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Tribology International
journal homepage: www.elsevier.com/locate/triboint
A R T I C LE I N FO A B S T R A C T
Keywords: Ionic liquids (ILs) are highly attractive lubricant additives for their nonflammability, low vapor pressures,
Oil-dispersible ILs structural diversity and reasonable tribological properties. A convenient synthesis route to oil-dispersible ILs has
Phosphite been presented in this paper. Phosphite binds to aliphatic acid as anion and triethylbenzylammonium serve as a
Fatty acid cation, which could be applied as lubricant additives in mineral oil (5CST) and refined vegetable oil (RSO).
Surface analysis
Results demonstrated that these ILs could effectively enhance the antiwear, friction-reducing and extreme
pressure properties of 5CST and RSO. The chain length and unsaturation of fatty acid is significant in improving
the tribological properties of base oil. TEY and FY mode K-edge XANES analysis of the formed tribofilms showed
that the improvement of anti-wear and friction-reducing properties was closely related to the content of phos-
phate species on the near surface.
∗
Corresponding author.
E-mail address: thren@sjtu.edu.cn (T. Ren).
https://doi.org/10.1016/j.triboint.2018.03.028
Received 4 January 2018; Received in revised form 26 March 2018; Accepted 26 March 2018
Available online 27 March 2018
0301-679X/ © 2018 Elsevier Ltd. All rights reserved.
G. Zheng et al. Tribology International 123 (2018) 316–324
been reported as a lubricant additive recently [34]. Fatty acid can (m, 32H), 1.46–1.50 (t, 4H), 1.55–1.67 (m, 2H), 2.24–2.37 (m, 2H),
produce metal soap and avoid the direct contact of asperities, but its 3.38–3.43 (t, 3H), 3.67–3.69 (s, 4H), 4.70–4.75 (s, 2H), 4.85–5.1
tribological properties could not meet the requirement of severe lu- (s,2H), 7.42–7.56 (m, 5H). 13C NMR (100 MHz, CDCl3) δ 8.27, 14.12,
brication conditions. Quaternary ammonium base has good phase 22.63, 24.91, 29.36, 31.97, 34.12, 51.48, 127.17, 129.50, 130.77,
transfer, adsorption and dispersion characteristics over a wide range of 132.43, 174.37, 177.22.
base liquids [35]. PAPN: 1H NMR (500 MHz, CDCl3) δ 0.88–0.92 (t, 6H), 1.26–1.39 (t,
Combined with the benefits of ILs, fatty acid and phosphite, we 40H), 1.60–1.68 (m, 4H), 1.95–2.10 (m, 8H), 2.32–2.38 (m, 4H),
report the synthesis, characterization, tribo-evaluation and lubrication 2.60–2.85 (m, 6H), 3.61–3.65 (m, 4H), 3.66–3.69 (t, 6H), 3.70–3.73 (t,
mechanism of phosphite-based halogen-free ILs additives for vegetable 6H), 3.73–3.80 (m, 4H), 4.22–4.28 (m, 4H), 7.41–7.49 (m, 5H). 13C
oil and mineral oil. We focus on the influence of ILs concentration on NMR (100 MHz, CDCl3) δ 14.08, 22.42, 24.59, 24.90, 27.22, 29.12,
tribological properties of the base oil. The tribological performance of 31.53, 34.20, 61.65, 63.35, 69.27, 70.53, 72.55, 127.78, 130.22,
ILs as lubricant additive was evaluated using a four-ball tester. A 174.10.
KEYENCE vk-x200 laser scanning microscope (CLSM) was used to ex- SAPN: 1H NMR (500 MHz, CDCl3) δ 0.88–0.93 (t, 6H), 1.26–1.39 (t,
amine the morphology and wear volume of steel ball surface. XANES 60H), 1.47–1.51 (t, 4H), 1.58–1.68 (m,4H), 1.96–2.12 (m, 4H),
analysis was carried out to examine the chemical composition on the 2.28–2.37 (m, 4H), 2.72–2.84 (m, 2H), 3.37–3.42 (m, 2H), 3.67–3.90
wear scar and the possible tribochemical changes involved in the fric- (s, 2H), 4.03–4.20 (m, 2H), 7.46–7.54 (m, 5H). 13C NMR (100 MHz,
tional process. CDCl3) δ 8.21, 14.13, 22.56, 24.95, 25.64, 27.23, 29.16, 31.54, 31.85,
34.07, 51.46, 52.78, 127.90, 128.04, 129.52, 174.44.
