Abstract
The enantioselective hydrogenation of ethyl pyruvate to (R)-ethyl lactate has been studied using gases under supercritical conditions as solvents. The catalyst was a 5 wt% Pt/alumina modified with cinchonidine. In supercritical ethane the reaction time could be reduced by a factor of 3.5 compared to toluene under similar conditions, without any loss in enantioselectivity. A further advantage of ethane is that the enantioselectivity remains high even at high catalyst/reactant ratio, which is interesting in view of a possible application of a continuous fixed-bed reactor for this reaction. A strong catalyst deactivation was observed in supercritical CO2, which is due to the reduction of CO2 on Pt as indicated by FTIR.
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References
Y. Orito, S. Imai and S. Niwa, J. Chem. Soc. Japan (1980) 670.
H.U. Blaser, Chem. Rev. 92 (1992) 935.
A. Baiker, DGMK Tagungsber. 9305 (ISBN 3-928-16461-9) 119 (1992).
J.T. Wehrli, A. Baiker, D.M. Monti, H.U. Blaser and H.P. Jalett, J. Mol. Catal. 57 (1989) 245.
H.U. Blaser, H.P. Jalett and J. Wiehl, J. Mol. Catal. 68 (1991) 215.
B. Minder, T. Mallat, P. Skrabal and A. Baiker, Catal. Lett. 29 (1994) 115.
B. Minder, T. Mallat, A. Baiker, G. Wang, T. Heinz and A. Pfaltz, J. Catal., in press.
C. Reichardt,Solvents and Solvent Effects in Organic Chemistry (VCH, Weinheim, 1988) p. 359.
B. Minder, M. Schüreh, T. Mallat and A. Baiker, Catal. Lett. 31 (1995) 143.
V. Krukonis, G. Brunner, M. Perrut,Proc. 3rd Int. Symp. on Supercritical Fluids, Strasbourg 1994.
B. Subramaniam and A. McHugh, Ind. Eng. Chem. Process Des. Dev. 25 (1986) 1.
L. Book, B. Wu, C. LaMarca, M. Klein and S. Paspek, CHEMTECH 12 (1992) 719.
P.G. Jessop, T. Ikariya and R. Noyori, Nature 368 (1994) 231.
G. Kaupp, Angew. Chem. 106 (1994) 1519.
A. Heintz and W.B. Streett, J. Chem. Eng. Data 27 (1982) 465.
C.Y. Tsang and W.B. Streett, Chem. Eng. Sci. 36 (1981) 993.
J.T. Wehrli, A. Baiker, D.M. Monti and H.U. Blaser, J. Mol. Catal. 61 (1990) 207.
T.E. Daubert and R.P. Danner, eds.,Physical and Thermodynamic Properties of Pure Chemicals: Data Compilation (Taylor and Francis, Washington, 1993).
J.T. Wehrli, PhD Thesis, ETH-Zürich, No. 8833 (1989).
H.U. Blaser, H.P. Jalett, D.M. Monti, J.F. Reber and J.T. Wehrli, Stud. Surf. Sci. Catal. 41 (1988) 153.
H.U. Blaser, H.P. Jalett, D.M. Monti, A. Baiker and J.T. Wehrli, Stud. Surf. Sci. Catal. 67 (1991) 147.
E. Talas, L. Botz, J. Margitfalvi, O. Sticher and A. Baiker, J. Planar Chrom. 5 (1992) 28.
K. Steiner and K.H. Pickel, unpublished.
T. Inoue and T. Iizuka, J. Chem. Soc. Faraday Trans. 82 (1986) 1681.
S. Taguchi and A. Aramata, Electrochim. Acta 39 (1994) 2533.
E. Morallòn, J.L. Vàzquez, J.M. Pèrez and A. Aldaz, J. Electroanal. Chem. 380 (1995) 47.
M. Freifelder, in:Practical Catalytic Hydrogenation (Wiley-Interscience, New York, 1971).
A.W. Frahm,Methoden der Organischen Chemie (Thieme, Stuttgart, 1980).
M. Primet, J.M. Basset, M.V. Mathieu and M. Prettre, J. Catal. 29 (1973) 213.
N.D. Parkyns, J. Chem. Soc. A (1967) 1910.
B. Minder, M. Schürch, T. Mallat, A. Baiker, T. Heinz and A. Pfaltz, J. Catal., submitted.
Z.M. Liu, Y. Zhou, F. Solymosi and J.M. White, Surf. Sci. 245 (1991) 289.
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Minder, B., Mallat, T., Pickel, K.H. et al. Enantioselective hydrogenation of ethyl pyruvate in supercritical fluids. Catal Lett 34, 1–9 (1995). https://doi.org/10.1007/BF00808315
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DOI: https://doi.org/10.1007/BF00808315