Insights into the tribological behavior of choline chloride–urea and choline chloride–thiourea deep eutectic solvents

Yuting LI; Yuan LI; Hao LI; Xiaoqiang FAN; Han YAN; Meng CAI; Xiaojun XU; Minhao ZHU

doi:10.1007/s40544-021-0575-4

Friction 2023, 11(1): 76-92 https://doi.org/10.1007/s40544-021-0575-4

Research Article |

Open Access | Issue | Published: 25 April 2022

Insights into the tribological behavior of choline chloride–urea and choline chloride–thiourea deep eutectic solvents

Show Author's Information Hide Author's Information Yuting LI^¹, Yuan LI^¹, Hao LI^¹(

), Xiaoqiang FAN^¹(

), Han YAN^¹, Meng CAI^², Xiaojun XU^¹, Minhao ZHU^{¹^,²}

1 Key Laboratory of Advanced Technologies of Materials (Ministry of Education), School of Materials Science and Engineering, Southwest Jiaotong University, Chengdu 610031, China

2 Tribology Research Institute, School of Mechanical Engineering, Southwest Jiaotong University, Chengdu 610031, China

Keywords:

lubrication mechanism, deep eutectic solvents (DESs), tribo-chemical film, von Mises stress

Cite this article:

LI Y, LI Y, LI H, et al. Insights into the tribological behavior of choline chloride–urea and choline chloride–thiourea deep eutectic solvents. Friction, 2023, 11(1): 76-92. https://doi.org/10.1007/s40544-021-0575-4

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Abstract

Deep eutectic solvents (DESs) have been considered as novel and economic alternatives to traditional lubricants because of their similar physicochemical performance. In this study, choline chloride (ChCl) DESs were successfully synthesized via hydrogen-bonding networks of urea and thiourea as the hydrogen bond donors (HBDs). The as-synthesized ChCl–urea and ChCl–thiourea DESs had excellent thermal stability and displayed good lubrication between steel/steel tribo-pairs. The friction coefficient and wear rate of ChCl– thiourea DES were 50.1% and 80.6%, respectively, lower than those of ChCl–urea DES for GCr15/45 steel tribo-pairs. However, for GCr15/Q45 steel, ChCl–urea DES decreased the wear rate by 85.0% in comparison to ChCl–thiourea DES. Under ChCl–thiourea DES lubrication, the tribo-chemical reaction film composed of FeS formed at the interfaces and contributed to low friction and wear. However, under high von Mises stress, the film could not be stably retained and serious wear was obtained through direct contact of friction pairs. This illustrated that the evolution of the tribo-chemical reaction film was responsible for the anti-friction and anti-wear properties of the DESs.

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Insights into the tribological behavior of choline chloride–urea and choline chloride–thiourea deep eutectic solvents

Show Author's information Hide Author's Information Yuting LI^¹, Yuan LI^¹, Hao LI^¹(

), Xiaoqiang FAN^¹(

), Han YAN^¹, Meng CAI^², Xiaojun XU^¹, Minhao ZHU^{¹^,²}

1 Key Laboratory of Advanced Technologies of Materials (Ministry of Education), School of Materials Science and Engineering, Southwest Jiaotong University, Chengdu 610031, China

2 Tribology Research Institute, School of Mechanical Engineering, Southwest Jiaotong University, Chengdu 610031, China

Abstract

Keywords: lubrication mechanism, deep eutectic solvents (DESs), tribo-chemical film, von Mises stress

References(53)

[1]

Abbott A P, Ahmed E I, Harris R C, Ryder K S. Evaluating water miscible deep eutectic solvents (DESs) and ionic liquids as potential lubricants. Green Chem 16(9): 4156–4161 (2014)

DOI Google Scholar

[2]

Zhou Y, Dyck J, Graham T W, Luo H M, Leonard D N, Qu J. Ionic liquids composed of phosphonium cations and organophosphate, carboxylate, and sulfonate anions as lubricant antiwear additives. Langmuir 30(44): 13301–13311 (2014)

DOI Google Scholar

[3]

Boyde S. Green lubricants. Environmental benefits and impacts of lubrication. Green Chem 4(4): 293–307 (2002)

DOI Google Scholar

[4]

Hörner D. Recent trends in environmentally friendly lubricants. J Synth Lubr 18(4): 327–347 (2002)

