Pop-up English-Chinese

Preparation and tribological properties of nitrogen-containing heterocyclic ester or amide derivatives

YU Lei1,2 DAI Kangxu2 LU Hao2 FANG Yanxiong1 CAO Hua3 HAN Lifen2 ZHAO Hongbin2 LI Shijuan2

(1.School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, Guangdong, China 510000)
(2.School of Chemical Engineering and Energy Technology, Dongguan University of Technology, Dongguan, Guangdong, China 523808)
(3.Foshan Delian Automotive Accessories Co., Ltd., Foshan, Guangdong, China 528247)
【Knowledge Link】substitution effect

【Abstract】Four nitrogen heterocyclic ester or amide derivatives based lubricant additives, namely Ⅰ—Ⅳ, were designed and synthesized. The molecular structures were characterized by 1H NMR and MALDI-TOF-MS. The oil solubility, thermal stability and corrosion resistance of these additives were studied. The tribological properties of additives in liquid paraffin (LP) were systematically investigated on a four-ball test machine. The surfaces morphology and elementary composition of the wear scar were recorded on a scanning electron microscope (SEM) and an energy dispersive spectrometer (EDS). The results show that the four additives exhibit excellent oil solubility, high thermal stability and good corrosion resistance. When the addition of additive Ⅰ is 1% (mass fraction), the wear scar diameter (WSD) and coefficient of friction Are 33% and 26% lower than those in non-added liquid paraffin. The SEM images suggest that the addition of all the four additives can significantly reduce WSD and decrease surface wear. The EDS results indicate that the additives form a complex reaction film in the process of friction.

【Keywords】 synthesis; lubricant additive; attrition; surface; tribological properties;


【Funds】 Social Science and Technology Development Foundation of Dongguan (2015108101003) Characteristic Innovation Foundation of Ordinary Universities of Guangdong Province (2017KTSCX179, 2015KTSCX136)

Download this article


    [1] GUAN Z J. Views and suggestions on current tribological work [J]. Lubes & Fuels, 2016, 26 (Z1): 6–12 (in Chinese).

    [2] DOHHEN K C, SWAMI K K, MONDAL P K, et al. Lubricant compositions for internal combustion engines: US6339052 [P]. 2002–01–15.

    [3] YANG J J, GAO H. Present status and development trend of Chinese lubricant industry [J]. Lubricating Oil, 2009, 24 (1): 1–10 (in Chinese).

    [4] LIANG P, WU H, ZUO G, et al. Tribological performances of heterocyclic-containing ether and/or thioether as additives in the synthetic diester [J]. Lubrication Science, 2009, 21 (3): 111–121.

    [5] JIA Z, XIA Y, PANG X, et al. Tribological behaviors of different diamond-like carbon coatings on nitrided mild steel lubricated with benzotriazole-containing borate esters [J]. Tribology Letters, 2011, 41 (1): 247–256.

    [6] HE Z, XIONG L, LIANG Q, et al. Tribological properties and hydrolysis stability study of benzothiazole borate derivative [J]. Lubrication Science, 2014, 26 (2): 81–94.

    [7] WU H, ZENG X Q, REN T H. Tribological performance of 2-mercaptobenzothiazole derivatives as lubricating oil additives [J]. Industrial Lubrication & Tribology, 2008, 60 (4): 183–188.

    [8] TANG Z, LI S. A review of recent developments of friction modifiers for liquid lubricants (2007–present) [J]. Current Opinion in Solid State & Materials Science, 2014, 18 (3): 119–139.

    [9] ZHANG S W. Scientific and technological connotation and the prospects of green tribology [J]. Tribology, 2011, 31 (4): 417–424 (in Chinese).

    [10] ZHAO X W. Synthetic methods of diesters lubricants [J]. Synthetic Lubricants, 2013, 40 (4): 29–31 (in Chinese).

    [11] KANG J, ZHAO Y Z, ZONG M. Development of biodegradable grease [J]. Acta Petrolei Sinica (Petroleum Processing Section), 2011, 27 (s1): 110–114 (in Chinese).

    [12] YAO M. Study on properties of imidazolinium-based lubricity additives for promoting biodegradation [D]. Chongqing: Chongqing University of Technology, 2011 (in Chinese).

    [13] DENG C J. Study on the performance of N-fatty acyl amino acid lubricity additives for promoting biodegradation [D]. Chongqing: Chongqing University of Technology, 2011 (in Chinese).

