Aryl substituted pyridylamine iron-based catalyst and preparation method and application thereof

A technology of pyridinium amine iron series and pyridinium amine iron, applied in the polymerization of isoprene, preparation of catalysts, field of pyridinium amine iron series catalysts, can solve the problem of unclear active center of catalyst structure, low molecular weight of synthetic polymer, Poor selectivity and other issues, to achieve the effect of low cost, good industrial value, and high tolerance

Active Publication Date: 2019-01-04
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the nitrogen-containing ligands for the polymerization of isoprene catalyzed by iron catalysts are mainly sp 2 –N,sp 2 -N pyridine imines, but the system has catalyst structures or unclear active centers, low activity, poor selectivity, and low molecular weight of synthetic polymers

Method used

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  • Aryl substituted pyridylamine iron-based catalyst and preparation method and application thereof
  • Aryl substituted pyridylamine iron-based catalyst and preparation method and application thereof
  • Aryl substituted pyridylamine iron-based catalyst and preparation method and application thereof

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Effect test

Embodiment 1

[0030] The present embodiment prepares the pyridine imine iron complex shown in formula (A):

[0031] The 25mL Schlenk reaction tube was pumped and baked three times, and 15mL redistilled dichloromethane, equimolar ratio of anhydrous FeCl 2 and isopropyl substituted pyridine imine ligand (1.5 mmol) (structural formula LA), stirred at room temperature for 24 h. After the reaction, the dichloromethane was vacuum-dried, washed twice with 10 mL redistilled n-hexane (the filtrate was colorless and clear), and vacuum-dried to constant weight to obtain an off-white solid, structural formula:

[0032]

[0033] Mass Spectrometry: C 12 h 12 Cl 2 FeN 2 :[M-Cl] + : Theoretical value: 275.0033; measured value: 275.0042.

[0034] Elemental Analysis: C 12 h 12 Cl 2 FeN 2 : Theoretical value: C, 46.35; H, 3.89; N, 9.01; Measured value: C, 46.41%; H, 3.85%; N, 8.98%.

Embodiment 2

[0036] The preparation process of the pyridinium iron complex shown in formula (B) prepared in this embodiment is as follows:

[0037] The 25mL Schlenk reaction tube was pumped and baked three times, and 15mL redistilled dichloromethane, equimolar ratio of anhydrous FeCl 2 and tert-butyl-substituted pyridinimine ligand (1.5 mmol) (structural formula LB), and stirred at room temperature for 24 h. After the reaction, the dichloromethane was vacuum-dried, washed twice with 10 mL redistilled n-hexane (the filtrate was colorless and clear), and vacuum-dried to constant weight to obtain a light blue solid with the structural formula:

[0038]

[0039] Mass Spectrometry: C 18 h 24 Cl 2 FeN 2 [M-Cl] + : Theoretical value: 359.0972; measured value: 359.0968.

[0040] Elemental Analysis: C 18 h 24 Cl 2 FeN 2 : Theoretical value: C, 54.71; H, 6.12; N, 7.09; Measured value: C, 54.68%; H, 6.09%; N, 7.13%.

Embodiment 3

[0042] The pyridine imine iron complex shown in the formula (C) prepared in this embodiment, the preparation process is as follows:

[0043] The 10mL Schlenk reaction tube was pumped and baked three times, and 15mL redistilled dichloromethane, anhydrous FeCl 2 and cyclohexyl-substituted pyridine imine ligand (1.5 mmol) (structural formula LC), and stirred at room temperature for 48 h. After the reaction, the dichloromethane was vacuum-dried, washed twice with 10 mL redistilled n-hexane (the filtrate was colorless and clear), and vacuum-dried to constant weight to obtain a light red solid, structural formula:

[0044]

[0045] Mass Spectrometry: C 38 h 32 Cl 2 FeN 2 [M-Cl]+ : Theoretical value: 607.1598; measured value: 607.1601.

[0046] Elemental Analysis: C 38 h 32 Cl 2 FeN 2 : Theoretical value: C, 70.93; H, 5.01; N, 4.35; Measured value: C, 71.01%; H, 4.98%; N, 4.30%.

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Abstract

The invention discloses an aryl substituted pyridylamine iron-based catalyst and a preparation method and application thereof, and relates to the technical field of catalytic polymerization of conjugated diene. The iron-based catalyst comprises a main catalyst body and an auxiliary catalyst body, wherein the main catalyst body is an aryl substituted pyridylamine iron complex, the auxiliary catalyst body is methylaluminoxane or aluminum alkyl, and the molar ratio of the auxiliary catalyst body to the main catalyst body ranges from 100:1 to 2000:1. An iron-based catalyst system has high activityin isoprene polymerization, and an obtained polymer is high in molecular weight and narrow in molecular weight distribution. Meanwhile, the microstructure of the polymer can be controlled by adjusting the structure of the main catalyst body, and the reaction activity depends on main catalyst bodies with different substituent groups and different types of auxiliary catalyst bodies.

Description

technical field [0001] The invention relates to the field of catalytic polymerization of conjugated dienes, in particular to a pyridine amine iron-based catalyst, and also relates to a preparation method of the catalyst and its application in isoprene polymerization. Background technique [0002] In recent years, environmentally friendly late-transition metal-catalyzed olefin polymerization has attracted increasing attention from scientists. Iron-based catalysts have also received extensive attention in the polymerization of isoprene due to their environmental friendliness, economy, biocompatibility, and good tolerance to polar monomers. At present, the nitrogen-containing ligands for iron catalysts to catalyze the polymerization of isoprene are mainly sp 2 –N,sp 2 -N pyridine imines, but the system has catalyst structures or unclear active centers, low activity, poor selectivity, and low molecular weight of synthetic polymers. Contents of the invention [0003] In orde...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F136/08C08F4/70
CPCC08F136/08C08F4/7006
Inventor 王庆刚荆楚杨王亮王晓武赵梦梦咸漠
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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