Thiazole imine-cobalt compound as well as synthesis method and application thereof

A technology of thiazole imines and cobalt compounds, which is applied in the field of catalysts for catalyzing the polymerization of isoprene and its synthesis, can solve problems such as unsatisfactory output, and achieve high activity effects

Pending Publication Date: 2022-05-13
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the output of natural rubber is affected by conditions such as climate, and its output is far from meeting the growing needs of society. Therefore, it is extremely important to develop synthetic rubber.

Method used

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  • Thiazole imine-cobalt compound as well as synthesis method and application thereof
  • Thiazole imine-cobalt compound as well as synthesis method and application thereof
  • Thiazole imine-cobalt compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] The synthetic method of present embodiment thiazole imine-cobalt compound Co1 is as follows:

[0056] (1) In a round bottom flask, add 2-acetylthiazole (2.54g, 20mmol), 2,6-diisopropylaniline (3.55g, 20mmol), 50mL methanol, then add a few drops of formic acid as a catalyst, and reflux 48h with continuous stirring; after the reaction, part of the solvent was removed, and then recrystallized at -30°C, filtered, and the obtained solid was washed with pre-cooled anhydrous methanol, and dried to obtain ligand L1. Yellow solid; Yield: 51%, 2.91g; 1 H NMR (600MHz, CDCl 3)δ7.95(d,J=3.2Hz,1H),7.49(d,J=3.2Hz,1H),7.18–7.13(m,2H),7.11(dd,J=8.5,6.7Hz,1H), 2.74(hept, J=6.8Hz, 2H), 2.23(s, 3H), 1.15(dd, J=6.9, 3.1Hz, 12H); 13 C{ 1 H}(151MHz, CDCl 3 )δ 170.25, 161.52, 144.98, 143.82, 136.03, 124.20, 123.19, 123.06, 28.45, 23.09, 22.82, 17.58.

[0057] (2) In a Shrek bottle, add L1 (285.6 mg, 1 mmol) and anhydrous cobalt chloride (129.8 mg, 1 mmol), then add 10 mL of tetrahydrofura...

Embodiment 2

[0060] Present embodiment thiazole imine-cobalt compound Co The synthetic method is as follows:

[0061] (1) The amount of 2-acetylthiazole in step (1) of Example 1 is replaced by (3.82g, 30mmol), and 2,6-diisopropylaniline is replaced by 2,6-methylaniline (3.64 g, 30mmol), other synthesis methods are the same as Example 1 step (1); the purification method is replaced by silica gel column chromatography, developing agent (petroleum ether / dichloromethane=100 / 1), and run column with triethylamine; Obtain Ligand L2. Yellow oily liquid; Yield: 4.21g, 61%; 1 H NMR (600MHz, CDCl 3 )δ7.94(d, J=3.2Hz, 1H), 7.49(d, J=3.2Hz, 1H), 7.06(d, J=7.5Hz, 2H), 6.95(t, J=7.5Hz, 1H) ,2.20(s,3H),2.05(s,6H); 13 C{ 1 H}(151MHz, CDCl 3 ) δ 170.05, 161.78, 147.26, 143.78, 127.91, 125.71, 123.65, 123.11, 17.91, 17.06.

[0062] (2) The synthesis of compound Co2 is the same as the step (2) of Example 1. Green solid; Yield: 234.3mg, 64%; Elemental analysis: C 13 h 14 Cl 2 CoN 2 S: C, 43.35; H, 3...

Embodiment 3

[0064] The synthetic method of present embodiment thiazole imine-cobalt compound Co is as follows:

[0065] (1) Replace the amount of 2-acetylthiazole in step (1) of Example 1 with (1.27g, 10mmol), and replace 2,6-diisopropylaniline with 2,4,6-trimethyl Aniline (1.35g, 10mmol), other synthetic methods are the same as Example 1 step (1); the purification method is replaced by silica gel column chromatography, developing agent (petroleum ether / methylene chloride=40 / 1), and moistened with triethylamine column; Ligand L3 was obtained. Orange-yellow solid; Yield: 1.56g, 64%; 1 H NMR (600MHz, CDCl 3 )δ7.95(d,J=3.2Hz,1H),7.54(d,J=3.2Hz,1H),7.11–7.04(m,1H),7.00–6.93(m,2H),2.42(s,3H ); 13 C{ 1 H}(151MHz, CDCl 3 )δ170.23, 161.94, 144.78, 143.73, 132.89, 128.57, 125.55, 123.00, 20.74, 17.84, 17.00.

[0066] (2) The synthesis of compound Co3 is the same as step (2) of Example 1. Dark green solid; Yield: 293.1g; 78%; Elemental analysis: C 14 h 16 Cl 2 CoN 2 S: C, 44.94; H, 4.31;...

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Abstract

The invention discloses a thiazole imine-cobalt compound as well as a synthesis method and application thereof, and the synthesis method comprises the following steps: condensing 2-acetylthiazole and an aniline derivative under different conditions to obtain a corresponding thiazole imine ligand. And reacting the ligand with anhydrous cobalt chloride in tetrahydrofuran at normal temperature to obtain the thiazole imine-cobalt compound. The synthesized cobalt catalyst has different electronic effects and steric effects, and can be used for catalyzing isoprene polymerization.

Description

technical field [0001] The invention belongs to the technical field of polyolefin catalysts, and in particular relates to a catalyst for catalyzing the polymerization of isoprene, a synthesis method and application thereof. Background technique [0002] Rubber is an important polyolefin material, which has an extremely wide range of applications in modern society, such as tire manufacturing, medical equipment, aviation industry, etc. However, the output of natural rubber is affected by climate and other conditions, and its output is far from meeting the growing demand of the society. Therefore, it is extremely important to develop synthetic rubber. Polyisoprene is favored by researchers because it has the same monomer structure as natural rubber. [0003] The key to the synthesis of polyisoprene lies in the development and utilization of catalysts. At present, polyisoprene catalysts mainly include lithium series, early transition metal (Sc, Ti, V, Cr, etc.), late transitio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/06C08F36/08C08F4/70
CPCC07F15/065C08F36/08C07B2200/13C08F4/7006
Inventor 姜辉付联荣王慧珠王艳冰石林林郝新奇宋毛平
Owner ZHENGZHOU UNIV
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