DOI Google Scholar

[5]

Dugoni G C, di Pietro M E, Ferro M, Castiglione F, Ruellan S, Moufawad T, Moura L, Costa Gomes M F, Fourmentin S, Mele A. Effect of water on deep eutectic solvent/ β-cyclodextrin systems. ACS Sustainable Chem Eng 7(7): 7277–7285 (2019)

DOI Google Scholar

[6]

Zhang K, Ren S H, Yang X, Hou Y C, Wu W Z, Bao Y Y. Efficient absorption of low-concentration SO₂ in simulated flue gas by functional deep eutectic solvents based on imidazole and its derivatives. Chem Eng J 327: 128–134 (2017)

DOI Google Scholar

[7]

Wagle D V, Zhao H, Baker G A. Deep eutectic solvents: Sustainable media for nanoscale and functional materials. Acc Chem Res 47(8): 2299–2308 (2014)

DOI Google Scholar

[8]

Adhikari L, Larm N E, Bhawawet N, Baker G A. Rapid microwave-assisted synthesis of silver nanoparticles in a halide-free deep eutectic solvent. ACS Sustainable Chem Eng 6(5): 5725–5731 (2018)

DOI Google Scholar

[9]

Smith E L, Abbott A P, Ryder K S. Deep eutectic solvents (DESs) and their applications. Chem Rev 114(21): 11060–11082 (2014)

DOI Google Scholar

[10]

Zhang Q, De Oliveira Vigier K, Royer S, Jérôme F. Deep eutectic solvents: Syntheses, properties and applications. Chem Soc Rev 41(21): 7108–7146 (2012)

DOI Google Scholar

[11]

Chen Z, Greaves T L, Warr G G, Atkin R. Mixing cations with different alkyl chain lengths markedly depresses the melting point in deep eutectic solvents formed from alkylammonium bromide salts and urea. Chem Commun (Camb) 53(15): 2375–2377 (2017)

DOI Google Scholar

[12]

Weaver K D, Kim H J, Sun J Z, MacFarlane D R, Elliott G D. Cyto-toxicity and biocompatibility of a family of choline phosphate ionic liquids designed for pharmaceutical applications. Green Chem 12(3): 507–513 (2010)

DOI Google Scholar

[13]

Ilgen F, Ott D, Kralisch D, Reil C, Palmberger A, König B. Conversion of carbohydrates into 5-hydroxymethylfurfural in highly concentrated low melting mixtures. Green Chem 11(12): 1948–1954 (2009)

DOI Google Scholar

[14]

Li X Y, Hou M Q, Han B X, Wang X L, Zou L Z. Solubility of CO₂ in a choline chloride + urea eutectic mixture. J Chem Eng Data 53(2): 548–550 (2008)

DOI Google Scholar

[15]

Abbott A P, Capper G, Davies D L, Shikotra P. Processing metal oxides using ionic liquids. Miner Process Extr Metall 115(1): 15–18 (2006)

DOI Google Scholar

[16]

Morrison H G, Sun C C, Neervannan S. Characterization of thermal behavior of deep eutectic solvents and their potential as drug solubilization vehicles. Int J Pharm 378(1–2): 136–139 (2009)

DOI Google Scholar

[17]

Abbott A P, Cullis P M, Gibson M J, Harris R C, Raven E. Extraction of glycerol from biodiesel into a eutectic based ionic liquid. Green Chem 9(8): 868–872 (2007)

DOI Google Scholar

[18]

Karam A, Villandier N, Delample M, Koerkamp C K, Douliez J P, Granet R, Krausz P, Barrault J, Jérôme F. Rational design of sugar-based-surfactant combined catalysts for promoting glycerol as a solvent. Chem A Eur J 14(33): 10196–10200 (2008)

DOI Google Scholar

[19]

Lawes S D A, Hainsworth S V, Blake P, Ryder K S, Abbott A P. Lubrication of steel/steel contacts by choline chloride ionic liquids. Tribol Lett 37(2): 103–110 (2010)

DOI Google Scholar

[20]

Shi Y J, Mu L W, Feng X, Lu X H. Friction and wear behavior of CF/PTFE composites lubricated by choline chloride ionic liquids. Tribol Lett 49(2): 413–420 (2013)