2. Materials and experimental details The measured values of C, H, P, N elements are close to their cal-
culated values. The NMR, EA and FT-IR results confirmed that the de-
2.1. Materials signed molecules were successfully synthesized.
Oleic acid, linoleic acid, stearic acid, and palmitic acid were pur-
chased from KLK OLEO and used to synthesize four ILs without further 2.4. Lubricant preparation and oil solubility of ILs
treatment. RSO (trade name Arawana 1:1:1) was commercially avail-
able from Xi'an Jiali Oil and Grease Factory of China. A commercial The additives were mixed with RSO or 5CST at a fixed concentra-
mineral oil (referred to 5CST), was provided by Petro China Lanzhou tion, and the solution was stirred at fixed temperature (60 °C) for
Lubricating Oil R&D Institute in Lanzhou, China. T308B were obtained 10 min. And the solubility data of the synthesized ILs for both blends
from Zibo Hui Hua Chemical Corporation and used without further was measured at highest concentration (3 wt %)
purification. Other chemicals utilized in this article were all analytical
grade and procured commercially. The steel balls used in experiments 2.5. Tribological evaluation
were obtained from Shanghai Ningxing steel ball Co., Ltd. and had the
following specifications:φ12.7 mm; HRC59-61; GCr15 (chemical com- The tribological properties of ILs as additives in RSO and 5CST were
position: 0.95–1.05 wt % C; 0.15–0.35 wt % Si; 0.20–0.40 wt % Mn; evaluated using a MS-10J four-ball tester manufactured by Xia men
0.027 wt % P; 0.020 wt % S; 1.30–1.65 wt % Cr; 0.30 wt % Ni; 0.25 wt tenkey automation Co. Ltd, China. Four-ball tester consists of a mobile
% Cu). ball bearing that is rotated in contact with three fixed ball bearings
which are immersed in the test lubricant, as shown in Fig. 3. The an-
2.2. Preparation of additives tiwear and friction-reducing test were conducted on four-ball tester at a
speed of 1450 rpm, load 40 Kg and room temperature (25 °C) for
Four ILs with quaternary ammonium group, OAPN, LAPN, SAPN 30 min. The wear scar diameters (WSDs) were collected by an optical
and PAPN, were synthesized in three steps (Fig. 1). The desired mixture microscope with accuracy of ± 0.01 mm. The friction coefficient (COF)
1 was obtained from a slight excess of epoxy propane and aliphatic acid was automatically calculated from measured torque and load data. The
with triethylamine as the catalyst, and toluene as the solvent at 60 °C extreme pressure (EP) performance was conducted following GB12583-
after 8 h. The mixture 2 was prepared by mixing l and dimethyl phos- 98 test procedure: speed, 1760 rpm; temperature, ambient; load, vari-
phite stirring at about 120 °C until no CH3OH formed. In the third se- able; test duration, 10 s, which was similar to ASTMD-2783 method. EP
quence of reactions, mixture 3 was obtained by neutralization with tests were conducted with increasing loads until welding of steel balls is
quaternary ammonium base at 70 °C for 4 h. Finally it was obtained by occurred. The load before which welding occurs is called the maximum
filtration and reduced pressure distillation. Additionally, a commercial nonseized load (PB value), and the load is an EP property of the test
additive was also provided for compare and its chemical structure was lubricant. For each sample, three identical tests were performed so as to
shown in Fig. 1. minimize data scattering. After the tribological evaluation, the steel
balls were gently rinsed in acetone and dried with tissue paper.
