Skip to main content
SpringerLink
Log in

Isomerisation of α-Pinene Oxide to Campholenic Aldehyde Over Supported Ionic Liquid Catalysts (SILCAs)

  • Original Paper
  • Published:
Topics in Catalysis Aims and scope Submit manuscript

Abstract

The isomerisation of α-pinene oxide to campholenic aldehyde, an expensive ingredient utilized by e.g. flavor industry, was studied over Supported Ionic Liquid Catalysts (SILCAs) consisting of catalytically active species residing in ionic liquid. The ionic liquid, in turn, was immobilized on a solid support material. SILCAs were demonstrated as efficient catalysts for the transformation of α-pinene oxide into campholenic aldehyde, with the product distribution and activity being dependent on the nature of the ionic liquid.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Chapuis C, Jacoby D (2001) Appl Catal A 221:93

    Article  CAS  Google Scholar 

  2. Erman WF (1985) Chemistry of the monoterpenes. An Encyclopedic Handbook (Marcel Dekker, New York

    Google Scholar 

  3. Orloff G, Winter B, Fehr C (1991) In: Muller PM, Lamparsky D (eds) Perfumes, Art, Science and Technology. Elsevier, NewYork

    Google Scholar 

  4. Kaminska J, Schwegler MA, Hoefnagel AJ, van Bekkum H (1992) Recl Trav Chim Pays-Bas 111:432

    Article  CAS  Google Scholar 

  5. Da Silva Rocha KA, Kozhevnikov IV, Gusevskaya EV (2005) Appl Catal A 294:106

    Article  CAS  Google Scholar 

  6. Wilson K, Renson A, Clark JH (1999) Catal Lett 61:51

    Article  CAS  Google Scholar 

  7. Arbusow B (1935) Chem Ber 68:1430

    Google Scholar 

  8. Hölderich WF, Röseler J, Heitmann G, Liebens AT (1997) Catal Today 37:353

    Article  Google Scholar 

  9. Stekrova M, Kumar N, Aho A, Sinev I, Grunert W, Dahl J, Roine J, Arzumanov S.S, Maki-Arvela P and Yu. Murzin D (2013) Appl Catal A 470:162

  10. Kunkeler PJ, van der Waal JC, Bremmer J, Zuurdeeg BJ, Downing RS, van Bekkum H (1998) Catal Lett 53:135

    Article  CAS  Google Scholar 

  11. Flores-Moreno JL, Baraket L, Figueras F (2001) Catal Lett 77:113

    Article  CAS  Google Scholar 

  12. Ravasio N, Zaccheria F, Guidotti M, Psaro R (2004) Top Catal 27:157

    Article  CAS  Google Scholar 

  13. Mun J, Sim H (2012) Handbook of ionic liquids. Nova Science Publishers Inc., New York

    Google Scholar 

  14. Sheldon R (2001) Chem Commun (2001) 2399

  15. Gordon CM (2001) Appl Catal A 222:101. 14

  16. Virtanen P, Karhu H, Toth G, Kordas K, Mikkola J-P (2009) J Catal 263:209

    Article  CAS  Google Scholar 

  17. Valkenberg MH (2002) C. deCastro and W.F. Holderich. Green Chem. 4:88–93

    Article  CAS  Google Scholar 

  18. Mikkola J-P, Virtanen P, Karhu H, Salmi T, Murzin DY (2006) Green Chem 8:197

    Article  CAS  Google Scholar 

  19. Mehnert CP, Cook RA, Dispenziere NC, Afeworki M (2002) J Am Chem Soc 124:12932

    Article  CAS  Google Scholar 

  20. Hara P, Mikkola J-P, Murzin DY, Kanerva LT (2010) J Mol Catal B 67:129

    Article  CAS  Google Scholar 

  21. Shi F, Zhang Q, Li D, Deng Y (2005) Chem Eur J 11:5279

    Article  CAS  Google Scholar 

  22. Kim DW, Chi DY (2004) Angew Chem Int Ed 43:483

    Article  CAS  Google Scholar 

  23. Kernchen U, Etzold B, Korth W, Jess A (2007) Chem Eng Technol 30:985

    Article  CAS  Google Scholar 

  24. Coelho JV, Meireles ALP, Silva Rocha KA, Pereira MC, Oliveira LCA, Gusevskaya EV (2012) Appl Catal A 443–444:125

    Article  Google Scholar 

  25. Riisager A, Fehrmann R, Haumann M, Gorle BSK, Wasserscheid P (2005) Ind Eng Chem Res 44:9853

    Article  CAS  Google Scholar 

  26. Allahverdiev A, Irandoust S, Murzin DYu (1999) J Catal 185:352

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work is part of the activities at the Åbo Akademi Process Chemistry Centre. The Academy of Finland is gratefully acknowledged for financial support. In Sweden, the Bio4Energy programme and Kempe Foundations are acknowledged. The Cost action CM0903 (UbioChem) is also acknowledged. Hangzhou Grascent Co. is acknowledged for providing terpene samples.

Author information

Authors and Affiliations

  1. Department of Chemical Engineering, Process Chemistry Centre, Industrial Chemistry and Reaction Engineering, Åbo Akademi University, 20500, Abo/Turku, Finland

    Eero Salminen, Päivi Mäki-Arvela, Pasi Virtanen, Tapio Salmi & Jyri-Pekka Mikkola

  2. Department of Chemistry, Chemical-Biological Centre, Technical Chemistry, Umeå University, 90187, Umeå, Sweden

    Jyri-Pekka Mikkola

Authors
  1. Eero Salminen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Päivi Mäki-Arvela
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pasi Virtanen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tapio Salmi
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jyri-Pekka Mikkola
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Eero Salminen.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Salminen, E., Mäki-Arvela, P., Virtanen, P. et al. Isomerisation of α-Pinene Oxide to Campholenic Aldehyde Over Supported Ionic Liquid Catalysts (SILCAs). Top Catal 57, 1533–1538 (2014). https://doi.org/10.1007/s11244-014-0330-4

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11244-014-0330-4

Keywords

Search

Navigation