m,8H,Ph-H), 6.79(s,2H,Aryl-H),5.57(s,2H,-CHPh 2 ). 13 C NMR (100MHz, CDCl 3 , ppm): δ164.1, 153.7, 151.0, 146.2 (C=N), 144.5, 141.3, 137.4, 131.1, 129.2, 127.3, 124.2, 114.6, 112.7, 56.1 (-CHPh 2 ).Anal.Calc.for C 45 h 29 I 2 Cl 2 f 2 N 3 (974.45): C, 55.47; H, 3.00; N, 4.31. Found: C...

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Abstract

The invention discloses a pyridine diimine iron complex and a preparation method and application thereof. The preparation method comprises: methanol serving as a solvent, formic acid serving as a catalyst, mixing ortho-diphenyl methyl substituted aniline and 2, 6-pyridine dicarbonyl chloride, starting stirring, conducting a reflux reaction under the temperature condition, removing the solvent, obtaining a crude product, recrystallizing by using a C2H5OH / CH2Cl2 mixed solvent to separate out a solid precipitate, filtering and drying to obtain a pyridine diimine ligand; mixing a pyridine diimineligand with FeCl2. 4H2O by taking tetrahydrofuran as a solvent under the protection of nitrogen, starting stirring, reacting at room temperature, filtering the obtained precipitate, removing the solvent from mother liquor in vacuum, and washing residues with diethyl ether for multiple times, thereby obtaining the dark green solid catalyst. According to the pyridine diimine iron complex provided bythe invention, the ethylene insertion rate is greatly improved, so that the complex shows very good catalytic activity, and the complex has very high application value in the production process of polyolefin synthetic lubricating oil.

Description

technical field [0001] The invention belongs to the technical field of lubricating oil synthesis, and relates to polyolefin synthesizing lubricating oil technology, in particular to a pyridine diimine iron complex and its preparation method and application. Background technique [0002] With the increasingly stringent specifications of lubricating oil, the demand for high-quality lubricating oil is on the rise, and the demand for synthetic oil has increased significantly. Polyalphaolefin (PA0) in synthetic oil is one of the fastest growing varieties in the market demand. The production of PAO in foreign countries is mainly produced by ethylene oligomerization method, while in China it is mainly produced by paraffin cracking method, and its product quality has a large gap compared with foreign countries. [0003] PA0 synthetic oil is a type of long-chain alkanes obtained by polymerizing α-olefins (mainly trimers, tetramers and pentamers) under the action of a catalyst. Comp...

Claims

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Application Information

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IPC IPC(8): C07F15/02C07D213/78B01J31/22C10M107/04C07C2/22C07C11/02C08F110/02C08F4/70
CPCC07F15/025C07D213/78B01J31/1815C10M107/04C07C2/22C08F110/02B01J2531/842B01J2231/20C10M2205/0225Y02P20/52
Inventor 许春栋高琦张杨李为民
Owner JIANGSU ZHONGSHENG GAOKE ENVIRONMENTAL CO LTD
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