Abstract
When α,β-unsaturated aldehydes are reduced by hydrogen in supercritical carbon dioxide using an unmodified Pt/Al2O3 catalyst, unsaturated alcohols are highly selectively produced, in contrast to previous results with organic solvents in which such a selective hydrogenation is difficult to achieve with monometallic Pt catalysts. The selectivity of unsaturated alcohols depends mainly on pressure of carbon dioxide while the conversion depends on both carbon dioxide and hydrogen pressures. The selectivity increases with increasing pressure and then does not change so much at higher pressures.
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K.P. Johnston and J.M.L. Penninger, eds., Supercritical Fluid Science and Technology, ACS Symposium Series, Vol. 406 (Am. Chem. Soc., Washington, DC, 1989); (b) P.G. Jessop, T. Ikariya and R. Noyori, Science 269 (1995) 1065; (c) P.G. Jessop, T. Ikariya and R. Noyori, Organometallics 14 (1995) 1510.
G. Kaupp, Angew. Chem. Int. Ed. Engl. 33 (1994) 1452; (b) L. Boock, B. Wu, C. LaMarca, M. Klein and S. Paspek, CHEMTECH (1992) 719; (c) B. Subramaniam and M.A. McHugh, Ind. Eng. Chem. Process Des. Dev. 25 (1986) 1; (d) M.E. Paulaitis and G.C. Alexander, Pure Appl. Chem. 59 (1987) 61; (e) J.A. Hyatt, J. Org. Chem. 49 (1984) 5097.
J.M. DeSimone, Z. Guan and C.S. Elsbernd, Science 257 (1992) 945; (b) J.M. DeSimone, E.E. Maury, Y.Z. Menceloglu, J.B. McClain, T.J. Romack and J.R. Combes, Science 265 (1994) 356; (c) J.M. Tanko and J.F. Blackert, Science 263 (1994) 203; (d) J.W. Rathke, R.J. Klingler and T.B. Krause, Organometallics 10 (1991) 1350; (e) M. Jobling, S.M. Howdle, M.A. Healy and M.J. Poliakoff, J. Chem. Soc. Chem. Commun. (1990) 1287; (f) M.J. Burk, S. Feng, M.F. Gross and W. Tumas, J. Am. Chem. Soc. 117 (1995) 8277; (g) S. Kainz and W. Leitner, Catal. Lett. 55 (1998) 223; (h) D. Koch and W. Leitner, J. Am. Chem. Soc. 120 (1998) 13398; (i) P.G. Jessop, Y. Hsiao, T. Ikariya and R. Noyori, J. Am. Chem. Soc. 118 (1996) 344; (j) P.G. Jessop, Y. Hsiao T. Ikariya and R. Noyori, J. Chem. Soc. Chem. Commun. (1995) 707; (k) P.G. Jessop, T. Ikariya and R. Noyori, Nature 368 (1994) 231; (l) K.E. O'Shea, J.R. Combes, M.A. Fox and K.P. Johnston, Photochem. Photobiol. 54 (1991) 571.
M.J. Burk, F. Shaoguang, M.F. Gross and W.J. Tumas, J. Am. Chem. Soc. 117 (1995) 8277; (b) J. Xiao, C.A. Nefkens, P.G. Jessop, T. Ikariya and R. Noyori, Tetrahedron Lett. 37 (1996) 2813.
M.G. Hitzler and M. Poliakoff, J. Chem. Soc. Chem. Commun. (1997) 1667; (b) A. Bertucco, P. Canu, L. Devetta and A.G. Zwahlen, Ind. Eng. Chem. Res. 36 (1997) 2626; (c) L. Devetta, P. Canu, A. Bertucco and K. Steiner, Chem. Eng. Sci. 52 (1997) 4163; (d) B. Minder, T. Mallat, K.H. Pickel, K. Steiner and A. Baiker, Catal. Lett. 34 (1995) 1; (e) M. Harrod and P. Moller, Process Technol. Proc. 12 (1996) 43; (f) T. Tacke, S. Wieland and P. Panster, Process Technol. Proc. 12 (1996) 17; (g) M.G. Hitzler, F.R. Smail, S.K. Ross and M. Poliakoff, Org. Proc. Res. Dev. 2 (1998) 137.
P. Gallezot and D. Richard, Catal. Rev. Sci. Eng. 40 (1998) 81, and references therein; (b) V. Ponec, Appl. Catal. A 149 (1997) 27; (c) J.M. Grosselin, C. Mercier, G. Allmang and F. Grass, Organometallics 10 (1991) 2126.
M. Arai, H. Takahashi, M. Shirai, Y. Nishiyama and T. Ebina, Appl. Catal. A 176 (1999) 229; (b) M. Arai, A. Obata, K. Usui, M. Shirai and Y. Nishiyama, Appl. Catal. A 146 (1996) 381; (c) M. Arai, K. Usui, M. Shrai and Y. Nishiyama, Stud. Surf. Sci. Catal. 91 (1995) 923; (d) M. Arai, K. Usui and Y. Nishiyama, J. Chem. Soc. Chem. Commun. (1993) 1853.
T. Moriyoshi, T. Kita and Y. Uosaki, Ber. Bunsen Ges. Phys. Chem. 97 (1993) 589.
M. Arai, Y. Nishiyama and Y. Ikushima, J. Supercrit. Fluids 13 (1998) 149.
M. Arai, M. Mitsui, J. Ozaki and Y. Nishiyama, J. Colloid Interface Sci. 168 (1994) 473.
C.L. Young, ed., Hydrogen and Deuterium, Solubility Data Series, Vol. 5/6 (Pergamon, Oxford, 1981).
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Bhanage, B.M., Ikushima, Y., Shirai, M. et al. The selective formation of unsaturated alcohols by hydrogenation of α,β-unsaturated aldehydes in supercritical carbon dioxide using unpromoted Pt/Al2O3 catalyst. Catalysis Letters 62, 175–177 (1999). https://doi.org/10.1023/A:1019038820349
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DOI: https://doi.org/10.1023/A:1019038820349