Advertisement

Russian Journal of Organic Chemistry

, Volume 55, Issue 6, pp 771–774 | Cite as

Transesterification of Dialkyl Carbonates with 2,2,3,3-Tetrafluoropropan-1-ol

  • A. M. Semenova
  • M. G. Pervova
  • M. A. Ezhikova
  • M. I. Kodess
  • A. Ya. Zapevalov
  • A. V. PestovEmail author
Article
  • 9 Downloads

Abstract

Transesterification of dialkyl carbonates with 2,2,3,3-tetrafluoropropan-1-ol in the presence of various bases leads to the formation of mixtures of bis(2,2,3,3-tetrafluoropropyl) carbonate and alkyl 2,2,3,3-tetrafluoropropyl carbonate. The best catalyst for the synthesis of alkyl 2,2,3,3-tetrafluoropropyl carbonates was found to be tetramethylammonium hydroxide which ensured 81% selectivity for methyl 2,2,3,3-tetrafluoropropyl carbonate, the conversion of dimethyl carbonate being 50%. Lithium alkoxides showed a comparable catalytic efficiency.

Keywords

transesterification dialkyl carbonates alkoxides tetrafluoropropanol dimethyl carbonate phosgene 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Notes

Acknowledgments

This study was performed using the equipment of the Spectroscopy and Analysis of Organic Compounds joint center.

Funding

This study was performed in the framework of state assignment of the Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences.

References

  1. 1.
    Studnev, Yu.N., Frolovskii, VA., Kinash, O.F., and Stolyarov, V.P., Pharm. Chem. J., 2006, vol. 40, p. 76. doi  https://doi.org/10.1007/s11094-006-0062-2 CrossRefGoogle Scholar
  2. 2.
    Okazoe, T., Nagasaki, Y., and Okamoto, H., JPN Patent no. 86126, 2010; Chem. Abstr., 2011, vol. 155, no. 535 845.Google Scholar
  3. 3.
    Azimi, N., Weng, W., Takoudis, C., and Zhang, Z., Electrochem. Commun., 2013, vol. 37, p. 96. doi  https://doi.org/10.1016/j.elecom.2013.10.020 CrossRefGoogle Scholar
  4. 4.
    Nishikawa, D., Nakajima, T., Ohzawa, Y., Koh, M., Yamauchi, A., Kagawa, M., and Aoyama, H., J. Power Sources, 2013, vol. 243, p. 573. doi  https://doi.org/10.1016/j.jpowsour.2013.06.034 CrossRefGoogle Scholar
  5. 5.
    Matsuda, Y., Nakajima, T., Ohzawa, Y., Koh, M., Yamauchi, A., Kagawa, M., and Aoyama, H., J. Fluorine Chem., 2011, vol. 132, p. 1174. doi  https://doi.org/10.1016/j.jfluchem.2011.07.019 CrossRefGoogle Scholar
  6. 6.
    Babad, H. and Zeiler, A., Chem. Rev., 1973, vol. 73, p. 75. doi  https://doi.org/10.1021/cr60281a005 CrossRefGoogle Scholar
  7. 7.
    Okamoto, H., Tajima, K., and Okazoe, T., JPN Patent no. 312655, 2007; Chem. Abstr., 2009, vol. 151, no. 33110.Google Scholar
  8. 8.
    Hong, M.-C., Choi, Y.-S., Kwon, D.-E., and Kwak, J.-Y., Korean Patent no. 159015, 2016; Chem. Abstr., 2018, vol. 168, no. 523052.Google Scholar
  9. 9.
    Gao, M.-T., Nakazawa, A., Sakata, H., Tanaka, M., and Yamauchi, A., JPN Patent no. 26911, 2007; Chem. Abstr., 2008, vol. 149, no. 271609.Google Scholar
  10. 10.
    Petrova, T.D., Ryabichev, A.G., Savchenko, T.I., Kolesnikova, I.V., and Platonov, V.E., Zh. Org. Khim., 1988, vol. 24, p. 1513.Google Scholar
  11. 11.
    Okamoto, H., JPN Patent no. 178836, 2004; Chem. Abstr., 2005, vol. 144, no. 87956.Google Scholar
  12. 12.
    Arico, F. and Tundo, P., Russ. Chem. Rev., 2010, vol. 79, p. 479. doi  https://doi.org/10.1070/RC2010v079n06ABEH004113 CrossRefGoogle Scholar
  13. 13.
    Kuznetsov, V.A., Pervova, M.G., and Pestov, A.V., Russ. J. Org. Chem., 2014, vol. 50, p. 654. doi  https://doi.org/10.1134/S1070428014050066 CrossRefGoogle Scholar
  14. 14.
    Otera, J., Chem. Rev., 1993, vol. 93, p. 1449. doi  https://doi.org/10.1021/cr00020a004 CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • A. M. Semenova
    • 1
  • M. G. Pervova
    • 1
  • M. A. Ezhikova
    • 1
  • M. I. Kodess
    • 1
    • 2
  • A. Ya. Zapevalov
    • 1
  • A. V. Pestov
    • 1
    • 2
    Email author
  1. 1.Postovskii Institute of Organic Synthesis, Ural BranchRussian Academy of SciencesYekaterinburgRussia
  2. 2.Yeltsin Ural Federal UniversityYekaterinburgRussia

Personalised recommendations