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Synthesis method of dicyclohexyl-18-crown-6

A technology of dicyclohexyl and synthesis method, which is applied in the field of organic compound preparation, can solve problems such as low content and large product loss, and achieve the effect of reducing difficulty and making the preparation method simple and feasible

Inactive Publication Date: 2011-05-04
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the proportion of the cis isomer in the crude product after hydrogenation is about 1 / 3 to 2 / 3, and the content is relatively low. After further purification through steps such as column chromatography and recrystallization, dicyclohexyl The content of the cis-isomer in the -18-crown-6 product is 89%, and the pure product of the cis-isomer can be obtained by repeated recrystallization in n-heptane, but the product loss is relatively large
Since the content of the cis-isomer in the crude product obtained from hydrogenation is higher, the difficulty of subsequent separation and purification steps is less, but in the currently disclosed preparation method, the dicyclohexyl-18-crown-6 cis-isomer in the product is Construct content still needs to be further increased

Method used

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  • Synthesis method of dicyclohexyl-18-crown-6
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  • Synthesis method of dicyclohexyl-18-crown-6

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Experimental program
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Effect test

Embodiment 1

[0022] 1) Preparation of dicyclohexyl-18-crown-6

[0023] The reaction equation is as follows:

[0024]

[0025] 2.0 g (0.0055 mol) of dibenzo-18-crown-6 was added to the autoclave. Add 0.28g (0.0027mol) of nano-metal ruthenium catalyst to 10ml of n-butanol, ultrasonically 30min to make it fully dispersed, then add it to the autoclave, and repeatedly rinse the beaker containing the catalyst with 40ml of n-butanol to fully add the catalyst into the kettle. After nitrogen replacement for 3 times and hydrogen replacement for 1 time, 10MPa hydrogen gas was charged for reaction. Control the reaction temperature to 100° C., and stop the reaction after 2 hours of reaction. After being cooled to room temperature, the mixture of the reaction product and the catalyst was centrifuged, and the product was detected by gas chromatography to show that the yield of dicyclohexyl-18-crown-6 was 91.2%, the cis-isomer content was 86.4%, and the trans-isomer content was 86.4%. The conformat...

Embodiment 2

[0029] 1) Add 20g (0.055mol) of dibenzo-18-crown-6 into the autoclave. Add 0.07g (0.0007mol) nano-metal ruthenium catalyst to 10ml of n-octanol, ultrasonic 30min to make it fully dispersed, then add it to the autoclave, rinse the beaker containing the catalyst repeatedly with 300ml of n-octanol, so that all the catalyst is added into the kettle. After nitrogen replacement for 3 times and hydrogen replacement for 1 time, 2MPa hydrogen gas was charged for reaction. Control the reaction temperature to 200° C., and stop the reaction after 24 hours of reaction. After being cooled to room temperature, the mixture of the reaction product and the catalyst was centrifuged, and the gas chromatography detection of the product showed that the yield of dicyclohexyl-18-crown-6 was 92.7%, the cis-isomer content was 81.5%, and the trans-isomer content was 81.5%. The conformation content was 18.5%.

[0030] 2) the preparation of the used nano ruthenium metal catalyst of above-mentioned reac...

Embodiment 3

[0033] 1) Add 2g (0.0055mol) of dibenzo-18-crown-6 into the autoclave. Add 0.05g (0.0005mol) of nano-metal ruthenium catalyst to 10ml of toluene, ultrasonic 30min to make it fully dispersed, then add it to the autoclave, rinse the beaker containing the catalyst repeatedly with 40ml of toluene, so that all the catalyst is added to the kettle. After nitrogen replacement for 3 times and hydrogen replacement for 1 time, 7MPa hydrogen gas was charged for reaction. The reaction temperature was controlled at 135° C., and the reaction was stopped after 7 hours of reaction. After being cooled to room temperature, the mixture of the reaction product and the catalyst was centrifuged, and the gas chromatography detection of the product showed that the yield of dicyclohexyl-18-crown-6 was 90.5%, the cis-isomer content was 87.6%, and the trans-isomer content was 87.6%. The conformation content was 12.4%.

[0034] 2) the preparation of the used nano ruthenium metal catalyst of above-mentio...

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Abstract

The invention relates to a synthesis method of dicyclohexyl-18-crown-6 (DCH18C6), belonging to the technical field of preparation of an organic compound. The invention aims at increasing the content of cis-DCH18C6 isomer in the reaction product, thereby simplifying the purification process and improving the yield of cis-isomer. In the synthesis method, dibenzo-18-crown-6 is used as a raw material, and nano ruthenium metal powder is used as a catalyst to perform a catalytic hydrogenation reaction, wherein the reaction temperature is 100-200 DEG C, and the hydrogen pressure is 2-10 MPa. Although the method does not include any purification step, the content of the cis-isomer in the product can be up to 80% or above. The synthesis method has the characteristics of low cost and strong practicability and can be operated simply and conveniently.

Description

technical field [0001] The invention relates to a synthesis method of dicyclohexyl-18-crown-6, belonging to the technical field of organic compound preparation. Background technique [0002] Crown ether is a kind of macrocyclic polyether compound, because of its special complexing ability to alkali metal and alkaline earth metal cations, and with the change of heteroatom type, number of atoms and macrocyclic hole size in the macrocyclic ligand , showing obvious selectivity for the complexation of different metal ions, which has attracted extensive attention. Since Pedersen reported the discovery and preparation of crown ether ligands in 1967, crown ether compounds have been widely used in aspects including host-guest chemistry, ion-pair extraction, and phase-transfer catalytic reactions. Due to the selective nature of crown ethers to extract cations, they can be extracted from Na + Cs is separated from the solution with high content + and Sr 2+ , so crown ethers are wide...

Claims

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Application Information

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IPC IPC(8): C07D323/00B01J23/46
Inventor 高杰陈崧哲陈靖王建晨张平
Owner TSINGHUA UNIV
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