Equilibrium Studies on Liquid-Liquid Reactive Extraction of Phenylsuccinic Acid Enantiomers Using Hydrophilicβ-CD Derivatives Extractants
This paper deals with the enantioseparation of phenylsuccinic acid（H2A）enantiomers by liquid-liquid reactive extraction usingβ-CD derivatives as aqueous selectors.Cyclodextrin and its derivatives can interact with guest molecules selectively to form complexes with different stabilities.Cyclodextrin...
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| Published in | Chinese journal of chemical engineering Vol. 19; no. 3; pp. 397 - 403 |
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| Main Author | |
| Format | Journal Article |
| Language | English |
| Published |
Elsevier B.V
01.06.2011
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| Subjects | |
| Online Access | Get full text |
| ISSN | 1004-9541 2210-321X |
| DOI | 10.1016/S1004-9541(09)60227-5 |
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| Abstract | This paper deals with the enantioseparation of phenylsuccinic acid（H2A）enantiomers by liquid-liquid reactive extraction usingβ-CD derivatives as aqueous selectors.Cyclodextrin and its derivatives can interact with guest molecules selectively to form complexes with different stabilities.Cyclodextrin derivatives are not soluble in organic liquids,but highly soluble in water.In this work,hydroxypropyl-β-cyclodextrin（HP-β-CD）,hydroxyethyl- β-cyclodextrin（HE-β-CD）and methyl-β-cyclodextrin（Me-β-CD）were selected as chiral selectors in aqueous phase for the reactive extraction of phenylsuccinic acid enantiomers from organic phase to aqueous phase.The results show that the efficiency of the extraction depends,often strongly,on a number of process variables,including the types of organic solvents andβ-CD derivatives,the concentrations of the extractants and H2A enantiomers,pH and temperature.HP-β-CD,HE-β-CD and Me-β-CD have stronger recognition abilities for R-phenylsuccinic acid than for S-phenylsuccinic acid.Among the three kinds ofβ-CD derivatives,HP-β-CD has the strongest separation ability. Excellent enantioseparation was achieved under the optimal conditions of pH of 2.5 and temperature of 5°C with a maximum enantioselectivity（a）of 2.38.Reactive extraction of enantiomers with hydrophilicβ-CD derivatives is of strong chiral separation ability and can be hopeful for separations of various enantiomers at a large-scale. |
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| AbstractList | This paper deals with the enantioseparation of phenylsuccinic acid (H sub(2)A) enantiomers by liquid-liquid reactive extraction using beta -CD derivatives as aqueous selectors. Cyclodextrin and its derivatives can interact with guest molecules selectively to form complexes with different stabilities. Cyclodextrin derivatives are not soluble in organic liquids, but highly soluble in water. In this work, hydroxypropyl- beta -cyclodextrin (HP- beta -CD), hydroxyethyl- beta -cyclodextrin (HE- beta -CD) and methyl- beta -cyclodextrin (Me- beta -CD) were selected as chiral selectors in aqueous phase for the reactive extraction of phenylsuccinic acid enantiomers from organic phase to aqueous phase. The results show that the efficiency of the extraction depends, often strongly, on a number of process variables, including the types of organic solvents and beta -CD derivatives, the concentrations of the extractants and H sub(2)A enantiomers, pH and temperature. HP- beta -CD, HE- beta -CD and Me- beta -CD have stronger recognition abilities for R-phenylsuccinic acid than for S-phenylsuccinic acid. Among the three kinds of beta -CD derivatives, HP- beta -CD has the strongest separation ability. Excellent enantioseparation was achieved under the optimal conditions of pH of 2.5 and temperature of 5 degree C with a maximum enantioselectivity (a) of 2.38. Reactive extraction of enantiomers with hydrophilic beta -CD derivatives is of strong chiral separation ability and can be hopeful for separations of various enantiomers at a large-scale. This paper deals with the enantioseparation of phenylsuccinic acid (H 2A) enantiomers by liquid-liquid reactive extraction using β-CD derivatives as aqueous selectors. Cyclodextrin and its derivatives can interact with guest molecules selectively to form complexes with different stabilities. Cyclodextrin derivatives are not soluble in organic liquids, but highly soluble in water. In this work, hydroxypropyl- β-cyclodextrin (HP- β-CD), hydroxyethyl- β-cyclodextrin (HE- β-CD) and methyl- β-cyclodextrin (Me- β-CD) were selected as chiral selectors in aqueous phase for the reactive extraction of phenylsuccinic acid enantiomers from organic phase to aqueous phase. The results show that the efficiency of the extraction depends, often strongly, on a number of process variables, including the types of organic solvents and β-CD derivatives, the concentrations of the extractants and H 2A enantiomers, pH and temperature. HP- β-CD, HE- β-CD and Me- β-CD have stronger recognition abilities for R-phenylsuccinic acid than for S-phenylsuccinic acid. Among the three kinds of β-CD derivatives, HP- β-CD has the strongest separation ability. Excellent enantioseparation was achieved under the optimal conditions of pH of 2.5 and temperature of 5°C with a maximum enantioselectivity ( a) of 2.38. Reactive extraction of enantiomers with hydrophilic β-CD derivatives is of strong chiral separation ability and can be hopeful for separations of