2.3. Characterization
The structure of ILs was characterized by 1H, 13C NMR spectroscopy, 2.6. Analysis of the worn surface morphology and chemical composition
Fourier transform infrared (FT-IR) spectroscopy (see Fig. 2 and Table 1)
and Elemental Analysis (EA) (see Table 2). In order to estimate the The morphology of the worn surface was obtained using a KEYENCE
decomposition behavior of synthesized ILs under thermal conditions vk-x200 laser scanning microscope (CLSM). Chemical composition
(oxygen free), Tonset (thermal decomposition temperature) was de- measurement on the worn surface was carried out on an X-ray ab-
termined on a Perkin Elmer TGA 7 thermo-gravimetric analysis device. sorption near edge structure spectroscopy (XANES) which was located
OAPN: 1H NMR (500 MHz, CDCl3) δ 0.85–0.93 (t, 6H), 1.22–1.28 at the Institute of High-Energy Physics (IHEP), Chinese Academy of
(m, 44H), 1.29–1.35 (t, 9H), 1.46–1.51 (t, 6H), 1.56–1.66 (m, 4H), Science [36]. Sample spectra were collected in partial fluorescence
2.25–2.35 (m, 4H), 3.35–3.41 (t, 6H), 3.67–3.69 (s, 4H),4.65–4.70 (s, yield (FY) mode for bulk information or total electron yield (TEY) mode
2H), 4.85–5.1 (s,2H), 7.44–7.53 (m, 5H). 13C NMR (100 MHz, CDCl3) δ for near surface information. All spectras were recorded from 2140 to
8.25, 14.04, 22.66, 24.91, 29.50, 31.93, 34.13, 35.08, 51.45, 52.86, 2165eV with a step size of 1.0eV on the region of 2140–2145 eV,
61.15, 127.16, 129.27, 130.6, 130.83,132.39, 174.40, 177.87. 0.50 eV in pre-edge region of 2145–2150 eV, and 0.20 eV in near edge
LAPN: 1H NMR (500 MHz, CDCl3) δ 0.86–0.91 (t, 6H), 1.20–1.40 region of 2150–2165 eV.
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G. Zheng et al. Tribology International 123 (2018) 316–324
Table 2
The results of EA for ILs.
Items/(wt%) H C P N
a
Calculated value (oxygen being at balance).
Table 1
3. Results and discussion
IR spectra data of ILs.
Adsorption peaks OAPN(cm−1) LAPN(cm−1) PAPN SAPN(cm−1) 3.1. Oil solubility
(cm−1)
=CH(Ph) 3008 3009 _ _ From Fig. 4, there is almost no stratification in the container under
-CH3,-CH2, -CH 2927, 2927, 2915, 2851 2917, 2850 the highest addition, indicating that the synthesized additives could
2866,706 2855,708 disperse in the base oil commendably. The transparency of ILs blended
C=C 1638 1637 _ _ with RSO decreases with the increase of carbon chain length and the
-COO- 1739, 1212, 1742, 1243 1727, 1210, 1742, 1215,
number of “C=C”. However, the synthesized ILs in 5CST seems to be
1059 1062 1056
-C-N+ 904 916 902 905 different. SAPN and PAPN exhibits strong thickening properties in
O-P-O 830 836 850 883 5CST. The longer the carbon chain of ILs is, the better the thickening
Ph 755, 618 756, 619 736, 617 757 property is. The thickening property is obvious at room temperature
P-O 1007 1012 1009 1009
(25 °C) and is not significant at the high temperature (40–100 °C). ILs
with more “C=C” shows better transparency in 5CST. Additionally,
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G. Zheng et al. Tribology International 123 (2018) 316–324
their transparency do not change significantly over time. The antiwear performance of SAPN is the worst at the test concentra-
tion among the synthesized ILs, while OAPN, LAPN and PAPN are si-
3.2. Thermal stability milar at a relative wide test range (Fig. 6(b)). This phenomenon can be
attributed to the adsorption and tribochemical reaction of the additive
The thermogravimetry analysis (TGA) results of four ILs are shown on the metal surface. The free movement of anion and cation is re-
in Fig. 5. The anion structure of the synthesized ILs, plays a significant stricted by the minor polarity of base oil. The adsorption property of
effect on thermal stability of the whole molecule. Tonset (thermal de- additive molecule can be effectively ameliorated by polar group. ILs
composition temperature) of SAPN, PAPN, OAPN and LAPN follows the with more double bonds and shorter carbon chain length are more
order PAPN (310.5 °C) > SAPN (245.8 °C) > OAPN (232.5 °C) > easily to adsorb on the metal surface. SAPN contains saturated long
LAPN (211.5 °C) respectively (Fig. 5), indicating that the synthesized carbon chain, which is not conducive to its adsorption on the metal
ILs have a high thermal stability. The decrease of thermal stability with surface. In the friction process, the additive adsorbed on the metal
the increase of “C=C” due to the increasing unsaturated double bond of surface reacts with the metal asperity to produce a film with high
phosphite by inductive effect, promoting the breakdown of C-O bond. strength, which replaces the direct contact between asperities under
harsh frictional process [37]. The additive with poor adsorption capa-
city may not have enough active elements on the worn surface to
3.3. Antiwear performance produce a similar film. This situation could gradually improve with
increase of the additive concentration. Additionally, other reports have
WSDs of steel balls with different additive concentration in 5CST described that when the addition amount exceeds the optimum con-
and RSO are shown in Fig. 6. WSD decreases first and then remains centration, the tribological properties of additive may become worse or
relative stable with the increase of additive concentration. The antiwear even deteriorate [38]. The synthesized ILs could avoid that problem
performance of the synthesized ILs blended with 5CST decreases in the due to the protection of quaternary ammonium salt.
