Green synthesis and tribological behaviors of three novel benzothiazole-derived borate esters as lubricant additives in mineral oil

Abstract

Three ashless and nonphosphorus benzothiazole-derived borate esters were synthesized by a halide-free green synthesis method. The results show that the hydrolytic stability and tribological characteristics have been significantly improved. Scanning electron microscopy was used to analyze the morphologies of the rubbing surfaces. X-ray absorption near edge structure spectroscopy was also adopted to investigate the thermal films and tribofilms of the synthesized additives. The analysis results indicate that the thermal films are mainly composed of FeSO₄ and B₂O₃, while the tribofilms consist of the components of FeS, FeSO₄, and B₂O₃.

Keywords

Borate esters halide-free hydrolytic stability tribological properties surface analysis

Get full access to this article

View all access options for this article.

References

Han

Zheng

et al.

Tribological properties and worn surface analysis generated by ashless and phosphorus-free additive in water-based lubricant. Proc IMechE, Part J: J Engineering Tribology 2009; 223: 723–728.

Costello

Kasrai

. Study of surface films of overbased sulfonates and sulfurized olefins by X-Ray Absorption Near Edge Structure (XANES) spectroscopy. Tribol Lett 2006; 24: 163–169.

Qiao

et al.

XANES characteristics of tribofilms generated by dithiophosphate additive in water at different test temperatures and durations. Surf Interface Anal 2009; 41: 779–784.

Lee

S-H

Themelis

Castaldi

. High-temperature corrosion in waste-to-energy boilers. J Therm Spray Technol 2007; 16: 104–110.

Rudnick

. Lubricant additives - Chemistry and applications, 2nd ed. Wilmington, DE: Designed Materials Group, 2008.

Tysoe WT. Understanding the tribological chemistry of chlorine- and sulfur- and phosphorus-containing additives. In: World tribology congress III. New York: American Society of Mechanical Engineers, 2005.

Zhang

Zeng

et al.

The tribological chemistry of a novel borate ester additive and its interaction with ZDDP using XANES and XPS. Tribol Lett 2014; 53: 533–542.

Fan

Ren

et al.

Tribological study and mechanism of B-N and B-S-N triazine borate esters as lubricant additives in mineral oil. Tribol Int 2015; 88: 1–7.

Zhang

Liu

Xue

. The tribological properties of the heterocyclic compound containing S, N, O, and B as additive in liquid paraffin. Wear 1999; 224: 68–74.

10.

Shen

Zheng

Wan

et al.

Synergistic lubricating effects of borate ester with heterocyclic compound. Wear 2000; 246: 55–58.

11.

Sun

Xue

. Hydrolytic stability of S‐hydroxyethyl N,N‐dialkyl dithiocarbamate‐derived borates and their tribological behavior as additives in PAO. Ind Lubr Tribol 2010; 62: 70–77.

12.

Wang

Yue

et al.

Study on the tribological properties of plasma nitrided bearing steel under lubrication with borate ester additive. Tribol Int 2013; 66: 259–264.

13.

Mourhatch

Aswath

. Tribological behavior and nature of tribofilms generated from fluorinated ZDDP in comparison to ZDDP under extreme pressure conditions—Part 1: Structure and chemistry of tribofilms. Tribol Int 2011; 44: 187–200.

14.

Martin

Onodera

De Barros Bouchet

M-I

et al.

Anti-wear chemistry of ZDDP and calcium borate nano-additive. Coupling experiments, chemical hardness predictions, and MD calculations. Tribol Lett 2013; 50: 95–104.

15.

Fan

et al.

Tribological characteristics of ashless dithiocarbamate derivatives and their combinations with ZDDP as additives in mineral oil. Tribol Int 2008; 41: 1226–1231.

16.

Wang

Ren

. The tribological properties and action mechanism of non-active organic molybdate ester and its combination with ZDDP. Tribol Int 2012; 49: 90–95.

17.

et al.

The tribological behaviours of dithiocarbamate-triazine derivatives as additives in mineral oil. Surf Interface Anal 2009; 41: 151–156.