various enantiomers at a large-scale. This paper deals with the enantioseparation of phenylsuccinic acid（H2A）enantiomers by liquid-liquid reactive extraction usingβ-CD derivatives as aqueous selectors.Cyclodextrin and its derivatives can interact with guest molecules selectively to form complexes with different stabilities.Cyclodextrin derivatives are not soluble in organic liquids,but highly soluble in water.In this work,hydroxypropyl-β-cyclodextrin（HP-β-CD）,hydroxyethyl- β-cyclodextrin（HE-β-CD）and methyl-β-cyclodextrin（Me-β-CD）were selected as chiral selectors in aqueous phase for the reactive extraction of phenylsuccinic acid enantiomers from organic phase to aqueous phase.The results show that the efficiency of the extraction depends,often strongly,on a number of process variables,including the types of organic solvents andβ-CD derivatives,the concentrations of the extractants and H2A enantiomers,pH and temperature.HP-β-CD,HE-β-CD and Me-β-CD have stronger recognition abilities for R-phenylsuccinic acid than for S-phenylsuccinic acid.Among the three kinds ofβ-CD derivatives,HP-β-CD has the strongest separation ability. Excellent enantioseparation was achieved under the optimal conditions of pH of 2.5 and temperature of 5°C with a maximum enantioselectivity（a）of 2.38.Reactive extraction of enantiomers with hydrophilicβ-CD derivatives is of strong chiral separation ability and can be hopeful for separations of various enantiomers at a large-scale. |
| Author | 唐课文 苗家兵 周涛 刘永兵 |
| AuthorAffiliation | Department of Chemistry and Chemical Engineering, Htman Institute of Science and Technology, Yueyang 414006, China College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China |
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| Cites_doi | 10.1016/S0040-4039(01)02271-7 10.1016/j.tetasy.2007.09.031 10.1021/cg050579i 10.1021/ol015682p 10.1021/ac010153k 10.1021/cr970015o 10.1016/j.ces.2006.11.043 10.1016/j.chroma.2008.07.071 10.1021/ac0109218 10.1016/j.snb.2005.06.020 10.1016/S1004-9541(08)60238-4 10.1002/anie.198911473 10.1016/0376-7388(95)00176-X 10.1016/j.cep.2005.06.009 10.1016/S0021-9673(00)00532-X 10.1002/anie.200353072 10.1021/je020176b 10.1002/chir.10049 10.1021/ac000741i 10.1016/j.seppur.2006.07.010 10.1021/ac800662y 10.1016/j.cej.2010.01.009 10.1016/j.ces.2009.06.029 10.1016/j.jpba.2004.01.017 |
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| Keywords | solvent extraction enantiomer resolution β-CD derivatives phenylsuccinic acid enantiomers |
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| Notes | This paper deals with the enantioseparation of phenylsuccinic acid（H2A）enantiomers by liquid-liquid reactive extraction usingβ-CD derivatives as aqueous selectors.Cyclodextrin and its derivatives can interact with guest molecules selectively to form complexes with different stabilities.Cyclodextrin derivatives are not soluble in organic liquids,but highly soluble in water.In this work,hydroxypropyl-β-cyclodextrin（HP-β-CD）,hydroxyethyl- β-cyclodextrin（HE-β-CD）and methyl-β-cyclodextrin（Me-β-CD）were selected as chiral selectors in aqueous phase for the reactive extraction of phenylsuccinic acid enantiomers from organic phase to aqueous phase.The results show that the efficiency of the extraction depends,often strongly,on a number of process variables,including the types of organic solvents andβ-CD derivatives,the concentrations of the extractants and H2A enantiomers,pH and temperature.HP-β-CD,HE-β-CD and Me-β-CD have stronger recognition abilities for R-phenylsuccinic acid than for S-phenylsuccinic acid.Among the three kinds ofβ-CD derivatives,HP-β-CD has the strongest separation ability. Excellent enantioseparation was achieved under the optimal conditions of pH of 2.5 and temperature of 5°C with a maximum enantioselectivity（a）of 2.38.Reactive extraction of enantiomers with hydrophilicβ-CD derivatives is of strong chiral separation ability and can be hopeful for separations of various enantiomers at a large-scale. solvent extraction; enantiomer resolution; β-CD derivatives; phenylsuccinic acid enantiomers 11-3270/TQ TANG Kewen1,MIAO Jiabing 2 ,ZHOU Tao 2 and LIU Yongbing 1 1Department of Chemistry and Chemical Engineering,Hunan Institute of Science and Technology,Yueyang 414006,China2 College of Chemistry and Chemical Engineering,Central South University,Changsha 410083,China ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 23 |
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| Snippet | This paper deals with the enantioseparation of phenylsuccinic acid（H2A）enantiomers by liquid-liquid reactive extraction usingβ-CD derivatives as aqueous... This paper deals with the enantioseparation of phenylsuccinic acid (H 2A) enantiomers by liquid-liquid reactive extraction using β-CD derivatives as aqueous... This paper deals with the enantioseparation of phenylsuccinic acid (H sub(2)A) enantiomers by liquid-liquid reactive extraction using beta -CD derivatives as... |
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| SubjectTerms | Chemical engineering Cyclodextrins Derivatives enantiomer resolution Enantiomers Liquid-liquid extraction phenylsuccinic acid enantiomers Selectors Separation solvent extraction β-CD derivatives β-环糊精衍生物 亲水性 对映体 提取液 羟丙基-β-环糊精 苯基 萃取剂 |
| Title | Equilibrium Studies on Liquid-Liquid Reactive Extraction of Phenylsuccinic Acid Enantiomers Using Hydrophilicβ-CD Derivatives Extractants |
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