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Preparation method of dodecanoyl-beta cyclodextrin and preparation method of polysulfone membrane for tryptophan chiral resolution

A technology of dodecanoyl and cyclodextrin, applied in chemical instruments and methods, membrane technology, semipermeable membrane separation, etc., can solve the problems of cumbersome preparation, high cost, and high toxicity of tryptophan chiral separation membranes, etc. Achieve the effects of low preparation cost, good stability and simple preparation process

Inactive Publication Date: 2017-07-07
CHINA PHARM UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the problems of high cost, high toxicity and complicated preparation of tryptophan chiral separation membrane in the existing purification method of lauryl-β-cyclodextrin, one of the purposes of the present invention is to provide a kind of lauryl-β-cyclodextrin - The preparation method of cyclodextrin, the preparation of the chiral resolving agent lauryl-β-cyclodextrin, the purification link is the key step, according to the literature method using n-hexane purification, not only the cost is high, the toxicity is relatively high, but also low yield

Method used

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  • Preparation method of dodecanoyl-beta cyclodextrin and preparation method of polysulfone membrane for tryptophan chiral resolution
  • Preparation method of dodecanoyl-beta cyclodextrin and preparation method of polysulfone membrane for tryptophan chiral resolution
  • Preparation method of dodecanoyl-beta cyclodextrin and preparation method of polysulfone membrane for tryptophan chiral resolution

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Embodiment 1

[0033] First prepare the lauryl-β-cyclodextrin polysulfone membrane by the following steps, and then evaluate the concentration ratio of the two configurations in the filtrate filtered by the chiral membrane by a validated HPLC method to resolve chiral substances Split performance.

[0034] Synthesis of dodecanoyl-β-cyclodextrin:

[0035] Dry recrystallized β-cyclodextrin (5.675 g, 5 mmol) was slowly added to dry pyridine (100 mL) under magnetic stirring. After the β-cyclodextrin was completely dissolved, a certain mass of lauryl chloride (M β-环糊精 :M 十二酰氯 =1:7). The above mixed solution was shaken and reacted for 65 h at room temperature. After the reaction, the reaction liquid was evaporated to dryness in a rotary evaporator at 70° C. under reduced pressure to obtain a crude product of the reaction. Add 100 mL of water to the reaction crude product, stir magnetically at 100° C. for 10 min, and filter to obtain the reaction product. Dry the reaction product in a vacuum o...

Embodiment 2

[0049] The preparation method of lauryl-beta-cyclodextrin comprises the following steps:

[0050] (1) Add dry recrystallized β-cyclodextrin (3g, 2.64mmol) into anhydrous pyridine (50mL);

[0051] (2) After the β-cyclodextrin is completely dissolved, add lauryl chloride dropwise, (M β-环糊精 :M 十二酰氯 =1:6);

[0052] (3) The above mixed solution was shaken and reacted for 40 hours at room temperature;

[0053] (4) After the reaction, the reaction solution was evaporated to dryness at 60°C under reduced pressure to obtain the crude reaction product

[0054] (5) Add 50 mL of water to the reaction crude product, stir at 100°C for 20 minutes, filter to obtain the reaction product, and vacuum-dry the reaction product at 15°C to constant weight to obtain dodecanoyl-β-cyclodextrin.

[0055] The preparation method of lauryl-beta-cyclodextrin polysulfone chiral membrane comprises the following steps:

[0056] (1) Under stirring conditions, heat and stir 10% (7.5% PSF+2.5% lauryl-β-cyclo...

Embodiment 3

[0062] The preparation method of lauryl-beta-cyclodextrin comprises the following steps:

[0063] (1) Add dry recrystallized β-cyclodextrin (8g, 7mmol) into anhydrous pyridine (100mL);

[0064] (2) After the β-cyclodextrin is completely dissolved, add lauryl chloride dropwise, (M β-环糊精 :M 十二酰氯 =1:8);

[0065] (3) The above mixed solution was shaken and reacted for 80 hours at room temperature;

[0066] (4) After the reaction, the reaction solution was evaporated to dryness at 80°C under reduced pressure to obtain the crude reaction product

[0067] (5) Add 300 mL of water to the reaction crude product, stir at 70°C for 5 minutes, and filter to obtain the reaction product, which is vacuum-dried at 50°C to constant weight to obtain dodecanoyl-β-cyclodextrin.

[0068] The preparation method of lauryl-beta-cyclodextrin polysulfone chiral membrane comprises the following steps:

[0069] (1) Under stirring conditions, heat and stir 28% (18.5% PSF+9.5% dodecanoyl-β-cyclodextrin)...

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Abstract

The invention discloses a preparation method of dodecanoyl-beta cyclodextrin and a preparation method of a polysulfone membrane for tryptophan chiral resolution, and belongs to the technical field of chiral resolution. Amphipathic dodecanoyl-beta cyclodextrin is prepared from beta cyclodextrin and lauroyl chloride by adopting a one-step synthesis method to serve as a chiral selector, and a polysulfone material with high mechanical strength, compressive tightness, chemical stability, heat resistance, wide pH application range, low price and simple preparation method is used as basic membrane material to prepare the polysulfone membrane for resolution. Racemic tryptophan is used as a resolution object, the concentration and a concentration ratio of D-tryptophan and L-tryptophan are monitored by high performance liquid chromatography, and the prepared amphipathic chiral membrane has a stable resolution effect within 12h and good performance.

Description

technical field [0001] The invention belongs to the technical field of chiral resolution, and more specifically relates to a preparation method of dodecanoyl-β-cyclodextrin and a preparation method of a polysulfone membrane used for chiral resolution of tryptophan. Background technique [0002] Membrane separation method is to use the specific separation functional sites contained in the membrane or outside the membrane to resolve the vortex mixture. The membrane separation method has the advantages of low energy consumption, simple operation, large batch capacity, easy continuous operation, easy industrial scale-up, flexible device design and system application, and room temperature operation in most cases. According to the morphology of the membrane, the membrane separation method can be divided into two types: liquid membrane separation and solid membrane separation. Chiral liquid membranes have a common disadvantage that is difficult to overcome, that is, poor stability...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16B01D67/00B01D71/68
CPCB01D67/0002B01D71/68C08B37/0012
Inventor 季一兵柯健陈建秋
Owner CHINA PHARM UNIV
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