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Ketoprofen and mandelic acid enantiomers of chiral separation

Author: TianFengJuan
Tutor: JiangXinYu
School: Central South University
Course: Analytical Chemistry
Keywords: Biphasic Recognition Chiral extraction High - speed countercurrent chromatography Ketoprofen Mandelic acid
CLC: TQ463.2
Type: Master's thesis
Year: 2010
Downloads: 164
Quote: 1
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Abstract


In this paper, the chiral separation of racemic ketoprofen and mandelic acid two chiral drugs. Following major elements: 1. Chiral selector tartaric acid ester synthesis: experimental to L, D-tartaric acid and fatty alcohol for the synthesis of a series of chiral selector L, D-tartaric acid esters, and the target product was Infrared Characterization ; L-tartaric acid and isobutanol was synthesized from L-tartaric acid, isobutyl, for example, the amount of water-carrying agent, the molar ratio, catalyst amount and type of synthesis yield. The experimental results show that the optimum reaction conditions were as follows: the molar ratio of 2.8:1, the catalyst is 1.0g p-toluenesulfonic acid, with liquid toluene (45 mL). Biphasic Recognition Chiral Extraction Separation of ketoprofen enantiomers: study the distribution behavior of ketoprofen dissolved tartaric acid esters of organic phase and beta-cyclodextrin derivative in the aqueous phase extraction system; investigated organic solvents, tartaric acid esters and the type of cyclodextrin derivatives, extractant concentration and pH of factors such as the effect of separation. The experimental results show that: the beta-cyclodextrin derivative of the first identification of the S-enantiomer instead of the R-enantiomer, but the recognition ability of the L-tartrate opposite; 1,2 - dichloroethane as an organic solvent, Preferably, the extraction effect of the methyl-beta-cyclodextrin and L-tartaric acid, Titanium Dioxide chiral extractant; extractant concentration and pH value of the separation effect is significantly affected; trimethyl-beta-cyclodextrin Titanium Dioxide concentration and L-tartaric acid, respectively 0.1mol / L and 0.2 mol / L aqueous phase pH = 2.5 hours, the best separation effect. 3 bis (2 - ethylhexyl) phosphoric acid and tartaric acid derivatives mapping monomer complex extraction split mandelic acid enantiomers: study mandelic acid enantiomers containing di (2 - ethylhexyl) phosphoric acid (D2EHPA) tartaric acid derivatives map monomer complex chiral selector n-octanol and water two-phase systems extraction allocation behavior, tartaric acid derivatives mapping monomer types, the initial concentration of the initial concentration of D2EHPA, mandelic acid The initial concentration of the partition coefficient and separation factor. The experiments show that: the use of the composite chiral selector body can greatly improve the distribution coefficient and separation factor; mandelic acid and the concentration of the chiral selector is also relatively large influence on the distribution coefficient and separation factor. 4 high-speed countercurrent chromatography (HSCCC) Chiral separation of mandelic acid enantiomers explore: experiment by n-hexane - ethyl acetate - isopropanol - water at a different ratio HSCCC separation of the solvent system, the choice of L -DBTA and D-isobutyl tartrate as a chiral selector HSCCC chiral separation of mandelic acid enantiomers. Experimental results show that: the choice of solvent system of stationary phase retention rate reached 50% or more, but the racemate separation ineffective. Caused by the above results may be due to: the solvent system or inappropriate ratio; little different configuration of chiral selector of racemic selective difference or the amount added is not enough; chiral selector in the stationary phase. poor solubility; low speed countercurrent chromatography separation efficiency.

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