| Flurbiprofen is a kind of non-steroidal anti-inflammatory drug which has been widely used in clinic.It has been reported that S-flurbiprofen shows good performance on clinic rheumatoid arthritis and osteoarthritis treatment.R-enantiomer almost has no anti-inflammatory pharmacological activities while it has a certain therapeutic effect on Helmer's disease and inhibiting tumor growth.It has important practical values to obtain optically pure flurbiprofen enantiomers.Recently,chiral ionic liquids have been widely applied in chiral separation process because of good structural designability and chiral recognize ability.And the related studies have sustained grown.In this work,the enantioseparation of flurbiprofen was studied with chiral ionic liquids as chiral selectorsThe main content can be summarized as follows1.The interaction mechanism between chiral selectors and enantiomers was explored by the assistant of quantum chemistry calculations.And the interaction forces and interaction energies between different chiral amino acid ionic liquids and flurbiprofen enantiomers were also analyzed.The results can be used for the guidance of chiral ionic liquid selection.The complexation energy difference(?E)between enantiomers can evaluate the separation ability of selectors and the simulation results showed that 1-butyl-3-methylimidazolium L-tryptophan([BMIM][L-trp])has better recognition ability.It was verified by extraction experiments that the extraction system containing[BMIM][L-trp]has the higher enantioselectivity for flurbiprofen The influences of the organic solvent,the concentration of chiral extractant,the concentration of drug enantiomers,the pH of aqueous phase and the temperature on enantioseparation were also investigated.Moreover,a reverse extraction process was also carried out to separate and recover the aqueous phase with chiral ionic liquid2.To further improve the enantioselectivity,the biphasic recognition chiral extraction(BRCE)systems for flurbiprofen were performed with[BMIM][L-trp]as hydrophilic selector and tartaric ester as lipophilic selector.The influence of tartaric ester was investigated by extraction experiments and the interaction between selector and flubiprofen was further analyzed by quantum chemistry calculations.D-dioctyl tartrate was selected as the suitable chiral selector.The influences of organic solvent,D-dioctyl tartrate concentration,flurbiprofen concentration,temperature were also investigated.The enantioselectivity of BRCE were improved by synergistic extraction,compared with that of monophasic recognition,3.The liquid-liquid extraction system for flurbiprofen contains chiral ionic liquid and chiral ionic liquid mixtures system.And its industrialization process needs large amounts of basic physical properties data.Compared with the density and viscosity,the thermal conductivity measurements of chiral ionic liquids have been rarely reported.In this chapter,the thermal conductivities of[BMIM][L-trp]+water,[BMIM][L-trp]+ethanol,water+ethanol,[BMIM][L-trp]+methanol and[BMIM][L-trp]+water+ ethanol have been determined at room pressure from 283.15 K to 333.15 K.The experimental data were correlated by second-order Scheffe polynomial with high accuracy.4.To recycle the chiral ionic liquid and save costs,the immobilized imidazolium-based L-tryptophan ionic liquid was prepared using chemical bonding method.The influences of carrier type,solvent and material ratio were investigated.The products were characterized by Fourier transform infrared(FTIR),thermogravimetric analysis(TGA)and scanning electron microscope(SEM).The immobilized chiral ionic liquid was applied to the adsorption separation of flurbiprofen enantiomers in solution.The influence of flurbiprofen concentration,temperature,adsorption time and pH were investigated.The kinetic model and adsorption isotherm model were used to correlate the experimental data. |
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