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Chiral-separation solid membrane grafted by chiral identification body through dopamine pretreatment, and making method thereof

A chiral recognition and chiral separation technology, applied in organic chemistry methods, chemical instruments and methods, membrane technology, etc. Effects of modification, expanded selectivity, mild reaction conditions

Active Publication Date: 2014-02-19
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Methods such as blending and chemical modification may change the physical properties of the original film matrix; after composite modification, the coating may be unstable. As the use progresses, the composite layer will gradually separate from the film substrate; Branches, low-temperature plasma grafting, enzyme-induced grafting, etc. have high costs and small processing capacity, so they are not suitable for industrial operation

Method used

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  • Chiral-separation solid membrane grafted by chiral identification body through dopamine pretreatment, and making method thereof
  • Chiral-separation solid membrane grafted by chiral identification body through dopamine pretreatment, and making method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0036] (1) β-CD-NH 2 Preparation: 12.0g β-CD was added to 100mL distilled water, 1.32g NaOH was dissolved in 4mL water, and added dropwise to the β-CD solution, the original suspension gradually became uniform. Then 2.24g of p-toluenesulfonyl chloride was dissolved in 8mL of acetonitrile, and added dropwise to the β-CD solution, a white precipitate appeared, reacted at 25°C for 2h, and placed at 4°C overnight. The white solid was obtained by filtration, soaked in diethyl ether, filtered and washed twice with hot water, and dried under vacuum to obtain the intermediate 6-OTs-β-CD. Take 1.0g of 6-OTs-β-CD and react with 6g of ethylenediamine, reflux at 70°C for 4h, the obtained solution is slightly diluted with a certain amount of methanol, and precipitated in acetonitrile solution to obtain a white solid, which is and dried overnight to obtain β-CD-NH 2 . Dissolve 1 g of dopamine (Aladdin Reagent Co., Ltd.) in 1 L of Tris-buffer (pH 8.0) to prepare 1 g / L of dopamine Tris-buf...

Embodiment 2

[0042] (1) Soak the flat polyvinylidene fluoride membrane (Guangzhou Chaoyu Membrane Separation Technology Co., Ltd.) in isopropanol (98%) for 90 minutes to completely wet the membrane.

[0043] (2) Take out the soaked polyvinylidene fluoride flat film and soak it in 2g / L dopamine Tris buffer solution (pH8.5), expose it to the air at room temperature, stir for 24 hours, take out the film and wash it with water after the reaction is completed net.

[0044] (3) Soak the dopamine-treated solid film in 2g / L BSA-NH 2 In Tris buffer (pH8.5), react at 20°C for 2h. After the reaction, the membrane was washed repeatedly with water and dried to obtain a chiral resolution solid membrane.

[0045] The flow rate of polyvinylidene fluoride flat membrane before modification is 90L m -2 h -1 , the flow rate of modified polyvinylidene fluoride plate chiral separation membrane is 245L m -2 h -1. The resolution efficiency (e.e%) for D,L-histidine was 29%, and the resolution efficiency (e....

Embodiment 3

[0047] (1) Soak the polytetrafluoroethylene tubular membrane (Guangzhou Ruite Water Purification Technology Co., Ltd.) in isobutanol (98%) for 240 minutes to completely wet the membrane. Take 5 g of dopamine (Aladdin Reagent Co., Ltd.) and dissolve it in 1 L of Tris-buffer (pH9.0) to prepare 5 g / L dopamine Tris-buffer. Take 1g β-CD-NH 2 Dissolve in 5L of Tris-buffer (pH9.0) to prepare 5g / L of β-CD-NH 2 Tris-buffer.

[0048] (2) Take out the soaked polytetrafluoroethylene tubular membrane and soak it in 5g / L dopamine Tris buffer solution (pH9.0), expose it to the air at room temperature, stir for 48h, take out the membrane and wash it with water after the reaction is completed net.

[0049] (3) Soak the dopamine-treated solid film in 5g / L β-CD-NH 2 In Tris buffer (pH9.0), react at 70°C for 4h. After the reaction, the membrane was washed repeatedly with water and dried to obtain a chiral resolution solid membrane.

[0050] The flow rate of PTFE tubular membrane before mod...

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Abstract

The invention belongs to the technical field of polymer membrane materials, and discloses a chiral-separation solid membrane grafted by a chiral identification body through dopamine pretreatment, and a making method and an application thereof. The method includes the following concrete steps: 1, immersing a solid membrane in a dopamine solution, stirring for reacting, and flushing with clear water; and 2, immersing the flushed solid membrane in a solution of the chiral identification body, heating for reacting, washing, and carrying out vacuum drying to obtain the chiral-separation solid membrane grafted by the chiral identification body through dopamine pretreatment. Firm and stable fctive function groups comprising -NH2, -OH and -C=O are introduced to the surface of the solid membrane through the above immersion technology; and chiral recognition sites are introduced to the surface of the solid membrane through the above immersion technology without influencing the structure or performances of the membrane, so the chiral-separation solid membrane grafted by the chiral identification body through dopamine pretreatment can be used for the effective separation of racemes The making method has the advantages of realization of the implementation of above reactions in an aqueous solution for a whole course, and mild and unharsh reaction conditions, development of the modification selectivity of the solid membrane, simple process, and easy realization of the industrialized batch production.

Description

technical field [0001] The invention belongs to the technical field of polymer membrane materials, in particular to a chiral separation solid membrane of dopamine pretreatment grafted chiral recognition body and its preparation method and application. Background technique [0002] Chirality is getting more and more attention in the modern pharmaceutical industry. This is mainly due to the growing understanding that the enantiomers of racemic drugs have different pharmacological activities, different pharmacokinetics and pharmacodynamics. The human body is particularly sensitive to chiral selection. After the interaction of different enantiomers in racemic drugs with human organs, they are separately metabolized through different pathways, resulting in different pharmacological activities. Thus, one enantiomer may produce the desired therapeutic effect, while the other may not only have no effect, but worse, may produce undesired results. Such a tragedy occurred in 1960, wh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01D71/68B01D71/34B01D71/36B01D71/26B01D71/10B01D71/42B01D71/48B01D69/06B01D69/08B01D69/04B01D67/00C07B57/00C07D209/20C07D233/64
Inventor 胡继文杨洋苗磊李妃刘国军吴艳林树东刘峰邹海良涂园园胡盛逾
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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