Abstract
An oil-soluble antioxidant, alkylated diphenylamine (ADPA), was prepared by alkylation of diphenylamine. The influence of ADPA on the thermal-oxidative stability of poly-α-olefin (PAO8) was evaluated by thermogravimetry (TG). For comparison, the thermal-oxidative stability of PAO8 with zinc dialkyl dithiophosphate (ZDDP) was also investigated. Activation energy (Ea)of the corresponding thermal-oxidative degradation process was evaluated by the Flynn-Wall-Ozawa (FWO) and Kissinger-Akahira-Sunose (KAS) methods. To demonstrate the reliability of the kinetic study, the antioxidant performance of ADPA and ZDDP in PAO8 was also studied by the pressure drop (PDT) and accelerated oxidation (AOT) tests. The results indicate that ADPA has better antioxidant ability than ZDDP in increasing the Ea value and enhancing the oxidative stability of PAO8. Good correlation between the applied test methods was established.
Similar content being viewed by others
References
Cai, M. R., Liang, Y. M., Yao, M. H., **a, Y. Q., Zhou, F., & Liu, W. M. (2010). Imidazolium ionic liquids as antiwear and antioxidant additive in poly(ethylene glycol) for steel/steel contacts. ACS Applied Materials & Interfaces, 2 870–876. DOI: 10.1021/am900847j.
Chao, M. R., Li, W. M., & Wang, X. B. (2014). Antioxidant synergism between synthesised alkylated diphenylamine and dilauryl thiodipropionate in polyolefin base fluid. Journal of Thermal Analysis and Calorimetry, 117 925–933. DOI: 10.1007/s10973-014-3808-1.
de Sousa Rios, M. A., Matos Sales, F. A., & Mazzetto, S. E. (2009). Study of antioxidant properties of 5-n-pentadecyl-2-tert-amylphenol. Energy & Fuels, 23 2517–2522. DOI: 10.1021/ef800994j.
de Sousa Rios, M. A., Santiago, S. N., Sanders Lopes, A. A., & Mazzetto, S. E. (2010). Antioxidative activity of 5-n-pentadecyl-2-tert-butylphenol stabilizers in mineral lubricant oil. Energy & Fuels, 24 3285–3291. DOI: 10.1021/ef100262j.
de Sousa Rios, M. A., & Mazzetto, S. E. (2012). Effect of organophosphate antioxidant on the thermo-oxidative degradation of a mineral oil. Journal of Thermal Analysis and Calorimetry, 111 553–559. DOI: 10.1007/s10973-011-2160-y.
Du, D. C., Kim, S. S., Chun, J. S., Suh, C. M., & Kwon, W. S. (2002). Antioxidation synergism between ZnDTC and ZnDDP in mineral oil. Tribology Letters, 13 21–27. DOI: 10.1023/a:1016503703006.
El-Mekabaty, A., Habib, O. M. O., Hassan, H. M., & Moawad, E. B. (2012). Synthesis and evaluation of some new oxazolones and imidazolones as antioxidant additives for Egyptian lubricating oils. Petroleum Science, 9 389–399. DOI: 10.1007/s12182-012-0223-8.
General Administration of Quality Supervision, Inspection and Quarantine of the People’s Republic of China (2002). Chinese standard: Standard test method for acid and base number of petroleum products and lubricants by colour-indicator titration. GB/T 4945-2002. Bei**g, China.
Lin, C. Y., & Chiu, C. C. (2009). Effects of oxidation during long-term storage on the fuel properties of palm oil-based biodiesel. Energy & Fuels, 23 3285–3289. DOI: 10.1021/ef900105t.
Mamleev, V., Bourbigot, S., Le Bras, M., Duquesne, S., & Šesták, J. (2000). Modelling of nonisothermal kinetics in thermogravimetry. Physical Chemistry Chemical Physics, 2 4708–4716. DOI: 10.1039/b004355i.
Mangolini, F., Rossi, A., & Spencer, N. D. (2010). Substituent effect on the reactivity of alkylated triphenyl phosphorothionates in oil solution in the presence of iron particles. Tribology Letters, 40 375–394. DOI: 10.1007/s11249-010-9659-4.
Nagendramma, P., & Kaul, S. (2012). Development of ecofriendly/biodegradable lubricants: An overview. Renewable and Sustainable Energy Reviews, 16 764–774. DOI: 10.1016/j.rser.2011.09.002.
