The selective separation of (S)-amlodipine via a hollow fiber supported liquid membrane: Modeling and experimental verification

Chemical Engineering Journal

Volumn 180, Issue , 2012, Pages 299-308

  Sunsandee, Niti ^a   Leepipatpiboon, Natchanun ^a   Ramakul, Prakorn ^b   Pancharoen, Ura ^a  

^a CHULALONGKORN UNIVERSITY   (Thailand)

^b SILPAKORN UNIVERSITY   (Thailand)

Author keywords

(S) Amlodipine; Enantiosepartation; Flux model; HFSLM; O,O' Dibenzoyl (2S,3S) tartaric acid

Indexed keywords

AMLODIPINE; CHEMICAL PARAMETERS; CHIRAL SELECTOR; DISTRIBUTION RATIO; ENANTIOSEPARATIONS; ENANTIOSEPARTATION; EXPERIMENTAL DATA; EXPERIMENTAL VERIFICATION; EXTRACTION EQUILIBRIA; FEED PHASE; FLUX MODEL; HFSLM; HOLLOW FIBER SUPPORTED LIQUID MEMBRANE; MASS-TRANSFER COEFFICIENT; SELECTIVE SEPARATION; TARTARIC ACIDS; TRANSPORT MECHANISM;

CARRIER CONCENTRATION; EQUILIBRIUM CONSTANTS; LIQUID MEMBRANES; LIQUIDS; MASS TRANSFER; MATHEMATICAL MODELS; STEREOCHEMISTRY;

SOLVENT EXTRACTION;

EID: 84455205488     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2011.11.068     Document Type: Article

References (55)