DOI Google Scholar

[21]

Antunes M, Campinhas A S, de Sá Freire M, Caetano F, Diogo H P, Colaço R, Branco L C, de Saramago B. Deep eutectic solvents (DES) based on sulfur as alternative lubricants for silicon surfaces. J Mol Liq 295: 111728 (2019)

DOI Google Scholar

[22]

Hallett J E, Hayler H J, Perkin S. Nanolubrication in deep eutectic solvents. Phys Chem Chem Phys 22(36): 20253–20264 (2020)

DOI Google Scholar

[23]

Yue D Y, Jia Y Z, Yao Y, Sun J H, Jing Y. Structure and electrochemical behavior of ionic liquid analogue based on choline chloride and urea. Electrochimica Acta 65: 30–36 (2012)

DOI Google Scholar

[24]

Delgado-Mellado N, Larriba M, Navarro P, Rigual V, Ayuso M, García J, Rodríguez F. Thermal stability of choline chloride deep eutectic solvents by TGA/FTIR–ATR analysis. J Mol Liq 260: 37–43 (2018)

DOI Google Scholar

[25]

Yuan C S, Zhang X, Ren Y F, Feng S Q, Liu J B, Wang J, Su L. Temperature- and pressure-induced phase transitions of choline chloride–urea deep eutectic solvent. J Mol Liq 291: 111343 (2019)

DOI Google Scholar

[26]

Madhurambal G, Mariappan M, Mojumdar S C. Thermal, UV and FTIR spectral studies of urea–thiourea zinc chloride single crystal. J Therm Anal Calorim 100(3): 763–768 (2010)

DOI Google Scholar

[27]

Madhurambal G, Mariappan M, Ravindran B, Mojumdar S C. Thermal and FTIR spectral studies in various proportions of urea thiourea mixed crystal. J Therm Anal Calorim 104(3): 885–891 (2011)

DOI Google Scholar

[28]

Karimi M, Dadfarnia S, Haji Shabani A M. Hollow fibre- supported graphene oxide nanosheets modified with a deep eutectic solvent to be used for the solid-phase microextraction of silver ions. Int J Environ Anal Chem 98(2): 124–137 (2018)

DOI Google Scholar

[29]

Pandey A, Pandey S. Solvatochromic probe behavior within choline chloride-based deep eutectic solvents: Effect of temperature and water. J Phys Chem B 118(50): 14652–14661 (2014)

DOI Google Scholar

[30]

Bombard A J F, Gonçalves F R, Shahrivar K, Ortiz A L, de Vicente J. Tribological behavior of ionic liquid-based magnetorheological fluids in steel and polymeric point contacts. Tribol Int 81: 309–320 (2015)

DOI Google Scholar

[31]

Leyland A, Matthews A. On the significance of the H/E ratio in wear control: A nanocomposite coating approach to optimised tribological behaviour. Wear 246(1–2): 1–11 (2000)

DOI Google Scholar

[32]

McIntyre N S, Zetaruk D G. X-ray photoelectron spectroscopic studies of iron oxides. Anal Chem 49(11): 1521–1529 (1977)

DOI Google Scholar

[33]

Mills P, Sullivan J L. A study of the core level electrons in iron and its three oxides by means of X-ray photoelectron spectroscopy. J Phys D: Appl Phys 16(5): 723–732 (2000)

DOI Google Scholar

[34]

Kim Y I, Hatfield W E. Electrical, magnetic and spectroscopic properties of tetrathiafulvalene charge transfer compounds with iron, ruthenium, rhodium and iridium halides. Inorganica Chimica Acta 188(1): 15–24 (1991)

DOI Google Scholar

[35]

Brion D. Etude par spectroscopie de photoelectrons de la degradation superficielle de FeS₂, CuFeS₂, ZnS et PbS a l'air et dans l'eau. Appl Surf Sci 5(2): 133–152 (1980) (In French)

DOI Google Scholar

[36]

McIntyre N S, Zetaruk D G. X-ray photoelectron spectroscopic studies of iron oxides. Anal Chem 49(11): 1521–1529 (1977)

DOI Google Scholar

[37]

Rueda F, Mendialdua J, Rodriguez A, R Casanova, Barbaux Y, Gengembre L, Jalowiecki L. Characterization of Venezuelan laterites by X-ray photoelectron spectroscopy. J Electron Spectrosc Relat Phenom 82(3): 135–143 (1996)

