Skip to main content
SpringerLink
Log in

Synthesis of terpinyl acetate using octadecylamine ethoxylate ionic liquids as catalysts

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Terpinyl acetate, an important natural flavor, can be synthesized by esterification of α-pinene with acetic acid under acidic conditions. In this work, seven acidic ionic liquids were first synthesized, using octadecylamine ethoxylates (AC 1810, AC 1815, AC 1820, and AC 1830) as the cations, and characterized by FT-IR, 1H NMR, and 13C NMR spectroscopy. The ionic liquids were then used as catalysts in the synthesis of terpinyl acetate. The effect of preparation conditions on catalyst performance was examined. It was found that the acidic ionic liquid 1-(3-sulfonic acid)propyl-3-poly(ethylene glycol) octadecylamine polyoxyethylene ether tetrafluoroborate ([PAC1815]+[BF4]−) was an excellent catalyst for synthesis of terpinyl acetate. The effects of the conditions used for preparation of terpinyl acetate were examined in detail, and the optimum preparation conditions were obtained. Under the optimum conditions, the yield of terpinyl acetate reached 35.70 %. When the catalyst was reused for the 5th time, the yield of terpinyl acetate was still 32.00 %. The results showed that effective separation and recycling of catalyst could contribute to developing a new strategy for synthesis of terpinyl acetate.

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

Similar content being viewed by others

References

  1. G.W. Xu, B.Q. Li, Manual on synthesis of spices (China Business Press, Beijing, 1996)

  2. S.S. Lin, S.H. Fu, K.C. Zheng, Y.G. Li, B.Z. Zhan, J. Mole, Catal. (China) 8, 50 (1994)

    CAS  Google Scholar 

  3. G.J. Gainsford, C.F. Hosie, R.J. Weston, Appl. Catal. A: Gen. 209, 269 (2001)

    Article  CAS  Google Scholar 

  4. G. Fan, C. Lin, J. Fuzhou, Univ. Natur. Sci. 33, 679 (2005)

    CAS  Google Scholar 

  5. J.S. Liu, X.M. Zheng, Ind. Catal. 16, 49 (2008)

    CAS  Google Scholar 

  6. D.C. Forbes, K.J. Weaver, J. Mol. Catal. A: Chem. 214, 129 (2004)

    Article  CAS  Google Scholar 

  7. H.M. Wang, P. Cui, G. Zou, Tetrahedron 62, 3985 (2006)

    Article  CAS  Google Scholar 

  8. D.Q. Xu, W.L. Yang, S.P. Luo, Eur. J. Org. Chem. 6, 1007 (2007)

    Article  Google Scholar 

  9. J.H. Shen, H. Wang, H.C. Liu, J. Mol. Catal. A: Chem. 280, 24 (2008)

    Article  CAS  Google Scholar 

  10. M.H. Han, W.L. Yi, Q. Wu, Bioresource Tech. 100, 2308 (2009)

    Article  CAS  Google Scholar 

  11. Y.W. Zhao, J.X. Long, F.G. Deng, Catal. Commun. 10, 732 (2009)

    Article  CAS  Google Scholar 

  12. K. Przemyslaw, Prog. Polym. Sci. 12, 1333 (2009)

    Google Scholar 

  13. X.L. Tong, Y.D. Li, ChemSusChem. 3, 350 (2010)

    Article  CAS  Google Scholar 

  14. A.K. Ressmann, P. Gaertner, K. Bica, Green Chem. 13, 1442 (2011)

    Article  CAS  Google Scholar 

  15. S.W. Liu, C.X. Xie, S.T. Yu, Catal. Commun. 9, 1634 (2008)

    Article  CAS  Google Scholar 

  16. A.C. Cole, J.L. Jensen, D.A. Forbes, J. Am. Chem. Soc. 124, 5962 (2002)

    Article  CAS  Google Scholar 

  17. D.J. Fraga, K. Bourahla, J.P. Bazureau, Catal. Commun. 3, 185 (2002)

    Article  Google Scholar 

  18. T. Joseph, S. Sahoo, S.B. Halligudi, J. Mol. Catal. A: Chem. 234, 107 (2005)

    Article  CAS  Google Scholar 

  19. A. Atef, P.B. Jean, Org. Process Res. Dev. 9, 743 (2005)

    Article  Google Scholar 

  20. H.P. Zhu, F. Yang, J. Tang, Green Chem. 5, 38 (2003)

    Article  CAS  Google Scholar 

  21. Z.G. Zhang, H. Yin, Z.R. Chen, J. Tex. Res. 4, 134 (2005)

    Google Scholar 

  22. S. Fang, Prog. Chem. 22, 309 (2010)

    CAS  Google Scholar 

  23. M. Said, V. Alfons, Chem. Eng. Process. 18, 225 (1984)

    Article  Google Scholar 

Download references

Acknowledgments

The authors are grateful to the National Natural Science Foundation of China (31000275) and the Postdoctoral Science Foundation of China (20100471496) for financial support of this work.

Author information

Authors and Affiliations

  1. College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao, China

    Lu Li, Shiwei Liu, Yanjing Shi, Shitao Yu & Chunjie Qi

  2. College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao, China

    Congxia Xie

Authors
  1. Lu Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shiwei Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yanjing Shi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Shitao Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Congxia Xie
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Chunjie Qi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Lu Li.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Li, L., Liu, S., Shi, Y. et al. Synthesis of terpinyl acetate using octadecylamine ethoxylate ionic liquids as catalysts. Res Chem Intermed 39, 2095–2105 (2013). https://doi.org/10.1007/s11164-012-0741-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0741-4

Keywords

Search

Navigation