1. Thompson A.M., Hu T., Eshelbrenner C.L., Reynolds K., He J., Bazzano L.A. Antihypertensive treatment and secondary prevention of cardiovascular disease events among persons without hypertension: a meta-analysis. JAMA 2011, 305(9):913-922.
2. Guidelines Subcommittee World Health Organization International Society of Hypertension Guidelines for the management of hypertension. J. Hypertens. 1999, 17:151-183.
3. Mancia G., De G.B., Dominiczak A., Cifkova R., Fagard R., Germano G., Grassi G., Heagerty A.M. Guidelines for the management of arterial hypertension. J. Hypertens. 2007, 25:1105-1187.
4. Schachter M. Calcium antagonists and atherosclerosis. Int. J. Cardiol. 1997, 62(Suppl. 2):S9-S15.
5. Hardman J.G., Limbird L.E. Goodman and Gilman's the Pharmacological Basis of Therapeutics 2001, McGraw Hill Medical Publishing Division, New Delhi, pp. 853-860. 10th ed.
6. Abernethy D.R The pharmacokinetic profile of amlodipine. Am. Heart J. 1989, 118:1100-1103.
7. Mason R.P., Walter M.F., Trumbore M.W., Olmstead E.G., Mason P.E. Membrane antioxidant effects of the charged dihydropyridine calcium antagonist amlodipine. J. Mol. Cell. Cardiol. 1999, 31:275-281.
8. Park J.Y., Kim K.A., Park P.W., Lee O.J., Ryu J.H., Lee G.H., Ha M.C., Kim J.S., Kang S.W., Lee K.R. Pharmacokinetic and pharmacodynamic characteristics of a new S-amlodipine formulation in healthy Korean male subjects: a randomized open-label, two-period, comparative, crossover study. Clin. Ther. 2006, 28:1837-1847.
9. Yinghua S., Liang F., Meng Z., Wei L., Ping M., Li L., Zhonggui H. A drug-in-adhesive transdermal patch for S-amlodipine free base: in vitro and in vivo characterization. Int. J. Pharm. 2009, 382:165-171.
10. Breuer M., Ditrich K., Habicher T., Hauer B., Kesseler M., Sturmer R., Zelinski T. Industrial methods for the production of optically active intermediates. Angew. Chem. Int. 2004, 43:788-824.
11. R.J. Rohini, A.J. Ramesh, K.G. Mukund, A process for the preparation of S-(-)-amlodipine salts, EP Patent Application 1407773 A1, 14 April 2004.
12. Christians T., Diewald D., Wessler C., Otte Y., Lehmann J., Holzgrabe U. Resolution of newly synthesized racemic dihydropyridines with different chiral selectors by means of capillary electrophoresis. J. Chromatogr. A 1999, 853:455-460.
13. N. Zhong, X. Zhao, H.C. Ma, Method for the enantiomeric separation of optical active amlodipine, US Patent Application 2007/0093661 A1, 26 April 2007.
14. Owens P.K., Fell A.F., Coleman M.W., Berridge J.C. Effect of charged and uncharged chiral additives on the resolution of amlodipine enantiomers in liquid chromatography and capillary electrophoresis. J. Chromatogr. A 1998, 797:187-195.
15. Pancharoen U., Somboonpanya S., Chaturabul S., Lothongkum A.W. Selective removal of mercury as HgCl42- from natural gas well produced water by TOA via HFSLM. J. Alloys Compd. 2010, 489:72-79.
16. Arrowsmith J.E., Campbell S.F., Cross P.E., Stubbs J.K., Burges R.A., Gardiner D.G., Blackburn K.J. Long-acting dihydropyridine calcium antagonists. 1. 2-Alkoxymethyl derivatives incorporating basic substituents. J. Med. Chem. 1986, 29:1696-1702.
17. Arrowsmith J.E., Campbell S.F., Cross P.E., Stubbs J.K., Burges R.A., Gardiner D.G. Long acting dihydropyridine calcium antagonists. 2. 2-[2-Aminoheterocycloethoxy]methyl derivatives. J. Med. Chem. 1986, 32:562-568.
18. Lee H.W., Shin S.J., Yu H., Kang S.K., Yoo C.L. A novel chiral resolving reagent, bis((S)-mandelic acid)-3-nitrophthalate, for amlodipine racemate resolution: scalable synthesis and resolution process. Org. Process Res. Dev. 2009, 13:1382-1386.
19. Gotrane D.M., Deshmukh R.D., Ranade P.V., Sonawane S.P., Bhawal B.M., Gharpure M.M., Gurjar M.K. A novel method for resolution of amlodipine. Org. Process Res. Dev. 2010, 13:640-643.
20. Goldmann S., Stoltefuss J., Born L. 1,4-Dihydropyridines: effects of chirality and conformation on the calcium antagonist and calcium agonist activities. J. Angew. Chem. Int. Ed. Engl. 1991, 30:1559-1578.
21. Goldmann S., Stoltefuss J., Born L. Determination of the absolute configuration of the active amlodipine enantiomer as (-)-S: a correction. J. Med. Chem. 1992, 35:3341-3344.
22. Zandkarimi M., Shafaati A., Foroutan S.M., Lucy C.A. Rapid enantioseparation of amlodipine by highly sulfated cyclodextrins using short-end injection capillary electrophoresis. DARU 2009, 17(4):269-276.
23. Streel B., Laine C., Zimmer C., Sibenaler R., Ceccato A. Enantiomeric determination of amlodipine in human plasma by liquid chromatography coupled to tandem mass spectrometry. J. Biochem. Biophys. Methods 2002, 54:357-368.
24. Luksa J., Josic D.J., Podobnik B., Furlan B., Kremser M. Semi-preparative chromatographic purification of the enantiomers S-(-)-amlodipine and R-(+)-amlodipine. J. Chromatogr. B 1997, 693:367-375.
25. Fogassy E., Nógrádi M., Kozma D., Egri G., Pálovics E., Kiss V. Optical resolution methods. Org. Biomol. Chem. 2006, 4:3011-3030.
26. Schuur B., Winkelman J.G.M., Heeres H.J. Equilibrium studies on enantioselective liquid-liquid amino acid extraction using a cinchona alkaloid extractant. Ind. Eng. Chem. Res. 2008, 47:10027-10033.
