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Continuous Asymmetric Hydrogenation

  • Lasse Greiner
  • Stephan Laue
  • Jens Wöltinger
  • Andreas Liese
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 276)

Abstract

Asymmetric hydrogenation with homogeneous soluble catalysts is a key technology for the production of enantiomerically enriched fine chemicals. Hydrogen supply via dense membranes in combination with continuous membrane filtration of soluble macromolecular catalysts allows for continuous hydrogenation. A optimised reactor with minimized volume was realized and used for continuous enzymatic and homogeneous catalysis. The vital importance of catalyst stability for continuous application is discussed. Furthermore, activation kinetics of the Pyrphos catalyst was investigated and found to be dependent on the presence of substrate.

Keywords

Cinnamic Acid Continuous Application Tubular Membrane Asymmetric Hydrogenation Dense Membrane 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Notes

Acknowledgments

We thank Andreas Franz, Daniela H. Müller and Christian R. Reimers (all of Forschungszentrum Jülich) for skilful technical support. The research was made possible by financial support from the German Federal Ministry of Education and Research (BMBF) and Degussa AG.

References

  1. 1.
    Osborn JA, Jardin FH, Young JF, Wilkinson G (1966) J Chem Soc, p 1711 Google Scholar
  2. 2.
    Knowles WS, Sabacky MJ (1968) Chem Comm, p 1445 Google Scholar
  3. 3.
    Kagan HB, Dang T-P (1972) J Am Chem Soc 94:6429 CrossRefGoogle Scholar
  4. 4.
    Tang WJ, Zhang XM (2003) Chem Rev 103:3029 and references cited therein CrossRefGoogle Scholar
  5. 5.
    Brown JM, Chaloner PA (1980a) J Chem Soc-Chem Commun, p 344 Google Scholar
  6. 6.
    Brown JM, Chaloner PA (1980b) J Am Chem Soc 102:3040 CrossRefGoogle Scholar
  7. 7.
    Halpern J (1982) Science 217:401 CrossRefGoogle Scholar
  8. 8.
    Achiwa K (1976) J Am Chem Soc 98:8265 CrossRefGoogle Scholar
  9. 9.
    Nagel I (1984) Angew Chem 96:425 CrossRefGoogle Scholar
  10. 10.
    Burk MJ, Feaster JE, Nugent WA, Harlow RL (1993) J Am Chem Soc 115:10125 CrossRefGoogle Scholar
  11. 11.
    Pye PJ, Rossen K, Reamer RA, Tsou NN, Volante RP, Reider PJ (1997) J Am Chem Soc 119:6207 CrossRefGoogle Scholar
  12. 12.
    Togni A, Dorta R, Kollner C, Pioda G (1998) Pure Appl Chem 70:1477 CrossRefGoogle Scholar
  13. 13.
    Muniz K, Bolm C (2000) Chem Eur J 6:2309 CrossRefGoogle Scholar
  14. 14.
    Noyori R (1994) Asymmetric Catalysis in Organic Synthesis. Wiley, Tokyo Google Scholar
  15. 15.
    Koten Gv, Leeuwen PWv (1999) In: Santen RVv, Leeuwen PWv, Mouljin JA, Averil BA (eds) Catalysis: An integrated approach, Vol. 123. Elsevier Google Scholar
  16. 16.
    Bayer E, Schurig V (1975) Angew Chem 87:484 CrossRefGoogle Scholar
  17. 17.
    Lütz S, Rao N, Wandrey C (2005) Chem Ing Tech 77:1669 CrossRefGoogle Scholar
  18. 18.
    Kula M-R, Wandrey C (1987) Methods in Enzymology 136:9 CrossRefGoogle Scholar
  19. 19.
    Kragl U, Dwars T (2001) Trends in Biotechnology 19:45 CrossRefGoogle Scholar
  20. 20.
    Wöltinger J, Drauz K, Bommarius AS (2001) Appl Cat A 221:171 CrossRefGoogle Scholar
  21. 21.
    Mecking S (2005) In: Cornils B, Herrmann WA, Horváth IT, Leitner W, Mecking S, Olivier-Bourbigou H, Vogt D (eds) Multiphase Homogeneous Catalysis. Wiley, Weinheim, p 753 Google Scholar
  22. 22.
    Greiner L, Liese A (2006) In: Cornils B, Herrmann WA, Horvath IT, Leitner W, Mecking S, Olivier-Bourbigou H, Vogt D (eds) Multiphase Homogeneous Catalysis. Wiley, Weinheim, p 819 Google Scholar
  23. 23.
    Nagel U (1984) Angew Chem 96:425 CrossRefGoogle Scholar
  24. 24.
