Abstract
In this study, a multi-phenol antioxidant 2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenylthio)-1,3,5-triazine (THA) was synthesized. The thermal stability of THA and its oxidation resistance in triisodecyl trimellitate (TDTM) ester oil were evaluated compared with several commercial phenol antioxidants. Further investigations on the oxidation resistance and tribological performance of THA with dinonyl diphenylamine (Am) and ZDDP composites were conducted to determine the additive compatibility in TDTM. The results indicate that the THA possesses higher thermal stability and more effectiveness of oxidation resistance than the commercial phenol antioxidants. The synergistic anti-oxidative effect is confirmed for the THA/Am mixtures in TDTM ester oil. However, the addition of THA alone or THA/Am mixtures shows no improvement for the tribological performance of TDTM. Excitingly, the THA/Am/ZDDP composite additives not only have the superior oxidation resistance, but exhibit the effective friction and wear reductions. It suggests the excellent compatibility of the synthesized THA antioxidant with Am and ZDDP additives in TDTM ester oil.
References
Jin, Y., Duan, H., Wei, L., Chen, S., Qian, X., Jia, D., Li, J.: Online infrared spectra detection of lubricating oil during friction process at high temperature. Ind Lubr. Tribol. 70(7), 1294–1302 (2018)
Pfaendtner, J.; Broadbelt, L. J. Mechanistic modeling of lubricant degradation. 2. The autoxidation of decane and octane. Industrial & Engineering Chemistry Research 2008, 47 (9), 2897-2904
Chao, M., Li, W., Wang, X.: Influence of antioxidant on the thermal–oxidative degradation behavior and oxidation stability of synthetic ester. Thermochim. Acta 591, 16–21 (2014)
Xia, L., Long, J., Zhao, Y., Wu, Z., Dai, Z., Wang, L.: Molecular dynamics simulation on the aggregation of lubricant oxidation products. Tribol. Lett. 66(3), 104 (2018)
Qian, X., Xiang, Y., Shang, H., Cheng, B., Zhan, S., Li, J.: Thermal-oxidation mechanism of dioctyl adipate base oil. Friction 4(1), 29–38 (2016)
Wu, N., Zong, Z.M., Fei, Y.W., Ma, J., Guo, F.: Thermal oxidation stability of poly-α-olefin lubricating oil. Asia-Pac. J. Chem. Eng. 12(5), 813–817 (2017)
Siouris, S., Wilson, C.W.: Thermodynamic properties of pentaerythritol-based species involved in degradation of aviation gas turbine lubricants. Ind. Eng. Chem. Res. 49(23), 12294–12301 (2010)
Wei, L., Duan, H., Chen, S., Jia, D., Qian, X., Cheng, B., Liu, J., Li, J.: A field test method to quantitatively determine oxidation stability of gasoline engine oil. Lubr. Sci. 30(2), 57–64 (2018)
Adhvaryu, A., Sharma, B.K., Hwang, H.S., Erhan, S.Z., Perez, J.M.: Development of biobased synthetic fluids: application of molecular modeling to structure-physical property relationship. Ind. Eng. Chem. Res. 45(3), 928–933 (2006)
Nagendramma, P., Kaul, S.: Development of ecofriendly/biodegradable lubricants: an overview. Renew. Sustain. Energy Rev. 16(1), 764–774 (2012)
Yasa, S.R., Krishnasamy, S., Singh, R.K., Penumarthy, V.: Synthesis and characterization of iso-undecenoic and iso-undecanoic acids based polyol esters. Ind. Eng. Chem. Res. 56(26), 7423–7433 (2017)
He, Y., Zolper, T.J., Liu, P., Zhao, Y., He, X., Shen, X., Sun, H., Duan, Q., Wang, Q.: Elastohydrodynamic lubrication properties and friction behaviors of several ester base stocks. Friction 3(3), 243–255 (2015)
Singh, R.K., Kukrety, A., Sharma, O.P., Baranwal, S., Atray, N., Ray, S.S.: Study of a novel phenolic-ester as antioxidant additive in lube, biodiesel and blended diesel. J. Ind. Eng. Chem. 37, 27–31 (2016)
Singh, A., Gandra, R.T., Schneider, E.W., Biswas, S.K.: Studies on the aging characteristics of base oil with amine based antioxidant in steel-on-steel lubricated sliding. J. Phys. Chem. C 117(4), 1735–1747 (2013)
