Skip to main content
SpringerLink
Log in

Gold Catalysts for Selective Aerobic Oxidation of the Lignan Hydroxymatairesinol to Oxomatairesinol: Catalyst Deactivation and Regeneration

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

The lignan oxomatairesinol was synthesized from the biomass-derived lignan hydroxymatairesinol via selective aerobic oxidation over a heterogeneous gold catalyst. The catalyst was prepared by direct ion-exchange and characterized by XRD, TEM and ICP-OES methods. The reaction was carried out at 70 °C and atmospheric pressure in a semi-batch reactor. To reveal the origin of catalyst deactivation, spent catalysts were studied by TEM, XRD, nitrogen physisorption, ICP-OES, TPO, and DSC-TGA techniques. Several regeneration procedures were applied—extraction by several solvents and calcinations in the oxidizing atmosphere. The former one was found to be the most effective way for the catalyst regeneration.

Graphical Abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Adlercreutz H (1998) Phytoestrogens and human health. In: Korach K (ed) Reproductive and developmental toxicology. Marcel Dekker, New York, pp 299–371

    Google Scholar 

  2. Yamaguchi S, Sugahara T, Nakashima Y, Okada A, Akiyama K, Kishida T, Maruyama M, Masuda T (2006) Biosci Biotechnol Biochem 70:1934

    Article  Google Scholar 

  3. Korte H, Unkila M, Hiilovaara-Teijo M, Lehtola V-M, Ahotupa M (2003) Patent WO/2004/000304 A1

  4. Ahlnäs T (2008) Patent WO 2008/020112 A1

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

    Article  Google Scholar 

  6. Eklund PC, Sjöholm RE (2003) Tetrahedron 59:4515

    Article  CAS  Google Scholar 

  7. Willför S, Hemming J, Reunanen M, Eckerman C, Holmbom B (2003) Holzforschung 57:27

    Article  Google Scholar 

  8. Kawamura F, Miyachi M, Kaway S (1998) J Wood Sci 44:47

    Article  CAS  Google Scholar 

  9. Eklund P, Lindholm A, Mikkola J-P, Smeds A, Lehtilä R, Sjöholm R (2003) Org Lett 5:491

    Article  CAS  Google Scholar 

  10. Markus H, Plomp AJ, Sandberg T, Nieminen V, Bitter JH, Murzin DYu (2007) J Mol Catal A 274:42

    Article  CAS  Google Scholar 

  11. Bond GC, Louis C, Thompson DT (2006) Catalysis by gold. In: Hutchings GJ (ed) Catalysis science series, vol 6. Imperial College Press, London

    Google Scholar 

  12. Corma A, Domine ME (2005) Chem Commun 31:4042

    Article  Google Scholar 

  13. Simakova OA, Murzina EV, Mäki-Arvela P, Leino A-R, Campo BC, Kordás K, Willför S, Salmi T, Murzin DYu (2011) J Catal 282:54

    Article  CAS  Google Scholar 

  14. Besson M, Gallezot P (2003) Catal Today 81:547

    Article  CAS  Google Scholar 

  15. Ivanova S, Pitchon V, Zimmermann Y, Petit C (2006) Appl Catal A 298:57

    Article  CAS  Google Scholar 

  16. Markus H, Mäki-Arvela P, Kumar N, Kul’kova NV, Eklund P, Sjöhölm R, Holmbom B, Salmi T, Murzin DY (2005) Catal Lett 103:125

    Article  CAS  Google Scholar 

  17. Ollonqvist T, Murzin DY, Mäki-Arvela P, Lindroos M, Vayrynen J, Salmi T, Kumar N (2002) Catal. Org. React. Chap 50

  18. Gong J, Flaherty DW, Yan T, Mullins CB (2008) ChemPhysChem 9:2461

    Article  CAS  Google Scholar 

  19. Wilds AL (1944) Org React 2:178

    Google Scholar 

  20. Zanella R, Louis C (2005) Catal Today 107–108:768

    Article  Google Scholar 

  21. Simakova OA, Kusema BT, Campo BC, Leino A-R, Kordas K, Pitchon V, Maki-Arvela P, Murzin DYu (2011) J Phys Chem C 115:1036

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors express their gratitude to Dr. Lari Vähäsalo for HMR preparation and Mr. Markku Reunanen for product identification. Mr. Sten Lindholm is acknowledged for ICP-OES analysis.

Author information

Authors and Affiliations

  1. Laboratory of Industrial Chemistry and Reaction Engineering, Process Chemistry Centre, Åbo Akademi University, FI-20500, Turku, Finland

    Olga A. Simakova, Elena V. Murzina, Päivi Mäki-Arvela & Dmitry Yu Murzin

  2. Graduate School of Chemical Engineering, Åbo Akademi University, FI-20500, Turku, Finland

    Olga A. Simakova

  3. Microelectronics and Materials Physics Laboratories, EMPART Research Group of Infotech Oulu, University of Oulu, FI-90014, Oulu, Finland

    Anne-Riikka Leino

  4. Laboratory of Wood and Paper Chemistry, Process Chemistry Centre, Åbo Akademi University, FI-20500, Turku, Finland

    Stefan Willför

Authors
  1. Olga A. Simakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Elena V. Murzina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Anne-Riikka Leino
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Päivi Mäki-Arvela
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Stefan Willför
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Dmitry Yu Murzin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Dmitry Yu Murzin.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Simakova, O.A., Murzina, E.V., Leino, AR. et al. Gold Catalysts for Selective Aerobic Oxidation of the Lignan Hydroxymatairesinol to Oxomatairesinol: Catalyst Deactivation and Regeneration. Catal Lett 142, 1011–1019 (2012). https://doi.org/10.1007/s10562-012-0855-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-012-0855-8

Keywords

Search

Navigation