Abstract
To reduce harmful sulfur content in lubricant additives, making use of isosterism has been shown to be an effective strategy. When thiobenzothiazole compounds were used as templates, the exchange of sulfur atoms in the thiazole ring with oxygen atoms and NH groups produced twelve isosteres. Similarly, 2-benzothiazole- S-carboxylic acid esters were used as template molecules to produce six isosteres. About 30% of the isosteres exhibited a satisfactory deviation of ±5% relative to the template, ignoring the specific changes in the base oils, the differences in molecular structure, and the friction or wear properties. The template molecules and isosteres in triisodecyl trimellitate exhibited better tribological properties than in trimethylolpropane trioleate or bis(2- ethylhexyl) adipate. Comparative molecular field analysis (CoMFA)- and comparative molecular similarity index analysis (CoMSIA)-quantitative structure tribo-ability relationship (QSTR) models were employed to study the correlation of molecular structures between the base oils and additives. The models indicate that the higher the structural similarities of the base oils and additives are, the more synergetic the molecular force fields of the lubricating system are; the molecular force fields creating synergistic effects will improve tribological performance.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Spikes H. Low- and zero-sulphated ash, phosphorus and sulphur anti-wear additives for engine oils. Lubrication Science 20(2): 103–136 (2008)
Froeschmann R, Spruegel F. Sulfur and phosphorus bearing lubricant. U.S. Patent 3 840 463, Oct. 1974
Gao F, Kotvis P V, Tysoe W T. The surface and tribological chemistry of chlorine- and sulfur-containing lubricant additives. Tribology International 37(2): 87–92 (2004)
Zinke H, Lorenz J. Lubricant compositions containing sulfur-containing esters of phosphoric acid. U.S. Patent 4 197 209, Apr. 1980
Evans R D, More K L, Darragh C V, Nixonetal H P. Transmission electron microscopy of boundary-lubricated bearing surfaces. Part II: Mineral oil lubricant with sulfurand phosphorus-containing gear oil additives. Tribology Transactions 48(3): 299–307 (2005)
Coyle C L, Greaney M A, Stiefel E I, Francis J N, Beltzeretal M. Molybdenum sulfur antiwear and antioxidant lube additives. U.S. Patent 4 995 996, Feb. 1991
DiBiase S A, Pialet J W. Sulfur-containing lubricant and functional fluid compositions. U.S. Patent 4 800 031, Jan. 1989
Love D, Schlicht R C, Biasotti J B. Lubricant additive. U.S. Patent 4 765 918, Aug. 1988
Malec R E. Lubricant composition of improved friction reducing properties. U.S. Patent 4 201 684, May. 1980
Thornber C W. Isosterism and molecular modification in drug design. Chemical Society Reviews 8(4): 563–580 (1979)
Willett P, Barnard J M, Downs G M. Chemical similarity searching. Journal of Chemical Information and Computer Sciences 38(6): 983–996 (1998)
Nikolova N, Jaworska J. Approaches to Measure Chemical Similarity–A review. Qsar & Combinatorial Science 22(22): 1006–1026 (2004)
Lima L M, Barreiro E J. Bioisosterism: a useful strategy for molecular modification and drug design. Current Medicinal Chemistry 12(1): 23–49 (2005)
Patani G A, La Voi E J. Bioisosterism: A rational approach in drug design. Chemical Reviews 96(8): 3147–3176 (1996)
Meanwell N A. Synopsis of some recent tactical application of bioisosteres in drug design. Journal of Medicinal Chemistry 54(8): 2529–2591 (2011)
Brown N. Bioisosteres in Medicinal Chemistry. Methods & Principles in Medicinal Chemistry. Weinheim (GER): Wiley-VCH, 2012
Burger A. Isosterism and bioisosterism in drug design. In Progress in Drug Research. Basel (CH): Birkhauser, 1991: 287–371.
