Phenylene ethylenediamine derivatized beta-cyclodextrin bonded silica gel and application thereof

A phthaloyl ethylene diamine and phthaloyl ethylene diamine-based technology is applied in the field of preparation of bonded SBA-15 silica gel chiral stationary phase, and can solve the problem of poor chiral separation performance of chiral stationary phase materials and other problems, to achieve the effect of improving the chiral separation ability and range, low preparation cost and high bonding amount

Active Publication Date: 2016-09-21
NANCHANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The present invention aims at the technical defects of the prior art, and provides a kind of phthaloyl ethylenediamine derivatized β-cyclodextrin bonded silica gel to solve the problem of poor chiral separation performance of chiral stationary phase materials in the prior art. good technical questions

Method used

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  • Phenylene ethylenediamine derivatized beta-cyclodextrin bonded silica gel and application thereof
  • Phenylene ethylenediamine derivatized beta-cyclodextrin bonded silica gel and application thereof
  • Phenylene ethylenediamine derivatized beta-cyclodextrin bonded silica gel and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] (1) According to the ratio of phthalic acid (mmol): thionyl chloride (ml) of 1.0:2.0, add phthalyl and thionyl chloride into a round bottom flask, stir and place in a 75°C oil bath Heated to reflux for 1.5h. Then the unreacted thionyl chloride was evaporated under reduced pressure to obtain phthaloyl chloride;

[0066] (2) Under nitrogen atmosphere, according to 6-(ethylenediamino)-β-cyclodextrin (mmol): phthaloyl chloride (mmol): anhydrous N, N-dimethylformamide (ml) as 2.0~2.5:1.0:25~35 ratio, dissolve 6-(ethylenediamino)-β-cyclodextrin in anhydrous N,N-dimethylformamide, add phthaloyl chloride under ice bath , and then magnetically stirred at room temperature for 4h to 6h to obtain a solution containing 6-(phthaloylethylenediamine)-β-cyclodextrin. This step is not separated and purified, and the next step reaction is continued;

[0067] (3) Under nitrogen atmosphere, according to 6-(ethylenediamino)-β-cyclodextrin (mmol) in (2): 3-isocyanatopropyl trialkoxysilane ...

Embodiment 2

[0077] Take SBA-15 (400m 2 / g) Activated silica gel 2.5g as the base.

[0078] (1) According to the ratio of phthalic acid (mmol): thionyl chloride (ml) of 1.0:2.0, add phthalic acid and thionyl chloride into a round-bottomed flask, under stirring, in 75 ℃ oil The bath was heated to reflux for 1.5h. Then the unreacted thionyl chloride was evaporated under reduced pressure to obtain phthaloyl chloride;

[0079] (2) Under nitrogen atmosphere, according to 6-(ethylenediamino)-β-cyclodextrin (mmol): phthaloyl chloride (mmol): anhydrous N,N-dimethylformamide (ml) In the ratio of 2.0:1.0:25, dissolve 6-(ethylenediamino)-β-cyclodextrin in anhydrous N,N-dimethylformamide, add phthaloyl chloride under ice-cooling, room temperature The reaction was carried out under magnetic stirring for 4 hours to obtain a solution containing 6-(phthaloylethylenediamine)-β-cyclodextrin. This step is not separated and purified, and the next step reaction is continued;

[0080] (3) Under a nitrogen ...

Embodiment 3

[0087] Take SBA-15 (500m 2 / g) Activated silica gel 2.5g as the base.

[0088] (1) According to the ratio of phthalic acid (mmol): thionyl chloride (ml) of 1.0:2.0, add phthalyl and thionyl chloride into a round bottom flask, stir and heat at 75°C The bath was heated to reflux for 1.5h. Then the unreacted thionyl chloride was evaporated under reduced pressure to obtain phthaloyl chloride;

[0089] (2) Under nitrogen atmosphere, according to 6-(ethylenediamino)-β-cyclodextrin (mmol): phthaloyl chloride (mmol): anhydrous N,N-dimethylformamide (ml) In the ratio of 2.5:1.0:35, dissolve 6-(ethylenediamino)-β-cyclodextrin in anhydrous N,N-dimethylformamide, add phthaloyl chloride under ice-cooling, room temperature The reaction was carried out under magnetic stirring for 6 hours to obtain a solution containing 6-(phthaloylethylenediamine)-β-cyclodextrin. This step is not separated and purified, and the next step reaction is continued;

[0090] (3) Under a nitrogen atmosphere, p...

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Abstract

The invention provides phenylene ethylenediamine derivatized beta-cyclodextrin bonded silica gel and an application thereof. According to the technical scheme, 6-(ethylenediamino)-beta-cyclodextrin and phthalic acid are taken as raw materials, thionyl chloride is taken as a chlorinating agent and a solvent, phenylene chloride is generated under a heating condition, then stirring is performed at the room temperature to enable 6-(ethylenediamino)-beta-cyclodextrin to be subjected to a reaction with phenylene chloride, 6(phenylene ethylenediamino)-beta-cyclodextrin is prepared, and a novel chiral stationary phase is prepared in a follow-up stage with 3-isocyanatopropylsiloxane as a coupling agent and ordered mesopore SBA-15 silica gel as a bonding matrix. The product has large specific surface area and large bonded quantity, the method is simple and lower in cost, and a chromatographic column filled with the stationary phase has longer service life because cyclodextrin is stable in performance and is connected with silica gel in a bonding manner. Besides, the product and a solute have various stereoselectivity functions, and by means of good permeability and small mass transfer resistance of SBA-15, the chiral separation speed is high and the effect is outstanding.

Description

technical field [0001] The present invention relates to the technical field of organic synthesis, and further relates to the preparation method and application of bonded SBA-15 silica gel chiral stationary phase, in particular to the bonding of β-cyclodextrin derivatized with phthaloylethylenediamine as a ligand The preparation method and chiral separation application of SBA-15 silica gel chiral stationary phase. Background technique [0002] Chirality is one of the basic properties of nature, which refers to the property that a substance and its mirror image cannot overlap. Chiral drugs refer to a pair of enantiomers that are real objects and mirror images obtained after introducing a chiral center into the molecular structure of a drug. The physical and chemical properties of these enantiomers are basically similar, only the optical rotation is different, and they are named R-type (dextrorotary) or S-type (left-rotary) and racemic respectively. Chirality is closely relat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00C08B37/16B01J20/29B01J20/30
CPCB01J20/29C08B37/0012C08G83/001
Inventor 李来生曹志刚周仁丹程彪平曾春李良张宏福廖玉芹
Owner NANCHANG UNIV
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