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Mixed matrix membrane taking chiral metal organic molecular cage as filler as well as preparation and application of the mixed matrix membrane

A technology of metal-organic molecules and mixed matrix membranes, which is applied in membrane technology, semi-permeable membrane separation, chemical instruments and methods, etc., can solve problems such as uneven mixing, poor mechanical properties, and poor film-forming properties, and overcome uneven mixing , high stability, good flexibility

Active Publication Date: 2021-06-18
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The invention realizes the controllable synthesis of chiral metal-organic molecular cages, and prepares high-quality mixed matrix membranes through a phase inversion method, which improves the uneven mixing and film formation that are prone to occur in the synthesis process of existing chiral mixed matrix membranes. Poor properties, many defects, and poor mechanical properties, it has broad development prospects in applications such as the separation of chiral drugs

Method used

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  • Mixed matrix membrane taking chiral metal organic molecular cage as filler as well as preparation and application of the mixed matrix membrane
  • Mixed matrix membrane taking chiral metal organic molecular cage as filler as well as preparation and application of the mixed matrix membrane
  • Mixed matrix membrane taking chiral metal organic molecular cage as filler as well as preparation and application of the mixed matrix membrane

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] The preparation method of the mixed matrix membrane with the chiral metal-organic molecular cage as the filler comprises the following steps:

[0054] 1. Preparation of chiral binaphthalene dicarboxylic acid ligand functionalized with crown ether:

[0055]

[0056] Add 5.0 g of starting material compound S1 to a 250 mL dry two-necked round bottom flask, evacuate nitrogen three times, and then add 60.0 mL of dry CH 2 Cl 2 , and the temperature of the solution was lowered to -78° C., and 2.85 mL of boron tribromide in dichloromethane (20.0 mL) was added dropwise. Slowly return to room temperature and stir overnight. After the reaction was completed, the reaction solution was poured into an ice-water bath to quench the reaction. Dichloromethane was removed under reduced pressure, ethyl acetate was added to extract and the organic phase was collected, dried and spin-dried. The crude product was separated by a short silica gel column to obtain 4.5g of white compound S...

Embodiment 2

[0073] The preparation method of the mixed matrix membrane with the chiral metal-organic molecular cage as the filler comprises the following steps:

[0074] 1) Using 6,6'-dichloro-2,2'-diethoxy-[1,1'-binaphthalene]-4,4'-dicarboxylic acid as the starting material, successively deprotect the hydroxyl group, Esterification of carboxyl groups, functionalization of crown ethers and hydrolysis of ester groups to obtain chiral binaphthyl dicarboxylic acid ligands functionalized with crown ethers. The consumption of boron tribromide is 3 times of equivalents; the consumption of pentylene glycol di-p-toluenesulfonate is 5 times of equivalents; the consumption of lithium hydroxide is 5 times of equivalents. Specifically include:

[0075] 1-1) Compound S1, boron tribromide and dichloromethane were mixed, and the ethyl group of compound S1 was removed by reaction to obtain hydroxyl-containing compound S2; the reaction conditions were: stirring overnight at room temperature.

[0076] 1-...

Embodiment 3

[0084] The preparation method of the mixed matrix membrane with the chiral metal-organic molecular cage as the filler comprises the following steps:

[0085] 1) Using 6,6'-dichloro-2,2'-diethoxy-[1,1'-binaphthalene]-4,4'-dicarboxylic acid as the starting material, successively deprotect the hydroxyl group, Esterification of carboxyl groups, functionalization of crown ethers and hydrolysis of ester groups to obtain chiral binaphthyl dicarboxylic acid ligands functionalized with crown ethers. The consumption of boron tribromide is 6 times of equivalents; the consumption of pentylene glycol di-p-toluenesulfonate is 2 times of equivalents; the consumption of lithium hydroxide is 8 times of equivalents. Specifically include:

[0086] 1-1) Compound S1, boron tribromide and dichloromethane were mixed, and the ethyl group of compound S1 was removed by reaction to obtain hydroxyl-containing compound S2; the reaction conditions were: stirring overnight at room temperature.

[0087] 1-...

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Abstract

The invention relates to a mixed matrix membrane with a chiral metal organic molecular cage as filler and preparation and application thereof. The method includes 1) preparing a crown ether functionalized chiral binaphthyl dicarboxylic acid ligand by taking 6,6'-dichloro-2,2'-diethoxy-[1,1'-binaphthyl]-4,4'-dicarboxylic acid as an initial raw material; 2) preparing a chiral metal organic molecular cage crystal through a solvothermal method; 3) fully mixing with an activated polyethersulfone polymer matrix to obtain a membrane casting solution; and 4) preparing the mixed matrix membrane with the chiral metal organic molecular cage as the filler through a phase inversion method, wherein the mixed matrix membrane is used for chiral separation of racemic compounds. Compared with the prior art, the controllable synthesis of the chiral metal organic molecular cage is realized, the high-quality mixed matrix membrane is prepared by the phase inversion method, and the problems of non-uniform mixing, poor membrane forming property, many defects, poor mechanical property and the like which are easily generated in the existing chiral mixed matrix membrane synthesis process are solved; the mixed matrix membrane has a wide development prospect in the application aspects of separation of chiral drugs and the like.

Description

technical field [0001] The invention belongs to the technical field of chiral separation membranes, and relates to a mixed matrix membrane with a chiral metal-organic molecular cage as filler and its preparation and application. Background technique [0002] Chirality is a basic property of nature and is closely related to many aspects of life phenomena and people's daily life. Life activities such as molecular recognition and enzyme catalysis in organisms are carried out in a highly complex chiral microenvironment. The huge demand for chiral substances has promoted the development of chiral science. Therefore, obtaining a single chiral compound is one of the research priorities in the field of chemistry and materials in recent decades, and it is also very important in the application fields of biology, medicine and fine chemicals. link. [0003] Chiral membrane separation has incomparable advantages over traditional separation methods, such as simple equipment, low energy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01D67/00B01D69/12B01D71/68
CPCB01D71/06B01D71/68B01D69/12B01D67/0011
Inventor 崔勇刘玉豪袁晨付仕国刘燕
Owner SHANGHAI JIAO TONG UNIV
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