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, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
V. I. Babkin, A. A. Aleksashin, L. S. Yanovskii, et al., Dvigatel’ 83 (5), 6 (2012).
C. W. Tsai, K. H. Wu, C. C. Yang, and G. P. Wang, React. Funct. Polym. 91–92, 11 (2015).
C.-W. Tsai, J.-C. Wang, F.-N. Li, et al., Mater. Express 6, 220 (2016).
K. Tanaka, T. Hiraoka, F. Ishiguro, et al., RSC Adv 4, 28107 (2014).
T. Ouchi and Y. Nishimura, US Patent No. 8912366 (2014).
M.-Y. Huang, J.-C. Lin, K.-H. Lin, and J.-C. Wu, US Patent No. 7 488 859 (2009).
A. Kojima and M. Saito, US Patent No. 7 145 048 (2006).
Y. Ishii, T. Nakano, and N. Hirai, US Patent No. 6392104 (1998).
C. S. H. Chen, S. E. Schramm, and S. E. Wentzek, US Patent No. 5 397 488 (1995).
K. Honna and H. Seiki, US Patent No. 4 990 691 (1991).
K. Honna and H. Seiki, US Patent No. 4 963 292 (1990).
Modern Oxidation Methods, Ed. by J.-E. Bäckvall, 2nd Ed. (Wiley–VCH, Weinheim, 2010).
E. I. Bagrii and G. B. Maravin, Pet. Chem. 53, 418 (2013).
E. I. Bagrii, A. I. Nekhaev, and A. L. Maksimov, Pet. Chem. 57, 183 (2017).
E. A. Ivleva, M. R. Baimuratov, Yu. A. Zhuravleva, et al., Pet. Chem. 55, 133 (2015).
E. A. Ivleva, M. R. Baimuratov, Yu. A. Zhuravleva, et al., Pet. Chem. 56, 873 (2016).
E. A. Ivleva, M. R. Baimuratov, V. S. Gavrilova, et al., Pet. Chem. 55, 673 (2015).
T. M. Klapçtke, B. Krumm, and A. Widera, ChemPlusChem 83, 61 (2018).
S.-Q. Fu, J.-W. Guo, D.-Y. Zhu, et al., RSC Adv. 5, 67054 (2015).
S. M. Sayed, B.-P. Lin, and H. Yang, Soft Matter 12, 6148 (2016).
F. M. Menger and V. A. Migulin, J. Org. Chem. 64, 8916 (1999).
N. Pannier and W. Maison, Eur. J. Org. Chem., 1278 (2008).
P.-E. Alexandre, A. Schwenger, W. Frey, and C. Richert, Chem.-Eur. J. 23, 9018 (2017).
A. Schwenger, W. Frey, and C. Richert, Chem.-Eur. J. 21, 1 (2015).
A. Schwenger, W. Frey, and C. Richert, Angew. Chem., Int. Ed. Engl. 55, 1 (2016).
M. Tominaga, H. Masu, and I. Azumaya, J. Org. Chem. 74, 8754 (2009).
H. Zhu, J. Guo, C. Yang, et al., Synth. Commun. 43, 1161 (2013).
H. Yang, J. Guo, R. Tong, et al., Polymers 10, 443 (2018).
E. A. Ivleva, I. A. Platonov, and Yu. N. Klimochkin, Russ. J. Gen. Chem. 85, 1830 (2015).
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
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare no conflict of interest requiring the disclosure in this publication.
Additional information
Translated by E. Boltukhina
Rights and permissions
About this article
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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0965544119110082