The natural lignan hydroxymatairesinol was hydrogenolysed to a potential anticarcinogenic substance matairesinol over different carbon-supported palladium catalysts. The reaction was conducted in 2-propanol at 70 °C under hydrogen flow in a stirred glass reactor. The catalysts were characterised by N2-physisorption, CO pulse chemisorption and pH measurement of aqueous catalyst slurries. The most active catalyst (Degussa-Hüls) gave yields of matairesinol over 90% in 4 h. It was concluded that the acidity of the catalyst had a profound influence on the reaction rate.
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References
D.C. Ayres J.D. Loike (1990) Lignans – Chemical, Biological and Clinical Properties Cambridge University Press Cambridge
N.M. Saarinen A. Wärri S.I. Mäkelä C. Eckerman M. Reunanen M. Ahotupa S.M. Salmi A.A. Franke L. Kangas R. Santti (2000) Nutr. Cancer 36 207 Occurrence Handle10.1207/S15327914NC3602_10 Occurrence Handle10890032
S. Willför J. Hemming M. Reunanen C. Eckerman B. Holmbom (2003) Holzforschung 57 27 Occurrence Handle10.1515/HF.2003.005
P. Eklund R. Sillanpää R. Sjöholm (2002) J. Chem. Soc., Perkin Trans. 1 1906
S. Heinonen T. Nurmi K. Liukkonen K. Poutanen K. Wähälä T. Deyama S. Nishibe H. Adlercreutz (2001) J. Agric. Food Chem. 49 3178 Occurrence Handle10.1021/jf010038a Occurrence Handle11453749
H. Adlercreutz (2002) Lancet 3 364 Occurrence Handle10.1016/S1470-2045(02)00777-5
S.M. Willför M.O. Ahotupa J.E. Hemming M.H.T. Reunanen P.C. Eklund R.E. Sjöholm C.S.E. Eckerman S.P. Pohjamo B.R. Holmbom (2003) J. Agric. Food Chem. 51 7600 Occurrence Handle10.1021/jf030445h Occurrence Handle14664514
G.V. Smith F. Notheisz (1999) Heterogeneous Catalysis in Organic Chemistry Academic Press San Diego
S. Nishimura (2001) Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis John Wiley & Sons Inc. NewYork
N. Krishnankutty M.A. Vannice (1995) J. Catal. 155 312 Occurrence Handle10.1006/jcat.1995.1213
P. Eklund A. Lindholm J.-P. Mikkola A. Smeds R. Lehtilä R. Sjöholm (2003) Org. Lett. 5 491 Occurrence Handle10.1021/ol0273598 Occurrence Handle12583751
O. Hofstadt and K. Kartte, Patent EP0193889 (1986)
M. Gurrath T. Kuretzky H.P. Boehm L.B. Okhlopkova A.S. Lisitsyn V.A. Likholobov (2000) Carbon 38 1241 Occurrence Handle10.1016/S0008-6223(00)00026-9
T.A. Dorling R.L. Moss (1967) J. Catal. 378 Occurrence Handle10.1016/0021-9517(67)90166-2
P.C. Eklund F.J. Sundell A.I. Smeds R.E. Sjöholm (2004) Org. Biomol. Chem. 2 2229 Occurrence Handle10.1039/b402849j Occurrence Handle15280960
R. Schlögl, in: Handbook of Heterogeneous Catalysis, Vol. 1, eds. G. Ertl, H. Knözinger and J. Weitkamp (Verlagsgesellschaft mbH, Weinheim, 1997) ch. 2.1.9
H.P. Boehm (2002) Carbon 40 145 Occurrence Handle10.1016/S0008-6223(01)00165-8
M. Kang M.W. Song K.L. Kim (2002) React. Kinet. Catal. Lett. 76 207 Occurrence Handle10.1023/A:1016563323091
M.L. Studebaker (1957) Rubber Chem. Technol. 30 1400
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Markus, H., Mäki-Arvela, P., Kumar, N. et al. Hydrogenolysis of Hydroxymatairesinol Over Carbon-Supported Palladium Catalysts. Catal Lett 103, 125–131 (2005). https://doi.org/10.1007/s10562-005-6514-6
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DOI: https://doi.org/10.1007/s10562-005-6514-6