Research Article
Gas Chromatographic Enantioseparation of Fluorinated Anesthetics: Single-Column Performance and Scale-up Estimation
Ivana Mutavdžin,
Thomas Munkelt,
Dirk Enke,
Andreas Seidel-Morgenstern,
Corresponding Author
Ivana Mutavdžin
Max Planck Institute for Dynamics of Complex Technical Systems, Sandtorstrasse 1, 39106 Magdeburg, Germany
Correspondence: Ivana Mutavdžin ([email protected]), Max Planck Institute for Dynamics of Complex Technical Systems, Sandtorstrasse 1, 39106 Magdeburg, Germany.Search for more papers by this authorThomas Munkelt
Otto-von-Guericke University, Institute of Process Engineering, Universitätsplatz 2, 39106 Magdeburg, Germany
Search for more papers by this authorDirk Enke
Universität Leipzig, Institute of Chemical Technology, Linnéstrasse 3, 04103 Leipzig, Germany
Search for more papers by this authorAndreas Seidel-Morgenstern
Max Planck Institute for Dynamics of Complex Technical Systems, Sandtorstrasse 1, 39106 Magdeburg, Germany
Otto-von-Guericke University, Institute of Process Engineering, Universitätsplatz 2, 39106 Magdeburg, Germany
Search for more papers by this authorIvana Mutavdžin,
Thomas Munkelt,
Dirk Enke,
Andreas Seidel-Morgenstern,
Corresponding Author
Ivana Mutavdžin
Max Planck Institute for Dynamics of Complex Technical Systems, Sandtorstrasse 1, 39106 Magdeburg, Germany
Correspondence: Ivana Mutavdžin ([email protected]), Max Planck Institute for Dynamics of Complex Technical Systems, Sandtorstrasse 1, 39106 Magdeburg, Germany.Search for more papers by this authorThomas Munkelt
Otto-von-Guericke University, Institute of Process Engineering, Universitätsplatz 2, 39106 Magdeburg, Germany
Search for more papers by this authorDirk Enke
Universität Leipzig, Institute of Chemical Technology, Linnéstrasse 3, 04103 Leipzig, Germany
Search for more papers by this authorAndreas Seidel-Morgenstern
Max Planck Institute for Dynamics of Complex Technical Systems, Sandtorstrasse 1, 39106 Magdeburg, Germany
Otto-von-Guericke University, Institute of Process Engineering, Universitätsplatz 2, 39106 Magdeburg, Germany
Search for more papers by this authorAbstract
Results of a study devoted to provide the pure enantiomers of isoflurane and desflurane from racemic mixtures using gas chromatography are presented. For that purpose, a cyclodextrin-based selector described in earlier work was immobilized on porous glass beads. The adsorption isotherms were determined and applied to predict operating parameters which provide the highest possible productivity of the separation. The analysis included evaluation of the performance of larger columns applying simplifying scale-up considerations. Using repetitive batches, the method can provide per day with a laboratory scale column approximately 1 g pure enantiomer. Selected model predictions were validated experimentally.
References
- 1 D. A. Sidebotham, S. A. Schug, Clin. Exp. Pharmacol. Physiol. 1997, 24 (2), 126–130.
- 2 P. L. Polavarapu, A. L. Cholli, G. Vernice, J. Am. Chem. Soc. 1992, 114 (27), 10953–10955. DOI: https://doi.org/10.1021/ja00053a038
- 3 V. Schurig, M. Juza, B. S. Green, J. Horakh, A. Simon, Angew. Chem., Int. Ed. 1996, 35 (15), 1680–1682.
- 4 N. P. Franks, W. R. Lieb, Science 1991, 254 (5030), 427–430.
- 5 B. Harris, E. Moody, P. Skolnick, Eur. J. Pharmacol. 1992, 217 (2–3), 215–216. DOI: https://doi.org/10.1016/0014-2999(92)90875-5
- 6 R. Dickinson, I. White, W. R. Lieb, N. P. Franks, Anesthesiology 2000, 93 (3), 837–843.
