Skip to main content

Synthesis, Physicochemical Properties, and Thermo-Oxidative Stability of Triesters of 1,3,5-Adamantanetriol and 7-Ethyl-1,3,5-Adamantanetriol

Abstract

The synthesis of a series of triesters based on 1,3,5-adamantanetriol and 7-ethyl-1,3,5-adamantanetriol and C4–C6 aliphatic acids is executed, and their physicochemical and thermo-oxidative properties are studied. The properties of the obtained esters are compared to those of pentaerythritol esters. The synthesized esters have pour points below −40°C, the range of viscosities at 100°C varies from 4.361 to 9.912 mm2/s, and the values of the indices of thermo-oxidative stability are 221.6–240.3°C.

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

Fig. 1.
Fig. 2.

REFERENCES

  1. 1

    V. I. Babkin, A. A. Aleksashin, L. S. Yanovskii, et al., Dvigatel’ 83 (5), 6 (2012).

    Google Scholar 

  2. 2

    C. W. Tsai, K. H. Wu, C. C. Yang, and G. P. Wang, React. Funct. Polym. 91–92, 11 (2015).

    Article  Google Scholar 

  3. 3

    C.-W. Tsai, J.-C. Wang, F.-N. Li, et al., Mater. Express 6, 220 (2016).

    CAS  Article  Google Scholar 

  4. 4

    K. Tanaka, T. Hiraoka, F. Ishiguro, et al., RSC Adv 4, 28107 (2014).

    CAS  Article  Google Scholar 

  5. 5

    T. Ouchi and Y. Nishimura, US Patent No. 8912366 (2014).

  6. 6

    M.-Y. Huang, J.-C. Lin, K.-H. Lin, and J.-C. Wu, US Patent No. 7 488 859 (2009).

  7. 7

    A. Kojima and M. Saito, US Patent No. 7 145 048 (2006).

  8. 8

    Y. Ishii, T. Nakano, and N. Hirai, US Patent No. 6392104 (1998).

  9. 9

    C. S. H. Chen, S. E. Schramm, and S. E. Wentzek, US Patent No. 5 397 488 (1995).

  10. 10

    K. Honna and H. Seiki, US Patent No. 4 990 691 (1991).

  11. 11

    K. Honna and H. Seiki, US Patent No. 4 963 292 (1990).

  12. 12

    Modern Oxidation Methods, Ed. by J.-E. Bäckvall, 2nd Ed. (Wiley–VCH, Weinheim, 2010).

    Google Scholar 

  13. 13

    E. I. Bagrii and G. B. Maravin, Pet. Chem. 53, 418 (2013).

    CAS  Article  Google Scholar 

  14. 14

    E. I. Bagrii, A. I. Nekhaev, and A. L. Maksimov, Pet. Chem. 57, 183 (2017).

    CAS  Article  Google Scholar 

  15. 15

    E. A. Ivleva, M. R. Baimuratov, Yu. A. Zhuravleva, et al., Pet. Chem. 55, 133 (2015).

    CAS  Article  Google Scholar 

  16. 16

    E. A. Ivleva, M. R. Baimuratov, Yu. A. Zhuravleva, et al., Pet. Chem. 56, 873 (2016).

    CAS  Article  Google Scholar 

  17. 17

    E. A. Ivleva, M. R. Baimuratov, V. S. Gavrilova, et al., Pet. Chem. 55, 673 (2015).

    CAS  Article  Google Scholar 

  18. 18

    T. M. Klapçtke, B. Krumm, and A. Widera, ChemPlusChem 83, 61 (2018).

    Article  Google Scholar 

  19. 19

    S.-Q. Fu, J.-W. Guo, D.-Y. Zhu, et al., RSC Adv. 5, 67054 (2015).

    CAS  Article  Google Scholar 

  20. 20

    S. M. Sayed, B.-P. Lin, and H. Yang, Soft Matter 12, 6148 (2016).

    CAS  Article  Google Scholar 

  21. 21

    F. M. Menger and V. A. Migulin, J. Org. Chem. 64, 8916 (1999).

    CAS  Article  Google Scholar 

  22. 22

    N. Pannier and W. Maison, Eur. J. Org. Chem., 1278 (2008).

  23. 23

    P.-E. Alexandre, A. Schwenger, W. Frey, and C. Richert, Chem.-Eur. J. 23, 9018 (2017).

    CAS  Article  Google Scholar 

  24. 24

    A. Schwenger, W. Frey, and C. Richert, Chem.-Eur. J. 21, 1 (2015).

    Article  Google Scholar 

  25. 25

    A. Schwenger, W. Frey, and C. Richert, Angew. Chem., Int. Ed. Engl. 55, 1 (2016).

    Article  Google Scholar 

  26. 26

    M. Tominaga, H. Masu, and I. Azumaya, J. Org. Chem. 74, 8754 (2009).

    CAS  Article  Google Scholar 

  27. 27

    H. Zhu, J. Guo, C. Yang, et al., Synth. Commun. 43, 1161 (2013).

    CAS  Article  Google Scholar 

  28. 28

    H. Yang, J. Guo, R. Tong, et al., Polymers 10, 443 (2018).

    Article  Google Scholar 

  29. 29

    E. A. Ivleva, I. A. Platonov, and Yu. N. Klimochkin, Russ. J. Gen. Chem. 85, 1830 (2015).

    CAS  Article  Google Scholar 

Download references

Funding

This work was supported by the Ministry of Education and Science of the Russian Federation. agreement no. 14.577.21.0237 (project unique identifier RFMEFI57716X0237).

Author information

Affiliations

Authors

Corresponding author

Correspondence to E. A. Ivleva.

Ethics declarations

The authors declare no conflict of interest requiring the disclosure in this publication.

Additional information

Translated by E. Boltukhina

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Ivleva, E.A., Baimuratov, M.R., Malinovskaya, Y.A. et al. Synthesis, Physicochemical Properties, and Thermo-Oxidative Stability of Triesters of 1,3,5-Adamantanetriol and 7-Ethyl-1,3,5-Adamantanetriol. Pet. Chem. 59, 1235–1239 (2019). https://doi.org/10.1134/S0965544119110082

Download citation

Keywords:

  • esters
  • thermo-oxidative stability
  • adamantanetriol
  • thermally stable base oils