Side-by-side Chinese-English

含氮杂环的酯或酰胺类衍生物的制备及其摩擦学性能

余磊1,2 戴康徐2 鲁浩2 方岩雄1 曹华3 韩利芬2 赵鸿斌2 李诗娟2

(1.广东工业大学轻工化工学院, 广东广州 510000)
(2.东莞理工学院化学工程与能源技术学院, 广东东莞 523808)
(3.佛山德联汽车用品有限公司, 广东佛山 528247)

【摘要】设计合成了4种含氮杂环的酯或酰胺类衍生物润滑油添加剂 (Ⅰ~Ⅳ) 。采用核磁共振氢谱 (1H NMR) 和飞行时间质谱 (MALDI-TOF-MS) 对所得产物的结构进行了表征;研究了4种添加剂的油溶性、热稳定性和抗腐蚀性;在四球摩擦磨损试验机上系统考察了添加剂在液体石蜡中的摩擦学性能;利用扫描电子显微镜 (SEM) 和能谱分析仪 (EDS) 观察和分析了钢球磨斑的表面形貌和元素组成。结果表明, 4种添加剂均具有良好的油溶性、热稳定性和抗腐蚀性, 当添加剂Ⅰ的质量分数达到1.0%时, 钢球的磨斑直径 (WSD) 和摩擦系数分别比在液体石蜡中降低了33%和26%。SEM结果显示4种添加剂的加入能明显减小WSD, 减少表面磨损, EDS结果表明添加剂在摩擦过程中形成了复杂的反应膜。

【关键词】 合成;润滑油添加剂;磨损;表面;摩擦学性能;

【DOI】

【基金资助】 东莞市社会科技发展项目 (2015108101003) ; 广东省普通高校特色创新项目 (2017KTSCX179, 2015KTSCX136) ;

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)

【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;

【DOI】

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

Download this article
    References

    [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

ISSN:0438-1157

CN: 11-1946/TQ

Vol 69, No. 09, Pages 4083-4089

September 2018

Downloads:0

Share
Article Outline

Abstract

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