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A kind of synthetic method of dicyclohexyl crown ether

A synthetic method, dicyclohexyl technology, which is applied in the field of improved synthetic technology of dicyclohexyl crown ether compounds, can solve the problems of rare synthetic methods, and achieve the effects of low price, simple treatment, and cheap and easy-to-obtain raw materials

Active Publication Date: 2017-01-18
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis method of dicyclohexyl-18-crown-6 ether compound with substituent is rare

Method used

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  • A kind of synthetic method of dicyclohexyl crown ether
  • A kind of synthetic method of dicyclohexyl crown ether
  • A kind of synthetic method of dicyclohexyl crown ether

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Ni-Ru / γ-Al 2 o 3 Catalyst preparation, weigh γ-Al 2 o 3 (180m 2 / g, 50g) is ground into powder, and the powder particles are larger than 20 mesh. Weigh nickel acetate tetrahydrate (3.1g, 12.5mmol) and ruthenium trichloride trihydrate (3.27g, 12.5mmol), add the above materials into a 250mL round bottom flask, add water (50mL) to soak and stir for 12 hours. in N 2 Under protection, 20 mL of aqueous solution containing sodium borohydride (2.5 g) was dropped into the mixture under stirring, and heated to reflux at 100° C. for 10 hours of reaction. After cooling down to room temperature, the solid was obtained by suction filtration, and the solid was washed twice with 200 mL of water. Then the black solid was heated to 450° C. in a muffle furnace for 5 hours and then cooled to room temperature for use. According to inductively coupled plasma atomic emission spectrometry analysis, the Ni content is 1.5% (mass percentage); the Ru content is 2.5% (mass percentage).

Embodiment 2

[0024]

[0025] in N 2 Add 2-hydroxy-4-(tert-butyl)-phenol 2a (50.8g, 0.31mol), NaOH (12.4g, 0.31mol) and 500mL n-BuOH into a 2L reaction flask under atmosphere, stir and heat to reflux. A solution containing dichloroethyl ether (21.9 g, 0.15 mol) and n-BuOH (50 mL) was added dropwise into the reaction solution within 30 minutes, and the drop was completed within 30 minutes, and then refluxed for 1 hour. The reaction solution was cooled to below 90°C, another portion of NaOH (12.4 g, 0.31 mol) was added, and the temperature was raised to reflux for 30 min. Dichloroethyl ether (21.9 g, 0.15 mol) and n-BuOH (50 mL) were mixed and added dropwise to the reaction liquid, stirred, and refluxed for 15 hours. After the reaction is complete, cool to room temperature and adjust the pH value to 5 with concentrated hydrochloric acid. Evaporate the solvent n-BuOH, add an appropriate amount of water as the volume of the mixture decreases, and continue heating until the temperature of t...

Embodiment 3

[0027]

[0028] 4,4'(5')-bis(tert-butyl)diphenyl-18-crown-6 ether 4a (10g, 20.5mmol), catalyst Ni-Ru / γ-Al 2 o 3 (10.0g, the molar ratio of Ni to Ru is 1:1), tetrahydrofuran (100mL) was added into a 250mL pressure reactor, and sealed. h 2 Filled with H after replacement 3 times 2 To 8Mpa pressure, the oil bath is heated to 180 ℃ and stirred. React for 2 hours, put the reaction kettle into cold water and drop to room temperature, the pressure drops to 5MPa, add H 2 Continue to react overnight to 8MPa. After reacting for 24 hours, the reaction kettle was put into cold water and dropped to room temperature (pressure dropped to 2Mpa), supplemented with H 2 Continue to react to 8MPa, at this time the reaction speed is obviously slowed down, and the pressure drop is not obvious. After a total reaction of 30 hours, the reaction kettle was put into cold water and the pressure was lowered to 6 MPa at room temperature to stop the reaction. The reaction mixture was filtered to r...

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Abstract

The invention discloses a method for synthesizing dicyclohexyl crown ether compounds. Using catechol compounds and dichloroethyl ether as starting materials, through the Pedersen synthesis method, cyclization produces dibenzo-18-crown-6 ether compounds, and then undergoes catalytic hydrogenation to form dicyclohexyl- 18‑Crown‑6 ether compounds. The main feature of the present invention is that the heterogeneous metal catalyst is used to efficiently convert the dibenzocrown ether into the dicyclohexyl crown ether. After the reaction is completed, the product only needs simple treatment such as filtration and concentration, and the purity can reach more than 90%. The heterogeneous metal catalyst used is convenient to prepare, low in price, and can be recycled.

Description

technical field [0001] The invention relates to a synthesis method of dicyclohexyl crown ether compounds, in particular to an improved synthesis process of dicyclohexyl crown ether compounds. Background technique [0002] As an important extractant, crown ether is widely used in the extraction and separation of metal ions. In recent years, crown ethers have also been paid attention to and widely used as extractants of radionuclides in the field of nuclear fuel reprocessing. However, the synthesis of crown ether compounds, especially dicyclohexyl crown ether compounds, has been relatively restricted, and the market price has been relatively high. The main reason is that when preparing dicyclohexyl crown ether from dibenzocrown ether, due to the activity of catalyst hydrogenation, the yield has not been effectively improved, and after the reaction, complex separation and purification work is required to obtain the product . Tong Libin and others studied the preparation meth...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D323/00
CPCY02P20/582Y02P20/584
Inventor 余正坤赫巍吴苹王连弟
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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