    Malmström T, Andersson C (2000) J Mol Cat A 157:79 CrossRefGoogle Scholar
  25. 25.
    Engel GD, Gade LH (2002) Chem Eur J 8:4319 CrossRefGoogle Scholar
  26. 26.
    Bergbreiter D (2000) In: De Vos DE, Vankelecom IFJ, Jacobs PA (eds) Chiral Catalyst Immobilization and Recycling. Wiley, Weinheim Google Scholar
  27. 27.
    Nagel U, Kinzel E (1986) Chem Ber 119:1731 CrossRefGoogle Scholar
  28. 28.
    Beck W, Nagel U (1988) EP 0151282 Google Scholar
  29. 29.
    Laue S, Greiner L, Wöltinger J, Liese A (2001) Adv Synth Catal 343:711 CrossRefGoogle Scholar
  30. 30.
    Fogg PC, Gerrard W (1991) Solubility of gases in liquids: A critical evaluation of gas/liquid systems in theory and practice. Wiley, Chichester, UK Google Scholar
  31. 31.
    Compan V, López ML, Andrio A, López-Alemany A, Refojo MF (1999) J Appl Polym Sci 72:321 CrossRefGoogle Scholar
  32. 32.
    Rissom S, Schwarz-Linek U, Vogel M, Tishkov V, Kragl U (1997) Tetrahedron: Asymmetry 8:2523 CrossRefGoogle Scholar
  33. 33.
    Bongs J, Hahn D, Schörken U, Sprenger GA, Kragl U, Wandrey C (1997) Biotechnol Lett 19:213 CrossRefGoogle Scholar
  34. 34.
    Greiner L, Müller DH, van den Ban ECD, Wöltinger J, Wandrey C, Liese A (2003) Adv Synth Catal 342:679 CrossRefGoogle Scholar
  35. 35.
    Laue S, Greiner L, Wöltinger J, Liese A (2001) Adv Synth Catal 343:711 CrossRefGoogle Scholar
  36. 36.
    Giffels G, Beliczey J, Felder M, Kragl U (1998) Tetrahedron: Asymmetry 9:691 CrossRefGoogle Scholar
  37. 37.
    Wöltinger J, Bommarius AS, Drauz K, Wandrey C (2001) Org Proc Res Dev 5:241 CrossRefGoogle Scholar
  38. 38.
    Kragl U, Dreisbach C (1996) Angew Chem Int Ed Engl 35:642 CrossRefGoogle Scholar
  39. 39.
    Kula MR, Wandrey C (1987) Meth Enz 136:9 CrossRefGoogle Scholar
  40. 40.
    Iding H, Siegert P, Dünnwald T, Müller M, Greiner L, Liese A, Grötzinger J, Demir A, Pohl M (2000) Chem Eur J 6:1483 CrossRefGoogle Scholar
  41. 41.
    Greiner L, Brik Ternbach M (2004) Adv Synth Catal 346:1392 CrossRefGoogle Scholar
  42. 42.
    Mecking S (2005) In: Cornils B, Herrmann WA, Horváth IT, Leitner W, Mecking S, Olivier-Bourbigou H, Vogt D (eds) Multiphase Homogeneous Catalysis. Wiley, Weinheim, p 753 Google Scholar
  43. 43.
    Greiner L, Laue S, Liese A, Wandrey C (2006) Chem Eur J 12:1818 CrossRefGoogle Scholar
  44. 44.
    Börner A, Heller D (2001) Tetrahedron Lett 42:223 CrossRefGoogle Scholar
  45. 45.
    Cobley CJ, Lennon IC, McCague R, Ramsden JA, Zanotti-Gerosa A (2001) Tetrahedron Lett 42:7481 CrossRefGoogle Scholar
  46. 46.
    Nindakova LO, Shainyan BA (2001) Russ Chem Bull 50:1855 CrossRefGoogle Scholar
  47. 47.
    Greiner L, Müller DH, van den Ban ECD, Wöltinger J, Wandrey C, LieseA (2003) Adv Synth Catal 342:679 CrossRefGoogle Scholar
  48. 48.
    Mertens R, Wandrey C, Liese A (2005) Chem Ing Tech 77:609 CrossRefGoogle Scholar
  49. 49.
    Bergbreiter DE, Case BL, Liu U-S, Caraway JW (1998) Macromolecules 31:6053 CrossRefGoogle Scholar
  50. 50.
    Bergbreiter DE (2002) Chem Rev 102:3345 CrossRefGoogle Scholar
  51. 51.
    Malmström T, Andersson C (1999) J Mol Cat A: Chemical 139:259 CrossRefGoogle Scholar
  52. 52.
    Malmström T, Andersson C (2000) J Mol Cat A: Chemical 157:79 CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2006

Authors and Affiliations

  • Lasse Greiner
    • 1
  • Stephan Laue
    • 2
  • Jens Wöltinger
    • 3
  • Andreas Liese
    • 4
  1. 1.RWTH Aachen UniversityInstitut für Technische und Makromolekulare ChemieAachenGermany
  2. 2.Bu-PLS-P & T-PDBayer Material ScienceUerdingenGermany
  3. 3.Degussa AGHanau-WolfgangGermany
  4. 4.Institute of Technical BiocatalysisHamburg University of Technology TUHHHamburgGermany

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