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Manganese catalyst of 8-hydroxy quinoline derivative and its uses in olefin epoxidation

A technology of hydroxyquinoline and manganese catalysts, which is applied in the fields of physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., and can solve problems such as difficult synthesis, difficult recovery, and low practical value , to achieve high utilization rate, high epoxidation efficiency and mild reaction conditions

Inactive Publication Date: 2009-09-30
HUNAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because the ligands of this catalyst are difficult to synthesize, the recovery is difficult, and relatively toxic dichloromethane or acetonitrile are used as solvents, so the practical value is not high.

Method used

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  • Manganese catalyst of 8-hydroxy quinoline derivative and its uses in olefin epoxidation
  • Manganese catalyst of 8-hydroxy quinoline derivative and its uses in olefin epoxidation
  • Manganese catalyst of 8-hydroxy quinoline derivative and its uses in olefin epoxidation

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Experimental program
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Effect test

Embodiment 1

[0027] Embodiment 1: the synthesis of general formula (II) catalyst:

[0028] Dissolve 10mmol of the ligand of general formula (I) in 30-100ml of ethanol or methylene chloride, and add 20ml of Mn(OAc) containing 5mmol Mn(OAc) dropwise under stirring. 2 ethanol solution. Continue stirring at room temperature for 10 to 20 minutes. Filter with suction, wash with ethanol, and dry to obtain a solid that is the catalyst of general formula (II). The product yield is about 90%.

Embodiment 2

[0029] Embodiment 2: the synthesis of general formula (III) catalyst:

[0030] Dissolve 10mmol of the ligand of general formula (I) in 30-50ml

[0031] In tetrahydrofuran, add 20ml of 5mmol MnCl dropwise under stirring 2 ethanol solution. Then drop in 2-3mmol hydrogen peroxide, then drop in ammonia water to adjust the pH value of the solution to between 6-7 or drop in 4ml containing 10mmolNH 4 Aqueous solution of OAc. Continue to stir or reflux at room temperature for 1 to 2 hours. Filtrate with suction, wash with ethanol, and dry to obtain a catalyst (X=Cl) of general formula (III). The product yield is about 90%.

Embodiment 3

[0032] Embodiment 3: the synthesis of general formula (III) catalyst:

[0033] Dissolve 10mmol of a ligand of general formula (I) in 30-50ml of tetrahydrofuran, and add 20ml of Mn(OAc) containing 5mmol Mn(OAc) dropwise under stirring. 2 ethanol solution. Then add 2-3mmol hydrogen peroxide dropwise; continue to stir or reflux at room temperature for 1 to 2 hours; filter with suction, wash with ethanol, and dry to obtain a solid that is the desired catalyst (X=OAc); the product yield is about 90% .

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Abstract

The invention discloses a manganese catalyst of 8-hydroxyquinoline derivatives and its application in olefin epoxidation. The catalyst uses the 8-hydroxyquinoline derivative of the general formula (I) as a ligand and manganese ions to form a complex of the general formula (II) or (III). The application of the above-mentioned catalyst in catalyzing the epoxidation of olefin to prepare its epoxide is that in the presence of the catalyst, the olefin and the oxidant hydrogen peroxide react in a solvent, and the amount of the catalyst is 0.5-5% of the molar weight of the olefin. The catalyst of the present invention is simple to prepare, cheap, reusable, and has high chemoselectivity. When applied to the reaction of olefins and oxidant hydrogen peroxide in a solvent, the hydrogen peroxide utilization rate is high, the epoxidation efficiency is high, and the stability is good. The solvent is non-toxic or low-toxic, and the reaction conditions are mild.

Description

technical field [0001] The invention relates to a manganese catalyst of 8-hydroxyquinoline derivatives and its application in olefin epoxidation. Background technique [0002] Manganese is widely used as a catalyst in organic synthesis because of its cheapness, low toxicity, high activity and high selectivity, and has been used in the epoxidation of alkenes with hydrogen peroxide as an oxidant, but manganese ions have a strong decomposition of hydrogen peroxide capacity, resulting in very low utilization of hydrogen peroxide in the reaction process. People try to use various ligands to coordinate with manganese to improve the utilization rate of hydrogen peroxide, but the results are not very satisfactory. For example, the more Salen type manganese complexes reported at home and abroad are very effective catalysts for olefin epoxidation (a.E.N.Jacobsen, W.Zhang, A.R.Muci, J.R.Ecker, and L.Deng, J.Am.Chem.Soc., 1991,113,7063.b.Y.N.Ito and T.Katsuki, Bull.Chem.Soc.Jpn., 1999...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F13/00B01J31/22B01J31/32C07D301/12
Inventor 伏再辉衷晟熊东路谢芳尹笃林
Owner HUNAN NORMAL UNIVERSITY
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