following order: LAPN > OAPN > PAPN > SAPN > T308B (Fig. 6
(a)), while that in RSO is more obvious. The four-ball tester cannot even
start because of the poor antiwear performance of T308B at 0.25 wt%. 3.4. Friction-reducing performance
In Fig. 7, the friction coefficient of the base oil, T308B blends and
ILs blends are shown. The friction coefficient of 5CST is slightly lower
than that of RSO. When the concentration of synthesized ILs increases
in base oil, COF decreases initially and reduces drastically to relatively
low value at a particular concentration. But the contribution of T308B
to antifriction is very small or even worse at certain concentration
(0.25 wt %). Additionally, the COF difference of the four additives can
be explained by their different alkyl length and “C=C” groups. The
shorter alkyl chain and less “C=C” group can form effective lubricating
films on the rubbing surface in 5CST, resulting in lower COF. COFs
resulting from the four kinds of ILs rank as PAPN < SAPN <
OAPN < LAPN < T308B in 5CST. OAPN with long alkyl chain and
one “C=C” group exhibits the best friction-reducing performance in
RSO. While LAPN shows reasonable antiwear property and relatively
poor friction-reducing performance in RSO. This decrement in COFs can
be attributed to the physical and/or chemical reaction film initiated by
Fig. 5. TGA curves of the synthesized ILs. the additive during friction process. The shearing strength of the film is
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Fig. 6. Effects of the additive concentration on WSD (a), synthesized ILs and T308B in 5CST; (b) synthesized ILs and T308B in RSO (four-ball tester, load 392 N,
rotation speed 1450 rpm, 30 min).
less than that of the metal asperities, so asperities from one surface can
easily slide over the asperities of the other sliding surface, leading to the
decrease of COF compared to base oils [39]. The shear strength of
PAPN-tribofilm is lower than that of other synthesized ILs-tribofilm in
5CST. This may be because P content of PAPN is higher than that of
other synthesized ILs, which could form a more effective lubricating
film to avoid the direct contact of asperities. OAPN with reasonable
polarity could form an adsorption film, and then generate a layer of
reaction film induced by triboheat. The adsorption film and reaction
film might form a boundary lubricating film to alleviate COF of rubbing
surfaces in RSO. The polarity of LAPN is also large, but LAPN shows the
worst friction-reducing performance than other ILs in RSO. That is may
be because the thickness of adsorption film increases with the polarity
of RSO. The reasonable friction-reducing property of OAPN-tribofilm
may be due to the lower polymerization degree or content of phosphate
species formed by OAPN than other ILs [40].
Fig. 8. Wear volume of steel balls lubricated by the base oil and the base oil
3.5. Analysis of wear volumes
containing 3 wt% of synthesized ILs and T308B (four-ball tester, load 392 N,
rotation speed 1450 rpm, 30 min).
The wear volumes of steel balls lubricated by base oil containing
3 wt% of OAPN, LAPN, SAPN, PAPN and T308B under a load of 392 N
for 30 min are shown in Fig. 8. T308B can improve antiwear perfor- those of the base oil, but they are much higher than those of the other
mance of the base oil. But in comparison with the synthesized ILs, its blends. This result is basically consistent with WSD results of the four-
antiwear performance is not remarkable. The wear volume obviously ball tests. The wear volume results are better than WSD data in reflect
decreases with the addition of four additives, and the wear volume of the improvement of the wear resistance.
