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Bipyridyl iron complex and its preparation method and application in conjugated diene polymerization

A technology of iron bipyridine and conjugated diene is applied in the direction of iron organic compounds, iron group organic compounds without C-metal bonds, etc., can solve the problems of lack of efficient preparation and the like, and achieves simple and easy preparation, low cost and high activity. high effect

Active Publication Date: 2022-03-01
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

[0003] In view of the current lack of efficient methods for preparing highly branched and ultra-high molecular weight polyconjugated dienes, the present invention provides a bipyridyl iron complex and its preparation method and its use in the preparation of iron-based highly branched and ultra-high molecular weight polyconjugated dienes application in

Method used

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  • Bipyridyl iron complex and its preparation method and application in conjugated diene polymerization
  • Bipyridyl iron complex and its preparation method and application in conjugated diene polymerization
  • Bipyridyl iron complex and its preparation method and application in conjugated diene polymerization

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1. Preparation of bipyridyl iron complex catalyst 1 (structural formula is as follows).

[0043]

[0044] Add anhydrous Fe(acac) to a 50 mL Schlenk bottle under argon atmosphere 2 (127.0mg, 0.5mmol), dissolved in 6mL of absolute ethanol at 60°C; then a solution of 2,2'-bipyridine (78.0mg, 0.5mmol) in ethanol (4mL) was added dropwise to the system. React at 60°C for half an hour, then return to room temperature and stir overnight. The filtrate was collected by filtration, concentrated, washed twice with cold ethanol, and vacuum-dried for 12 h to obtain product 1 as a brown-yellow solid with a yield of 68%.

[0045] Mass Spectrometry: C 20 h 22 FeN 2 o 4 :[M+H]+: theoretical value: 411.1002; measured value: 410.0998.

[0046] Elemental Analysis: C 20 h 22 FeN 2 o 4 : Theoretical value: C, 58.55%; H, 5.41%; N, 6.83%; Measured value: C, 58.34%; H, 5.53%; N, 7.09%.

Embodiment 2

[0047] Example 2. Preparation of pyridine imine iron complex catalyst 2 (structural formula is as follows).

[0048]

[0049] Add anhydrous Fe(acac) to a 50 mL Schlenk bottle under argon atmosphere 3 (211.8mg, 0.6mmol), dissolved in 6mL of absolute ethanol at 60°C; then a solution of 2,2'-bipyridine (93.6mg, 0.6mmol) in ethanol (4mL) was added dropwise to the system. React at 60°C for half an hour, then return to room temperature and stir overnight. The filtrate was collected by filtration, concentrated, washed twice with cold ethanol, and dried in vacuum for 12 h to obtain product 2 as a reddish-brown solid with a yield of 78%.

[0050] Mass Spectrometry: C 25 h 29 FeN 2 o 6 :[M+H]+: theoretical value: 510.1448; measured value: 510.1443.

[0051] Elemental Analysis: C 25 h 29 FeN 2 o 6 : Theoretical value: C, 58.95%; H, 5.74%; N, 5.50%; Measured value: C, 58.54%; H, 5.61%; N, 5.85%.

Embodiment 3

[0052] Example 3. Preparation of pyridine imine iron complex catalyst 3 (structural formula is as follows).

[0053]

[0054] Add anhydrous Fe(acac) to a 50 mL Schlenk bottle under argon atmosphere 2 (127mg, 0.5mmol), dissolved in 6mL of absolute ethanol at 60°C; then, a solution of 5,5'-dimethyl-2,2'-bipyridine (92.0mg, 0.5mmol) in ethanol (4mL) was dropped added to the system. React at 60°C for half an hour, then return to room temperature and stir overnight. The filtrate was collected by filtration, concentrated, washed twice with cold ethanol, and dried in vacuum for 12 h to obtain tan solid product 3 with a yield of 55%.

[0055] Mass Spectrometry: C 22 h 26 FeN 2 o 4 :[M+H]+: theoretical value: 439.1315; measured value: 439.1319.

[0056] Elemental Analysis: C 22 h 26 FeN 2 o 4 : Theoretical value: C, 60.29%; H, 5.98%; N, 6.39%; Measured value: C, 59.90%; H, 6.21%; N, 6.65%.

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Abstract

The invention discloses a bipyridine iron complex, a preparation method thereof and an application in conjugated diene polymerization, belonging to the field of conjugated diene catalytic polymerization. Aiming at the technical problems of the high cost of catalysts used in the synthesis process of highly branched polyconjugated dienes and the poor ability to adjust the polymer molecular weight and microstructure, the invention provides a bipyridyl iron complex, the bipyridyl iron complex As the main catalyst in the polymerization of polypentadiene, it shows high activity and obtains a polymer with a high degree of branching. The polymer has the characteristics of high molecular weight, narrow molecular weight distribution, and the molecular weight of the polymer can be adjusted by chain transfer reagents. , The polyconjugated diene rubber has high branched chain content and ultra-high molecular weight. Because there are a large number of side groups on the molecular chain links of its rubber, it is mainly used to prepare high-performance tires with good wet skid resistance and low friction and heat generation and other related rubber products. The invention has the prospect of being applied to the industrialized production of polyconjugated diene.

Description

technical field [0001] The invention relates to the field of polymer synthesis, in particular to a bipyridine iron complex, a preparation method thereof and an application in conjugated diene polymerization. Background technique [0002] For a long time, the contradiction between rolling resistance and wet skid resistance of tire compounds has hindered the development and promotion of "green tires". Trans-1,4-polyisoprene rubber (TPI), high vinyl polybutylene rubber The emergence of new materials such as vinylene rubber (HVBR) and 3,4-polyisoprene rubber (3,4-PIP) has opened up a new way for the research and application of "green tires". High vinyl polybutadiene rubber (HVBR) and 3,4-polyisoprene (3,4-PIP) have high wet skid resistance, low rolling resistance and good shock absorption properties and can be used in manufacturing High-performance tires; the water resistance and airtightness of this rubber are close to butyl rubber; it can also be used together with ethylene-p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/02C08F4/70C08F136/06C08F136/08C08F236/06C08F236/08
CPCC07F15/025C08F136/08C08F136/06C08F236/08C08F236/06C08F4/7006
Inventor 王庆刚王亮朱广乾张献辉荆楚杨
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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