Bhattacharya A, Singh T, Verma V K, Nakayama K. The role of certain substituted 2-amino-benzothiazolylbenzoylthiocarbamides as additives in extreme pressure lubrication of steel bearing balls. Wear 136(2): 345–357 (1990)
Wan Y, Pu Q, Xue Q, Su Z. Antiwear and extreme pressure characteristics of 2-mercaptobenzothiazole derivative as the potential lubricating oil additive. Wear 192(1): 74–77 (1996)
Zhang J, Liu W, Xue Q. Tribological properties of the film formed by 2-(n-dodecyldithio)-benzothiazole as additive in liquid paraffin. Wear 236(1): 34–38 (1999)
Wu H, Fan K, Li J, Ren T, Ji K. Anti-wear performance and chemical property of films of nitrogen-containing heterocyclic lubricating oil additive. Acta Phys–Chim Sin 23(06): 911–915 (2007)
Li Z, Li X, Zhang Y, Ren T, Zhao Y, Zeng X. Tribological study of a highly hydrolytically stable phenylboronic acid ester containing benzothiazolyl in mineral oil. Applied Surface Science 308: 91–99 (2014)
Dai K, Gao X. Estimating Antiwear properties of lubricant additives using a quantitative structure tribo-ability relationship model with back propagation neural network. Wear 306(1–2): 242–247 (2013)
Gao X, Wang Z, Zhang H, Dai K, Wang T. Quantitative Structure Tribo-ability relationship model for ester lubricant base oils. Journal of Tribology 137(2): 021801–1–021801-7 (2015)
Gao X, Wang R, Wang Z, Dai K. BPNN-QSTR Friction model for organic compounds as potential lubricant base oils. Journal of Tribology 138(3): 031801–031801-8 (2016)
Gao X, Wang Z, Zhang H, Dai, K. Three dimensional quantitative tribo-ability relationship model. Journal of Tribology 137(2): 021802–1–021802-8 (2015)
Gao X, Dai K, Wang R, Wang Z, Wang T, He J. Establishing quantitative structure tribo-ability relationship model using Bayesian regularization neural network. Friction 4(2): 105–115 (2016)
Gao X, Liu D, Wang Z, Dai K. Quantitative structure triboability relationship for organic compounds as lubricant base oils using CoMFA and CoMSIA. Journal of Tribology 138(3): 031802–031802-7 (2016)
Liu D, Yang Q, Wang Y, Wang R, Dai K, He J. CoMFAQSTR and CoMSIA-QSTR models about N-containing Heterocyclic derivatives as lubricant additives about antiwear property. Tribology 36(4): 421–429 (2016)
Liu D. The study on the synthesis and tribological properties of green antiwear lubricant additives. Master dissertation. Wuhan (China): Wuhan Polytechnic University, 2016
Cramer R D III, Patterson D E, Bunce J D. Recent advances in comparative molecular field analysis (CoMFA). Prog Clin Biol 291: 161–165 (1989)
Cramer R D. III, Patterson D E, Bunce J D. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Chem Soc 110(18): 5959–5967 (1988)
Kubinyi H, Folkers G, Martin Y C. 3D QSAR in Drug Design, Recent Advances. Berlin (GER): Springer Netherlands, 1998.
Klebe G, Abraham U, Mietzner T. Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules tocorrelate and predict their biological activity. J Med Chem 37(24): 4130–4146 (1994)
Klebe G, Abraham U. Comparative molecular similarity index analysis (CoMSIA) to study hydrogen-bonding properties and to score combinatorial libraries. J Comput-Aided Mol Des 13: 1–10 (1999)
Acknowledgments
This project is supported by National Natural Science Foundation of China (Grant No. 51675395).
Author information
Authors and Affiliations
Corresponding author
Additional information
This article is published with open access at Springerlink.com
Xinlei GAO. She received her M.S. degree in 1996 from Huazhong Normal University in organic chemistry, and graduated from Wuhan Research Institute of Materials Protection in mechanical design and theory with Ph.D. degree in 2006. Currently she is a full professor at Wuhan Polytechnic University, member of Chinese Tribology Association. She is interested in tribology chemistry, chemical computing, and designation of lubricant.
Rights and permissions
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.
About this article
Cite this article
Gao, X., Liu, D., Song, Z. et al. Isosteric design of friction-reduction and anti-wear lubricant additives with less sulfur content. Friction 6, 164–182 (2018). https://doi.org/10.1007/s40544-017-0162-x
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s40544-017-0162-x