Pyridine imine ferrous acetylacetonate complex, preparation method thereof and method for catalyzing conjugated diene polymerization by using pyridine imine ferrous acetylacetonate complex

A technology of pyridinium acetyl and ferrous acetonate, which is applied in the direction of iron organic compounds, can solve the problems of poor solubility and low molecular weight of polymers, and achieve the effects of improved solubility, high activity, and clear molecular structure

Active Publication Date: 2020-06-05
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0004] The present invention provides a pyridine catalyst to solve the technical problems of poor solubility in the reaction system of the existing iron-based catalyst and the low molecular weight of the polymer catalyzed by it. Ferrous imine acetylacetonate complex and its preparation method and method of using it to catalyze the polymerization of conjugated diene

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  • Pyridine imine ferrous acetylacetonate complex, preparation method thereof and method for catalyzing conjugated diene polymerization by using pyridine imine ferrous acetylacetonate complex
  • Pyridine imine ferrous acetylacetonate complex, preparation method thereof and method for catalyzing conjugated diene polymerization by using pyridine imine ferrous acetylacetonate complex
  • Pyridine imine ferrous acetylacetonate complex, preparation method thereof and method for catalyzing conjugated diene polymerization by using pyridine imine ferrous acetylacetonate complex

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Experimental program
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specific Embodiment approach 1

[0050] Specific embodiment one: the structural formula of a kind of ferrous pyridinium acetylacetonate complex of the present embodiment is:

[0051]

[0052] Its preparation method is as follows: under argon atmosphere, first add anhydrous Fe(acac) to a 25mL Schlenk tube 2 (566.3mg, 2.23mmol), then the pyridine imine ligand L 1 (224.3mg, 2.23mmol) was added to the system, then 20mL of dichloromethane solvent was added, and the reaction was stirred at 25°C for 2 days. After the reaction was completed, the filtrate was collected by filtration, concentrated, washed twice with n-hexane, and dried in vacuum for 12h to obtain Brown solid product, namely ferrous pyridinium acetylacetonate complex (referred to as catalyst 1), 682 mg, yield 63.7%.

[0053] Mass Spectrometry: C 25 h 30 FeN 2 o 4 :[M+H] + : Theoretical value: 479.1628; measured value: 479.1577.

[0054] Elemental analysis: [C 25 h 30 FeN 2 o 4 +0.5CH 2 Cl 2 ]: Theoretical value: C, 58.81; H, 6.00; N, 5.3...

specific Embodiment approach 2

[0055] Specific embodiment two: the structural formula of a kind of ferrous pyridinium acetylacetonate complex of the present embodiment is:

[0056]

[0057] Its preparation method is as follows: under argon atmosphere, first add anhydrous Fe(acac) to a 25mL Schlenk tube 2 (216.21mg, 0.85mmol), then the pyridine imine ligand L 2 (150mg, 0.85mmol) was added to the system, then 20mL of dichloromethane solvent was added, and the reaction was stirred at 25°C for 2 days. After the reaction was completed, the filtrate was collected by filtration, concentrated, washed twice with n-hexane, and dried in vacuum for 12h to obtain a green solid The product, ferrous pyridinium acetylacetonate complex (referred to as catalyst 2), was 160 mg, and the yield was 43.7%.

[0058] Mass Spectrometry: C 21 h 30 FeN 2 o 4 :[M+H] + : Theoretical value: 431.1628; measured value: 431.1573.

[0059] Elemental Analysis: C 21 h 30 FeN 2 o 4 : Theoretical value: C, 58.61%; H, 7.03%; N, 6.51%...

specific Embodiment approach 3

[0060] Specific embodiment three: the structural formula of a kind of ferrous pyridine imide acetylacetonate complex of the present embodiment is:

[0061]

[0062] Its preparation method is as follows: under argon atmosphere, first add anhydrous Fe(acac) to a 25mL Schlenk tube 2 (254.06mg, 1mmol)), then the pyridine imine ligand L 3 (240mg, 1mmol) was added to the system, then 20mL of dichloromethane solvent was added, and the reaction was stirred at 25°C for 2 days. After the reaction was completed, the filtrate was collected by filtration, concentrated, washed twice with n-hexane, and dried in vacuum for 12h to obtain a brown solid product , that is, ferrous pyridinium acetylacetonate complex (referred to as catalyst 3), 345.8 mg, yield 70%.

[0063] Mass Spectrometry: C 26 h 34 FeN 2 o 4 :[M+H] + : Theoretical value: 495.1941; measured value: 495.1899.

[0064] Elemental analysis: [C 26 h 34 FeN 2 o 4 +0.5C 6 h 14 ]: Theoretical value: C, 64.80%; H, 7.69%; ...

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Abstract

The invention relates to a pyridine imine ferrous acetylacetonate complex, a preparation method thereof and a method for catalyzing conjugated diene polymerization by using the pyridine imine ferrousacetylacetonate complex. The invention belongs to the field of conjugated diene catalytic polymerization. The invention aims to solve the technical problems of poor solubility of the existing iron-based catalyst in the reaction system and low molecular weight of the polymer catalyzed and polymerized by the iron-based catalyst. The pyridine imine ferrous acetylacetonate complex disclosed by the invention is prepared by reacting a dichloromethane solution of pyridine imine with ferrous acetylacetonate; the pyridine imine ferrous acetylacetonate complex serves as a main catalyst in conjugated diene polymerization, the catalyst is good in solubility in a reaction system and high in activity, the obtained polymer is high in molecular weight and narrow in molecular weight distribution, and the method can be used for industrial production of poly conjugated diene.

Description

technical field [0001] The invention belongs to the field of catalytic polymerization of conjugated diene, and in particular relates to a ferrous pyridine imine acetylacetonate complex, a preparation method thereof and a method for catalyzing the polymerization of conjugated diene. Background technique [0002] Trans (trans)-1,4-polyisoprene (TPI for short) is a synthetic rubber mainly composed of trans-1,4 structure, with a relative molecular weight of about 50,000. It has the similar structure and properties of natural Eucommia gum and gutta-percha. Trans-1,4-polyisoprene is a raw material for manufacturing high-performance "green tires" such as radial tires, air springs and other dynamic products due to its low dynamic heat generation, low rolling resistance, excellent wear resistance and dynamic fatigue performance one. And its trans order makes it easy to crystallize at room temperature, has a certain hardness and tensile strength, and it melts at 60 degrees Celsius, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/02C08F136/06C08F136/08C08F236/06C08F236/08C08F4/70
CPCC07F15/02C08F136/08C08F136/06C08F236/08C08F236/06C08F4/7006
Inventor 王庆刚王亮憨振宇朱广乾杨伟颖
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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