PAPN containing lubricants are smaller than those of OAPN, LAPN and
SAPN at the same concentration, indicating that the antiwear perfor- 3.6. Extreme pressure performance
mance of PAPN is better than that of OAPN, LAPN and SAPN in four-
ball tests. The wear volume for RSO blended with 3.0 wt % SAPN and PB value of as-prepared lubricants are summarized in Fig. 9. PB
5CST blended with 3.0 wt% OAPN are also considerably smaller than value of 5CST and RSO is 52 Kg and 40 Kg, respectively. The
Fig. 7. Friction-reducing performance of different ILs blends (a), ILs in 5CST; (b) ILs in RSO (four-ball tester, load 392 N, rotation speed 1450 rpm, duration 30 min).
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G. Zheng et al. Tribology International 123 (2018) 316–324
Fig. 10. CLSM image of worn surface of lower balls lubricated by base oil and base oil blended with 3 wt% of ILs and T308B (applied load 392 N, rotary speed
1450 rpm, duration 30 min).
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G. Zheng et al. Tribology International 123 (2018) 316–324
Fig. 11. XANES spectra of tribofilms: (a) TEY P K-edge spectra of the synthesized ILs in RSO; (b) TEY P K-edge spectra of the synthesized ILs in 5CST; (c) FY P K-edge
spectra of the synthesized ILs in RSO; (d) FY P K-edge spectra of the synthesized ILs in 5CST.
(1) Four novel aliphatic acid containing phosphite–based ILs, OAPN, [6] Peterson CL, Phillips AI. Vegetable oil as a diesel fuel: status and research priorities.
LAPN, PAPN and SAPN, were prepared and were used as lubricant Acta Bot Bras 1986;29(5):1413–22.
[7] Martins MAG. Vegetable oils, an alternative to mineral oil for power transformers-
additives in RSO and 5CST. The prepared ILs exhibits excellent experimental study of paper aging in vegetable oil versus mineral oil. IEEE Electr
tribological performance with low wear volume in the reference Insul Mag 2010;26(6):7–13.
base oils, and the additive with long carbon chain and small po- [8] Saurín N, Minami I, Sanes J, Bermúdez MD. Study of the effect of tribo-materials
and surface finish on the lubricant performance of new halogen-free room tem-
larity is not conductive to the improvement of antiwear properties. perature ionic liquids. Appl Surf Sci 2016;366:464–74.
The additives have reasonable compatibility with the base oil and [9] Zhou Y, Qu J. Ionic liquids as lubricant additives: a review. ACS Appl Mater
acquire excellent friction-reducing, extreme pressure performance. Interfaces 2017;9(4):3209–22.
[10] Zhou F, Liang YM, Liu WM. Ionic liquid lubricants: designed chemistry for en-
The tribological properties of the prepared ILs are better than
gineering applications. Chem Soc Rev 2009;38:2590–9.
T308B. [11] Li H, Somers AE, Rutland MW, Howlett PC, Atkin R. Combined nano- and macr
(2) Using TEY and FY mode XANES analyses, we could demonstrate otribology studies of titania lubrication using oil of ionic liquid mixtures. ACS
Sustainable Chem Eng 2016;4:5005–12.
that phosphate species protective layer form on the wear traces. The
[12] Mahrova M, Pagano F, Pejakovic V, Valea A, Kalin M, Igartua A, Tojo E. Pyridinium
effectiveness of the antiwear and friction-reducing performance based dicationic ionic liquids as base lubricants or lubricant additives. Tribol Int
could be attributed to the variation of phosphate species content on 2015;82:245–54.
the near surface. The base oil with minor polarity is more likely to [13] Song ZH, Yu QL, Cai MR, Huang GW, Yao MH, Li DM, Liang YM, Fan MJ, Zhou F.
Green ionic liquid lubricants prepared from anti-inflammatory drug. Tribol Lett
generate phosphate with high polymerization 2015;60(3):38.
[14] Viesca JL, Mallada MT, Blanco D, Fernández-González A, Espina-Casado J,
Acknowledgements González R, Battez AH. Lubrication performance of an ammonium cation-based
ionic liquid used as an additive in a polar oil. Tribol Int 2017;116:422–30.
[15] Sánchez FL, Otero I, López ER, Fernández LJ. Tribological properties of two bis
The authors are grateful to the National Natural Science Foundation (trifluoromethylsulfonyl)imide-based ionic liquids on steel-steel contact. Tribol
of China (Grant No. 21272157), Beijing Synchrotron Radiation Facility Trans 2014;57(4):637–46.
[16] Phillips BS, Zabinski JS. Ionic Liquid lubrication effects on ceramics in a water
(Grant No. SR06033) for financial support of the work reported in this environment. Tribol Lett 2004;17(3):533–41.
article. [17] Fan MJ, Song ZH, Liang YM, Zhou F, Liu WM. Laxative inspired ionic liquid lu-
bricants with good detergency and no corrosion. ACS Appl Mater Interfaces
2014;6(5):3233–41.
References [18] Totolin V, Minami I, Gabler C, Brenner J, Dörr N. Lubrication mechanism of
phosphonium phosphate ionic liquid additive in alkylborane-imidazole complexes.
[1] Bartz WJ. Lubricants and the environment. Tribol Int 1998;31(1–3):35–47. Tribol Lett 2014;53(2):421–32.
[2] Boyde S. Green lubricants. Environmental benefits and impacts of lubrication. Green [19] Palacio M, Bhushan B. A review of ionic liquids for green molecular lubrication in
Chem 2002;4:293–307. nanotechnology. Tribol Lett 2010;40(2):247–68.
[3] Shashidhara YM, Jayaram SR. Vegetable oils as a potential cutting fluid-An evolu- [20] Barnhill WC, Luo H, Meyer HM, Ma C, Chi M. Tertiary and quaternary ammonium-
tion. Tribol Int 2010;43(5–6):1073–81. phosphate ionic liquids as lubricant additives. Tribol Lett 2016;63(2):1–11.
[4] Kammann KP, Phillips AI. Sulfurized vegetable oil products as lubricant additives. J [21] Espinosa T, Sanes J, Jiménez AE, Bermúdez MD. Surface interactions, corrosion
Am Oil Chem Soc 1985;62(5):917–23. processes and lubricating performance of protic and aprotic ionic liquids with
[5] Erhan SZ, Sharma BK, Perez JM. Oxidation and low temperature stability of vege- OFHC copper. Appl Surf Sci 2013;273:578–97.
table oil-based lubricants. Ind Crop Prod 2006;24(3):292–9. [22] Fu XS, Sun LG, Zhou XG, Li ZP, Ren TH. Tribological study of oil-miscible
323
G. Zheng et al. Tribology International 123 (2018) 316–324
quaternary ammonium phosphites ionic liquids as lubricant additives in PAO. Acta B 2014;10:1–5.
Tribol Lett 2015;60(2):23. [37] Chen H, Yan JC, Ren TH, Zhao YD, Zheng L. Tribological behavior of some long-
[23] Zheng GL, Zhang GQ, Ding TM, Xiang XZ, Li F, Ren TH, Liu SH, Zheng L. chain dimercaptothiadiazole derivatives as multifunctional lubricant additives in
Tribological properties and surface interaction of novel water-soluble ionic liquid in vegetable oil and investigation of their tribochemistry using xanes. Tribol Lett
water-glycol. Tribol Int 2017;116:440–8. 2012;45(3):465–76.
[24] Westerholt A, Weschta M, Bösmann A, Tremmel S, Korth Y, Wolf M, Schlücker E, [38] Fu XS, Sun LG, Zhou XG, Li JC, Fan BJ, Ren TH. Tribochemical behaviors of
Wehrum N, Lennert A, Uerdingen M, Holweger W, Wartzack S, Wasserscheid P. phosphite esters and their combinations with alkyl amines. Appl Surf Sci
Halide-free synthesis and tribological performance of oil-miscible ammonium and 2015;357:1163–70.
phosphonium-based ionic liquids. Ind Eng Chem Res 2013;52:15829–37. [39] Li ZP, Li YL, Zhang YW, Ren TH, Zhao YD. Tribological study of hydrolytically
[25] Yu B, Bansal DG, Qu J, Sun XQ, Luo HM, Dai S, Blau PJ, Bunting BG, Mordukhovich stable S-containing alkyl phenylboric esters as lubricant additives. RSC Adv
G, Smolenski DJ. Oil-miscible and non-corrosive phosphonium-based ionic liquids 2014;4:25118–26.
