Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation technology of 4'4'' (5'')-di-tert-butyl-di-benzo-18-crown-6

A technology for the preparation of di-tert-butyldibenzo, which is applied in the field of organic synthesis, can solve the problems of difficult removal of impurities, long time, cumbersome decomplexation process, etc., to reduce solvation, increase conversion rate, and increase concentration and the effect of cationic activity

Active Publication Date: 2010-12-29
XI AN JIAOTONG UNIV
View PDF0 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Like the complexing solvent, the decomplexing solvent also has many requirements, the preparation is difficult, and the decomplexing process is cumbersome, and the impurities brought in during the separation of the complex are difficult to remove. The yield of tert-butyldibenzo-18-crown-6 is low, the purity is not high, and the process is cumbersome and complicated, the time is long, and the cost is high

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation technology of 4'4'' (5'')-di-tert-butyl-di-benzo-18-crown-6
  • Preparation technology of 4'4'' (5'')-di-tert-butyl-di-benzo-18-crown-6
  • Preparation technology of 4'4'' (5'')-di-tert-butyl-di-benzo-18-crown-6

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] a. Weigh 8.3g (0.05mol) of p-tert-butylcatechol and 35.8g (0.11mol) of cesium carbonate and dissolve them in 500ml of tetrahydrofuran, wherein the cesium carbonate is added in two equal amounts. A certain amount of diethylene glycol xylene sulfonate was weighed, dissolved in 250ml tetrahydrofuran twice, and added dropwise in a constant pressure dropping funnel. The reaction was carried out at 60°C for 48 hours, and the reaction conversion rate was 52.3%.

[0032] b. Filtrate the mixture obtained by reacting according to the above step a, and take the filtrate for vacuum distillation. The residue was dissolved in methanol, filtered, and the filtrate was vacuum distilled. Dichloromethane elutes the residue, washes repeatedly with 1N HCl and hot sodium thiosulfate aqueous solution, separates the organic phase, and dries it with anhydrous magnesium sulfate for use.

[0033] c. Weigh 5 g of the mixture treated according to the above step b, add 250 g of basic alumina and 5...

Embodiment 2

[0035] a. Weigh 8.3g (0.05mol) of p-tert-butylcatechol and 37.6g (0.115mol) of cesium carbonate and dissolve them in 400ml of tetrahydrofuran, wherein the cesium carbonate is added in two equal amounts. A certain amount of diethylene glycol xylene sulfonate was weighed, dissolved in 200ml tetrahydrofuran twice, and added dropwise in a constant pressure dropping funnel. The reaction was carried out at 50°C for 36 hours, and the reaction conversion rate was 43.8%.

[0036] b. Filtrate the mixture obtained in step a above, and get the filtrate for vacuum distillation. Methanol strips the residue, continues to filter, and then takes the filtrate for vacuum distillation. Dichloromethane elutes the residue, washes repeatedly with 1N HCl and hot sodium thiosulfate aqueous solution, separates the organic phase, and dries it with anhydrous magnesium sulfate for use.

[0037] c. Weigh 100 g of 200-300 mesh column chromatography silica gel, and dry-pack the column. Weigh 1 g of the mi...

Embodiment 3

[0039] a. Weigh 8.3g (0.05mol) of p-tert-butylcatechol and 40.6g (0.125mol) of cesium carbonate and dissolve them in 300ml of tetrahydrofuran, wherein the cesium carbonate is added in two equal amounts. A certain amount of diethylene glycol xylene sulfonate was weighed, dissolved in 150ml tetrahydrofuran twice, and added dropwise in a constant pressure dropping funnel. The reaction was carried out at 40°C for 24 hours, and the reaction conversion rate was 33.7%.

[0040] b. Filtrate the mixture obtained in step a above, and get the filtrate for vacuum distillation. Methanol strips the residue, continues to filter, and then takes the filtrate for vacuum distillation. Dichloromethane elutes the residue, washes repeatedly with 1N HCl and hot sodium thiosulfate aqueous solution, separates the organic phase, and dries it with anhydrous magnesium sulfate for use.

[0041] c. Weigh 60 g of 200-300 mesh column chromatography silica gel, and dry-pack the column. Weigh 1 g of the mix...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a preparation technology of 4'4'' (5'')-di-tert-butyl-di-benzo-18-crown-6, which is characterized by comprising the following steps: selecting para-tert-butylcatechol as a raw material, caesium carbonate as a template agent, and tetrahydrofuran or acetonitrile as a solvent, adding the reaction materials to an agitated reactor, and synthesizing to obtain a mixture containing the expected product 4'4'' (5'')-di-tert-butyl-di-benzo-18-crown-6 at 40-80 DEG C under the protection of nitrogen atmosphere; and after finishing the reaction, adopting a silica gel alumina backflow co-heat technology or an eluant with different compositions and proportioning to perform column chromatography gradient elution, and isolating and purifying the expected product 4'4'' (5'')-di-tert-butyl-di-benzo-18-crown-6. Compared with the reportorial preparation technology, the invention simplifies the procedures of synthesis as well as separation and purification and improves the reaction conversion rate and the purity and yield of the products.

Description

technical field [0001] The invention relates to a novel synthesis, separation and purification process of a crown ether compound 4'4"(5")-di-tert-butyldibenzo-18-crown-6, which belongs to the technical field of organic synthesis. Background technique [0002] Because the macrocyclic structure of the crown ether compound has specific selectivity to metal ions, especially to alkali metals and alkali metals, it has shown super selectivity and coordination ability, and has become an effective method for removing high-level radioactive waste in recent years. 137 One of the research hotspots of Cs and other radioactive ions. [0003] Simple aliphatic or aromatic crown ethers are generally synthesized from diphenols and polyethylene glycols (diols) or polyethylene glycol dihalides via the Williamson reaction. The templating agent base required in the reaction generally depends on the size of the ether hole of the crown ether to be synthesized, and commonly used bases are sodium hy...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D323/00
Inventor 杨伯伦范娟伊春海蔡静
Owner XI AN JIAOTONG UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com