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Topics in Catalysis

, Volume 57, Issue 17–20, pp 1576–1581 | Cite as

Enantioselective Hydrogenation of Ethyl Benzoylformate, from Mechanism and Kinetics to Continuous Reactor Technology

  • Gerson Martin
  • Päivi Mäki-Arvela
  • Johan Wärnå
  • Dmitry Yu. Murzin
  • Tapio SalmiEmail author
Original Paper
  • 154 Downloads

Abstract

The enantioselective hydrogenation of ethyl benzoylformate over (−)-cinchonidine (CD)-modified Pt/Al2O3 catalyst in semi-batch and continuous fixed bed reactors was studied as a function of the modifier concentration and reaction temperature. The kinetic results from the semibatch reactor showed a higher enantioselectivity and lower initial rate as the amount of modifier was increased. The results from the fixed bed reactor demonstrates that continuous enantioselective hydrogenation is possible and that continuous feeding of (−)-CD is needed to maintain a high steady-state enantioselectivity.

Keywords

Enantioselective hydrogenation Pt catalyst (−)-Cinchonidine Continuous operation 

Notes

Acknowledgments

This work is part of the activities at the Åbo Akademi University Process Chemistry Centre (ÅA-PCC). Financial support from the Academy of Finland is gratefully acknowledged.

References

  1. 1.
    Toukoniitty E, Mäki-Arvela P, Kalantar Neyestanaki A, Salmi T, Murzin DYu (2002) Appl Catal A Gen 235:125–138CrossRefGoogle Scholar
  2. 2.
    Orito Y, Imai S, Niwa S (1979) Nippon Kagaku Kaishi 8:1118–1120CrossRefGoogle Scholar
  3. 3.
    Schürch M, Schwalm O, Mallat T, Weber J, Baiker A (1997) J Catal 169:275–286CrossRefGoogle Scholar
  4. 4.
    Schürch M, Künzle N, Mallat T, Baiker A (1998) J Catal 176:569–571CrossRefGoogle Scholar
  5. 5.
    Studer M, Burkhardt S, Blaser H-U (1999) Chem Commun 17:1727–1728CrossRefGoogle Scholar
  6. 6.
    Künzle N, Szabo A, Wang Z, Schürch M, Mallat T, Baiker A (1998) J Chem Soc, Chem Commun 13:1377–1378CrossRefGoogle Scholar
  7. 7.
    von Arx M, Mallat T, Baiker A (2000) J Catal 193:161–164CrossRefGoogle Scholar
  8. 8.
    Mallat T, Bodmer M, Baiker A (1997) Catal Lett 44:95–99CrossRefGoogle Scholar
  9. 9.
    Bodmer M, Mallat T, Baiker A (1998) In: Herkes FE (ed) Catalysis of organic reactions. Marcel Dekker, New York, pp 75–87Google Scholar
  10. 10.
    Wang GZ, Mallat T, Baiker A (1997) Tetrahedron 8:2113–2140Google Scholar
  11. 11.
    Bartók M, Felföldi K, Török B, Bartók T (1998) Chem Commun 23:2605–2606CrossRefGoogle Scholar
  12. 12.
    Sutyinszki M, Szöri K, Felföldi K, Bartók M (2002) Catal Commun 3:125–127CrossRefGoogle Scholar
  13. 13.
    Diezi S, Reinmann S, Bonalumi N, Mallat T, Baiker A (2006) J Catal 239:255CrossRefGoogle Scholar
  14. 14.
    Szőllősi G, Cserényi S, Füllöp F, Bartók M (2008) J Catal 260:245CrossRefGoogle Scholar
  15. 15.
    Tokarev AV, Kirilin AV, Murzina EV, Eränen K, Kustov LM, Murzin DYu, Mikkola JP (2010) Int J Hydrogen Energy 35:12642–12649CrossRefGoogle Scholar
  16. 16.
    Toukoniitty E, Wärnå J, Murzin DYu, Salmi T (2010) Chem Eng Sci 65:1076–1087CrossRefGoogle Scholar
  17. 17.
    Leyshon R, Jenkins A (2007) The enantioselective hydrogenation of pyruvate estesr over cinchona alkaloid modifier platinum catalysts. ProQuest LLC, CardiffGoogle Scholar
  18. 18.
    Toukoniitty E, Mäki-Arvela P, Kalantar Neyestanaki A, Salmi T, Sjöholm R, Leino R, Laine E, Kooyman PJ, Ollonqvist T, Väyrynen J (2001) Appl Catal A 216:73–83CrossRefGoogle Scholar
  19. 19.
    Bartók M, Szöllösi Gy, Balázsik K, Bartók T (2002) J Mol Catal A 177:299–305CrossRefGoogle Scholar
  20. 20.
    Morawsky V, Prüsse U, Witte L, Vorlop KD (2000) Catal Commun 1:15–20CrossRefGoogle Scholar
  21. 21.
    Sutherland M, Ibbotson A, Moyes RB, Well PB (1990) J Catal 125:77–88CrossRefGoogle Scholar
  22. 22.
    Hájek J, Murzin DYu (2004) Ind Eng Chem Res 43:2030–2038CrossRefGoogle Scholar
  23. 23.
    Bürgi T, Baiker A (1998) J Am Chem Soc 120:12920–12926CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • Gerson Martin
    • 1
  • Päivi Mäki-Arvela
    • 1
  • Johan Wärnå
    • 1
  • Dmitry Yu. Murzin
    • 1
  • Tapio Salmi
    • 1
    Email author
  1. 1.Process Chemistry CentreÅbo Akademi UniversityTurku/ÅboFinland

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