AI Chat Paper
Note: Please note that the following content is generated by AMiner AI. SciOpen does not take any responsibility related to this content.
{{lang === 'zh_CN' ? '文章概述' : 'Summary'}}
{{lang === 'en_US' ? '中' : 'Eng'}}
Chat more with AI
Powered by AMiner. Clicking this button will take you away from SciOpen.
Home Friction Article
PDF (2.4 MB)
Cite
EndNote(RIS) BibTeX
Collect
Submit Manuscript AI Chat Paper
Show Outline
Outline
Show full outline
Hide outline
Outline
Show full outline
Hide outline
Research Article | Open Access

Thermal-oxidation mechanism of dioctyl adipate base oil

Xuzheng QIAN1, Yaling XIANG, Hongfei SHANG2, Bingxue CHENG, Shengpeng ZHAN, Jian LI( )
State Key Laboratory of Special Surface Protection Materials and Application Technology, Wuhan Research Institute of Materials Protection, Wuhan 430030, China
State Key Laboratory of Tribology, Tsinghua University, Beijing 100084, China
Show Author Information

Abstract

The ester base oil of dioctyl adipate (DOA) was oxidized in an oven at 200 ℃ for 30 h, and variations in the physicochemical and tribological properties were studied. To investigate the thermal-oxidation mechanism, the thermal-oxidation products were analyzed by gas chromatography–mass spectrometry (GC−MS), and the thermal-oxidation process was simulated using visual reactive force field molecular dynamics (ReaxFF MD). The results indicated that the total acid number (TAN) increased significantly because of the presence of 14% carboxylic acids and low molecular weight monoesters. The tribological properties were improved by the formation of the strongly polar carboxylic acids. Additionally, the increase in kinematic viscosity was limited due to the formation of high molecular weight polymerization products and low molecular weight degradation products. Thermal-oxidative degradation and polymerization mechanisms were proposed by combining ReaxFF MD simulations and GC−MS results.