as candidate lubricant additives. Wear 2012;289(15):58–64. [40] Fu XS, Li JC, Sun LG, Zhou XG, Fan BJ, Ren TH. Synergistic effect between organic
[26] Gusain R, Gupta P, Saran S, Khatri OP. Halogen-free bis (imidazolium)/bis (am- borate esters and phosphorus-based additives on tribological performances as lu-
monium)-di [bis (salicylato) borate] ionic liquids as energy-efficient and en- bricant additives in mineral oil. P I Mech Eng O-J Ris 2017;231(8). 1330–1040.
vironmentally friendly lubricant additives. ACS Appl Mater Interfaces [41] Biresaw G, Asadauskas SJ, Mcclure TG. Polysulfide and biobased extreme pressure
2014;17(6):15318–28. additive performance in vegetable vs paraffinic base oils. Ind Eng Chem Res
[27] Song ZH, Liang YM, Fan MJ, Zhou F, Liu WM. Ionic liquids from amino acids: fully 2011;51(1):262–73.
green fluid lubricants for various surface contacts. RSC Adv 2014;37(4):19396–402. [42] Zeng XQ, Li J, Wu XD, Ren TH, Liu WM. The tribological behaviors of hydroxyl-
[28] Fischer TE. Tribochemistry. Annu Rev Mater Sci 1988;18:303–23. containing dithiocarbamate-triazine derivatives as additives in rapeseed oil. Tribol
[29] Xue QJ, Liu WM. Tribochemistry and the development of AW and EP oil additives-a Int 2007;40(3):560–6.
review. Lubric Sci 2010;7(1):81–92. [43] Kim BH, Sharma V, Aswath PB. Chemical and mechanistic interpretation of thermal
[30] Scharf TW, Prasad SV. Solid lubricants: a review. J Mater Sci 2013;48(2):511–31. films formed by dithiophosphates using xanes. Tribol Int 2017;114:15–26.
[31] Shah FU, Glavatskih S, Antzutkin ON. Boron in Tribology: from borates to ionic [44] Li YR, Pereira G, Kasrai M, Norton PR. Studies on ZDDP anti-wear films formed
liquids. Tribol Lett 2013;51(3):281–301. under different conditions by XANES spectroscopy, atomic force microscopy and
[32] Saba CS, Forster NH. Reactions of aromatic phosphate esters with metals and their 31P NMR. Tribol Lett 2007;28(3):319–28.
oxides. Tribol Lett 2002;12(2):135–46. [45] Zheng GL, Ding TM, Zhang GQ, Xiang XZ, Xu Y, Ren TH, Li F, Zheng L. Surface
[33] Papay AG. Antiwear and extreme-pressure additives in lubricants. Lubric Sci analysis of tribofilm formed by phosphorus-nitrogen (p-n) ionic liquid in synthetic
1998;10(3):209–24. ester and water-based emulsion. Tribol Int 2017;115:212–21.
[34] Gusain R, Dhingra S, Khatri OP. Fatty-acid-constituted halogen-free ionic liquids as [46] Yan JC, Bu JM, Bai XF, Li J, Ren TH, Zhao YD. The tribological study of novel
renewable, environmentally friendly, and high-performance lubricant additives. Ind phosphorous–nitrogen type phosphoramidate additives in rapeseed oil. P. I. Mech.
Eng Chem Res 2016;55(4):856–65. Eng. C-J. Mec 2012;226(J5):377–88.
[35] Starks CM, Liotta CL, Halpern ME. Phase transfer catalysis: fundamentals. In phase- [47] Ma HB, Li J, Chen H, Zuo GZ, Yu Y, Ren TH, Zhao YD. XPS and XANES char-
transfer catalysis. Netherlands: Springer; 1994. p. 48–122. acteristics of tribofilms and thermal films generated by two P- and/or S-containing
[36] Zheng L, Zhao YD, Ma CY, Hong CH, Han Y, Cui MQ, Guo ZY. A new experiment additives in water-based lubricant. Tribol Int 2009;42(6):940–5.
station on beamline 4B7A at Beijing Synchrotron Radiation Facility. Spectrochim
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