Optical resolution of racemic lysine monohydrochloride by novel enantioselective thin film composite membrane

Desalination

Volumn 305, Issue , 2012, Pages 54-63

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

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

Author keywords

Enantiomeric excess; Enantioselective thin film membrane; Optical resolution; Trans 1,4 diaminocyclohexane; Trimesoyl chloride

Indexed keywords

ENANTIOMERIC EXCESS; OPTICAL RESOLUTION; THIN FILM MEMBRANE; TRANS-1,4-DIAMINOCYCLOHEXANE; TRIMESOYL CHLORIDE;

AMINO ACIDS; ATOMIC FORCE MICROSCOPY; CHIRALITY; CHLORINE COMPOUNDS; ENANTIOMERS; ENANTIOSELECTIVITY; INFRARED SPECTROSCOPY; MEMBRANES; SCANNING ELECTRON MICROSCOPY; TRANSMISSION ELECTRON MICROSCOPY;

COMPOSITE MEMBRANES;

AMINO ACID; AQUEOUS SOLUTION; ATOMIC FORCE MICROSCOPY; MEMBRANE; OPTICAL METHOD; SCANNING ELECTRON MICROSCOPY; TRANSMISSION ELECTRON MICROSCOPY;

EID: 84866154382     PISSN: 00119164     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.desal.2012.08.015     Document Type: Article

References (43)

