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Heterochain polymer chiral stationary phase and process for preparing same

A chiral stationary phase and polymer technology, which is applied in the field of heterochain polymer chiral stationary phase and its preparation, can solve the problems of high cost, cumbersome operation, and high price of chiral chromatographic columns, and simplify the preparation steps , easy preparation, and high practical value

Inactive Publication Date: 2005-03-16
WUHAN CHEM COLLEGE
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Problems solved by technology

The introduction of all these groups must be achieved through chemical reactions, so the preparation of chiral stationary phases often requires several steps of reactions to complete, the operation is cumbersome, and most chiral reagents are very expensive. Each additional step of reaction, Its yield has just declined, so the price of chiral chromatographic columns is very expensive now, and the price of each chiral chromatographic column is more than 10,000 yuan

Method used

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  • Heterochain polymer chiral stationary phase and process for preparing same
  • Heterochain polymer chiral stationary phase and process for preparing same
  • Heterochain polymer chiral stationary phase and process for preparing same

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preparation example Construction

[0036] 2. Preparation method of heterochain polymer chiral stationary phase

[0037] It is formed by connecting a carrier and a chiral polymer through an amide bond or a urea bond, and the carrier is 3-aminopropyl silica gel.

[0038] The chiral polymer is one of polyamide, polyester, polyurethane, poly(ester-amide), poly(ester-urethane), or poly(amide-urea). Chiral polymers are polymerized by monomers, that is, through chiral diamines or chiral diols or chiral diphenols or chiral alcohol amines, and one or both of excess diacid chlorides and diisocyanates It is polymerized from species (that is, including diacyl chloride and diisocyanate), and the end segment has an acid chloride or isocyanate active group that can react with the functional group on the silica gel. One or both of diacyl chloride and diisocyanate are calculated based on the moles of monomers charged during the reaction, and the excess range is 1 to 20%.

[0039] Among the above-mentioned monomers used, at le...

Embodiment 1

[0040] Example 1. Preparation of polyamide chiral stationary phase

[0041] Add 5.22 grams of terephthaloyl dichloride and 5.22 grams of D-1,2-diphenylethylenediamine into 50 milliliters of dimethylformamide (DMF), stir, then add 10 milliliters of triethylamine, at 30-100 Reaction at ℃ for 5-15 hours. DMF was evaporated under reduced pressure, and the residue was washed with n-hexane. The washed solid was transferred to a three-neck flask, 30 ml of DMF, 3 ml of triethylamine and 4 g of 3-aminopropyl silica gel were added, and the reaction was stirred at 20-70° C. for 8 hours. Filter, extract the solid with acetone, and dry to constant weight. The measured elemental analysis results of the chiral stationary phase are: C: 18.31%; H: 2.647%; N: 3.632%. Infrared spectral data (cm -1 , KBr): 3423 (-NH-CO-), 1691 (-NH-CO-), 1530 (-NH-CO-).

Embodiment 2

[0042] Example 2. Preparation of Polyurethane Chiral Stationary Phase

[0043] Add 3.38 g of p-phenyl diisocyanate and 4.65 g of diisopropyl tartrate into 40 ml of pyridine, and react at 30-100° C. for 5-15 hours. The reaction mixture was dropped into toluene to obtain a solid. The solid was redissolved with pyridine and precipitated three times with toluene. The precipitated polymer was dissolved in pyridine, 4 g of 3-aminopropyl silica gel was added, and the reaction was stirred at 20-70° C. for 12 hours. After filtration, the solid was extracted with acetone and dried to constant weight. The measured elemental analysis results of the chiral stationary phase are: C: 20.81%; H: 2.932%; N: 3.809%. Infrared spectral data (cm -1 , KBr): 3410 (-NH-CO-), 1721 (-CO 2 -), 1642 (-NH-CO-).

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Abstract

The invention relates to a heterochain polymer chiral stationary phase and process for preparing same, wherein the heterochain polymer chiral stationary phase is formed by carriers and chiral macromolecules through the connection of polyamide bonds or carbamide bonds, the carrier being 3-amino propyl silica gel. The obtained chiral stationary phase has good chiral identification capability.

Description

technical field [0001] The invention relates to a heterochain polymer chiral stationary phase and a preparation method thereof. Background technique [0002] A pair of enantiomers of chiral molecules often have very different physiological or pharmacological activities. For example, in chiral drugs, one enantiomer can treat diseases, while the other enantiomer may be ineffective for treating diseases, or even toxic, side effect. So the separation of chiral molecules, especially the separation of chiral drugs is very important. The detection technique related to chiral separation is mainly chiral high performance liquid chromatography, which can be used to determine the content of a certain enantiomer. Unlike commonly used chromatographic columns, stationary phases for chiral chromatography must contain chiral molecules. The chiral molecules used to prepare chiral stationary phases include natural chiral macromolecules, oligosaccharides and chiral small molecules. These ch...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/76C08G69/48C08J3/00
Inventor 柏正武黄少华尹传奇
Owner WUHAN CHEM COLLEGE
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