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A method for extracting and separating flurbiprofen racemate using amino acid ionic liquid

A technology of ionic liquid and flurbiprofen, which is applied in the field of amino acid ionic liquid for splitting flurbiprofen enantiomers, can solve the problems of difficult recovery of extractant, poor extraction effect, complicated system, etc., and achieves green and safe dosage and operation. Simple, simple-to-equip effect

Active Publication Date: 2020-06-23
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to provide a method for extraction and separation of flurbiprofen using amino acid chiral ionic liquids to solve the problems of high cost, complex system, difficult recovery of extraction agent, and poor extraction effect of the existing flurbiprofen extraction and separation method. The method of Fen enantiomers, the amino acid ionic liquid mentioned here is 1-butyl-3-methylimidazole L-tryptophanate (directly purchased from Shanghai Chengjie Chemical Co., Ltd.), which is used as an extractant to carry out flurbirol The method for extraction and separation of fen comprises the steps:

Method used

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  • A method for extracting and separating flurbiprofen racemate using amino acid ionic liquid
  • A method for extracting and separating flurbiprofen racemate using amino acid ionic liquid
  • A method for extracting and separating flurbiprofen racemate using amino acid ionic liquid

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Effect test

Embodiment 1

[0023] Configure 0.1mol / L phosphate buffer solution (pH=2) and methanol volume ratio 95:5 to mix, add a certain amount of 1-butyl-3-methylimidazolium L-tryptophan salt ionic liquid to prepare ionic liquid Aqueous phase with a concentration of 0.005mol / L. Flurbiprofen racemate was dissolved in dichloroethane to obtain 20 ppm oily phase. Take 3ml each of the water phase and the oil phase in a test tube, and shake in a constant temperature water bath shaking tank for 2 hours, and the extraction temperature is controlled at 25°C. After the extraction is completed, let it stand for stratification. After the interface between the two phases is clear, take a small amount of the lower oil phase to analyze and detect the concentration of S-flurbiprofen and R-flurbiprofen, and calculate the partition coefficient and selectivity of the enantiomers. coefficient.

[0024] The results showed that the distribution coefficients of R-flurbiprofen and S-flurbiprofen were 18.68 and 22.28, resp...

Embodiment 2

[0027] Configure 0.3mol / L phosphate buffer solution (pH=2) and mix methanol with a volume ratio of 90:10, add a certain amount of 1-butyl-3-methylimidazolium L-tryptophan ionic liquid to prepare ionic liquid Aqueous phase with a concentration of 0.02mol / L. Flurbiprofen racemate was dissolved in dichloroethane to obtain 50 ppm oily phase. Take 3ml each of the water phase and the oil phase in a test tube, and shake in a constant temperature water bath shaking tank for 2 hours, and the extraction temperature is controlled at 25°C. After the extraction is completed, let it stand for stratification. After the interface between the two phases is clear, take a small amount of the lower oil phase to analyze and detect the concentration of S-flurbiprofen and R-flurbiprofen, and calculate the partition coefficient and selectivity of the enantiomers. coefficient. The results showed that the distribution coefficients of R-flurbiprofen and S-flurbiprofen were 21.40 and 25.91, respectivel...

Embodiment 3

[0030]Configure 0.5mol / L phosphate buffer solution (pH=2) and methanol volume ratio 80:20 to mix, add a certain amount of 1-butyl-3-methylimidazolium L-tryptophan salt ionic liquid to prepare ionic liquid Aqueous phase with a concentration of 0.05mol / L. Flurbiprofen racemate was dissolved in dichloroethane to obtain 100 ppm oil phase. Take 3ml each of the water phase and the oil phase in a test tube, and shake in a constant temperature water bath shaking tank for 2 hours, and the extraction temperature is controlled at 25°C. After the extraction is completed, let it stand for stratification. After the interface between the two phases is clear, take a small amount of the lower oil phase to analyze and detect the concentration of S-flurbiprofen and R-flurbiprofen, and calculate the partition coefficient and selectivity of the enantiomers. coefficient. The results showed that the partition coefficients of R-flurbiprofen and S-flurbiprofen were 27.10 and 31.81, respectively, and...

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Abstract

The invention discloses a method of extracting and separating flurbiprofen racemate through amino ionic liquids (AILs), and belongs to the technical field of chemical separation. The method comprisesthe following steps: methanol is added into a phosphate buffered solution, 1-butyl-3-methylimidazole L-tryptophan salty ion liquid is added to serve as a water phase, the flurbiprofen racemate is added into dichloroethane to serve as an oil phase, the water phase and the oil phase are oscillated and extracted at the room temperature, still standing for separation is conducted after phase equilibrium is reached, R-flurbiprofen is enriched in the water phase, and S-flurbiprofen is enriched in the oil phase; the extracted water phase is collected and mixed with the dichloroethane, oscillation isconducted at the temperature of 5-25 DEG C for a reextraction process, still standing for separation is conducted after reextraction is conducted until phase equilibrium is reached, and the upper-layer water phase is recycled. The method adopts the AILs which are difficult to volatile, easy to recycle and stable in property as an extraction agent, environmental pollution is small, the system is easy, operation is easy, the condition is mild, the good selectivity is achieved, and the method is suitable for scale production.

Description

technical field [0001] The invention relates to the technical field of chemical separation, in particular to a method for splitting flurbiprofen enantiomers with an amino acid ionic liquid. [0002] technical background [0003] The chemical name of flurbiprofen is (±)-2-(2-fluoro-4-biphenyl)-propionic acid, which is a non-steroidal anti-inflammatory chiral drug commonly used in clinical practice and is the currently known One of the stronger drugs (the anti-inflammatory effect of labor pain is better than that of aspirin and ibuprofen), which contains a pair of S and R enantiomers, and is mainly used for the treatment of rheumatoid arthritis, osteoarthritis and other diseases. Its S-type enantiomer has high pharmacological activity, while its R-type enantiomer has almost no therapeutic effect and has some toxic side effects on the human body. Recent studies have found that R-type flurbiprofen has a certain therapeutic effect on Helmers' disease and can be used to inhibit tu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C57/58C07C51/48
Inventor 崔兴何潮洪朱海丁琦单若妮练伟平刘敏
Owner ZHEJIANG UNIV