Skip to main content
Log in

Hydrogenolysis of Hydroxymatairesinol Over Carbon-Supported Palladium Catalysts

  • Published:
Catalysis Letters Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. D.C. Ayres J.D. Loike (1990) Lignans – Chemical, Biological and Clinical Properties Cambridge University Press Cambridge

    Google Scholar 

  2. 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

    Article  PubMed  Google Scholar 

  3. S. Willför J. Hemming M. Reunanen C. Eckerman B. Holmbom (2003) Holzforschung 57 27 Occurrence Handle10.1515/HF.2003.005

    Article  Google Scholar 

  4. P. Eklund R. Sillanpää R. Sjöholm (2002) J. Chem. Soc., Perkin Trans. 1 1906

    Google Scholar 

  5. 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

    Article  PubMed  Google Scholar 

  6. H. Adlercreutz (2002) Lancet 3 364 Occurrence Handle10.1016/S1470-2045(02)00777-5

    Article  Google Scholar 

  7. 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

    Article  PubMed  Google Scholar 

  8. G.V. Smith F. Notheisz (1999) Heterogeneous Catalysis in Organic Chemistry Academic Press San Diego

    Google Scholar 

  9. S. Nishimura (2001) Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis John Wiley & Sons Inc. NewYork

    Google Scholar 

  10. N. Krishnankutty M.A. Vannice (1995) J. Catal. 155 312 Occurrence Handle10.1006/jcat.1995.1213

    Article  Google Scholar 

  11. P. Eklund A. Lindholm J.-P. Mikkola A. Smeds R. Lehtilä R. Sjöholm (2003) Org. Lett. 5 491 Occurrence Handle10.1021/ol0273598 Occurrence Handle12583751

    Article  PubMed  Google Scholar 

  12. O. Hofstadt and K. Kartte, Patent EP0193889 (1986)

  13. 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

    Article  Google Scholar 

  14. T.A. Dorling R.L. Moss (1967) J. Catal.   378 Occurrence Handle10.1016/0021-9517(67)90166-2

    Article  Google Scholar 

  15. P.C. Eklund F.J. Sundell A.I. Smeds R.E. Sjöholm (2004) Org. Biomol. Chem. 2 2229 Occurrence Handle10.1039/b402849j Occurrence Handle15280960

    Article  PubMed  Google Scholar 

  16. 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

  17. H.P. Boehm (2002) Carbon 40 145 Occurrence Handle10.1016/S0008-6223(01)00165-8

    Article  Google Scholar 

  18. M. Kang M.W. Song K.L. Kim (2002) React. Kinet. Catal. Lett. 76 207 Occurrence Handle10.1023/A:1016563323091

    Article  Google Scholar 

  19. M.L. Studebaker (1957) Rubber Chem. Technol. 30 1400

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Dmitry Yu. Murzin.

Rights and permissions

Reprints and permissions

About this article

Cite this article

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

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-005-6514-6

Keywords

Navigation