Enantioseparation of (S)-amlodipine from pharmaceutical industry wastewater by stripping phase recovery via HFSLM: Polarity of diluent and membrane stability investigation

Separation and Purification Technology

Volumn 116, Issue , 2013, Pages 405-414

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

^a CHULALONGKORN UNIVERSITY   (Thailand)

^b SILPAKORN UNIVERSITY   (Thailand)

Author keywords

Cyclodextrin; (S) Amlodipine; Enantioseparation; HFSLM; Pharmaceutical industry wastewater

Indexed keywords

AMLODIPINE; ENANTIOSEPARATIONS; HFSLM; LIQUID MEMBRANE PHASE; PHARMACEUTICAL INDUSTRY; PHARMACEUTICAL WASTEWATER; PHARMACEUTICALLY ACTIVE COMPOUNDS; SUPPORTED LIQUID MEMBRANE;

CYCLODEXTRINS; DICHLOROMETHANE; EXTRACTION; STEREOCHEMISTRY;

LIQUID MEMBRANES;

EID: 84880057863     PISSN: 13835866     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.seppur.2013.06.014     Document Type: Article

References (57)

1. Z. Chen, N. Ren, A. Wang, Z.P. Zhang, and Y. Shi A novel application of TPAD-MBR system to the pilot treatment of chemical synthesis-based pharmaceutical wastewater Water Res. 42 2008 3385 3392
2. Y.A. Oktem, O. Ince, P. Sallis, T. Donnelly, and B.K. Ince Anaerobic treatment of a chemical synthesis-based pharmaceutical wastewater in a hybrid upflow anaerobic sludge blanket reactor Bioresour. Technol. 99 2007 1089 1096
3. N. Nakada, K. Kiri, H. Shinohara, A. Harada, K. Kuroda, S. Takizawa, and H. Takada Evaluation of pharmaceuticals and personal care products as water-soluble molecular markers of sewage Environ. Sci. Technol. 42 2008 6347 6353
4. A.B.A. Boxall The environmental side effects of medication Eur. Mol. Biol. Org. 5 2004 1110 1116 (Pubitemid 40103600)
5. A.L. Batt, D.D. Snow, and D.S. Aga Occurrence of sulfonamide antimicrobials in private water wells in Washington County, Idaho, USA Chemosphere 64 2006 1963 1971 (Pubitemid 44160469)
6. I. Rodriguez-Donis, V. Gerbaud, A. Arias-Barreto, and X. Joulia Heterogeneous batch distillation processes for waste solvent recovery in pharmaceutical industry Comp. Aided Chem. Eng. 27 2009 1119 1124
7. D.S. Suman Raj, and Y. Anjaneyulu Evaluation of biokinetic parameters for pharmaceutical wastewaters using aerobic oxidation integrated with chemical treatment Proc. Biochem. 40 2005 165 175 (Pubitemid 39197406)
8. M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Kesseler, R. Stürmer, and T. Zelinski Industrial methods for the production of optically active intermediates Angew. Chem. Int. 43 2004 788 824 (Pubitemid 39256206)
9. A.M. Thompson, T. Hu, C.L. Eshelbrenner, K. Reynolds, J. He, and L.A. Bazzano Antihypertensive treatment and secondary prevention of cardiovascular disease events among persons without hypertension: a meta-analysis JAMA 305 2011 913 922
10. G.S. Liu, K. Wang, and M.H. Zhang Comparative effect of amlodipine and levamlodipine on nocturnal hypertension in hypertensive patients J. Med. Postgrad. 14 2001 496 499
11. J.Y. Park, K.A. Kim, P.W. Park, O.J. Lee, J.H. Ryu, G.H. Lee, M.C. Ha, J.S. Kim, S.W. Kang, and K.R. Lee 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. 28 2006 1837 1847
12. Y.Z. Cheng, X.G. Wu, and X.Y. Chen Clinical trial of therapeutic effects and adverse drug reaction of S-amlodipine Chin. J. Med. Guide 4 2002 198 200
13. R.X. Wang, W.P. Jiang, X.R. Li, and L.H. Lai Effects of (S)-amlodipine and (R)-amlodipine on L-type calcium channel current of rat ventricular myocytes and cytosolic calcium of aortic smooth muscle cells Pharmazie 63 2008 470 474
14. Y. Sun, L. Fang, M. Zhu, W. Li, P. Meng, L. Li, and Z. He A drug-in-adhesive transdermal patch for S-amlodipine free base: in vitro and in vivo characterization Int. J. Pharm. 382 2009 165 171
15. F. Liu, M. Qiu, and S.D. Zhai Tolerability and effectiveness of (S)-amlodipine compared with racemic amlodipine in hypertension: a systematic review and meta-analysis Curr. Ther. Res. 71 2010 1 29
16. B. Schuur, B.J. Verkuijl, A.J. Minnaard, J.G. de Vries, H.J. Heeres, and B.L. Feringa Chiral separation by enantioselective liquid-liquid extraction Org. Biomol. Chem. 9 2011 36 51