1. Newcomb M., Helgeson R.C., Cram D.J. Enantiomer differentiation in transport through bulk liquid membranes. J. Am. Chem. Soc. 1974, 96:7367-7369.
2. Nakagawa T., Toyokawa Y., Abe M., Higuchi A. Synthesis of membranes having a saccharide side chain and their optical resolution properties for d-/lglucose mixtures. Macromol. Symp. 1994, 84:209-226.
3. Higuchi A., Tamaid M., Koe Y.A., Tagawad Y.I., Wu Y.H., Freeman B.D., Bin J.T., Chang Y., Ling Q.D. Polymeric membranes for chiral separation of pharmaceuticals and chemicals. Polym. Rev. 2010, 50:113-143.
4. 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.
5. 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.
6. Aoki T., Shinohara K., Oikawa E. Optical resolution through the solid membrane from (+)-poly{1-[dimethyl(10-pinanyl)-silyl]-1-propyne}. Makromol. Chem. Rapid Commun. 1992, 13:565-570.
7. Aoki T., Tomizawa S., Oikawa E. Enantioselective permeation through poly γ-[3-pentamethyldisiloxanyl) propyl]-l-glutamate membranes. J. Membr. Sci. 1995, 99:117-125.
8. 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.
9. Gumi T., Minguillon C., Palet C. Separation of propranolol enantiomers through membranes based on chiral derivatized polysulfone. Polymer 2005, 46:12306-12312.
10. Xie R., Chu L.Y., Deng J.G. Membranes and membrane processes for chiral resolution. Chem. Soc. Rev. 2008, 37:1243-1263.
11. Kim J.H., Kim J.H., Jegal J., Lee K.H. Optical resolution of α-amino acids through enantioselective polymeric membranes based on polysaccharides. J. Membr. Sci. 2003, 213:273-283.
12. Singh K., Ingole P.G., Bajaj H.C., Gupta H. Preparation, characterization and application of β-cyclodextrin-glutaraldehyde crosslinked membrane for the enantiomeric separation of amino acids. Desalination 2012, 298:13-21.
13. Singh K., Ingole P.G., Chaudhary 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.
14. Petersen R., Cadotte J. Thin film composite reverse osmosis membranes. Handbook of Industrial Membrane Technology 1990, 307-348. Noyes Publications, Park Ridge, NJ, cbe. M. Portr (Ed.).
15. Wang H.D., Chu L.Y., Song H., Yang J.P., Xie R., Yang M. Preparation and enantiomer separation characteristics of chitosan/β-cyclodextrin composite membranes. J. Membr. Sci. 2007, 297:262-270.
16. 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.
17. 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.
18. K. Singh, H.C. Bajaj, P.G. Ingole, International PCT granted, Title: A method for preparation enantioselective composite membrane, Patent Number(s): WO2010109490-A1; IN200900629-I1.
19. 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.
20. Zhou Z., Cheng J.H., Chung T.S., Alan Hatton T., Toriida M., Nishiura K., Tamai S. Enantiomeric resolution of tryptophan via stereoselective binding in an ion-exchange membrane partitioned free flow isoelectric focusing system. Chem. Eng. J. 2011, 174:522-529.
21. Zhao M., Xu X.L., Jiang Y.D., Sun W.Z., Wang W.F., Yuan L.M. Enantioseparation of trans-stilbene oxide using a cellulose acetate membrane. J. Membr. Sci. 2009, 336:149-153.
22. Xiao Y., Lim H.M., Chung T.S., Raj R. Acetylation of β-cyclodextrin surface-functionalized cellulose dialysis membranes with enhanced chiral separation. Langmuir 2007, 23:12990-12996.
23. Zhou Z., Xiao Y., Chung T.S., Hatton T.A. Effects of spacer arm length and benzoation on enantioseparation performance of β-cyclodextrin functionalized cellulose membranes. J. Membr. Sci. 2009, 339:21-27.
24. Yudiato A., Dewi E., Kokugan T. Separation of isomers by ultrafiltration using modified cyclodextrins. Sep. Purif. Technol. 2000, 19:103-112.
25. Kakuchi T., Takaoka T., Yokota K. Polymeric chiral crown ether 6 optical resolution of alpha-amino-acid by polymers incorporating 1,3-4,6-di-O-benzylidene-d-mannitol residues. Polym. J. 1990, 22:199-205.
26. Higuchi A., Hayashi A., Kanda N., Sanui K., Kitamura H. Chiral separation of amino acids in ultrafiltration through DNA-immobilized cellulose membranes. J. Mol. Struct. 2005, 739:145-152.
27. Higuchi A., Higuchi Y., Furuta K., Yoon B.O., Hara M., Maniwa S., Saitoh M., Sanui K. Chiral separation of phenylalanine by ultrafiltration through immobilized DNA membranes. J. Membr. Sci. 2003, 221:207-218.
28. K. Singh, H.C. Bajaj, P.G. Ingole, A method for preparation of l-enantioselective composite membrane for optical resolution of α-amino acids, Patent Number(s): 0327DEL2012 (0111NF2011).
29. Lakshmi B.B., Martin C.R. Enantioseparation using apoenzymes immobilized in a porous polymeric membrane. Nature 1997, 388:758-760.
30. Higuchi A., Hara M., Horiuchi T., Nakagawa T. Optical resolution of amino acids by ultrafiltration membranes containing serum albumin. J. Membr. Sci. 1994, 93:157-164.
31. Wang H., Li Y., Chung T.S. A fine match between the stereoselective ligands and membrane pore size for enhanced chiral separation. AICHE J. 2009, 55:2284-2291.
32. 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.
33. Morgan P.W., Kwolek S.J. Condensation polymers by interfacial and solution methods. Polym. Sci. 1959, 40:299-327.
34. Darcy H. Les Fontaines Publiques de le Ville deDijon 1956, Victor Delmont, Paris.
35. Hancock Nathan T., Cath T.Y. Solute coupled diffusion in osmotically driven membrane processes. Environ. Sci. Technol. 2009, 43:6769-6775.
36. Ingole P.G., Bajaj H.C., Singh K. Enantiomeric separation of α-amino acids by imprinted terpolymer membrane. Arabian J. Chem. 2011, 10.1016/j.arabjc.2011.10.011.
37. Carey F.A. Organic Chemistry 2000, McGraw Hill Publication. 4th edition.
38. Freger V. Kinetics of film formation by interfacial polycondensation. Langmuir 2005, 21:1884-1894.
39. Elimelech M., Zhu X., Childress A.E., Hong S. Role of membrane surface morphology in colloidal fouling of cellulose acetate and composite aromatic polyamide reverse osmosis membranes. J. Membr. Sci. 1997, 127:101-109.
40. Vrijenhoek E.M., Hong S., Elimelech M. Influence of membrane surface properties on initial rate of colloidal fouling of reverse osmosis and nanofiltration membranes. J. Membr. Sci. 2001, 188:115-128.
41. Kwak S.Y., Ihm D.W. Use of atomic force microscopy and solid-state NMR spectroscopy to characterize structure-property-performance correlation in high-flux reverse osmosis (RO) membranes. J. Membr. Sci. 1999, 158:143-153.
42. Vito L., Punzi V.L. A comparison of solute rejection models in RO membrane. Ind. Eng. Chem. Res. 1990, 29:259-263.
43. Mulder M. Basic Principles of Membrane Technology 1997, 123-129. Kluwer Academic Publishers.