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Synthetic method of amino-substituted cyclohexyl crown ether

The technology of a radical crown ether and a synthesis method, which is applied in the synthesis field of amino group-substituted cyclohexyl crown ether, can solve the problems of high catalyst cost, harsh reaction conditions, cumbersome steps, etc., and achieves low catalyst dosage, reaction temperature and pressure. The effect of mild conditions and simple process

Inactive Publication Date: 2012-07-11
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a synthesis method of amino-substituted cyclohexyl crown ether, which solves the problems of cumbersome synthesis process steps, harsh reaction conditions and high catalyst cost in the existing amino-substituted cyclohexyl crown ether

Method used

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  • Synthetic method of amino-substituted cyclohexyl crown ether
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  • Synthetic method of amino-substituted cyclohexyl crown ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1: Synthesis of diaminodicyclohexyl-18-crown-6

[0019] Using dinitrodibenzo-18-crown-6 as a substrate, under the action of Pichler ruthenium catalyst, the reaction equation for the one-step synthesis of diaminodicyclohexyl-18-crown-6 using high-pressure hydrogen is as follows:

[0020]

[0021] Dissolve 5.0 g of dinitrodibenzo-18-crown-6 in 450 mL of ethanol and add it to an autoclave with a volume of 3L. Weigh 1 g of the newly activated Pichler ruthenium catalyst, disperse it in 50 mL of ethanol, and add it to the kettle. The reactor was closed and locked, the air in the kettle was replaced by nitrogen gas three times, and the nitrogen gas was replaced by hydrogen gas three times, and then hydrogen gas with a pressure of 6 MPa was introduced. Keep stirring, control the temperature in the kettle to 100°C, stop the reaction after 8 hours of reaction, and release the pressure after the entire system is cooled. Filtration, separation and recovery of Pichler ruthenium...

Embodiment 2

[0022] Example 2: Synthesis of amino-substituted cyclohexyl-12-crown-4

[0023] Under the action of Pichler ruthenium catalyst, mononitro substituted benzo-12-crown-4 uses high-pressure hydrogen to react in one step to generate amino-substituted cyclohexyl-12-crown-4. The reaction equation is as follows:

[0024]

[0025] Weigh 10.0 g of nitro-substituted benzo-12-crown-4 and dissolve in 700 mL of n-butanol in a 3L autoclave. Weigh 0.8 g of newly activated Pichler ruthenium catalyst, disperse it in 100 mL of n-butanol, and add it to the kettle. The reactor was closed and locked, the air in the kettle was replaced by nitrogen gas three times, and the nitrogen gas was replaced by hydrogen gas three times, and then hydrogen gas with a pressure of 7 MPa was introduced. Keep stirring, control the temperature in the kettle to 85°C, stop the reaction after 10 hours of reaction, and release the pressure after the entire system is cooled. Filtration, separation and recovery of Pichler rut...

Embodiment 3

[0026] Example 3: Synthesis of diaminodicyclohexyl-15-crown-5

[0027] Under the action of Pichler ruthenium catalyst, use high pressure hydrogen to reduce dinitrodibenzo-15-crown-5 in one step to produce diaminodicyclohexyl-15-crown-5. The reaction equation is as follows:

[0028]

[0029] Dissolve 5.0 g of dinitrodibenzo-15-crown-5 in 300 mL of ethylene glycol dimethyl ether and add it to an autoclave with a volume of 1 L. Weigh 0.3 g of newly activated Pichler ruthenium catalyst, disperse it in 50 mL of ethylene glycol dimethyl ether, and add it to the kettle. The reactor was closed and locked, the air in the kettle was replaced by nitrogen gas three times, and the nitrogen gas was replaced by hydrogen gas three times, and then hydrogen gas with a pressure of 9 MPa was introduced. Keep stirring, control the temperature in the kettle to 110°C, stop the reaction after 5 hours, and release the pressure after the entire system cools down. After filtering, separating and recovering...

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Abstract

The invention discloses a synthetic method of amino-substituted cyclohexyl crown ether, which belongs to the technical field of synthetic technique of organic compound. The synthetic method uses nitro-substituted benzo crown ether as a substrate, uses high-activity Pichler ruthenium as a catalytic agent, uses high pressure hydrogen to achieve reduction of nitro and hydrogenation of phenyl group in substrate molecules simultaneously in one-step reaction, and accordingly obtains needed amino-substituted cyclohexyl crown ether products. The synthetic method enables the existing two-step reaction to be merged in a same system, and operation is greatly simplified. The temperature and the pressure of the needed reaction are relative mild, occurrence of side reaction is well avoided, and purity of obtained products is guaranteed. The ruthenium catalytic agent is high in catalytic activity, while cost is relatively lower than that of rhodium, platinum and the like, and the synthetic method has the cost advantage. Simultaneously, after reaction ends, the catalytic agent can be well separated and recycled.

Description

Technical field [0001] The invention belongs to the technical field of organic compound synthesis, and specifically relates to a method for synthesizing an amino group substituted cyclohexyl crown ether. Background technique [0002] In recent years, crown ether compounds have attracted the attention of coordination chemistry, extraction chemistry, water treatment and other research fields due to their selective extraction ability of metal ions in solution. In the crown ether family, alicyclic crown ethers tend to have relatively better extraction and complex ability for metal ions, and have better solubility and stability in organic solvents, so their uses are more extensive. For example, dicyclohexyl-18-crown-6 paired Pb in solution 2+ The extremely high complex coefficient makes it very promising in the field of lead-containing wastewater treatment (Wu Chengtai et al., "Crown Ether Chemistry", Science Press, 1992). At the same time, in the extraction and separation of high-re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D323/00
CPCY02P20/584
Inventor 叶钢韦继超白飞飞王建晨陈靖
Owner TSINGHUA UNIV
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