Modeling, simulation, and experimental evaluation of continuous chromatographic separation of ketamine enantiomers on MCTA

Journal of Liquid Chromatography and Related Technologies

Volumn 31, Issue 20, 2008, Pages 3057-3076

  Barreto Jr , Amaro Gomes ^a   Silva Jr , Ivanildo José Da ^b   Dos Santos, Marco Antônio Garcia ^c   Veredas, Vinicius De ^c   Santana, Cesar Costapinto ^c  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b Grupo de Pesquisa Em Separacoes Por Adsorcao GPSA   (Brazil)

^c UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Chiral separation; Equilibrium theory; Ketamine; Liquid chromatography; Simulated moving bed

Indexed keywords

AMINES; ATMOSPHERIC TEMPERATURE; CELLULOSE DERIVATIVES; CHIRALITY; CHROMATOGRAPHIC ANALYSIS; CHROMATOGRAPHY; COLUMN CHROMATOGRAPHY; COLUMNS (STRUCTURAL); ENANTIOMERS; EXPERIMENTS; FLOW OF GASES; HIGH PRESSURE LIQUID CHROMATOGRAPHY; ISOMERS; SEPARATION;

CHIRAL SEPARATION; CHIRAL SEPARATIONS; CHROMATOGRAPHIC SEPARATIONS; CONTINUOUS; EQUILIBRIUM THEORY; EXPERIMENTAL DATUM; EXPERIMENTAL EVALUATIONS; IDEAL EFFECTS; INTERNAL PROFILES; KETAMINE; LINEAR ISOTHERMS; MICROCRYSTALLINE CELLULOSE TRIACETATES; MODELING; RAFFINATE STREAMS; SIMULATED MOVING BED; SIMULATED MOVING BEDS; SIMULATION APPROACHES; STEADY STATES; TRUE MOVING BED (TMB);

LIQUID CHROMATOGRAPHY;

KETAMINE;

ARTICLE; ENANTIOMER; LIQUID CHROMATOGRAPHY; SIMULATION; STEADY STATE;

AMINES; EXTRACTION; ISOTHERMS; KETONES; LIQUID CHROMATOGRAPHY; MICROCRYSTALLINE CELLULOSE; SIMULATION;

EID: 54349123107     PISSN: 10826076     EISSN: 1520572X     Source Type: Journal    
DOI: 10.1080/10236660802479507     Document Type: Article

References (30)

