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Pyridine imine oxime iron catalyst, preparation method thereof and application of pyridine imine oxime iron catalyst in conjugated diene polymerization

A technology of pyridine imidoxime and iron catalyst, which is applied in the direction of iron organic compounds and chemical recovery, can solve the problems of high production cost and low molecular weight, and achieve the effects of low price, simple preparation and high catalytic activity

Active Publication Date: 2022-08-09
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

Liquid farnesene rubber prepared by anionic polymerization usually has a lower molecular weight and is more expensive to produce

Method used

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  • Pyridine imine oxime iron catalyst, preparation method thereof and application of pyridine imine oxime iron catalyst in conjugated diene polymerization
  • Pyridine imine oxime iron catalyst, preparation method thereof and application of pyridine imine oxime iron catalyst in conjugated diene polymerization
  • Pyridine imine oxime iron catalyst, preparation method thereof and application of pyridine imine oxime iron catalyst in conjugated diene polymerization

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Experimental program
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Effect test

Embodiment 1

[0026] Embodiment 1: the preparation method of a kind of pyridine imidoxime iron catalyst of the present embodiment is carried out according to the following steps:

[0027] Under an argon atmosphere, first add anhydrous FeCl to a 25 mL Schlenk tube 2 (1.27 mg, 10 μmol, 1 equiv.), then the pyridine imine ligand L1 (2.72 mg, 20 μmol, 2 equiv.) was added to the system, and then 20 mL of dichloromethane solvent was added, and the reaction was stirred at 25 ° C for 24 h, the reaction was completed After that, the filtrate was collected by filtration, concentrated to solid, washed with anhydrous n-hexane for 3 times, and dried in vacuum for 12 h to obtain iron pyridine imidoxime catalyst A (referred to as main catalyst A).

[0028] Mass spectrometry: C 14 H 16 Cl 2 FeN 4 O 2 : [M-Cl - ] + : theoretical value 363.0311, actual value: 363.0421.

[0029] Elemental analysis: Theoretical value: C, 42.14%; H, 4.04%; N, 14.04%; Actual value: C, 41.84%, H, 3.94%, N, 13.80%.

Embodiment 2

[0030] Embodiment 2: the preparation method of a kind of pyridine imidoxime iron catalyst of the present embodiment is carried out according to the following steps:

[0031] Under an argon atmosphere, first add anhydrous FeCl to a 25 mL Schlenk tube 2 (1.27mg, 10μmol, 1equiv.), then pyridineimine ligand L2 (3.0mg, 20μmol, 2equiv.) was added to the system, then 20mL of dichloromethane solvent was added, and the reaction was stirred at 25 ° C for 24h, the reaction was completed Afterwards, the filtrate was collected by filtration, concentrated to solid, washed with anhydrous n-hexane for 3 times, and dried in vacuum for 12 h to obtain iron pyridine imidoxime catalyst B (referred to as main catalyst B).

[0032] Mass spectrometry: C 14 H 20 Cl 2 FeN 4 O 2 : [M-Cl - ] + : theoretical value 391.0624, actual value: 391.0121.

[0033] Elemental Analysis: Theoretical: C, 44.99%; H, 4.72%; N, 13.12%; Actual: C, 45.34%; H, 4.51%; N, 13.40%.

Embodiment 3

[0034] Embodiment 3: the preparation method of a kind of pyridine imidoxime iron catalyst of the present embodiment is carried out according to the following steps:

[0035] Under an argon atmosphere, first add anhydrous FeCl to a 25 mL Schlenk tube 2 (1.27 mg, 10 μmol, 1 equiv.), then the pyridine imine ligand L3 (3.96 mg, 20 μmol, 2 equiv.) was added to the system, and then 20 mL of dichloromethane solvent was added, and the reaction was stirred at 25 ° C for 24 h, the reaction was completed After that, the filtrate was collected by filtration, concentrated to solid, washed with anhydrous n-hexane for 3 times, and dried in vacuum for 12 h to obtain iron pyridine imidoxime catalyst C (referred to as main catalyst C).

[0036] Mass spectrometry: C24 H 20 Cl 2 FeN 4 O 2 : [M-Cl - ] + : theoretical value 487.0624, actual value: 487.0421.

[0037] Elemental analysis: Theoretical value: C, 55.10%; H, 3.85%; N, 10.71%; Actual value: C, 54.91%; H, 3.56%; N, 11.13%.

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Abstract

The invention relates to a pyridine imine oxime iron catalyst, a preparation method thereof and application of the pyridine imine oxime iron catalyst in conjugated diene polymerization. The invention belongs to the field of conjugated diene polymerization. The invention develops a green and efficient catalyst which can be used for preparing farnesene rubber with higher molecular weight and high 1, 4 selectivity, shows high catalytic activity on conjugated dienes such as butadiene, isoprene and myrcene, and has better reaction universality. The application method of the pyridine imine oxime iron catalyst in conjugated diene polymerization comprises the following steps: adding a solvent, a main catalyst, a cocatalyst and a conjugated diene monomer into a reactor according to any sequence under the protection of inert gas, and polymerizing for 10-240 minutes at 0-100 DEG C under the condition of stirring, so as to obtain the pyridine imine oxime iron catalyst. And adding a quenching agent and an anti-aging agent into the reaction system for quenching reaction, repeatedly washing with ethanol, and carrying out vacuum drying to obtain the poly-conjugated diene, the main catalyst being a pyridine imine oxime iron catalyst.

Description

technical field [0001] The invention belongs to the field of conjugated diene polymerization, and in particular relates to an iron pyridine imidoxime catalyst, a preparation method thereof, and an application in conjugated diene polymerization. Background technique [0002] Daily life is full of various synthetic rubber and natural rubber products, which are convenient for people's lives. With the fossil energy crisis and environmental concerns, it is particularly important to develop sustainable bio-based polymers to replace petroleum derivatives. β-Farnesene is a class of bio-based terpene monomers with long side chains. Due to the special bottlebrush / comb-like structure of its polymers, it has great application potential in rubber, adhesives, lubricating materials, etc. In the literature, Raynaud J found that the iron catalyst supported by iminopyridine can obtain polyfarnesene with a high content of 1,4, the weight average molecular weight is 110,000 g / mol, and the reac...

Claims

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Application Information

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IPC IPC(8): C08F4/70C08F136/22C07F15/02
CPCC08F4/7006C08F136/22C07F15/025Y02P20/584
Inventor 王庆刚王亮刘天罡匡佳憨振宇
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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