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Chiral covalent organic skeleton composite film and preparation method and application thereof

A covalent organic framework and composite membrane technology, applied in chemical instruments and methods, and other chemical processes, can solve problems such as limiting chiral separation membrane capabilities, MOFs structure damage, solvent instability, etc., to achieve the applicable surface of the preparation method Wide range, simple synthesis method, uniform pore size distribution

Active Publication Date: 2019-10-29
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the instability of most chiral MOFs (metal-organic coordination polymers) in water, organic solvents, and acidic environments greatly limits their ability to be used as chiral separation membranes.
At the same time, the solvent instability of chiral MOFs materials will lead to the destruction of the MOFs structure, and new impurities will be introduced during the chiral separation process.

Method used

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  • Chiral covalent organic skeleton composite film and preparation method and application thereof
  • Chiral covalent organic skeleton composite film and preparation method and application thereof
  • Chiral covalent organic skeleton composite film and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] A kind of preparation method of chiral covalent organic framework composite film (CPAF-1, CPAF-2 and CPAF-3), see figure 2 and image 3 ,Specific steps are as follows:

[0034] The first step: preparation of nylon-6 membrane with surface modified cyanuric chloride:

[0035] Nylon-6 membrane is placed in a 100mL beaker, add 40mL of 0.1mol / L hydrochloric acid solution, and soak at room temperature for 24 hours. Then wash with water until neutral. Finally, soak in 40 mL of 0.1 mol / L sodium hydroxide solution for 12 hours, wash neutral with water, and dry under vacuum at 80°C for 12 hours to obtain an activated nylon-6 membrane.

[0036] The activated nylon-6 film, 0.37g of cyanuric chloride and 0.83g of potassium carbonate were reacted at 0°C for 12 hours with anhydrous 1,4-dioxane as a solvent to obtain surface-modified triuric chloride Cyanide nylon-6 membrane.

[0037] The second step: preparation of chiral covalent organic framework composite membrane:

[0038] ...

Embodiment 2

[0043] Application of the chiral covalent organic framework membrane of the present invention as a chiral separation membrane in the selective adsorption of chiral aromatic alcohol drugs

[0044] 1. The separation of RS-3-chloro-1-phenylpropanol and R / S-limonene by CPAF-1, CPAF-2 and CPAF-3 membranes as an example.

[0045] The specific chromatographic method is:

[0046] Chromatographic conditions for R / S-3-chloro-1-phenylpropanol: Chromatographic column: FLM Chiral INB (4.6×250mm, 5μm); Mobile phase: n-hexane / isopropanol (v / v=90:10); Flow rate: 0.7mL / min; column temperature: 25°C, detection wavelength: 254nm.

[0047] Chromatographic conditions of R / S-limonene: Chromatographic column: FLM Chiral INB (4.6×250mm, 5μm); mobile phase: n-hexane / isopropanol (v / v=95:5); flow rate: 1.0mL / min; column Temperature: 25°C, detection wavelength: 240nm.

[0048] 2. Separation of CPAF-1, CPAF-2 and CPAF-3 membranes, such as Figure 6 As shown, take the selective separation of R / S-3-chlo...

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PUM

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Abstract

The invention discloses a chiral covalent organic skeleton composite film (CPAF-1, CPAF-2 and CPAF-3). The chiral covalent organic skeleton composite film has the porous performance and can provide aplurality of chiral recognition sites. The invention further provides a preparation method of the chiral covalent organic skeleton composite film. According to the chiral covalent organic skeleton composite film, the chiral covalent organic skeleton composite film is synthesized by controlling the reaction temperature, and formed by linking covalent bonds, more chiral monomers are arranged in a network skeleton with a molecular structure, and the extraordinary chiral recognition ability is given; and in addition, functional groups in a chiral covalent organic skeleton structure can provide sites with a variety of action such as size selection action and hydrogen-bond interaction, and can be used as application of chiral separation films to selective adsorption of chiral aromatic alcohol drugs.

Description

technical field [0001] The invention relates to separation materials, in particular to a chiral covalent organic framework composite membrane and its preparation method and application. Background technique [0002] The separation of chiral drugs plays an extremely important role in the pharmaceutical industry, and their enantiomers often exhibit different pharmacological and toxicological properties. So far, chiral recognition and separation is still an important technical problem. Especially the separation of polar chiral compounds is one of the most challenging research. Chromatography is currently an attractive technique for the separation of chiral compounds. However, chromatography has low throughput and high cost. Membrane separation has the advantages of simple operation and low cost. In recent years, chiral solid membrane separation technology has gradually shown great potential in the separation of chiral drugs. The design and synthesis of chiral membrane mate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J20/22B01J20/30
CPCB01J20/226
Inventor 李攻科陈彦龙李亮卢梓程胡玉玲
Owner SUN YAT SEN UNIV
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