Method for preparing cucurbituril and cucurbituril derivative

A technology of cucurbituril and derivatives, which is applied in the field of preparation of cucurbituril and cucurbituril derivatives, can solve the problems of corrosiveness, high equipment requirements, environmental pollution, etc., and achieve strong corrosiveness, serious acid pollution, and low yield Effect

Inactive Publication Date: 2014-09-03
DALIAN UNIV OF TECH
View PDF6 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The above method is catalyzed by strong inorganic acid, which is corrosive and requires high equi

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
  • Method for preparing cucurbituril and cucurbituril derivative
  • Method for preparing cucurbituril and cucurbituril derivative
  • Method for preparing cucurbituril and cucurbituril derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Glycoluril-formaldehyde polymer (0.250g), 1-methyl-3-(3-sulfonic acid) propylimidazolium bisulfate ([C 3 SO 3 Hmim] HSO 4 ) ionic liquid (1.000g) and water (2.000g) were mixed, heated to 160° C. for 30 minutes by microwave (800W). After the reaction solution was left to stand for 1-2 days, the cucurbit [6] urea product crystallized (0.070 g), and the ionic liquid could be recycled.

Embodiment 2

[0031] Glycoluril-formaldehyde polymer (0.250g), 1-methyl-3-(3-sulfonic acid) propylimidazole tetrafluoroborate ([C 3 SO 3 Hmim] BF 4 ) ionic liquid (1.000g) and water (2.000g) were mixed, heated to 160° C. for 30 minutes by microwave (800W). After the reaction solution was cooled, a large amount of cucurbit [6] urea product crystallized (0.141 g), and the ionic liquid could be recycled.

Embodiment 3

[0033] Glycoluril-formaldehyde polymer (0.250g), 1-methyl-3-(3-sulfonic acid) propylimidazolium bisulfate ([C 3 SO 3 Hmim] HSO 4 ) ionic liquid (1.000g) and water (2.000g) were mixed, heated to 160° C. for 30 minutes by microwave (800W). The reaction solution was poured into methanol to form a white precipitate, which was filtered and vacuum-dried to obtain 0.238 g of cucurbituril product, with a yield of 95.2%, in which cucurbit[5]uril, cucurbit[6]uril and cucurbit[7]uril each accounted for 12% , 57% and 31%. After the filtrate is dried, the ionic liquid is recycled.

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 belongs to the field of organic synthesis and chemical engineering, which relates to a method for preparing cucurbituril and a cucurbituril derivative. The method comprises the following steps: carrying out a mixed reaction on a glycoluril-aldehyde polymer, an acidic ionic liquid and a solvent or carrying out the mixed reaction on glycoluril, aldehyde, the acidic ionic liquid and the solvent for 1 second to 300 hours at a reaction temperature of 0 DEG C to 300 DEG C; and standing a reaction liquid and cooling after the reaction, thereby separating out the cucurbituril or the cucurbituril derivative in a crystallization manner; or adding an organic solvent after the cooling of the reaction liquid, thereby separating out the cucurbituril or the cucurbituril derivative in a precipitation manner. Compared with the background technology which is strong in corrosivity, serious in acid pollution and low in yield, the synthesis process provided by the invention is environmental friendly, economical and efficient, and has the advantages that the acidic ionic liquid is used for replacing the traditional inorganic strong acid to serve as a catalyst, thereby being environmental friendly; the acidic ionic liquid can be recycled, thereby being economical; the microwave radiation is optimally adopted as a heat source, thereby being efficient.

Description

technical field [0001] The invention belongs to the field of organic synthesis and chemical industry, and relates to a method for preparing cucurbituril and cucurbituril derivatives. Background technique [0002] In 1905, R. Behrend et al. found that glycoluril-formaldehyde polymers could generate macrocyclic compounds of unknown structure after treatment with concentrated sulfuric acid (Liebigs Ann. Chem. 1905, 1, 339). In 1981, W. Mock et al. repeated the experiment, and analyzed the macrocyclic compound by X-ray single crystal diffraction to be a cyclic hexamer connected by glycoluril through a methylene group, named cucurbit [6] urea (J.Am. Chem. Soc. 1981, 103, 7367). At present, cucurbituril (CB) has been used in many fields such as drug delivery, catalyst, molecular machine, sensor, ion channel, and wastewater treatment. [0003] In traditional CB[n] synthesis methods, strong inorganic acids (such as concentrated sulfuric acid and concentrated hydrochloric acid) are...

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): C07D487/22
CPCC07D487/22
Inventor 刘莉
Owner DALIAN UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap