Preparation, characterization and application of β-cyclodextrin-glutaraldehyde crosslinked membrane for the enantiomeric separation of amino acids

Desalination

Volumn 298, Issue , 2012, Pages 13-21

  Singh, Kripal ^a   Ingole, Pravin G ^a   Bajaj, Hari C ^a   Gupta, Hariom ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

Cyclodextrin; Amino acids; Crosslinked membrane; Glutaraldehyde; Optical resolution

Indexed keywords

ATR FTIR; ATTENUATED TOTAL REFLECTANCE FOURIER TRANSFORM INFRARED SPECTROSCOPY; CHIRAL ENVIRONMENT; CROSS LINKED MEMBRANES; CROSSLINKED; CROSSLINKED STRUCTURES; ENANTIOMER SEPARATION; ENANTIOMERIC SEPARATION; GLUTARALDEHYDES; HYDROGEN BONDING INTERACTIONS; MEMBRANE CHARACTERISTICS; N ,N-DIMETHYLFORMAMIDE; OPTICAL RESOLUTION; PHASE INVERSION TECHNIQUES; POLYSULFONE MEMBRANES; XRD STUDIES;

ALDEHYDES; AMIDES; AMINO ACIDS; ATOMIC FORCE MICROSCOPY; CHIRALITY; DEGRADATION; ENANTIOMERS; ENANTIOSELECTIVITY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROGEN BONDS; SCANNING ELECTRON MICROSCOPY; SEPARATION; X RAY DIFFRACTION;

MEMBRANES;

ALDEHYDE; AMINO ACID; DEGRADATION; HYDROGEN; MEMBRANE; OSMOSIS; POLYMER; SEPARATION;

EID: 84862172604     PISSN: 00119164     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.desal.2012.04.023     Document Type: Article

References (46)

