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Improved systhesizing process for dicyclohexyl-18-crown-6

A technology of dicyclohexyl and synthesis process, applied in the field of preparation of crown ether compounds, can solve the problems of low synthesis yield, low content of active ingredient DCH18C6 cis-stereoisomer, etc., and achieve the effect of shortening reaction time

Inactive Publication Date: 2005-12-21
TSINGHUA UNIV
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Problems solved by technology

[0008] In order to solve the problem that the synthesis yield of existing dicyclohexyl 18 crown 6 (DCH18C6) is relatively low, and the content of active ingredient DCH18C6 cis-syn-cis is not high, the invention provides a bicyclo An improved synthesis process of hexylna-18-crown 6. The synthesis process uses diethylene glycol as a raw material to obtain dibenzo-18-crown 6 through chlorination and condensation, and then obtains dicyclohexyl-18-crown 6 through catalytic hydrogenation reduction reaction. It is characterized by:

Method used

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preparation example Construction

[0021] 1) Preparation of intermediate bis(2-chloroethyl)ether: add thionyl chloride to diethylene glycol, the molar ratio of the two is (2~3):1, and rapidly heat up to 110~120°C for reaction, The acid gas produced by the reaction is introduced into the lye for absorption, and the reaction is completed when no acid gas escapes, and the bis(2-chloroethyl)ether product is obtained by distillation under reduced pressure;

[0022] 2) Preparation of the intermediate dibenzo-18-crown 6: catechol, n-butanol, and tetrabutylammonium bromide are added at one time, and the molar ratio of the three is 1: (8-11): (0.02-0.04); Sodium oxide and bis(2-chloroethyl)ether are added in twice, and the amount of the first addition can be 20-80% (mass). Wherein the molar ratio of sodium hydroxide and bis(2-chloroethyl) ether to catechol is (4.1~4.5):(1~1.2):1, and the reflux reaction time is more than 10 hours, preferably 11~15 hours . After the system is acidified to acidity, n-butanol is distille...

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Abstract

This is the modified synthesizing craft of dicyclohexyl-18-crown-6 (DCH18C6) belonging to the preparation field of crown ether compound. To solve the problems that the synthesizing production rate of the present DCH18C6 is low and the content of the cis three-dimensional isomereffective of the component DCH18C6 is low. The invention discloses the modified synthesizing craft and simple purifying method of cis three-dimensional isomereffective. In the systemization of DCH18C6, add tetrabutylammonium bromide to increase production rate and reduce reaction time, meantime it brings forward the purifying method of adopting toluene to have recrystallization. In the hydrogenation reaction, use acidic picher-ruthenium catalyst, increase temperature to 130 -140 Deg. C, the production rate can be increased to 90%, and promote the preparation of cis three-dimensional isomereffective; purify DCH18C6 cis three-dimensional isomereffective by the method of crystallizing in n-heptane. The synthesizing craft has strong practicability, low cost and high feasibility.

Description

technical field [0001] The invention belongs to the field of preparation of crown ether compounds, in particular to an improved synthesis process of dicyclohexyl-18-crown-6 applied in the fields of organic synthesis, extraction chemistry, biochemistry, analytical chemistry and the like. Background technique [0002] Crown ethers are a class of macrocyclic polyethers neutral compounds. Crown ethers have been widely used in selective catalytic reactions and preparation of ion-selective electrodes, but they are more widely used as important extractants for the extraction and separation of metal ions. In addition, in recent years, crown ether has also attracted extensive attention and application as an extractant for removing radioactive strontium-90 in the field of nuclear fuel reprocessing. The formation of complexes with cations is one of the main characteristics of crown ethers. As host molecules, crown ethers form host-guest complexes with various metal ions as guests, suc...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D323/00
Inventor 王海荣张平王建晨陈靖
Owner TSINGHUA UNIV
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