Nong, W. J., Chen, X. P., Wang, L. L., Liang, J. Z., Zhong, L. P., & Tong, Z. F. (2011). Nonisothermal decomposition kinetics of abietic acid in argon atmosphere. Industrial & Engineering Chemistry Research, 50 13727–13731. DOI: 10.1021/ie201863n.
Papageorgiou, D. G., Roumeli, E., Chrissafis, K., Lioutas, Ch., Triantafyllidis, T. K., Bikiaris, D., & Boccaccini, A. R. (2014). Thermal degradation kinetics and decomposition mechanism of PBSu nanocomposites with silica-nanotubes and strontium hydroxyapatite nanorods. Physical Chemistry Chemical Physics, 16 4830–4842. DOI: 10.1039/c3cp55103b.
Prosenko, A. E., Terakh, E. I., Gorokh, E. A., Nikulina, V. V., & Grigor’ev, I. A. (2003). Synthesis and antioxidant properties of bis[ω-(3,5-dialkyl-4-hydroxyphenyl)alkyl] sulfides. Russian Journal of Applied Chemistry, 76 248–252. DOI: 10.1023/a:1024650612317.
Purkayastha, D. D., Das, N., & Bhattacharjee, C. R. (2014). Synthesis and antioxidant activity of cupric oxide nanoparticles accessed via low-temperature solid state thermal decomposition of bis(dimethylglyoximato)copper(II) complex. Materials Letters, 123 206–209. DOI: 10.1016/j.matlet.2014.02.097.
Ruiz-Agudo, E., Martín-Ramos, J. D., & Rodriguez-Navarro, C. (2007). Mechanism and kinetics of dehydration of epsomite crystals formed in the presence of organic additives. The Journal of Physical Chemistry B, 111 41–52. DOI: 10.1021/jp064460b.
Singh, A., Gandra, R. T., Schneider, E. W., & Biswas, S. K. (2011). Lubricant degradation and related wear of a steel pin in lubricated sliding against a steel disc. ACS Applied Materials & Interfaces, 3 2512–2521. DOI: 10.1021/am200375a.
Venkatesh, M., Ravi, P., & Tewari, S. P. (2013). Isoconversional kinetic analysis of decomposition of nitroimidazoles: Friedman method vs Flynn-Wall-Ozawa method. The Journal of Physical Chemistry A, 117 10162–10169. DOI: 10.1021/jp407526r.
Wang, C. A., Liu, Y. H., Zhang, X. M., & Che, D. F. (2011). A study on coal properties and combustion characteristics of blended coals in Northwestern China. Energy & Fuels, 25 3634–3645. DOI: 10.1021/ef200686d.
Wang, X. F., **ng, W. Y., Tang, G., Hong, N. N., Hu, W. Z., Zhan, J., Song, L., Yang, W., & Hu, Y. (2013). Synthesis of a novel sulfur-bearing secondary antioxidant with a high molecular weight and its comparative study on antioxidant behavior in polypropylene with two commercial sulfur-bearing secondary antioxidants having relatively low molecular weight. Polymer Degradation and Stability, 98 2391–2398. DOI: 10.1016/j.polymdegradstab.2013.08.030.
Wiklund, P. (2007). The response to antioxidants in base oils of different degrees of refining. Lubrication Science, 19 169–182. DOI: 10.1002/ls.38.
Yadav, G. D., & Doshi, N. S. (2002). Development of a green process for poly-α-olefin based lubricants. Green Chemistry, 4 528–540. DOI: 10.1039/b206081g.
Yang, G. B., Zhang, J. F., Zhang, S. M., Yu, L. G., Zhang, P. Y., & Zhu, B. L. (2013a). Preparation of triazine derivatives and evaluation of their tribological properties as lubricant additives in poly-alpha olefin. Tribology International, 62 163–170. DOI: 10.1016/j.triboint.2013.02.024.
Yang, Q., Yang, X. P., Li, X. D., Shi, L., & Sui, G. (2013b). The curing and thermal transition behavior of epoxy resin: a molecular simulation and experimental study. RSC Advances, 3 7452–7459. DOI: 10.1039/c3ra40699g.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Chao, MR., Li, WM., Zhu, LL. et al. Effect of alkylated diphenylamine on thermal-oxidative degradation behavior of poly-α-olefin. Chem. Pap. 69, 1004–1011 (2015). https://doi.org/10.1515/chempap-2015-0104
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1515/chempap-2015-0104