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Research Papers: Lubricants

A Quantitative Structure Tribo-Ability Relationship Model for Ester Lubricant Base Oils

[+] Author and Article Information
Xinlei Gao

School of Chemical and
Environmental Engineering,
Wuhan Polytechnic University,
Wuhan, Hubei Province 430023, China
e-mail: gaoxl0131@163.com

Zhan Wang, Tingting Wang

School of Chemical and
Environmental Engineering,
Wuhan Polytechnic University,
Wuhan, Hubei Province 430023, China

Kang Dai

College of Pharmacy,
South-Central University for Nationalities,
Wuhan, Hubei Province 430074, China

1Corresponding author.

Contributed by the Tribology Division of ASME for publication in the JOURNAL OF TRIBOLOGY. Manuscript received December 21, 2013; final manuscript received December 2, 2014; published online January 29, 2015. Assoc. Editor: Hong Liang.

J. Tribol 137(2), 021801 (Apr 01, 2015) (7 pages) Paper No: TRIB-13-1255; doi: 10.1115/1.4029332 History: Received December 21, 2013; Revised December 02, 2014; Online January 29, 2015

Friction tests with point–point contact were carried out using a microtribometer to investigate the tribological characteristics of steel/steel rubbing pair immersed in 57 kinds of esters as lubricant base oils. A set of 57 esters and their wear data were included in the back-propagation neural network (BPNN)-quantitative structure tribo-ability relationship (QSTR) model with two-dimensional (2D) and three-dimensional (3D) QSTR descriptors. The predictive performance of the BPNN-QSTR model is acceptable. The findings of the BPNN-QSTR model show that the extent of polar groups cannot be too large in the molecule to achieve good antiwear performance; and the polar groups with a high degree of relative concentrated charge are favorable for antiwear. A low degree of molecular hydrophobicity of lubricant base oil is beneficial for antiwear behavior. Large molecular dipole moment is disadvantageous for antiwear properties. It is necessary to maintain one large molecular surface in one plane, to have a long and short chain length to be present within the same molecule, and to keep small difference between the long and short chain length to enhance the antiwear performance. Finally, lubricant base oil candidate molecules will have beneficial antiwear properties that they should contain more N groups with three single bonds and more C groups with one double bond and two single bonds; the presence of O atoms with any bonds or CH groups with three single bonds leads to a decrease in the wear resistance performance.

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References

Mortier, R. M., Fox, M. F., and Orszulik, S. T., eds., 2010, Chemistry and Technology of Lubricants, 3rd ed., Springer, The Netherlands.
Mang, T., and Dresel, W., 2001, Lubricants and Lubrication, Wiley VCH, Weinheim, Germany.
Dai, K., and Gao, X., 2013, “Estimating Antiwear Properties of Lubricant Additives Using a Quantitative Structure Tribo-Ability Relationship Model With Back Propagation Neural Network,” Wear, 306(1–2), pp. 242–247. [CrossRef]
Gao, X., Wang, Z., Zhang, H., and Dai, K., 2015, “A Three Dimensional Quantitative Structure–Tribological Relationship Model,” ASME J. Tribol. (submitted).
Gao, X., Dai, K., Wang, Z., and Wang, T., 2015, “Application of Quantitative Structure Tribo-Ability Relationship Model With Bayesian Regularization Neural Network,” Friction (submitted).
Hansch, C., and Steward, A. R., 1964, “The Use of Substituent Constants in the Analysis of the Structure–Activity Relationship in Penicillin Derivatives,” J. Med. Chem., 7(6), pp. 691–694. [CrossRef] [PubMed]
Prasanna, S., and Doerksen, R. J., 2009, “Topological Polar Surface Area: A Useful Descriptor in 2D-QSAR,” Curr. Med. Chem., 16(1), pp. 21–41. [CrossRef] [PubMed]
Cramer, R. D., III, Patterson, D. E., and Bunce, J. D., 1988, “Comparative Molecular Field Analysis (CoMFA). 1. Effect of Shape on Binding of Steroids to Carrier Proteins,” J. Am. Chem., 110(18), pp. 5959–5967. [CrossRef]
Ferguson, A. M., Heritage, T., Jonathon, P., Pack, S. E., Phillips, L., Rogan, J., and Snaith, P. J., 1997, “EVA: A New Theoretically Based Molecular Descriptor for Use in QSAR/QSPR Analysis,” J. Comput. Aided Mol. Des., 11(2), pp. 143–152. [CrossRef] [PubMed]
Ginn, C. M. R., Turner, D. B., Willett, P., Ferguson, A. M., and Heritage, T. W., 1997, “Similarity Searching in Files of Three-Dimensional Chemical Structures: Evaluation of the EVA Descriptor and Combination of Rankings Using Data Fusion,” J. Chem. Inf. Modell., 37(1), pp. 23–37. [CrossRef]
Turner, D. B., Willett, P., Ferguson, A. M., and Heritage, T., 1997, “Evaluation of a Novel Infra-Red Range Vibration-Based Descriptor (EVA) for QSAR Studies: 1. General Application,” J. Comput. Aided Mol. Des., 11(4), pp. 409–422. [CrossRef] [PubMed]
Heritage, T. W., Ferguson, A. M., Turner, D. B., and Willett, P., 1998, “EVA: A Novel Theoretical Descriptor for QSAR Studies,” Perspect. Drug Discovery Des., 9–11, pp. 381–398. [CrossRef]
Venkataramani, P. S., Kalra, S. L., and Raman, S. V., 1989, “Synthesis, Evaluation and Applications of Complex Ester as Lubricants: A Base Study,” J. Synth. Lubr., 5(4), pp. 271–289. [CrossRef]
Ponnekanti, N., and Savita, K., 2012, “Development of Ecofriendly/Biodegradable Lubricants: An Overview,” Renewable Sustainable Energy Rev., 16(1), pp. 764–774. [CrossRef]
Sommers, E. A., and Crowell, T. L., 1953, “High Temperature Anti-Oxidants for Synthetic Oils: 3.The Thermal Decomposition of Di-(2-Ethylhexyl) Sebacate,” Wright Air Development Center Technical Report, pp. 1–68, Report No. 53–293.
Barnes, R. S., and Fainman, M. Z., 1957, “Synthetic Ester Lubricants,” Lubr. Eng., pp. 454–457.
Eychenne, V., and Mouloungui, Z., 1998, “Relationships Between Structure and Lubricating Properties of Neopentylpolyol Esters,” Ind. Eng. Chem. Res., 37(12), pp. 4835–4843. [CrossRef]
Keenan, M. J., Krevalis, M. A., and David, W. T., 2001, “High Hydroxyl Content Glycerol Di-Esters,” U.S. Patent No. 6,255,262.
Beale, M. H., Hagan, M. T., and Demuth, H. B., 2010, Multilayer Neural Network Architecture, Neural Network ToolboxTM 7 User's Guide (matlab), the MathWorks Inc., Boston, MA, pp. 3-3–3-4.
Bonchev, D., Mekenyan, O., and Trinajstic, N., 1981, “Isomer Discrimination by Topological Information Approach,” J. Comput. Chem., 2(2), pp. 127–148. [CrossRef]
Stanton, D. T., and Jurs, P. C., 1990, “Development and Use of Charge Partial Surface Area Structural Descriptors in Computer-Assisted Quantitative Structure–Property Relationship Studies,” Anal. Chem., 62(21), pp. 2323–2329. [CrossRef]
Zhang, J., 1999, “The Relationship Between Additives Molecular Structure and Their Tribological Properties and the Mechanism of Boundary Lubrication,” Ph.D. thesis, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, China.