Keywords

tribological propertiesdioctyl adipateGC−MSphysicochemical propertiesReaxFF MD

References

[1]
Stanisław G. Enzyme catalysed synthesis of some adipic esters. J Mol Catal B-Enzym 15: 9–13 (2001)
Crossref Google Scholar
[2]
Kolwzan B, Gryglewicz S. Synthesis and biodegradability of some adipic and sebacic esters. J Synthetic Lubric 20: 99–107 (2003)
Crossref Google Scholar
[3]
He Y F, Zolper T J, Liu P Z, Zhao Y Z, He X L, Shen X J, Sun H W, Duan Q H, Wang Q. Elastohydrodynamic lubrication properties and friction behaviors of several ester base stocks. Friction 3(3): 243–255 (2015)
Crossref Google Scholar
[4]
Sander J. The aspects of designing lubricants using an environmental product assessment. NLGI Spokesman 61(11): 18–27 (1998)
Google Scholar
[5]
Maleville X, Faure D, Legros A, Hipeaux J C. Oxidation of mineral base oils of petroleum origin: The relationship between chemical composition, thickening, and composition of degradation products. Lubr Sci 9(1): 1–60 (1996)
Crossref Google Scholar
[6]
Li H, Hsu S M, Wang J C. Thermal-oxidative characteristics of some high-temperature diesel lubricants. J Syn Lubr 13(2): 129–149 (1996)
Crossref Google Scholar
[7]
Maduako A U C, Ofunne G C, Ojinnak C M. Carbonyl peak index technique in the study of lubricant oxidation. Lubr Sci 5(1): 43–54 (1992)
Crossref Google Scholar
[8]
Wu Y X, Li W M, Zhang M, Wang X B. Improvement of oxidative stability of trimethylolpropane trioleate lubricant. Thermochim Acta 569: 112–118 (2013)
Crossref Google Scholar
[9]
Jumat S, Nadia S, Emad Y. Improvement of pour point and oxidative stability of synthetic ester basestocks for biolubricant applications. Arab J Chem 5: 193–200 (2012)
Crossref Google Scholar
[10]
Liu Z S, Sharma B K, Erhanc S Z, Biswas A, Wang R P, Schuman T P. Oxidation and low temperature stability of polymerized soybean oil-based lubricants. Thermochim Acta 601: 9–16 (2015)
Crossref Google Scholar
[11]
Lewis S W, Worsfold P J, Lynes A, McKerrell E H. Determination of carboxylic acids in oxidised engine oils by liquid chromatography with chemiluminescence detection. Anal Chim Acta 266(2): 257–264 (1992)
Crossref Google Scholar
[12]
lvanov S K, Kalitchin Z D. The use of chemiluminescence in determining the thermal and oxidative i stability of motor oils. Lubr Sci 4: 135–153 (1992)
Crossref Google Scholar
[13]
Zhang B T, Zhao L X, Lin J M. Study on superoxide and hydroxyl radicals generated in indirect electrochemical oxidation by chemiluminescence and UV-Visible spectra. J Environ Sci 20: 1006–1011 (2008)
Crossref Google Scholar
[14]
Omrania H, Dudelzaka A E, Hollebonec B P, Loocka H P. Assessment of the oxidative stability of lubricant oil using fiber-coupled fluorescence excitation–emission matrix spectroscopy. Anal Chim Acta 811: 1–12 (2014)
Crossref Google Scholar
[15]
Amat S, Braham Z, Dréau Y L, Kister J, Dupuy N. Simulated aging of lubricant oils by chemometric treatment of infrared spectra: Potential antioxidant properties of sulfur structures. Talanta 107: 219–224 (2013)
Crossref Google Scholar
[16]
Walo M, Przybytniak G, Sadło J. Radiation-induced radicals in aliphatic poly (ester urethane)s studied by EPR spectroscopy. J Mol Struct 1036: 488–493 (2013)
Crossref Google Scholar
[17]
Zhang X, Davida D J, Miesch M, Geoffroy P, Raul F, Roussi S, Werner D A, Marchioni E. Identification and quantitative analysis of β-sitosterol oxides in vegetable oils by capillary gas chromatography–mass spectrometry. Steroids 70: 896–906 (2005)
Crossref Google Scholar
[18]
Dunn R O. Effect of antioxidants on the oxidative stability of methyl soyate (biodiesel). Fuel Process Technol 86: 1071–1085 (2005)
Crossref Google Scholar
[19]
Qiu C, Han S, Cheng X G, Ren T H. Determining the antioxidant activities of organic sulfides by rotary bomb oxidation test and pressurized differential scanning calorimetry. Thermochim Acta 447: 36–40 (2006)
Crossref Google Scholar
[20]
Nadia S, Jumat S, Emad Y. The physicochemical and tribological properties of oleic acid based trimester biolubricants. Ind Crops Prod 34:1089–1096 (2011)
Crossref Google Scholar
[21]
Richaud E, Audouin L, Fayolle Br, Verdu J, Rychlá L M, Rychlý J. Rate constants of oxidation of unsaturated fatty esters studied by chemiluminescence. Chem Phys Lipids 16: 753–759 (2012)
Crossref Google Scholar
[22]
Filho P A C. Developing a rapid and sensitive method for determination oftrans-fatty acids in edible oils using middle- infrared spectroscopy. Food Chem 158: 1–7 (2014)
Crossref Google Scholar
[23]
Gracia N, Thomas S, Bazin P, Duponchel L, Thibault-Starzyk F, Lerasle O. Combination of mid-infrared spectroscopy and chemometric factorization tools to study the oxidation of lubricating base oils. Catal Today 155: 255–260 (2010)
Crossref Google Scholar
[24]
Hahn S, Dott W, Eisentraeger A. Characterization of ageing behaviour of environmentally acceptable lubricants based on trimethylolpropane esters. J Syn Lubr 23: 223–236 (2006)
Crossref Google Scholar
[25]
Carrasco A, Ortiz-Ruiz V, Martinez-Gutierrez R, Tomas V, Tudela J. Lavandula stoechas essential oil from Spain: Aromatic profile determined by gas chromatography–mass spectrometry, antioxidant and lipoxygenase inhibitory bioactivities. Ind Crop Prod 73: 16–27 (2015)
Crossref Google Scholar
[26]
Wu Y X, Li W M, Zhang M, Wang X B. Oxidative degradation of synthetic ester and its influence on tribological behavior. Tribol Int 64:16–23 (2013)
Crossref Google Scholar
[27]
Diao Z J, Zhao Y M, Chen B, Duan C L, Song S. ReaxFF reactive force field for molecular dynamics simulations of epoxy resin thermal decomposition with model compound. J Anal Appl Pyrol 104: 618–624 (2013)
Crossref Google Scholar
[28]
Stoliarova S I, Lyon R E, Nyden M R. A reactive molecular dynamics model of thermal decomposition in polymers. II. Polyisobutylene. Polymer 45: 8613–8621 (2004)
Crossref Google Scholar
[29]
Stuart S J, Li Y, Kum O, Mintmire J W, Voter A F. Reactive bond-order simulations using both spatial and temporal approaches to parallelism. Struct Chem 15: 479–486 (2004)
Crossref Google Scholar
[30]
Nomura K I, Kalia R K, Nakano A, Vashishta P. A scalable parallel algorithm for large-scale reactive force-field molecular dynamics simulations. Compu Phys Commun 178: 73–87 (2008)
Crossref Google Scholar
[31]
Chen B, Diao Z J, Zhao Y L, Ma X X. A ReaxFF molecular dynamics (MD) simulation for the hydrogenation reaction with coal related model compounds. Fuel 154: 114–122 (2015)
Crossref Google Scholar
[32]
Zhang J L, Weng X X, Han Y, Li W, Cheng J Y, Gan Z X, Gu J J. The effect of supercritical water on coal pyrolysis and hydrogen production: A combined ReaxFF and DFT study. Fuel 108: 682–690 (2013)
Crossref Google Scholar
[33]
Shahabuddin M, Kalam M A, Masjuki H H, Bhuiya M M K, Mofijur M. An experimental investigation into biodiesel stability by means of oxidation and property determination. Energy 44: 616–622 (2012)
Crossref Google Scholar
Friction
Volume 4 Issue 1,
March 2016
Pages 29-38
DOI: 10.1007/s40544-015-0099-x
Cite this article:
QIAN X, XIANG Y, SHANG H, et al. Thermal-oxidation mechanism of dioctyl adipate base oil. Friction, 2016, 4(1): 29-38. https://doi.org/10.1007/s40544-015-0099-x

774

Views

21

Downloads

30

Crossref

N/A

Web of Science

34

Scopus

3

CSCD

Altmetrics
Received: 25 August 2015
Revised: 23 October 2015
Accepted: 26 November 2015
Published: 13 January 2016
© The author(s) 2015

This article is published with open access at Springerlink.com

Open Access: The articles published in this journal are distributed under the terms of the Creative Commons Attribution 4.0 International License (http:// creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
Return