Equilibrium of liquid-liquid extraction of 2-phenylbutyric acid enantiomers: Experiment and model
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  • 英文篇名:Equilibrium of liquid-liquid extraction of 2-phenylbutyric acid enantiomers: Experiment and model
  • 作者:Weifeng ; Xu ; Guilin ; Dai ; Kewen ; Tang ; Panliang ; Zhang ; Biquan ; Xiong ; Yu ; Liu
  • 英文作者:Weifeng Xu;Guilin Dai;Kewen Tang;Panliang Zhang;Biquan Xiong;Yu Liu;Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology;
  • 英文关键词:Model;;Simulation;;Enantioselective extraction;;2-Phenylbutyric acid;;Hydrophilic selector
  • 中文刊名:ZHGC
  • 英文刊名:中国化学工程学报(英文版)
  • 机构:Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology;
  • 出版日期:2018-04-15
  • 出版单位:Chinese Journal of Chemical Engineering
  • 年:2018
  • 期:v.26
  • 基金:Supported by the National Basic Research Program of China(2014CB260407)
  • 语种:英文;
  • 页:ZHGC201804005
  • 页数:7
  • CN:04
  • ISSN:11-3270/TQ
  • 分类号:42-48
摘要
The utilization of liquid–liquid extraction for the separation of 2-phenylbutyric acid(2-PBA) enantiomers was proposed. Factors affecting the extract process were investigated, including organic solvents, β-cyclodextrin derivatives, cyclodextrin concentration, p H and temperature. A model was proposed to describe the separation process based on the homogeneous phase reaction mechanism. Important parameters of this model were determined experimentally. The physical distribution coefficients for molecular and ionic 2-PBA were0.129 and 7.455, respectively. The equilibrium constants of the complexation reactions were 89.36 and36.78 L·mol~(-1) for(+)-and(-)-2-PBA, respectively. The model was verified by experiments and proved to be an excellent means to optimize the separation system. Through modeling prediction and experiment, the best conditions(e.g., pH value of 3.00, extractant concentration of 0.1 mol·L~(-1), temperature of 5.0 °C) were acquired. Under this condition, the maximum enantioselectivity(2.096) was obtained.
        The utilization of liquid–liquid extraction for the separation of 2-phenylbutyric acid(2-PBA) enantiomers was proposed. Factors affecting the extract process were investigated, including organic solvents, β-cyclodextrin derivatives, cyclodextrin concentration, p H and temperature. A model was proposed to describe the separation process based on the homogeneous phase reaction mechanism. Important parameters of this model were determined experimentally. The physical distribution coefficients for molecular and ionic 2-PBA were0.129 and 7.455, respectively. The equilibrium constants of the complexation reactions were 89.36 and36.78 L·mol~(-1) for(+)-and(-)-2-PBA, respectively. The model was verified by experiments and proved to be an excellent means to optimize the separation system. Through modeling prediction and experiment, the best conditions(e.g., pH value of 3.00, extractant concentration of 0.1 mol·L~(-1), temperature of 5.0 °C) were acquired. Under this condition, the maximum enantioselectivity(2.096) was obtained.
引文
[1]I.W.Wainer,Drue stereochemistry,2nd ed.,Anal.Methods Pharmacol.,Marcel Dekker,New York,1993.
    [2]H.Y.Aboul-Enein,I.W.Wainer,The Impact of Stereochemistry on Drug Development and Use,Wiley,New York,1997.
    [3]G.T.Liu,K.Nagahama,Application of rapid expansion of supercritical solutions in the crystallization separation,Ind.Eng.Chem.Res.35(1996)4626–4634.
    [4]T.J.Ward,B.A.Baker,Chiral separations,Anal.Chem.80(2008)4363–4372.
    [5]C.A.M.Afonso,J.G.Crespo,Recent advances in chiral resolution through membranebased approaches,Angew.Chem.Int.Ed.43(2004)5293–5295.
    [6]V.Prelog,M.Kovakevic,M.Egli,Lipophilic tartaric acid esters as enantioselective ionophores,Angew.Chem.Int.Ed.Engl.28(1989)1147–1152.
    [7]K.W.Tang,J.M.Yi,Y.B.Liu,X.Y.Jiang,Y.Pan,Enantioselective separation of R,S-phenylsuccinic acid by biphasic recognition chiral extraction,Chem.Eng.Sci.64(2009)4081–4088.
    [8]M.Steensma,N.J.Kuipers,A.B.de Haan,G.Kwant,Influence of process parameters on extraction equilibria for the chiral separation of amines and amino-alcohols with a chiral crown ether,J.Chem.Technol.Biotechnol.81(2006)588–597.
    [9]M.Pietraszkiewicz,M.Kozbia,O.Pietraszkiewicz,Chiral discrimination of amino acids and their potassium or sodium salts by optically active crown ether derived from D-mannose,J.Membr.Sci.138(1998)109–113.
    [10]J.Koska,C.A.Haynes,Modelling multiple chemical equilbria in chiral partition systems,Chem.Eng.Sci.56(2001)5853–5864.
    [11]B.Schuur,J.G.M.Winkelmam,H.J.Heeres,Equilibrium studies on enantioselective liquid-liquid amino acid extraction using a cinchona alkaloid extractant,Ind.Eng.Chem.Res.47(2008)10027–10033.
