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Research on Chemical Intermediates

, Volume 39, Issue 5, pp 2095–2105 | Cite as

Synthesis of terpinyl acetate using octadecylamine ethoxylate ionic liquids as catalysts

  • Lu Li
  • Shiwei Liu
  • Yanjing Shi
  • Shitao Yu
  • Congxia Xie
  • Chunjie Qi
Article

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.

Keywords

α-Pinene Acidic ionic liquid Esterification Terpinyl acetate Octadecylamine ethoxylates 

Notes

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.

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Copyright information

© Springer Science+Business Media B.V. 2012

Authors and Affiliations

  • Lu Li
    • 1
  • Shiwei Liu
    • 1
  • Yanjing Shi
    • 1
  • Shitao Yu
    • 1
  • Congxia Xie
    • 2
  • Chunjie Qi
    • 1
  1. 1.College of Chemical EngineeringQingdao University of Science and TechnologyQingdaoChina
  2. 2.College of Chemistry and Molecular EngineeringQingdao University of Science and TechnologyQingdaoChina

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