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.
References
Cai, M. R., Liang, Y. M., Yao, M. H., Xia, 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.10.1021/am900847jSearch in Google Scholar PubMed
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/s10973-014-3808-1.10.1007/s10973-014-3808-1Search in Google Scholar
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.10.1021/ef800994jSearch in Google Scholar
de Sousa Rios, M. A., Santiago, S. N., Sanders Lopes, A. A., & Mazzetto, S. E. (2010). Antioxidative activity of 5-npentadecyl-2-tert-butylphenol stabilizers in mineral lubricant oil. Energy & Fuels, 24, 3285-3291. DOI: 10.1021/ef100262j.10.1021/ef100262jSearch in Google Scholar
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.Search in Google Scholar
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:1016503703006.10.1023/A:1016503703006Search in Google Scholar
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/s12182-012-0223-8.10.1007/s12182-012-0223-8Search in Google Scholar
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. Beijing, China.Search in Google Scholar
Lin, C. Y., & Chiu, C. C. (2009). Effects of oxidation during long-term storage on the fuel properties of palm oilbased biodiesel. Energy & Fuels, 23, 3285-3289. DOI: 10.1021/ef900105t.10.1021/ef900105tSearch in Google Scholar
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.10.1039/b004355iSearch in Google Scholar
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/s11249-010-9659-4.10.1007/s11249-010-9659-4Search in Google Scholar
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.Search in Google Scholar
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.10.1021/ie201863nSearch in Google Scholar
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.10.1039/c3cp55103bSearch in Google Scholar PubMed
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:1024650612317.10.1023/A:1024650612317Search in Google Scholar
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.2014.02.097.10.1016/j.matlet.2014.02.097Search in Google Scholar
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.10.1021/jp064460bSearch in Google Scholar PubMed
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.10.1021/am200375aSearch in Google Scholar PubMed
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.10.1021/jp407526rSearch in Google Scholar PubMed
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.10.1021/ef200686dSearch in Google Scholar
Wang, X. F., Xing, 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 sulfurbearing secondary antioxidants having relatively low molecular weight. Polymer Degradation and Stability, 98, 2391-2398. DOI: 10.1016/j.polymdegradstab.2013.08.030.10.1016/j.polymdegradstab.2013.08.030Search in Google Scholar
Wiklund, P. (2007). The response to antioxidants in base oils of different degrees of refining. Lubrication Science, 19, 169-182. DOI: 10.1002/ls.38.10.1002/ls.38Search in Google Scholar
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.10.1039/B206081GSearch in Google Scholar
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.2013.02.024.10.1016/j.triboint.2013.02.024Search in Google Scholar
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. 10.1039/c3ra40699gSearch in Google Scholar
© 2015 Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
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Articles in the same Issue
- Voltammetric determination of B1 and B6 vitamins using a pencil graphite electrode
- An electrochemical sensor for sensitive determination of nitrites based on Ag–Fe3O4–graphene oxide magnetic nanocomposites
- Effect of influent nitrogen concentration on feasibility of short-cut nitrification during wastewater treatment in activated sludge systems
- Assessment of Urtica as a low-cost adsorbent for methylene blue removal: kinetic, equilibrium, and thermodynamic studies
- Electrode and electrodeless impedance measurement for determination of orange juices parameters
- Evaluation of oxidative stability of vegetable oils enriched with herb extracts by EPR spectroscopy
- Electrosynthesis of poly(p-phenylene) and poly(p-phenylene/pyrrole) films under controlled humidity
- Synthesis, characterisation, and electrical properties of novel nanostructured conducting poly(aniline-co-m-chloroaniline) with incorporated silver particles
- Heterocyclisation of substituted ylidenethiocarbonohydrazides using dimethyl acetylenedicarboxylate
- Newly synthesized indolizine derivatives – antimicrobial and antimutagenic properties
- Synthesis and insecticidal activity of anthranilic diamides with hydrazone substructure
- Effect of alkylated diphenylamine on thermal-oxidative degradation behavior of poly-α-olefin
- Novel pathways of interaction of maleic anhydride derivatives with phosphorus(III) compounds: synthesis and characterisation of N,N,N′,N′ -tetraethyl-2,3-diphenylbut-2-enediamide and 3-dihydrofuranylidene-4-phosphorylidene–oxolane-2,5,5′-trione
- Efficient method for the synthesis of polysubstituted 2,6-dicyanoanilines by one-pot three-component tandem reaction of malononitrile with α,β-unsaturated imines