17. C. Klein, R.J. Schneider, M.T. Meyer, and D.S. Aga Enantiomeric separation of metolachlor and its metabolites using LC-MS and CZE Chemosphere 62 2006 1591 1599
18. K.W. Tang, L.T. Song, Y.B. Liu, Y. Pan, and X.Y. Jiang Separation of flurbiprofen enantiomers by biphasic recognition chiral extraction Chem. Eng. J. 158 2010 411 417
19. J.E. Arrowsmith, S.F. Campbell, P.E. Cross, J.K. Stubbs, R.A. Burges, D.G. Gardiner, and K.J. Blackburn Long-acting dihydropyridine calcium antagonists. 1. 2-alkoxymethyl derivatives incorporating basic substituents J. Med. Chem. 29 1986 1696 1702 (Pubitemid 16018197)
20. J. Luksa, D. Josic, B. Podobnik, B. Furlan, and M. Kremser Semi-preparative chromatographic purification of the enantiomers S-(-)-amlodipine and R-(+)-amlodipine J. Chromatogr. B 693 1997 367 375 (Pubitemid 27250298)
21. M. Zandkarimi, A. Shafaati, S.M. Foroutan, and A. Lucy Charles Rapid enantioseparation of amlodipine by highly sulfated cyclodextrins using short-end injection capillary electrophoresis DARU 17 2009 269 276
22. D.M. Gotrane, R.D. Deshmukh, P.V. Ranade, S.P. Sonawane, B.M. Bhawal, M.M. Gharpure, and M.K. Gurjar A novel method for resolution of amlodipine Org. Process Res. Dev. 13 2010 640 643
23. J.V. Sonawane, A.K. Pabby, and A.M. Sastre Pseudo-emulsion based hollow fibre strip dispersion (PEHFSD) technique for permeation of Cr(VI) using Cyanex-923 as carrier J. Hazard. Mater. 174 2010 541 547
24. P. Dzygiel, and P.P. Wieczorek Supported liquid membranes and their modifications: definition, classification, theory, stability, application and perspectives V.S. Kislik, Liquid membranes 2010 Elsevier Amsterdam 72 140
25. A.W. Lothongkum, U. Pancharoen, and T. Prapasawat Treatment of heavy metals from industrial wastewaters using hollow fiber supported liquid membrane K. Demadis, Water Treatment Processes 2012 Nova Science Publishers Hauppauge NY 299 332
26. S.H. Lin, and R.S. Juang Mass-transfer in hollow-fiber modules for extraction and back-extraction of copper(II) with LIX64N carriers J. Membr. Sci. 188 2001 251 262
27. S. Panja, P.K. Mohapatra, S.C. Tripathi, and V.K. Manchanda Facilitated transport of uranium(VI) across supported liquid membranes containing T2EHDGA as the carrier extractant J. Hazard. Mater. 188 2011 281 287
28. A.W. Lothongkum, S. Suren, S. Chaturabul, N. Thamphiphit, and U. Pancharoen Simultaneous removal of arsenic and mercury from natural-gas-co- produced water from the Gulf of Thailand using synergistic extractant via HFSLM J. Membr. Sci. 369 2011 350 358
29. G. Schulz Separation techniques with supported liquid membranes Desalination 68 1988 191 202
30. R. Prasad, and K.K. Sirkar Dispersion-free solvent extraction with microporous hollow-fiber modules AIChE J. 34 1988 177 183
31. N. Sunsandee, N. Leepipatpiboon, P. Ramakul, and U. Pancharoen The selective separation of (S)-amlodipine via a hollow fiber supported liquid membrane: modeling and experimental verification Chem. Eng. J. 180 2012 299 308
32. I. Kmecz, B. Simándi, E. Székely, and E. Fogassy Resolution of Nmethylamphetamine enantiomers with tartaric acid derivatives by supercritical fluid extraction Tetrahedron: Asymm. 15 2004 1841 1845 (Pubitemid 38780915)
33. B. Tan, G.S. Luo, and J.D. Wang Enantioseparation of amino acids by co-extractants with di(2-ethylhexyl)phosphoric acid and tartaric acid derivatives Tetrahedron-Asymm. 17 2006 883 891 (Pubitemid 44389427)
34. K.W. Tang, P.L. Zhang, C.Y. Pan, and H.J. Li Equilibrium studies on enantioselective extraction of oxybutynin enantiomers by hydrophilic β-cyclodextrin derivatives AIChE J. 57 2011 3027 3036
35. B. Schuur, J.G.M. Winkelman, and H.J. Heeres Equilibrium studies on enantioselective liquid-liquid amino acid extraction using a cinchona alkaloid extractant Ind. Eng. Chem. Res. 47 2008 10027 10033
36. K.W. Tang, J.M. Yi, Y.B. Liu, X.Y. Jiang, and Y. Pan Enantioselective separation of R,S-phenylsuccinic acid by biphasic recognition chiral extraction Chem. Eng. Sci. 64 2009 4081 4088
37. C. Kassai, Z. Juvancz, J. Bálint, E. Fogassy, and D. Kozma Optical resolution of racemic alcohols via diastereoisomeric supramolecular compound formation with O,O′-dibenzoyl-(2R,3R)-tartaric acid Tetrahedron 56 2000 8355 8359