18.

Yan

Zeng

van der Heide

et al.

The tribological performance and tribochemical analysis of novel borate esters as lubricant additives in rapeseed oil. Tribol Int 2014; 71: 149–157.

19.

Ren

et al.

Hydrolytic stability and tribological properties of N-containing heterocyclic borate esters as lubricant additives in rapeseed oil. Tribol Int 2014; 73: 101–107.

20.

Zhang

et al.

Tribological study of hydrolytically stable S-containing alkyl phenylboric esters as lubricant additives. RSC Adv 2014; 4: 25118–25126.

21.

Sun

Xue

. Tribological properties and action mechanism of N,N-dialkyl dithiocarbamate-derived S-hydroxyethyl borate esters as additives in rapeseed oil. Wear 2009; 266: 917–924.

22.

Roy

Brown

. Stability of boronic esters – Structural effects on the relative rates of transesterification of 2-(phenyl)-1,3,2-dioxaborolane. J Organomet Chem 2007; 692: 784–790.

23.

Dong

Chen

et al.

Preparation and tribological properties of nanoparticle lanthanum borate. Wear 2000; 243: 43–47.

24.

Wang

et al.

Tribological studies on a novel borate ester containing benzothiazol-2-yl and disulfide groups as multifunctional additive. Tribol Int 2010; 43: 1048–1053.

25.

Xiong

Liang

et al.

Tribological properties and hydrolysis stability study of benzothiazole borate derivative. Lubr Sci 2014; 26: 81–94.

26.

Zhang

et al.

Tribological study of a highly hydrolytically stable phenylboronic acid ester containing benzothiazolyl in mineral oil. Appl Surf Sci 2014; 308: 91–99.

27.

Schaut

Lobello

Mueller

et al.

Characterization of boroaluminosilicate glass surface structures by B K-edge NEXAFS. J Non-Cryst Solids 2011; 357: 3416–3423.

28.

Nicholls

Najman

Zhang

et al.

The contribution of XANES spectroscopy to tribology. Can J Chem 2007; 85: 816–830.

29.

Roy

Brown

. A comparative study of the relative stability of representative chiral and achiral boronic esters employing transesterification. Monatsh Chem 2007; 138: 879–887.

30.

Yan

Zhou

Wang

et al.

Propylene oxide assisted one-pot, tandem synthesis of substituted-1,3,4-oxadiazole-2(3H)-ones in water. Tetrahedron 2012; 68: 7978–7983.

31.

Zhang

et al.

Tribological study of hydrolytically stable S-containing alkyl phenylboric esters as lubricant additives. RSC Adv 2014; 4: 25118–25126.

32.

Wang

Ren

. Tribological study of a novel borate ester containing dialkylthiophosphate group as multifunctional additive. Ind Lubr Tribol 2009; 61: 33–39.

33.

Shah

Glavatskih

Antzutkin

. Boron in tribology: From borates to ionic liquids. Tribol Lett 2013; 51: 281–301.

34.

Zeng

Shao

Rao

et al.

Tribological study of trioctylthiotriazine derivative as lubricating oil additive. Wear 2005; 258: 800–805.

35.

Zeng

et al.

The tribological behaviors of hydroxyl-containing dithiocarbamate-triazine derivatives as additives in rapeseed oil. Tribol Int 2007; 40: 560–566.

36.

Ren

et al.

The tribological chemistry of polysulfides in mineral oil and synthetic diester. Appl Surf Sci 2008; 254: 7232–7236.

37.

Caretti

Albella

Jiménez

. Tribological study of amorphous BC4N coatings. Diam Relat Mater 2007; 16: 63–73.

38.

Wang

et al.

Tribological study of boron-containing soybean lecithin as environmentally friendly lubricant additive in synthetic base fluids. Tribol Lett 2012; 47: 381–388.

39.

Morina

Neville

. Understanding the composition and low friction tribofilm formation/removal in boundary lubrication. Tribol Int 2007; 40: 1696–1704.