    [14] SPIKES H. Low and zero-sulphated ash, phosphorus and sulphur antiwear additives for engine oils [J]. Lubrication Science, 2008, 20 (2): 103–136.

    [15] LI Z P, LI Y L, ZHANG Y W, et al. Tribological study of hydrolytically stable S-containing alkyl phenylboric esters as lubricant additives [J]. RSC Advances, 2014, 4 (48): 25118–25126.

    [16] YANG G B, TIAN Y, ZHANG J F, et al. Preparation and tribological properties of N-containing heterocyclic borates as lubricant additives [J]. Tribology, 2012, 32 (4): 384–389 (in Chinese).

    [17] XIE E Q, ZHAO X N, ZHANG Y H, et al. Lubricant extreme pressure anti-wear additives applied research progress and direction [J]. Coal and Chemical Industry, 2013, 36 (5): 25–27 (in Chinese).

    [18] LI J S. Molecule design, synthesis and the relationship between structure and tribological properties of additives used in biodegradable lubricant [D]. Shanghai: Shanghai Jiao Tong University, 2001 (in Chinese).

    [19] WANG T T, DAI K, WANG Z, et al. Quantitative structure–triboability relationship about the antiwear properties of N-containing heterocyclic derivatives [J]. Tribology, 2014, 34 (2): 187–192 (in Chinese).

    [20] MA P L. Design, synthesis and testing of a new nitrogen containing conjugated heterocyclic lubricant for extreme pressure and antiwear additive [D]. Xi’an: Northwest University, 2011 (in Chinese).

    [21] ZHAO H B, PENG W L, LIU R D, et al. Synthesis, characterization and tribological properties of butoxy dithiocarbonate acetic ester as lubricating additives [J]. Tribology, 2011, 31 (5): 515–520 (in Chinese).

    [22] ZHAO H B, LIU Y L, CHANG H, et al. Synthesis, characterization and tribological properties of 1-H benzotriazole chloroacetate derivatives [J]. Lubrication Engineering, 2008, 33 (2): 714–720 (in Chinese).

    [23] ZHANG Z G, ZHAO H B, CHANG H, et al. Synthesis and tribological study of 1, 4-di (dithiocarbamate acetate) piperazine as lubricating oil additive [J]. Lubrication Engineering, 2008, 33 (1): 86–89 (in Chinese).

    [24] WANG Q H. Synthesis, characterization and properties of lubricating oil multifunctional additives containing nitrogen heterocyclic compound derivatives [D]. Chongqing: PLA Logistics Engineering College, 2001 (in Chinese).

    [25] LI J S, FENG Y, REN T H. The tribological study of organic borate esters as additives in rapeseed oil [J]. Lubricating Oil, 2004, 19 (2): 32–34 (in Chinese).

    [26] LUO H T, ZHANG L, SUN L G, et al. Research status and application analysis of nitrogen-containing heterocyclic extreme pressure antiwear additives [J]. Lubes & Fuels, 2014, 24 (Z1): 7–11 (in Chinese).

    [27] OUYANG P, CHEN G X, ZHANG X M. Performance of zerosulphur/phosphorus quinazolinone amine as multifunctional lubricating oil additive [J]. Acta Petrolei Sinica (Petroleum Processing Section), 2013, 29 (3): 447–452 (in Chinese).

    [28] OUYANG P, ZHANG X M, CHEN G X. Preparation and properties of nitrogen-containing heterocyclic lubricating additive [J]. Chemical Research & Application, 2013, 25 (2): 174–178 (in Chinese).

    [29] YAN J C, ZENG X Q, EMILE V, et al. The tribological performance and tribochemical analysis of novel borate esters as lubricant additives in rapeseed oil [J]. Tribology International, 2014, 71 (1): 149–157.

    [30] HUANG Y H, LI F F, YOU J W, et al. The tribological properties of hydroxyl-containing dithiocarbamate derivatives as additives in rapeseed oil [J]. Petroleum Processing and Petrochemicals, 2010, 41 (3): 60–64.

This Article


CN: 31-1012/F

Vol 44, No. 12, Pages 31-43

December 2018


Article Outline



  • Introduction
  • 1 Experimental materials and methods
  • 2 Experimental results and discussion
  • 3 Conclusion
  • References