38. Y.S. Liu, Y.Y. Dai, and J.D. Wang Distribution behavior of L-tryptophane by extraction with di(2-ethylhexyl) phosphoric acid Sep. Sci. Technol. 35 2000 1439 1454
39. R.S. Juang, and Y.Y. Wang Amino acid separation with D2EHPA by solvent extraction and liquid surfactant membranes J. Membr. Sci. 207 2002 241 252
40. B. Tan, G.S. Luo, X. Qi, and J.D. Wang Extractive separation of amino acid enantiomers with co-extractants of tartaric acid derivative and aliquat-336 Sep. Purif. Technol. 53 2007 330 336 (Pubitemid 46108669)
41. M. Steensma, N.J.M. Kuipers, A.B. de Haan, and G. Kwant Identification of enantioselective extractants for chiral separation of amines and amino alcohols Chirality 18 2006 314 328 (Pubitemid 43672680)
42. B. Schuur, J.G.M. Winkelman, J.G. de Vries, and H.J. Heeres Experimental and modeling studies on the enantio-separation of 3,5-dinitrobenzoyl-(R),(S)- leucine by continuous liquid-liquid extraction in a cascade of centrifugal contactor separators Chem. Eng. Sci. 65 2010 4682 4690
43. M. Kazusaki, H. Kawabata, and H. Matsukura Influence of temperature on enantioseparation employing an amylose-derivative stationary phase J. Liquid. Chromatogr. Rel. Technol. 23 2000 2937 2946 (Pubitemid 32973380)
44. P.R. Danesi A simplified model for the coupled transport of metal ions through hollow-fiber supported liquid membranes J. Membr. Sci. 20 1984 231 248 (Pubitemid 14012130)
45. U. Pancharoen, T. Wongsawa, and A.W. Lothongkum A reaction flux model for extraction of Cu(II) with LIX84I in HFSLM Sep. Sci. Technol. 46 2011 2183 2190
46. X. Zhang, Resolution of the enantiomers of amlodipine, U.S. Patent Number 6646131, 2003.
47. N. Sunsandee, P. Ramakul, N. Thamphiphit, U. Pancharoen, and N. Leepipatpiboon The synergistic effect of selective separation of (S)-amlodipine from pharmaceutical wastewaters via hollow-fiber supported liquid membrane Chem. Eng. J. 209 2012 201 214
48. N. Sunsandee, N. Leepipatpiboon, P. Ramakul, T. Wongsawa, and U. Pancharoen The effects of thermodynamics on mass transfer and enantioseparation of (R,S)-amlodipine across a hollow fiber supported liquid membrane Sep. Purif. Technol. 102 2013 50 61
49. N. Sunsandee, U. Pancharoen, P. Rashatasakhon, P. Ramakul, N. Leepipatpiboon, Enantioselective separation of racemic amlodipine by two-phase chiral Extraction containing O,O'-dibenzoyl-(2S,3S)-tartaric acid as chiral selector, Sep. Sci. Technol. in press.
50. F. Valenzuela, C. Fonseca, C. Basualto, O. Correa, C. Tapia, and J. Sapag Removal of copper ions from a waste mine water by a liquid emulsion membrane method Miner. Eng. 18 2005 33 40
51. G. Kyuchoukov, D. Yankov, J. Albet, and J. Molinier Mechanism of lactic acid extraction with quaternary ammonium chloride (Aliquat 336) Ind. Eng. Chem. Res. 44 2005 5733 5739
52. P.K. Mohapatra, D.S. Lakshmi, and V.K. Manchanda Diluent effect on Sr(II) extraction using di-tert-butyl cyclohexano 18 crown 6 as the extractant and its correlation with transport data obtained from supported liquid membrane studies Desalination 198 2006 166 172 (Pubitemid 44542448)
53. C.L. Yaws Chemical Properties Handbook 1999 McGraw-Hill New York
54. K.R. Chitra, A.G. Gaikwad, G.D. Surender, and A.D. Damodaran Studies on ion transport of some rare earth elements through solvating extractants immobilised on supported liquid membrane J. Membr. Sci. 125 1997 257 268
55. T. O'Brien, L. Crocker, R. Thompson, K. Thompson, P.H. Toma, D.A. Conlon, B. Feibush, C. Moeder, G. Bicker, and N. Grinberg Mechanistic aspects of chiral discrimination on modified cellulose Anal. Chem. 69 1997 1999 2007
56. M. Zandkarimi, A. Shafaati, and S.M. Foroutan Chiral separation of basic and zwitterionic drugs by highly sulfated cyclodextrins using short-end injection capillary electrophoresis Iran. J. Pharm. Res. 7 2008 275 281
57. W. Pattaveekongka, N. Vijitchalermpong, and U. Pancharoen Selective recovery of palladium from used aqua regia by hollow fiber supported with liquid membrane Korean J. Chem. Eng. 20 2003 1092 1096