1. Migliorini, C.; Mazzotti, M.; Zenoni, G.; Morbidelli, M. Simulated moving-bed units with extra-column dead volume. AIChE J. 1999, 45, 1411-1421.
2. Francotte, E.; Richert, P.; Mazzotti, M.; Morbidellim, M. Simulated moving bed chromatographic resolution of a chiral antitussive. J. Chromatogr. A. 1998, 796, 239-248.
3. Bae, Y.-S.; Moon, J.-H.; Lee, C.-H. Effects of feed concentration of the startup and performance behaviors of simulated moving bed chromatography. Ind. Eng. Chem. Res. 2006, 45, 777-790.
4. Silva Jr., I.J.; Veredas, V.; Santos, M.A.G.; Santana, C.C.; Carpes, M.J.S.; Correia, C.R.D. Simulated moving bed chromatography in the wide scale production of enantiomerically pure compounds. Quím. Nova. 2006, 29, 1027-1037.
5. Veredas, V.; Carpes, M.J.S.; Correia, C.R.D.; Santana, C.C. Continuous chromatographic separation of a baclofen precursor (N-Boc-4-[p-chlorophenyl]-2-pyrolidone) in a simulated moving bed using a polyssaccharide carbamate as chiral stationary phase. J. Chromatogr. A. 2006, 1119, 156-162.
6. Juza, M.; Mazzotti, M.; Morbidelli, M. Simulated moving bed and its application to chiral technology. Trends in Biotechnol. 2000, 18, 108-118.
7. Santos, M.A.G.; Veredas, V.; Silva Junior, I. J.; Correia, C.R.D.; Furlan, L. T.; Santana, C.C. Simulated moving-bed adsorption for separation of racemic mixtures, Braz. J. of Chem. Eng. 2004, 21, 127-136.
8. Yu, H.W.; Ching, C.-B. Modeling, simulation and operation performance of a simulated moving bed for enantioseparation of fluoxetine on new β-cyclodextrin columns. Adsorption. 2003, 9, 213-223.
9. Stanley, B.J.; Foster, C.R.; Guiochon, G. On the rproducibility of column performance in liquid chromatography and the role of the packing density. J. Chromatogr. A. 1997, 761, 41-51.
10. Mihlbachler, K.; Fricke, J.; Yun, T., Seidel-Morgenstern, A.; Schmidt-Traub, H.; Guiochon, G. Effect of the homogeneity of the column set on the performance of a simulated moving bed unity: I. theory. J. Chromatogr. A. 2001, 908, 49-70.
11. Mihlbachler, K.; Kaczmarski, K.; Seidel-Morgenstern, A.; Guiochon, G. Measurement and modeling of the equilibrium behavior of the trögeŕs base enantiomers on an amylose-based chiral stationary phase. J. Chromatogr. A. 2002, 955, 35-52.
12. Milhlbachler, K.; Seidel-Morgenstern, A.; Guiochon, G. Detailed study of tröger's base separation by SMB. Process AIChE J. 2004, 50, 611-624.
13. Yanagihara, Y.; Ohtani, M.; Kariya, S.; Uchino, K.; Aoyama, T.; Yamamura, Y.; Iga, T. Stereoselective high-performance liquid chromatographic determination of ketamine and its active metabolic, norketamine, in humam plasm. J. Chromatogr. B. 2000, 746, 227-231.
14. Svensson, J.; Gustafsson, L.L. Determination of ketamine and norketamine enantiomers in plasma by solid-phase extraction and high-performance liquid chromatography. J. Chromatogr. B. 1996, 678, 373-376.
15. Nishizawa, N.; Nakao, S.; Nagata, A.; Hirose, T.; Masuzawa, M.; Shingu, K. The effect of ketamine isomers on both mice behavioral responses and c-fos expression in the posterior cingulate and retrosplenial córtices. Brain Res. 2000, 857, 188-192.
16. Steiner, K.; Gangkofner, S.; Gruenwald, J-M. Racemic Separation of Ketamine. US2000/6040479, March, 21, 2000.
17. Russo, V.F.T; Russo, E.M.S. Process of Obtainment of Racemic Ketamine Enantiomers: Process of Obtainment of Pharmaceutically Acceptable Salts from Racemic Ketamine Enantiomers and Use of Pharmaceutically Acceptable Salts Obtained by Means of Said Mentioned Process. US2003/0212143A1, Nov.13, 2003.
18. Wang, X.J.; Wiehler, H.; Ching, C.B. Study of the Characterization and crystallization of 4-hydroxy-2-pyrrolidone. Chirality 2004, 16, 220-227.
19. Silva Jr., I.J.; Santos, M.A.G.; Veredas, V.; Santana, C.C. Experimental determination of chromatographic separation parameters of ketamine enantiomers on MCTA. Sep. Purif. Technol. 2005, 43, 103-110.
20. Silva Jr., I.J.; Santos, M.A.G.; Veredas, V.; Santana, C.C. Effect of temperature on chiral separation of ketamine enantiomers by high-performance liquid chromatography. Sep. Sci. Technol. 2005, 40, 2593-2611.
21. Barros, G.O.F.; Tamagawa, R.E.; Santana, C.C.; Miranda, E.A. Ternary Phase Diagram of Ketamine ((R/S)-2-(2-chlorophenyl)2-methylamine cyclohexanone) in Ethanol and Preliminary Studies Aiming to the Fractional Crystallization of S-ketamine, submitted for publication, 2007.
22. Azevedo, D.C.S. Separation/reaction in Simulated Moving Bed: Application to the Production of Industrial Sugars. PhD Thesis, Universidade do Porto, Porto, Portugal, 2001.
23. Azevedo, D.C.S.; Rodrigues, A.E. Design of a simulated moving bed in the presence of mass-transfer resistances. AIChE J. 1999, 45, 956-966.
24. Minceva, M.; Rodrigues, A.L. Two-level optimization of an existing SMB for p-xylene separation. Comp. Chem. Eng. 2005, 29, 2215-2228.
25. Barreto Jr, A.G. Design of Chromatographic Systems to Lapachol Separation, PhD Thesis, COPPE/UFRJ, Rio de Janeiro/RJ/Brasil, 2005, Available in Portuguese.
26. a Edição, LTC Editora, São Paulo, Brasil, 2004, Available in Portuguese.
27. IMSL, Fortran subroutine for mathematical applications, Visual Numerics, Inc., 1997.
28. Zenoni, G.; Pedeferri, M.; Mazzotti, M.; Morbidelli, M. On-line monitoring of enantiomer concentration in chiral simulated moving bed chromatography. J. Chromatogr. A. 2000, 888, 73-83.
29. Mazzotti, M.; Storti, G.; Morbidelli, M. Optimal operation of simulated moving bed units for nonlinear chromatographic separations. J. Chromatogr. A. 1997, 769, 3-24.
30. Migliorini, C.; Mazzotti, M.; Zenoni, G.; Morbidelli, M. Continuous chromatographic separation through simulated moving beds under linear and nonlinear conditions. J. Chromatogr. A. 1998, 827, 161-173.