1. Keurentjes J.T.F., Nabuurs L.J.W.M., Vegter E.A. Liquid membrane technology for the separation of racemic mixtures. J. Membr. Sci. 1996, 113:351-360.
2. Fogassy E., Nogradi M., Kozma D., Egri G., Palovics E., Kiss V. Optical resolution methods. Org. Biomol. Chem. 2006, 4:3011-3030.
3. Jacques J., Collet A. Enantiomers, Racemates and Resolutions 1981, Wiley Interscience, New York. 2nd Ed.
4. Haginaka J. Enantiomer separation of drugs by capillary electrophoresis using proteins as chiral selectors. J. Chromatogr. A 2000, 875:235-254.
5. Mack M., Hauck H.E. Separation of enantiomers in thin-layer chromatography. Chromatographia 1988, 26:197-205.
6. Pietraszkiewicz M., Kozbial M., Pietraszkiewicz O. Chiral discrimination of amino acids and their potassium or sodium salts by optically active crown ether derived from d-mannose. J. Membr. Sci. 1998, 138:109-113.
7. Maier N.M., Franco P., Lindner W. Separation of enantiomers: needs, challenges, perspectives. J. Chromatogr. A 2001, 906:3-33.
8. Thoelen C., De bruyn M., Theunisse E., Vankelecom I.F.J., Yoshikawa M., Jacobs P.A. Membranes based on poly (γ-methyl-l-glutamate): synthesis, characterization and use in chiral separations. J. Membr. Sci. 2001, 186:153-163.
9. Aoki T., Shinohara K., Oikawa E. Optical resolution through the solid membrane from (+)-poly {1-[dimethyl(10-pinanyl)-silyl]-1-propyne}. Macromol. Chem. Rapid Commun. 1992, 13:565-570.
10. Aoki T., Tomizawa S., Oikawa E. Enantioselective permeation through poly(γ-[3-(pentamethyldisiloxanyl) propyl]-l-glutamate) membranes. J. Membr. Sci. 1995, 99:117-125.
11. Aoki T., Maruyama A., Shinohara K., Oikawa E. Optical resolution by use of surface modified poly(methyl methacrylate) membrane containing (-)-oligo(methyl(10-pinanyl) siloxane). Polymer 1995, 27:547-550.
12. Mandal D.K., Guha A.K., Sirkar K.K. Isomer separation by a hollow fiber contained liquid membrane permeator. J. Membr. Sci. 1998, 144:13-24.
13. Canet L., Vanel P., Aouad N., Tronel-Peyroz E., Palmeri J., Seta P. Impedance and electrical potential across supported liquid membranes: role of interfacial potentials on the active transport of a metal cation. J. Membr. Sci. 1999, 163:109-121.
14. Armstrong D.W., Jin H.L. Enrichment of enantiomers and other isomers with aqueous liquid membranes containing cyclodextrin carriers. Anal. Chem. 1987, 59:2237-2241.
15. K. Singh, P.G. Ingole, H.C. Bajaj, A method for preparation enantioselective composite membrane. Patent Number(s): WO2010109490-A1; IN200900629-I1.
16. Ingole P.G., Singh K., Bajaj H.C. Enantioselective polymeric composite membrane for optical resolution of racemic mixtures of α-amino acids. Sep. Sci. Technol. 2011, 46:1898-1907.
17. Ingole P.G., Singh K., Bajaj H.C. Enantioselective permeation of α-amino acid isomers through polymer membrane containing chiral metal-Schiff base complexes. Desalination 2011, 281:413-421.
18. van der Ent E.M., van't Riet K., Keurentjes J.T.F., van der Padt A. Design criteria for dense permeation-selective membranes for enantiomer separations. J. Membr. Sci. 2001, 185:207-221.
19. Singh K., Bajaj H.C., Ingole P., Bhattacharya A. Comparative study of enantioseparation of racemic tryptophan by ultrafiltration using BSA-immobilized and BSA-interpenetrating network polysulfone membranes. Sep. Sci. Technol. 2010, 45:346-354.
20. Ingole P.G., Singh K., Bajaj H.C. Optical resolution of α-amino acid derivative through membrane process. Ind. J. Chem. Technol. 2011, 18:197-206.
21. Singh K., Ingole P.G., Bajaj H.C., Bhattacharya A., Brahmbhatt H.R. Optical resolution of α-amino acids by reverse osmosis using enantioselective polymer membrane containing chiral metal-Schiff base complex. Sep. Sci. Technol. 2010, 45:1374-1384.
22. Singh K., Ingole P.G., Bhrambhatt H., Bhattacharya A., Bajaj H.C. Preparation, characterization and performance evaluation of chiral selective composite membranes. Sep. Purif. Technol. 2011, 78:138-146.
23. Singh K., Ingole P.G., Chaudhari J., Bhrambhatt H., Bhattacharya A., Bajaj H.C. Resolution of racemic mixture of α-amino acid derivative through composite membrane. J. Membr. Sci. 2011, 378:531-540.
24. Szejtli J. Cyclodextrin and Their Inclusion Complexes 1982, Akademiai, Kiado, Budapest.
25. Cramer F., Dietsche W. Occlusion compounds. XV. Resolution of racemates with cyclodextrins. Chem. Ber. 1959, 92:378-384.
26. Szejtli J. Cyclodextrin Technology 1988, Kluwer, Boston.
27. Breslow R. Adv. Chemother. Ser. 1980, 191:1.
28. Saenger W. Cyclodextrin inclusion compounds in research and industry. Angew. Chem. Int. Ed. 1980, 19:344-362.
29. Inclusion Compounds 1984, 3:331. Academic Press, New York. J. Szejtli, J.L. Atwood, J.E.D. Davies, D. Mac Nicol (Eds.).
30. Chiral Separation by HPLC 1982, Wiley, New York. D. Sybilska, J. Zukowaik, A.M. Krstulovic (Eds.).
31. Chiral Liquid Chromatography 1989, Blackie, London. L. Coventry, W.J. Lough (Eds.).
32. Sreenivasan K. Absorption characteristics of a novel semi-IPN membrane based on β-cyclodextrin toward testosterone and progesterone. J. Appl. Polym. Sci. 1996, 60:2245-2252.
33. Marchese J., Pagliero C.L. Characterization of asymmetric polysulfone membranes for gas separation. Gas Sep. Purif. 1991, 5:215.
34. Chiral Separation by Liquid Chromatography 1991, American Chemical Society, Washington. S. Ahuja (Ed.).
35. Kim A.S., Chen H. Diffusive tortuosity factor of solid and soft cake layers: a random walk simulation approach. J. Membr. Sci. 2006, 279:129-139.
36. Hadik P., Szabbb L.P., Nagy E. d,l-lactic acid and d,l-alanine enantioseparation by membrane process. Desalination 2002, 148:193-198.
37. Williams M.E. A Review of Reverse Osmosis Theory 2003, EET Corporation and Williams Engineering Services Company, Inc.
38. Leob S., Sourirajan S. Reverse Osmosis 1985, National Research Council of Canada, Ottawa, Canada.
39. Masuelli M.A., Grasselli M., Marchese J., Ochoa N.A. Preparation, structural and functional characterization of modified porous PVDF membranes by γ-irradiation. J. Membr. Sci. 2012, 389:91-98.
40. Singh K., Bhattacharya A. Porometric study of polysulfone membranes and their co-relation with the performance. J. Indian Chem. Soc. 2006, 83:201-204.
41. Darcy H. Les Fontaines Publiques de le Ville deDijon 1956, Victor Delmont, Paris.
42. Kraume M., Meng F. Fouling in Membrane Processes Used for Water and Wastewater Treatment, Membrane Technologies and Applications 2011, CRC Press, pp. 231-253.
43. Wakeman R.J., Tarleton E.S. Solid Liquid Separation, Principal of Industrial Separation 2005.
44. Dalgliesh C.E. The optical resolution of aromatic amino acids on paper chromatograms. J. Chem. Soc. 1952, 137:3940-3942.
45. Hadik P., Szabó L.-P., Nagy E., Farkas Zs. Enantioseparation of D,L-lactic acid by membrane techniques. J. Membr. Sci. 2005, 251:223-232.
46. Xie R., Chu L.Y., Deng J.G. Membranes and membrane processes for chiral resolution. Chem. Soc. Rev. 2008, 37:1243-1263.