Figures

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Fig. 1

Sketch map of the ball–disk rubbing pair

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Fig. 2

The wear scar diameter of each upper steel specimen lubricated with structurally similar esters. Wear scar diameters for (A) butyloctanoate, (B) butylcaprate, (C) butyllaurate, (D) butylmyristate, (E) butylpalmitate, and (F) butyloleate lubricants.

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Fig. 3

The wear scar diameter of each upper steel specimen lubricated with structurally similar esters. Wear scar diameters for (A) pentaerythritol tetravalerate, (B) pentaerythrityl tetraheptanoate, (C) pentaerythritol tetraoctanoate, and (D) pentaerythritol tetraoleate lubricants.

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Fig. 4

The wear scar diameter of each upper steel specimen lubricated with structurally similar esters. Wear scar diameters for (A) tripropionin, (B) tributyrin, (C) trivalerin, (D) trioctanoin, and (E) triolein lubricants.

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Fig. 5

The wear scar diameter of each upper steel specimen lubricated with structurally similar esters. Wear scar diameters for (A) neopentyl glycol dioctanoate, (B) neopentyl glycol dicaprate, and (C) neopentyl glycol dilaurate lubricants.

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Fig. 6

The wear scar diameter of each upper steel specimen lubricated with structurally similar esters. Wear scar diameters for (A) ethyleneglycol diheptanoate, (B) 1,4-dioctyl succinate, (C) ethyleneglycol dilaurate, and (D) butylene glycol oleate lubricants.

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Fig. 7

The wear scar diameter of each upper steel specimen lubricated with structurally similar esters. Wear scar diameters for (A) 1,2-propylene glycol dioctanoate, (B) 1,2-propylene glycol dicaprate, and (C) 1,2-propylene glycol dioleate lubricants.

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Fig. 8

The wear scar diameter of each upper steel specimen lubricated with structurally similar esters. Wear scar diameters for (A) ethyl octanoate, (B) methyl decanoate, (C) methyl laurate, (D) ethyl dodecanoate, (E) methyl palmitate, and (F) ethyl palmitate lubricants.

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Fig. 9

The wear scar diameter of each upper steel specimen lubricated with structurally similar esters. Wear scar diameters for (A) octyl acetate, (B) 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, (C) isopropyl myristate, (D) isopropyl palmitate, and (E) 2-ethylhexyl trans-4-methoxycinnamate lubricants.

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Fig. 10

The wear scar diameter of each upper steel specimen lubricated with structurally similar esters. Wear scar diameters for (A) cyclohexyl methacrylate, (B) 2-ethylhexyl methacrylate, (C) isodecyl methacrylate, (D) stearyl methacrylate, and (E) 2-(diethylamino)ethyl methacrylate lubricants.

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Fig. 11

The wear scar diameter of each upper steel specimen lubricated with structurally similar esters. Wear scar diameters for (A)1,3-glycerol dimethacrylate, (B) 1,3-butanediol dimethacrylate, (C) di(ethylene glycol) dimethacrylate, (D) dibutyl maleate, and (E) di-n-octyl sebacate lubricants.

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Fig. 12

The wear scar diameter of each upper steel specimen lubricated with structurally similar esters. Wear scar diameters for (A) diisobutyl phthalate, (B) dipentyl phthalate, (C) di-n-octyl phthalate, (D) di(2-ethylhexyl)phthalate, (E) dinonyl phthalate, and (F) diisodecyl phthalate lubricants.

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Fig. 13

The wear scar diameter of each upper steel specimen lubricated with structurally similar esters. Wear scar diameters for (A) glyceryl triacetate, (B) tributyl citrate, and (C) triethyl 2-acetylcitrate lubricants.

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Fig. 14

Predicted (PRE WSD) versus observed (WSD) values of wear data for the investigated lubricant base oils

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Fig. 15

Sensitivity of 2D and 3D descriptors about wear performance

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