Bipyridine iron complex, preparation method thereof and application of complex in conjugated diene polymerization

A technology of bipyridyl iron and conjugated diene, which 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, etc., and achieve simple and easy preparation, good solubility, low cost effect

Active Publication Date: 2019-11-15
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 ...

Method used

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  • Bipyridine iron complex, preparation method thereof and application of complex in conjugated diene polymerization
  • Bipyridine iron complex, preparation method thereof and application of complex in conjugated diene polymerization
  • Bipyridine iron complex, preparation method thereof and application of complex 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 as well as a preparation method thereof and an application of the complex in conjugated diene polymerization, and belongs to the field of conjugated diene catalytic polymerization. The invention provides the bipyridine iron complex aiming at the technical problems that in the prior art, a catalyst used in a synthetic process of a polyconjugated diene with a high branched-chain degree has high costs, and the polymer molecular weight and microstructure adjusting capability is poor. The bipyridine iron complex is used as a main catalyst in polypentadiene polymerization and shows high activity, the obtained polymer with a high branched-chain degree has the characteristics that the polymer has a high molecular weight, the molecular weight distribution is narrower, the polymer molecular weight can be adjusted through a chain transfer reagent and the like, and the obtained polyconjugated diene rubber has the characteristics of a high branched-chain content and an ultra-high molecular weight; because a large number of side groups exist on molecular chain links of the rubber, the rubber is mainly used for preparing high-performance tires having good wet skid resistance and low friction heat generation and other related rubber products; and the complex has the prospect of being applied to industrial production of the 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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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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