27. 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. 2007, 53:224-234.
28. Tang K.W., Chen Y.Y., Liu J.J. Resolution of zopiclone enantiomers by biphasic recognition chiral extraction. Sep. Purif. Technol. 2008, 62:683-688.
29. Schuur B., Hallett A.J., Winkelman J.G.M., de Vries J.G., Heeres H.J. Scalable enantioseparation of amino acid derivatives using continuous liquid-liquid extraction in a cascade of centrifugal contactor separators. Org. Process Res. Dev. 2009, 13:911-914.
30. Schlosser S., Kertész R., Marták J. Recovery and separation of organic acids by membrane-based solvent extraction and pertraction-an overview with a case study on recovery of MPCA. Sep. Purif. Technol. 2005, 41:237-266.
31. Maximini A., Chmiel H., Holdik H., Maier N.W. Development of a supported liquid membrane process for separating enantiomers of N-protected amino acid derivatives. J. Membr. Sci. 2006, 276:221-231.
32. 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.
33. Afonso C.A.M., Crespo J.G. Recent advances in chiral resolution through membrane-based approaches. Angew. Chem. Int. Ed. 2004, 43:5293-5295.
34. Coelhoso I.M., Cardoso M.M., Viegas R.M.C., Crespo J.P.S.G. Transport mechanisms and modelling in liquid membrane contactors. Sep. Purif. Technol. 2000, 19:183-197.
35. Rogers J.D., Long R. Modeling hollow fiber membrane contactors using film theory, Voronoi tessellations, and facilitation factors for systems with interface reactions. J. Membr. Sci. 1997, 134:1-17.
36. Giorno L., Drioli E. Enantiospecific membrane processes. Membr. Technol. 1999, 106:6-11.
37. Hadik P., Szabó L.P., Nagy E. d,l-Lactic acid and d,l-alanine enantioseparation by membrane process. Desalination 2002, 148:193-198.
38. Tang K.W., Zhou C.S., Jiang X.Y. Racemic ofloxacin separation by supported-liquid membrane extraction with two organic phase. Sci. China (Ser. B) 2003, 46:96-103.
39. Tang K.W., Zhou C.S. Enantioselective extraction of terbutaline enantiomers by lipophilic tartaric acid. J. Cent. South Univ. Technol. 2003, 10:44-48.
40. Gumía T., Valientea M., Paleta C. Characterization of a supported liquid membrane based system for the enantioseparation of SR-propanolol by N-hexadecyl-l-hydroxyproline. Sep. Sci. Technol. 2004, 39:431-477.
41. Hadik P., Kotsis L., Eniszné-Bódogh M., Szabó L.P., Nagy E. Lactic acid enantioseparation by means of porous ceramic disc and hollow fiber organic membrane. Sep. Purif. Technol. 2005, 41:299-304.
42. Jiao F.P., Huang K.L., Peng X.H., Zhao X.H., Yu J.G. Hollow fiber liquid-supported membrane technology for enantioseparation of racemic salbutamol by combinatorial chiral selector. J. Cent. South Univ. Technol. 2006, 13:39-43.
43. Huang D.S., Huang K.L., Chen S.P., Liu S.Q. Rapid reaction diffusion model for the enantioseparation of phenylalanine across hollow fiber supported liquid membrane. Sep. Sci. Technol. 2008, 43:259-272.
44. Huang D.S., Huang K.L., Chen S.P., Liu S.Q., Yu J.G. Enantioseparation of racemic α-cyclohexyl-mandelic acid across hollow fiber supported liquid membrane. J. Braz. Chem. Soc. 2008, 19:557-562.
45. Jiao F.P., Chen X.Q., Jiang X.Y. Enantioselective extraction of ofloxacin enantiomers using ester alcohol l-tartarate as chiral selector. Iran. J. Chem. Chem. Eng. 2009, 28:7-11.
46. Wang Z., Cai C., Lin Y., Bian Y., Guo H., Chen X. Enantioselective separation of ketoconazole enantiomers by membrane extraction. Sep. Purif. Technol. 2011, 79:63-71.
47. Prasad R., Sirkar K.K. Dispersion-free extraction with microporous hollow fibre modules. AIChE J. 1988, 34:177.
48. Jiao F.P., Chen X.Q., Lin Y., Hu Y.H. Enantioselective extraction of mandelic acid enantiomers using ester alcohol l-tartarate as chiral selector. Latin Am. Appl. Res. 2008, 38:249-252.
49. Danesi P.R. A simplified model for the coupled transport of metal ions through hollow-fiber supported liquid membranes. J. Membr. Sci. 1984, 20:231-248.
50. El Aamrania F.Z., Kumara A., Beyerb L., Floridoa A., Sastrea A.M. Mechanistic study of active transport of silver (I) using sulphur containing novel carriers across liquid membrane. J. Membr. Sci. 1999, 152:263-275.
51. Lin S.H., Juang R.S. Mass-transfer in hollow fiber module for extraction and back-extraction of copper(II) with LIX64N carriers. J. Membr. Sci. 2001, 188:251-262.
52. Wannachod P., Chaturabul S., Pancharoen U., Lothongkum A.W., Patthaveekongka W. The effective recovery of praseodymium from mixed rare earths via a hollow fiber supported liquid membrane and its mass transfer related. J. Alloys Compd. 2011, 509:354-361.
53. Y.S. Chung, M.C. Ha, Resolution of the enantiomers of amlodipine, US Patent Application 2003/6,646,131 B2, 11 November 2003.
54. Ramakul P., Songkun E., Pattaweekongka W., Hronec M., Pancharoen U. Permeation study on the hollow-fiber supported liquid membrane for the extraction of cobalts (II). Korean J. Chem. Eng. 2006, 23(1):117-123.
55. Pancharoen U., Ramakul P., Patthaveekongka W. Purely extraction and separation of mixure of cerium(IV) and lanthanum(III) via hollow fiber supported liquid membrane. J. Ind. Eng. Chem. 2005, 11(6):926-931.