- 7 A. C. Hall, W. R. Lieb, N. P. Franks, Brit. J. Pharmacol. 1994, 112 (3), 906–910. DOI: https://doi.org/10.1111/j.1476-5381.1994.tb13166.x
- 8 E. J. Moody, B. D. Harris, P. Skolnick, Trends Pharmacol. Sci. 1994, 15 (10), 387–391. DOI: https://doi.org/10.1016/0165-6147(94)90160-0
- 9 H. Y. Aboul-Enein, J. Bojarski, J. Szymura-Oleksiak, Biomed. Chromatogr. 2000, 14 (4), 213–218. DOI: https://doi.org/10.1002/1099-0801(200006)14:4<213::AID-BMC975>3.0.CO;2-R
- 10 L. A. Rozov, C. G. Huang, D. F. Halpern, G. G. Vernice, K. Ramig, Tetrahedron: Asymmetry 1997, 8 (18), 3023–3025. DOI: https://doi.org/10.1016/S0957-4166(97)00382-0
- 11 H. A. Haeberle, H. G. Wahl, G. Aigner, K. Unertl, H. J. Dieterich, Eur. J. Anaesthesiol. 2004, 21 (2), 144–150. DOI: https://doi.org/10.1017/S026502150400211X
- 12
R. Schmidt, H. G. Wahl, H. Häberle, H. J. Dieterich, V. Schurig, Chirality
1999, 11 (3), 206–211. DOI: https://doi.org/10.1002/(SICI)1520-636X(1999)11:3<206::AID-CHIR6>3.0.CO;2-R
10.1002/(SICI)1520-636X(1999)11:3<206::AID-CHIR6>3.0.CO;2-R CAS PubMed Web of Science® Google Scholar
- 13 M. Juza, H. Jakubetz, H. Hettesheimer, V. Schurig, J. Chromatogr. B: Biomed. Sci. Appl. 1999, 735 (1), 93–102. DOI: https://doi.org/10.1016/S0378-4347(99)00409-0
- 14 C. G. Huang, L. A. Rozov, D. F. Halpern, G. G. Vernice, J. Org. Chem. 1993, 58 (26), 7382–7387.
- 15 K. Ramig, Synthesis 2002, 17, 2627–2631.
- 16
V. Schurig, in Differentiation of Enantiomers I (Ed: V. Schurig), Springer, Heidelberg
2013, 153–207.
10.1007/128_2013_440 Google Scholar
- 17 W. Saenger, Angew. Chem., Int. Ed. 1980, 19 (5), 344–362.
- 18 V. Schurig, H. P. Nowotny, Angew. Chem., Int. Ed. 1990, 29 (9), 939–957.
- 19 V. Schurig, H. Grosenick, B. S. Green, Angew. Chem., Int. Ed. 1993, 32 (11), 1662–1663.
- 20 A. Shitangkoon, D. U. Staerk, G. Vigh, J. Chromatogr. A 1993, 657 (2), 387–394. DOI: https://doi.org/10.1016/0021-9673(93)80294-I
- 21 J. Meinwald, W. R. Thompson, D. L. Pearson, W. A. König, T. Runge, W. Francke, Science 1991, 251 (4993), 560–561.
- 22 W. A. König, R. Krebber, P. Mischnick, J. High Resolut. Chromatogr. 1989, 12 (11), 732–738. DOI: https://doi.org/10.1002/jhrc.1240121108
- 23 V. Schurig, H. Grosenick, J. Chromatogr. A 1994, 666, 617–625.
- 24 M. Juza, E. Braun, V. Schurig, J. Chromatogr. A 1997, 769 (1), 119–127. DOI: https://doi.org/10.1016/S0021-9673(97)00024-1
- 25 G. Biressi, A. Rajendran, M. Mazzotti, M. Morbidelli, Sep. Sci. Technol. 2002, 37 (11), 2529–2543. DOI: https://doi.org/10.1081/ss-120004451
- 26 T. Munkelt, C. Küster, C. Hamel, D. Enke, A. Seidel-Morgenstern, Chem. Ing. Tech. 2013, 85 (11), 1686–1693. DOI: https://doi.org/10.1002/cite.201300076
- 27 M. Juza, O. Di Giovanni, G. Biressi, V. Schurig, M. Mazzotti, M. Morbidelli, J. Chromatogr. A 1998, 813 (2), 333–347. DOI: https://doi.org/10.1016/S0021-9673(98)00322-7
- 28 G. Biressi, F. Quattrini, M. Juza, M. Mazzotti, V. Schurig, M. Morbidelli, Chem. Eng. Sci. 2000, 55 (20), 4537–4547. DOI: https://doi.org/10.1016/S0009-2509(00)00109-3
- 29 G. Biressi, M. Mazzotti, M. Morbidelli, J. Chromatogr. A 2002, 957 (2), 211–225. DOI: https://doi.org/10.1016/S0021-9673(02)00319-9
- 30 J. Bentley, Q. Huang, Y. Kawajiri, M. Eic, A. Seidel-Morgenstern, Adsorption 2011, 17 (1), 159–170. DOI: https://doi.org/10.1007/s10450-010-9299-x
- 31 K. P. Kostroski, P. C. Wankat, Ind. Eng. Chem. Res. 2008, 47 (9), 3138–3149. DOI: https://doi.org/10.1021/ie071000b
- 32 G. Guiochon, A. Felinger, D. G. Shirazi, A. M. Katty, Fundamentals of Preparative and Nonlinear Chromatography, 2nd ed., Academic Press, Boston 2006.