Singh, A., Gandra, R.T., Schneider, E.W., Biswas, S.K.: Lubricant degradation and related wear of a steel pin in lubricated sliding against a steel disc. ACS Appl. Mater. Interfaces 3(7), 2512–2521 (2011)
Nagendramma, P.: Study of pentaerythritol tetraoleate ester as industrial gear oil. Lubr. Sci. 23(8), 355–362 (2011)
da Silva, J.A.C., Habert, A.C., Freire, D.M.G.: A potential biodegradable lubricant from castor biodiesel esters. Lubr. Sci. 25(1), 53–61 (2013)
Miao, C., Zhang, L., Zheng, K., Cui, Y., Zhang, S., Yu, L., Zhang, P.: Synthesis of ploy (p-methoxyphenol) and evaluation of its antioxidation behavior as an antioxidant in several ester oils. Tribol. Int. 88, 95–99 (2015)
Miao, C., Yu, D., Huang, L., Zhang, S., Yu, L., Zhang, P.: Synthesis of 1, 3, 5-tris (phenylamino) benzene derivatives and experimental and theoretical investigations of their antioxidation mechanism. Ind. Eng. Chem. Res. 55(7), 1819–1826 (2016)
Zhang, J., Spikes, H.: On the mechanism of ZDDP antiwear film formation. Tribol. Lett. 63(2), 24 (2016)
Fan, K., Li, J., Ma, H., Wu, H., Ren, T., Kasrai, M., Bancroft, G.M.: Tribological characteristics of ashless dithiocarbamate derivatives and their combinations with ZDDP as additives in mineral oil. Tribol. Int. 41(12), 1226–1231 (2008)
Parsaeian, P., Ghanbarzadeh, A., Van Eijk, M.C., Nedelcu, I., Neville, A., Morina, A.: A new insight into the interfacial mechanisms of the tribofilm formed by zinc dialkyl dithiophosphate. Appl. Surf. Sci. 403, 472–486 (2017)
Barnes, A.M., Bartle, K.D.: Thibon VR (2001) A review of zinc dialkyldithiophosphates (ZDDPS): characterisation and role in the lubricating oil. Tribol. Int. 34(6), 389–395 (2001)
Spikes, H.: The history and mechanisms of ZDDP. Tribol. Lett. 17(3), 469–489 (2004)
Wang, G., Xue, Y., An, L., Zheng, Y., Dou, Y., Zhang, L., Liu, Y.: Theoretical study on the structural and antioxidant properties of some recently synthesised 2,4,5-trimethoxy chalcones. Food Chem. 171, 89–97 (2015)
Cao, H., Cheng, W.X., Li, C., Pan, X.L., Xie, X.G., Li, T.H.: DFT study on the antioxidant activity of rosmarinic acid. J. Mol. Struct. (Thoechem) 719(1–3), 177–183 (2005)
Nenadis, N., Sigalas, M.P.: A DFT study on the radical scavenging potential of selected natural 3′, 4′-dihydroxy aurones. Food Res. Int. 44(1), 114–120 (2011)
Xue, Y., Zhang, L., Li, Y., Yu, D., Zheng, Y., An, L., Gong, X., Liu, Y.: A DFT study on the structure and radical scavenging activity of newly synthesized hydroxychalcones. J. Phys. Org. Chem. 26(3), 240–248 (2013)
Yokoyama, H.; Yamamoto, T.; Inoue, H. Method for producing 2,6-di-tert-butyl-4-mercaptophenol and 4,4′-isopropylidenedithiobis [2,6-di-tert-butylphenol]. U.S. Patent US 20080119672 A1, 2008
Tanaka, H., Tokumaru, Y., Fukui, K.I., Kuroboshi, M., Torii, S., Jutand, A., Amatore, C.: Chemo-and product-selective electrooxidation of 3-(arylthiomethyl)-Δ3-cephems. Synthesis 20, 3449–3459 (2009)
Perdew, J.P., Burke, K., Ernzerhof, M.: Generalized gradient approximation made simple. Phys. Rev. Lett. 77(18), 3865 (1996)
Rudnick, L.R.: Lubricant Additives: Chemistry and Applications. CRC Press, Boca Raton (2017)
Acknowledgements
We are grateful for the financial support from National Natural Science Foundation of China (No. 51575402).
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Electronic Supplementary Material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Jin, Y., Duan, H., Cheng, B. et al. Synthesis of a Multi-phenol Antioxidant and Its Compatibility with Alkyl Diphenylamine and ZDDP in Ester Oil. Tribol Lett 67, 58 (2019). https://doi.org/10.1007/s11249-019-1167-6
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s11249-019-1167-6