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Petroleum Chemistry

, Volume 59, Issue 11, pp 1235–1239 | Cite as

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

  • E. A. IvlevaEmail author
  • M. R. Baimuratov
  • Yu. A. Malinovskaya
  • Yu. N. Klimochkin
  • V. A. Tyshchenko
  • I. A. Kulikova
  • V. V. Pozdnyakov
  • K. A. Ovchinnikov
Article
  • 16 Downloads

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.

Keywords:

esters thermo-oxidative stability adamantanetriol thermally stable base oils 

Notes

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).

CONFLICT OF INTEREST

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

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).CrossRefGoogle Scholar
  3. 3.
    C.-W. Tsai, J.-C. Wang, F.-N. Li, et al., Mater. Express 6, 220 (2016).CrossRefGoogle Scholar
  4. 4.
    K. Tanaka, T. Hiraoka, F. Ishiguro, et al., RSC Adv 4, 28107 (2014).CrossRefGoogle Scholar
  5. 5.
    T. Ouchi and Y. Nishimura, US Patent No. 8912366 (2014).Google Scholar
  6. 6.
    M.-Y. Huang, J.-C. Lin, K.-H. Lin, and J.-C. Wu, US Patent No. 7 488 859 (2009).Google Scholar
  7. 7.
    A. Kojima and M. Saito, US Patent No. 7 145 048 (2006).Google Scholar
  8. 8.
    Y. Ishii, T. Nakano, and N. Hirai, US Patent No. 6392104 (1998).Google Scholar
  9. 9.
    C. S. H. Chen, S. E. Schramm, and S. E. Wentzek, US Patent No. 5 397 488 (1995).Google Scholar
  10. 10.
    K. Honna and H. Seiki, US Patent No. 4 990 691 (1991).Google Scholar
  11. 11.
    K. Honna and H. Seiki, US Patent No. 4 963 292 (1990).Google Scholar
  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).CrossRefGoogle Scholar
  14. 14.
    E. I. Bagrii, A. I. Nekhaev, and A. L. Maksimov, Pet. Chem. 57, 183 (2017).CrossRefGoogle Scholar
  15. 15.
    E. A. Ivleva, M. R. Baimuratov, Yu. A. Zhuravleva, et al., Pet. Chem. 55, 133 (2015).CrossRefGoogle Scholar
  16. 16.
    E. A. Ivleva, M. R. Baimuratov, Yu. A. Zhuravleva, et al., Pet. Chem. 56, 873 (2016).CrossRefGoogle Scholar
  17. 17.
    E. A. Ivleva, M. R. Baimuratov, V. S. Gavrilova, et al., Pet. Chem. 55, 673 (2015).CrossRefGoogle Scholar
  18. 18.
    T. M. Klapçtke, B. Krumm, and A. Widera, ChemPlusChem 83, 61 (2018).CrossRefGoogle Scholar
  19. 19.
    S.-Q. Fu, J.-W. Guo, D.-Y. Zhu, et al., RSC Adv. 5, 67054 (2015).CrossRefGoogle Scholar
  20. 20.
    S. M. Sayed, B.-P. Lin, and H. Yang, Soft Matter 12, 6148 (2016).CrossRefGoogle Scholar
  21. 21.
    F. M. Menger and V. A. Migulin, J. Org. Chem. 64, 8916 (1999).CrossRefGoogle Scholar
  22. 22.
    N. Pannier and W. Maison, Eur. J. Org. Chem., 1278 (2008).Google Scholar
  23. 23.
    P.-E. Alexandre, A. Schwenger, W. Frey, and C. Richert, Chem.-Eur. J. 23, 9018 (2017).CrossRefGoogle Scholar
  24. 24.
    A. Schwenger, W. Frey, and C. Richert, Chem.-Eur. J. 21, 1 (2015).CrossRefGoogle Scholar
  25. 25.
    A. Schwenger, W. Frey, and C. Richert, Angew. Chem., Int. Ed. Engl. 55, 1 (2016).CrossRefGoogle Scholar
  26. 26.
    M. Tominaga, H. Masu, and I. Azumaya, J. Org. Chem. 74, 8754 (2009).CrossRefGoogle Scholar
  27. 27.
    H. Zhu, J. Guo, C. Yang, et al., Synth. Commun. 43, 1161 (2013).CrossRefGoogle Scholar
  28. 28.
    H. Yang, J. Guo, R. Tong, et al., Polymers 10, 443 (2018).CrossRefGoogle Scholar
  29. 29.
    E. A. Ivleva, I. A. Platonov, and Yu. N. Klimochkin, Russ. J. Gen. Chem. 85, 1830 (2015).CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • E. A. Ivleva
    • 1
    Email author
  • M. R. Baimuratov
    • 1
  • Yu. A. Malinovskaya
    • 1
  • Yu. N. Klimochkin
    • 1
  • V. A. Tyshchenko
    • 2
  • I. A. Kulikova
    • 2
  • V. V. Pozdnyakov
    • 1
    • 3
  • K. A. Ovchinnikov
    • 3
  1. 1.Samara State Technical UniversitySamaraRussia
  2. 2.Middle Volga Oil Refining Research InstituteNoνokuibysheνskRussia
  3. 3.AO VNII NPMoscowRussia

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