- 33 A. Seidel-Morgenstern, J. Chromatogr. A 2004, 1037 (1–2), 255–272. DOI: https://doi.org/10.1016/j.chroma.2003.11.108
- 34 A. Cavazzini, A. Felinger, K. Kaczmarski, P. Szabelski, G. Guiochon, J. Chromatogr. A 2002, 953 (1–2), 55–66. DOI: https://doi.org/10.1016/S0021-9673(02)00150-4
- 35 P. Forssén, J. Lindholm, T. Fornstedt, J. Chromatogr. A 2003, 991 (1), 31–45. DOI: https://doi.org/10.1016/S0021-9673(03)00213-9
- 36 A. Felinger, D. Zhou, G. Guiochon, J. Chromatogr. A 2003, 1005 (1–2), 35–49. DOI: https://doi.org/10.1016/s0021-9673(03)00889-6
- 37 I. Mutavdžin, A. Seidel-Morgenstern, M. Petkovska, Chem. Eng. Sci. 2013, 89, 21–30. DOI: https://doi.org/10.1016/j.ces.2012.11.032
- 38 E. V. Dose, S. Jacobson, G. Guiochon, Anal. Chem. 1991, 63, 833–839.
- 39 D. Antos, W. Piatkowski, K. Kaczmarski, Acta Chromatogr. 1999, 9, XI–XII.
- 40 F. James, M. Sepúlveda, F. Charton, I. Quinones, G. Guiochon, Chem. Eng. Sci. 1999, 54 (11), 1677–1696. DOI: https://doi.org/10.1016/S0009-2509(98)00539-9
- 41 P. Forssén, R. Arnell, T. Fornstedt, Comput. Chem. Eng. 2006, 30 (9), 1381–1391. DOI: https://doi.org/10.1016/j.compchemeng.2006.03.004
- 42 L. Jacob, G. Guiochon, J. Chromatogr. A 1972, 65 (1), 19–27. DOI: https://doi.org/10.1016/S0021-9673(00)86914-9
- 43 J. Roles, G. Guiochon, J. Chromatogr. 1992, 589, 223–230.
- 44 D. M. Ruthven, S. Farooq, K. S. Knaebel, Pressure Swing Adsorption, VCH Publishers, New York 1994.
- 45 Preparative Chromatography, 2nd ed. (Eds: H. Schmidt-Traub, M. Schulte, A. Seidel-Morgenstern), Wiley-VCH, Weinheim 2013.
- 46 D. M. Ruthven, Principles of Adsorption and Adsorption Processes, John Wiley & Sons New York 1984.
- 47 A. T. James, A. J. Martin, Biochem. J. 1952, 50 (5), 679–690.
- 48 R. Kaiser, Gas Phase Chromatography, Vol. I, Butterworths, London 1963.
- 49 Gas Chromatography, Sub- and Supercritical Fluid Chromatography, Vol. 3, 1st ed. (Eds: J. L. Anderson, A. Berthod, V. Pino, A. M. Stalcup), Wiley-VCH, Weinheim 2015.
- 50 S. Golshan–Shirazi, G. Guiochon, Anal. Chem. 1989, 61 (11), 1276–1287.
- 51 C. Heuer, P. Hugo, G. Mann, A. Seidel-Morgenstern, J. Chromatogr. A 1996, 752 (1–2), 19–29. DOI: https://doi.org/10.1016/S0021-9673(96)00496-7
- 52 K. Unger, Handbuch der HPLC, Teil 2: Präparative Säulenflüssig-Chromatographie, GIT Verlag, Darmstadt 1994.
- 53 P. Rouchon, M. Schonauer, P. Valentin, G. Guiochon, Sep. Sci. Technol. 1987, 22 (8–10), 1793–1833. DOI: https://doi.org/10.1080/01496398708057614
- 54 M. Münzner, G. Dornberg, C. Küster, D. Enke, Chem. Ing. Tech. 2016, 88 (11), 1761–1769. DOI: https://doi.org/10.1002/cite.201600053
- 55 C. Küster, B. Reinhardt, M. Fröba, D. Enke, Z. Anorg. Allg. Chem. 2014, 640 (3–4), 565–569. DOI: https://doi.org/10.1002/zaac.201300456
- 56 A. Inayat, B. Reinhardt, J. Herwig, C. Küster, H. Uhlig, S. Krenkel, E. Raedlein, D. Enke, New J. Chem. 2016, 40 (5), 4095–4114. DOI: https://doi.org/10.1039/c5nj03591k
- 57 V. Schurig, M. Schleimer, S. Mayer, 1994. DE4324636
- 58 I. Mutavdžin, Ph.D. Thesis, Otto von Guericke University Magdeburg 2017.
- 59 A. Felinger, G. Guiochon, J. Chromatogr. A 1992, 591 (1–2), 31–45. DOI: https://doi.org/10.1016/0021-9673(92)80220-O
- 60 J. Jänchen, J. B. Brückner, H. Stach, Eur. J. Anaesthesiol. 1998, 15 (3), 324–329.
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