Edge Article
Chemical Science
the temperature. We have also validated these systems towards 17 M. Leeman, G. Brasile, E. Gelens, T. Vries, B. Kaptein and
multistage processes by demonstrating their catalytic efficiency R. Kellogg, Angew. Chem., Int. Ed., 2008, 47, 1287–1290.
in a U-tube system and have taken advantage of its unique 18 G. Subramanian, Chiral Separation Techniques: A Practical
properties to develop a novel triphasic extraction system. We Approach, Wiley-VCH, Weinheim, 2001.
conclude that these hosts, in view of the results obtained, could 19 K. W. Busch and M. A. Busch, Chiral Analysis, Elsevier,
be used in an industrial-scale racemate separation process. We Amsterdam, 2004.
are currently continuing our studies on the mode of action of 20 F. Toda, Enantiomer Separation: Fundamentals and Practical
these systems based on the initial observation made.
Methods, Kluwer Academic Publishers, Dordrecht, 2004.
21 G. Guebitz and M. G. Schmid, Chiral Separations, Humana
Press, Totowa (NJ), 2004.
22 S. Ahuja, Chiral Separations: Application and Technology, ACS,
Washington DC, 1997.
Conflicts of interest
There are no conicts of interest to declare.
¨
23 T. Jira, A. Bunke, M. G. Schmid and G. Gubitz, J. Chromatogr.
A, 1997, 761, 269–275.
24 V. A. Davankov, J. Chromatogr. A, 1994, 666, 55–76.
Acknowledgements
Financial support from STW through project no. 11404 (Chiral 25 M. Steensma, N. J. M. Kuipers, A. B. De Haan and G. Kwant,
Separations by Kinetic Extractive Resolution in Microuidic Chirality, 2006, 18, 314–328.
Devices), from the Swiss National Science Foundation (SNSF) 26 G. B. Cox, Preparative Enantioselective Chromatography,
and from the Ministry of Education, Culture and Science
Blackwell Publishing Ltd, 2007.
(Gravitation Program 024.001.035 to BLF) are all gratefully 27 E. Gavioli, N. M. Maier, C. Minguillon and W. Lindner, Anal.
´
acknowledged.
Chem., 2004, 76, 5837–5848.
28 R. Xie, L.-Y. Chu and J.-G. Deng, Chem. Soc. Rev., 2008, 37,
1243–1263.
29 A. Maximini, H. Chmiel, H. Holdik and N. W. Maier, J.
Membr. Sci., 2006, 276, 221–231.
30 C. A. M. Afonso and J. G. Crespo, Angew. Chem., Int. Ed., 2004,
43, 5293–5295.
31 G. Zenoni, F. Quattrini, M. Mazzotti, C. Fuganti and
M. Morbidelli, Flavour Fragrance J., 2002, 17, 195–202.
32 E. Francotte, T. Leutert, L. La Vecchia, F. Ossola, P. Richert
and A. Schmidt, Chirality, 2002, 14, 313–317.
33 J. T. F. Keurentjes, L. J. W. M. Nabuurs and E. A. Vegter, J.
Membr. Sci., 1996, 113, 351–360.
Notes and references
1 D. J. Ager, Handbook of Chiral Chemicals, Marcel Dekker, New
York, 2005.
2 H. Lorenz and A. Seidel-Morgenstern, Angew. Chem., Int. Ed.,
2014, 53, 1218–1250.
3 P. K. Ajikumar, K. Tyo, S. Carlsen, O. Mucha, T. H. Phon and
G. Stephanopoulos, Mol. Pharm., 2008, 5, 167–190.
4 M. J. Waites, Industrial Microbiology, Blackwell Science,
Oxford, 2001.
5 D. Cascaval, C. Oniscu and A. I. Galaction, Biochem. Eng. J.,
2001, 7, 171–176.
˜
34 B. Baragana, A. G. Blackburn, P. Breccia, A. P. Davis, J. de
´
¨
6 M. Reschke and K. Schugerl, Chem. Ing. Tech., 1984, 56, 141.
Mendoza, J. M. Padron-Carrillo, P. Prados, J. Riedner and
7 J. G. de Vries, G. A. Molander and P. A. Evans, Science of
J. G. de Vries, Chem.–Eur. J., 2002, 8, 2931–2936.
Synthesis, Stereoselective Synthesis, Georg Thieme Verlag 35 R. M. C. Viegas, C. A. M. Afonso, J. G. Crespo and
KG, Stuttgart, 2011, vol. 1–3.
8 R. A. Sheldon, J. Chem. Technol. Biotechnol., 1996, 67, 1–14.
9 A. N. Collins, G. N. Sheldrake and J. Crosby, Chirality in
I. M. Coelhoso, Sep. Purif. Technol., 2007, 53, 224–234.
36 M. Steensma, N. J. M. Kuipers, A. B. de Haan and G. Kwant,
Chem. Eng. Sci., 2007, 62, 1395–1407.
Industry II: The Commercial Manufacture and Applications of 37 J. Koska and C. A. Haynes, Chem. Eng. Sci., 2001, 56, 5853–
Optically Active Compounds, Wiley and Sons, New York, 1997.
5864.
10 N. M. Maier, P. Franco and W. Lindner, J. Chromatogr. A, 38 A. B. de Haan and B. Simandi, Extraction Technology for the
2001, 906, 3–33.
11 J. G. de Vries and A. H. M. de Vries, Eur. J. Org. Chem., 2003,
5, 799–811.
12 K. Reuter, WO 97/32644, 1997.
13 A. Bruggink, Rational Design in Resolutions, in Chirality in
Separation of Optical Isomers, in Ion Exchange and Solvent
Extraction, ed. Y. Marcus, M. M. Sharma and J. A.
Marinsky, Marcel Dekker, Inc, New York, 2001, pp. 255–294.
39 P. J. Pickering and J. B. Chaudhuri, Chem. Eng. Sci., 1997, 52,
377–386.
Industry II, ed. A. N. Collins, G. N. Sheldrake and J. Crosby, 40 J. C. Godfrey and M. J. Slater, Liquid–Liquid Extraction
John Wiley & sons Ltd., Chichester, 1997.
Equipment, John Wiley & Sons, New York, 1994.
14 D. Kozma, CRC Handbook of Optical Resolutions Via 41 E. Eliel, S. Wilen and L. Mander, Stereochemistry of Organic
Diastereomeric Salt Formation, CRC Press LLC Boca Raton,
2002.
15 E. Fogassy, M. Nogradi, D. Kozma, G. Egri, E. Palovics and
V. Kiss, Org. Biomol. Chem., 2006, 4, 3011–3030.
Compounds, John Wiley & Sons, New York, 1994.
42 M. Steensma, N. J. M. Kuipers, A. B. de Haan and G. Kwant,
Chemical Engineering and Processing: Process Intensication,
2007, 46, 996–1005.
´
´
´
16 F. Faigl, E. Fogassy, M. Nogradi, E. Palovics and J. Schindler,
Tetrahedron: Asymmetry, 2008, 19, 519–536.
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