Equilibrium studies on liquid-liquid reactive extraction of phenylsuccinic acid enantiomers using hydrophilic β-CD derivatives extractants

Chinese Journal of Chemical Engineering

Volumn 19, Issue 3, 2011, Pages 397-403

  Tang, Kewen ^a   Miao, Jiabing ^b   Zhou, Tao ^b   Liu, Yongbing ^a  

^a HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY   (China)

^b CENTRAL SOUTH UNIVERSITY   (China)

Author keywords

Enantiomer resolution; Phenylsuccinic acid enantiomers; Solvent extraction; CD derivatives

Indexed keywords

CHIRALITY; CYCLODEXTRINS; ENANTIOMERS; HYDROPHILICITY; LIQUIDS; SEPARATION; SOLVENT EXTRACTION; STEREOCHEMISTRY;

CHIRAL SEPARATIONS; CYCLODEXTRIN DERIVATIVES; ENANTIOMER RESOLUTION; OPTIMAL CONDITIONS; PHENYLSUCCINIC ACIDS; REACTIVE EXTRACTION; RECOGNITION ABILITIES; SEPARATION ABILITY;

EXTRACTION;

EID: 84860395378     PISSN: 10049541     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1004-9541(09)60227-5     Document Type: Article

References (26)

1. Wang, X.J., Wiehler, H., Ching, C.B., "Physicochemical properties and the crystallization thermodynamics of the pure enantiomer and the racemate for n-methylephedrine", J Chem Eng Data, 48, 1092-1098
2. Wang, X., Wang, X.J., Ching, C.B., "Solubility, metastable zone width, and racemic characterization of propanolol hydrochloride", Chirality, 14, 318-324 (2002). (Pubitemid 34326737)
3. Tang, K.W., Chen, Y.Y., Huang, K.L., Liu, J.J., "Enantioselective resolution of chiral aromatic acids by biphasic recognition chiral extraction", Tetrahedron: Asymmetry, 18, 2399-2408 (2007).
4. Yokota, M., Doki, N., Shimizu, K., "Chiral separation of a racemic compound induced by transformation of racemic crystal structures: DL-glutamic acid", Cryst. Growth Des., 6, 1588-1590 (2006). (Pubitemid 44166188)
5. Gübitz, G., Schmid, M.G., "Chiral separation by capillary electromigration techniques", J Chromatogr A, 1204, 140-156 (2008).
6. Hefnawy, M.M., Aboul-Enein, H.Y., "A validated LC method for the determination of vesamicol enantiomers in human plasma using vancomycin chiral stationary phase and solid phase extraction", J. Pharm. Biomed. Anal. 35, 535-543 (2004). (Pubitemid 38609373)
7. Houlton, S., "Resolution and racemisation of chiral drugs", Manuf. Chem., 72, 16-17 (2001).
8. Maier, N.M., Franco, P., Lindner, W., "Separation of enantiomers: needs, challenges, perspectives", J. Chromatogr. A, 906, 3-33 (2001).
9. Steensma, M., Kuipers, N.J.M., De Haan, A.B., Kwant, G., "Modelling and experimental evaluation of reaction kinetics in reactive extraction for chiral separation of amines, amino acids and amino-alcohols", Chem. Eng. Sci., 62, 1395-1407 (2007). (Pubitemid 46109433)
10. Viegas, R.M.C., Afonso, C.A.M., Crespo, J.G., Coelhoso, I.M., "Modelling of the enantio-selective extraction of propranolol in a biphasic system", Sep. Purif. Technol., 53, 224-234 (2007). (Pubitemid 46108661)
11. Ward, T.J., Baker, B.A., "Chiral Separations", Anal. Chem., 80, 4363-4372 (2008). (Pubitemid 351842326)
12. Huerta, F.F., Backvall, J.E., "Enantioselective synthesis of beta-hydroxy acid derivatives via a one-pot aldol reaction-dynamic kinetic resolution", Org. Lett., 3, 1209-1212 (2001). (Pubitemid 33627101)
13. Ginesta, X., Pericas, M.A., Riera, A., "Straightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain", Tetrahedron Lett., 43, 779-782 (2002).
14. Yang, G.S., Ying, L., Ou, Z.M., Yao, S.J., "Resolution of ibuprofen ester by catalytic antibodies in water-miscible organic-solvents", Chin. J. Chem. Eng., 17 (3), 506-512 (2009).
15. Makino, K., Goto, T., Hiroki, Y., Hamada, Y., "Stereoselective synthesis of anti-beta-hydroxy-alpha-amino acids through dynamic kinetic resolution", Angew Chem. Int. Ed., 43, 882-884 (2004). (Pubitemid 39256221)
16. De Haan, A.B., Simandi, B., "Extraction technology for the separation of optical isomers", Ion Exchange Solvent Extraction, 15, 255-294 (2002).
17. Keurentjes ,J.T.F., Nabuurs, L.W.M., Vegter, E.A., "Liquid membrane technology for the separation of racemic mixtures", J. Membr. Sci., 113, 354-360 (1996).
18. Tang, K.W., Song, L.T., Liu, Y.B., Jiang, X.Y., Pan, Y., "Separation of flurbiprofen enantiomers by biphasic recognition chiral extraction", Chem. Eng. J., 158, 411-417 (2010).
19. Yamauchi, A., Hayashita, T., Kato, A., Nishizawa, S., Watanabe, M., Teramae, N., "Selective potassium ion recognition by benzo-15-crown-5 fluoroionophore β-cyclodextrin complex sensors in water", Anal. Chem., 72, 5841-5846 (2000). (Pubitemid 32002339)
20. Wang, X., Zeng, H.L., Wei ,Y.L., Li, J.M., "A reversible fluorescence sensor based on insoluble β-cyclodextrinpolymer for direct determination of bisphenol A (BPA)", Sens. Actuators B, 114, 565-572 (2006).
21. Zhang, X.B., Guo, C.C., Li, Z.Z., Shen, G.L, Yu, R.Q., "An opticalfiber chemical sensor for mercury ions based on a porphyrin dimmer", Anal. Chem., 74, 821-825 (2002).
22. Vladimir, P., Miće, K., Martin, E., "Lipophilic tartaric acid esters as enantioselective ionophores", Angew Chem., 28, 1147-1152 (1989).
23. Lynam, C., Jennings, K., Nolan, K., Kane, P., McKervey, M.A., Diamond, D., "Tuning and enhancing enantioselective quenching of calixarene hosts by chiral guest amines", Anal. Chem., 74, 59-66 (2002). (Pubitemid 34044424)
24. Rekharsky, M.V., Inoue, Y., "Complexation thermodynamics of cyclodextrins", Chem. Rev., 98, 875-1918 (1998).
25. Meindersma, G.W., van Schoonhoven, T., Kuzmanovic, B., de Haan, A.B., "Extraction of toluene, o-xylene from heptane and benzyl alcohol from toluene with aqueous cyclodextrins", Chem. Eng. Process, 45, 175-183 (2006).
26. Tang, K.W., Yi, J.M., Liu, Y.B., Jiang, X.Y., Pan, Y., "Enantioselective separation of R,S-phenylsuccinic acid by biphasic recognition chiral extraction", Chem. Eng. Sci., 64, 4081-4088 (2009).