Skip to main content

Preparation of α-terpineol and perillyl alcohol using zeolites beta

Abstract

The preparation of α-terpineol by direct hydration of limonene catalyzed by zeolites beta was studied. The same catalyst was used to prepare perillyl alcohol by isomerization of β-pinene oxide in the presence of water. The aim was to optimize the reaction conditions to achieve high conversions of starting material and high selectivity to the desired products. In the case of limonene, it was found that the highest selectivity to α-terpineol was 88% with conversion of 36% under the conditions: 50 wt% of catalyst beta 25, 10% aqueous acetic acid (10 mL) (volume ratio limonene:H2O = 1:4.5), temperature 50 °C, after 24 h. In the case of β-pinene oxide, it was found that the highest selectivity to perillyl alcohol, which was 36% at total conversion, was obtained in the reaction under the following conditions: dimethyl sulfoxide as solvent (volume ratio β-pinene oxide:DMSO = 1:5), catalyst beta 25 without calcination (15 wt%), demineralized water (molar ratio β-pinene oxide:H2O = 1:8), temperature 70 °C, 3 h. The present study shows that the studied reactions are suitable for the selective preparation of chosen compounds.

This is a preview of subscription content, access via your institution.

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

References

  1. Yi. Li, L. Li, Yu. Jihong, Chem 3, 928 (2017)

    CAS  Article  Google Scholar 

  2. J. Čejka, N. Žilková, Chem. Listy 94, 278 (2000)

    Google Scholar 

  3. W.F. Hölderich, J. Röseler, G. Heitmann, A.T. Liebens, Catal. Today 37, 353 (1997)

    Article  Google Scholar 

  4. G. Sartori, R. Maggi, Chem. Rev. 106, 1077 (2006)

    CAS  Article  Google Scholar 

  5. J.C. Jansen, E.J. Creyghton, S.L. Njo, H. van Koningsveld, H. van Bekkum, Catal. Today 38, 205 (1997)

    CAS  Article  Google Scholar 

  6. G. Bellusi, G. Pazzuconi, C. Perego, G. Girotti, G. Terzoni, J. Catal. 157, 227 (1995)

    Article  Google Scholar 

  7. K.P. de Jong, C.M.A.M. Mesters, D.G.R. Peferoen, P.T.M. van Brugge, C. de Groot, Chem. Eng. Sci. 51, 2053 (1996)

    Article  Google Scholar 

  8. K. Smith, A. Musson, G.A. DeBoos. Chem. Commun. (4), 469–470 (1996)

  9. E. Vrbková, T. Prejza, M. Lhotka, E. Vyskočilová, L. Červený. Catal. Lett. 151, 1993–2003 (2021)

  10. E.T.C. Vogt, B.M. Weckhuysen, Chem. Soc. Rev. 44, 7342 (2015)

    CAS  Article  Google Scholar 

  11. U. Freese, F. Heinrich, F. Roessner, Catal. Today 49, 237 (1999)

    CAS  Article  Google Scholar 

  12. R. Sheldon, I. Arends, U. Hanefeld, Green Chemistry and Catalysis (Wiley-VCH, Weinheim, 2007)

    Book  Google Scholar 

  13. J.L.F. Monteiro, C.O. Veloso, Top. Catal. 27, 169 (2004)

    CAS  Article  Google Scholar 

  14. M. Soleimani, M. Sheikholeslami, S. Ghafghazi et al., Iran. J. Basic Med. Sci. 22(12), 1445 (2019)

    PubMed  PubMed Central  Google Scholar 

  15. M.K. Yadav, M.V. Patil, R.V. Jasra, J. Mol. Catal. A Chem 279, 101 (2009)

    Article  Google Scholar 

  16. T. Chen, C. Fonseca, A. Schonthal, Am. J. Cancer Res. 5(5), 1580 (2015)

    PubMed  PubMed Central  Google Scholar 

  17. D.E. Chastain, W.E. Sanders, C.C. Sanders. Patent US5110832A (1992)

  18. K. Bauer, D. Garde, H. Surburg, Common Fragrance and Flavor Materials, 4th edn. (Wiley-VCH, Weinheim, 2001)

    Book  Google Scholar 

  19. E. Vyskočilová, J. Dušek, M. Babirádová, J. Krupka, I. Paterová, L. Červený, Res. Chem. Intermed. 44, 3971 (2018)

    Article  Google Scholar 

  20. D.E. Chastain, N. Mody, G. Majetich. Patent US5994598A (1999)

  21. M. Štekrová, I. Paterová-Dudková, E. Vyskočilová-Leitmannová, L. Červený, Res. Chem. Intermed. 38(8), 2075 (2012)

    Article  Google Scholar 

  22. E. Vyskočilová, M. Malý, A. Aho, J. Krupka, L. Červený, React. Kinet. Mech. Cat. 118, 235 (2016)

    Article  Google Scholar 

  23. E. Vrbková, B. Šteflová, M. Zapletal, E. Vyskočilová, L. Červený, Res. Chem. Intermed. 46, 4047 (2020)

    Article  Google Scholar 

  24. R.P. Bell, Acid–base reaction. Encyclopedia Britannica (2020). Accessed 9 Mar 2021

  25. J.P. Guthrie, Can. J. Chem. 56, 2342 (1987)

    Article  Google Scholar 

  26. R. Mungroo, N.C. Pradhan, V.V. Goud, A.K. Dalai, J. Am. Oil Chem. Soc. 85(9), 887 (2008)

    CAS  Article  Google Scholar 

  27. P.A. Robles-Dutenhefner, K.A. da Silva, M.R.H. Siddiqui, I.V. Kozhevnikov, E.V. Gusevskaya, J. Mol. Catal. A Chem. 175, 33 (2001)

    CAS  Article  Google Scholar 

  28. Y. Yuasa, Y. Yuasa, Org. Process Res. Dev. 10, 1231 (2006)

    CAS  Article  Google Scholar 

  29. P. Mäki-Arvela, N. Kumar, S.F. Diáz, A. Aho, M. Tenho, J. Salonen, A.R. Leino, K. Kordas, P. Laukkanen, J. Dahl, I. Sinev, T. Salmi, D.Y. Murzin, J. Mol. Catal. A Chem. 366, 228 (2013)

    Article  Google Scholar 

  30. M.C. Cruz, J.E. Sánchez-Velandia, S. Causíl, A.L. Villa. Catal. Lett. 151, 2279–2290 (2021)

  31. A. Corma, M. Renz, M. Susarte, Top. Catal. 52, 1182 (2009)

    CAS  Article  Google Scholar 

  32. E. Salminen, L. Rujana, P. Mäki-Arvela, P. Virtanen, T. Salmi, J.P. Mikkola, Catal. Today 257, 318 (2015)

    CAS  Article  Google Scholar 

  33. O. De La Torre, M. Renz, A. Corma, Appl. Catal. A Gen. 380, 165 (2010)

    Article  Google Scholar 

Download references

Acknowledgements

We thank Eva Vrbková, Ph.D. (Department of Organic Technology, UCT Prague) for providing TPD measurements. This work was supported from the grant of Specific university research—Grant No. A1_FCHT_2021_005.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Eliška Vyskočilová.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Zítová, K., Vyskočilová, E. & Červený, L. Preparation of α-terpineol and perillyl alcohol using zeolites beta. Res Chem Intermed 47, 4297–4310 (2021). https://doi.org/10.1007/s11164-021-04515-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-021-04515-6

Keywords

  • Hydration
  • Zeolites
  • α-Terpineol
  • Perillyl alcohol
  • Heterogeneous catalysis