    [12]H.I.Kim,K.W.Lee,D.Mishra,K.M.Yi,J.H.Hong,M.K.Jun,H.K.Park,Separation of molybdenum and vanadium from oxalate leached solution of spent residue hydrodesulfurization(RHDS)catalyst by liquid–liquid extraction using amine extractant,J.Ind.Eng.Chem.21(2015)1265–1269.
    [13]N.Sunsandee,P.Ramakul,M.Hronec,U.Pancharoen,N.Leepipatpiboon,Mathematical model and experimental validation of the synergistic effect of selective enantioseparation of(S)-amlodipine from pharmaceutical wastewater using a HFSLM,J.Ind.Eng.Chem.20(2014)1612–1622.
    [14]A.J.Hallett,G.J.Kwant,J.G.de Vries,Continuous separation of racemic3,5-dinitrobenzoyl-amino acids in a centrifugal contact separator with the aid of cinchona-based chiral host compounds,Chem.A Eur.J.15(2009)2111–2120.
    [15]B.Schuur,J.G.M.Winkelmam,H.J.Heeres,Equilibrium studies on enantioselective liquid-liquid amino acid extraction using a cinchona alkaloid extractant,Ind.Eng.Chem.Res.47(2008)10027–10033.
    [16]X.Chen,J.Wang,F.Jiao,Efficient enantioseparation of phenylsuccinic acid enantiomers by aqueous two-phase system-based biphasic recognition chiral extraction:phase behaviors and distribution experiments,Process Biochem.9(2015)1468–1478.
    [17]P.Zhang,J.Luo,K.Tang,J.Yi,C.Yang,Kinetics study on reactive extraction of d-p-hydroxyphenylglycine by BINAP–palladium complex in Lewis cell,Chem.Eng.Process:Process Intensif.93(2015)50–55.
    [18]S.E.Evans,P.Davies,A.Lubben,B.Kasprzyk-Hordern,Determination of chiral pharmaceuticals and illicit drugs in wastewater and sludge using microwave assisted extraction,solid-phase extraction and chiral liquid chromatography coupled with tandem mass spectrometry,Anal.Chim.Acta 882(2015)112–126.
    [19]A.Holbach,J.Godde,R.Mahendrarajah,N.Kockmann,Enantioseparation of chiral aromatic acids in process intensified liquid–liquid extraction columns,AICh E J.61(2015)266–276.
    [20]B.J.Verkuijl,A.J.Minnaard,J.G.de Vries,B.L.Feringa,Chiral separation of underivatized amino acids by reactive extraction with palladium-BINAP complexes,J.Org.Chem.74(2009)6526–6533.
    [21]K.Tang,G.Wu,P.Zhang,C.Zhou,J.Liu,Experimental and model study on enantioselective extraction of phenylglycine enantiomers with BINAP-metal complexes,Ind.Eng.Chem.Res.51(2012)15233–15241.
    [22]M.Asztemborska,M.Mi?kiewicz,D.Sybilska,Separation of some chiral flavanones by micellar electrokinetic chromatography,Electrophoresis 24(2003)2527–2531.
    [23]C.Akbay,S.A.A.Rizvi,S.A.Shamsi,Simultaneous enantioseparation and tandem UV-MS detection of eightβ-blockers in micellar electrokinetic chromatography using a chiral molecular micelle,Anal.Chem.77(2005)1672–1683.
    [24]S.Fanali,Enantioselective determination by capillary electrophoresis with cyclodextrins as chiral selectors,J.Chromatogr.A 875(2000)89–122.
    [25]K.Tang,H.Zhang,Y.Liu,Experimental and simulation on enantioselective extraction in centrifugal contactor separators,AICh E J.59(2013)2594–2602.
    [26]G.Wang,L.Yang,F.Wu,N.Deng,Carboxymethyl-β-cyclodextrin enhanced Ti O2removal of acid red R and lead ions in suspended solutions,J.Chem.Technol.Biotechnol.89(2014)297–304.
    [27]Z.Ren,Y.Zeng,Y.Hua,Y.Cheng,Z.Guo,Enantioselective liquid-liquid extraction of racemic ibuprofen by L-tartatic acid derivatives,J.Chem.Eng.Data 59(2014)2517–2522.
    [28]J.Szejtli,Cyclodextrins and their Inclusion Complexes,Akademiai Kiado,Budapest,1982.
    [29]Y.Yamashoji,T.Ariga,S.Asano,M.Tanaka,Chiral recognition and enantiomeric separation of alanineβ-naphthylamide by cyclodextrins,Anal.Chim.Acta 268(1992)39–47.
    [30]K.Tang,P.Zhang,C.Pan,H.Li,Equilibrium studies on enantioselective extraction of oxybutynin enantiomers by hydrophilic-β-cyclodextrin derivatives,AICh E J.57(2011)3027–3036.
    [31]Y.Zheng,J.Yan,S.Tong,X.Li,C.Chu,High performance liquid chromatographic enantioseparation of 2-phenylpropionic acid chiral mobile phase additive,Chin.J.Pharm.Anal.33(2013)827–830.
    [32]T.O'Brien,L.Crocker,R.Thompson,K.Thompson,P.H.Toma,D.A.Conlon,B.Feibush,C.Moeder,G.Bicker,N.Grinberg,Mechanistic aspects of chiral discrimination on modified cellulose,Anal.Chem.69(1997)1999–2007.
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