DOI Google Scholar

[38]

Marcus P, Grimal J M. The anodic dissolution and passivation of NiCrFe alloys studied by ESCA. Corros Sci 33(5): 805–814 (1992)

DOI Google Scholar

[39]

Tan B J, Klabunde K J, Sherwood P M A. X-ray photoelectron spectroscopy studies of solvated metal atom dispersed catalysts. Monometallic iron and bimetallic iron–cobalt particles on alumina. Chem Mater 2(2): 186–191 (1990)

DOI Google Scholar

[40]

Zhou Y F, Li L L, Shao W, Chen Z H, Wang S F, Xing X L, Yang Q X. Mechanical and tribological behaviors of Ti-DLC films deposited on 304 stainless steel: Exploration with Ti doping from micro to macro. Diam Relat Mater 107: 107870 (2020)

DOI Google Scholar

[41]

Carver J C, Schweitzer G K, Carlson T A. Use of X-ray photoelectron spectroscopy to study bonding in cr, mn, Fe, and co compounds. J Chem Phys 57(2): 973–982 (1972)

DOI Google Scholar

[42]

Laajalehto K, Kartio I, Nowak P. XPS study of clean metal sulfide surfaces. Appl Surf Sci 81(1): 11–15 (1994)

DOI Google Scholar

[43]

Panzmer G, Egert B. The bonding state of sulfur segregated to α-iron surfaces and on iron sulfide surfaces studied by XPS, AES and ELS. Surf Sci 144(2–3): 651–664 (1984)

DOI Google Scholar

[44]

Hawn D D, DeKoven B M. Deconvolution as a correction for photoelectron inelastic energy losses in the core level XPS spectra of iron oxides. Surf Interface Anal 10(2–3): 63–74 (1987)

DOI Google Scholar

[45]

Becker K H, Haaks D. Measurement of the natural lifetimes and quenching rate constants of OH (²Σ⁺, v = 0,1) and OD (²Σ⁺, v = 0,1) radicals. Zeitschrift Für Naturforschung A 28(2): 249–256 (1973)

DOI Google Scholar

[46]

Yu X R, Liu F, Wang Z Y, Chen Y. Auger parameters for sulfur-containing compounds using a mixed aluminum– silver excitation source. J Electron Spectrosc Relat Phenom 50(2): 159–166 (1990)

DOI Google Scholar

[47]

Bare S R, Griffiths K, Lennard W N, Tang H T. Generation of atomic oxygen on Ag(111) and Ag(110) using NO₂: A TPD, LEED, HREELS, XPS and NRA study. Surf Sci 342(1–3): 185–198 (1995)

DOI Google Scholar

[48]

Allen G C, Curtis M T, Hooper A J, Tucker P M. ChemInform abstract: X-ray photoelectron spectroscopy of iron–oxygen systems. Chemischer Informationsdienst 5(41) (1974)

DOI Google Scholar

[49]

Siriwardane R V, Cook J M. Interactions of SO₂ with sodium deposited on silica. J Colloid Interface Sci 108(2): 414–422 (1985)

DOI Google Scholar

[50]

Paparazzo E. XPS and auger spectroscopy studies on mixtures of the oxides SiO₂, Al₂O₃, Fe₂O₃ and Cr₂O₃. J Electron Spectrosc Relat Phenom 43(2): 97–112 (1987)

DOI Google Scholar

[51]

Kutty T R N. A controlled copper-coating method for the preparation of ZnS: Mn DC electroluminescent powder phosphors. Mater Res Bull 26(5): 399–406 (1991)

DOI Google Scholar

[52]

Binder H, Fischer R. The reaction between boron trifluoride and tertiary phosphites. Zeitschrift Für Naturforschung B 27(7): 753–759 (1972) (In German)

DOI Google Scholar

[53]

Ho W Y, Chen M D, Lin C L, Ho W Y. Characteristics of TiVN and TiVCN coatings by cathodic arc deposition. In: Proceedings of the 6th International Conference on Mechatronics, Materials, Biotechnology and Environment, Yinchuan, China, 2016: 597–601.

DOI

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Publication history

Received: 22 June 2021

Revised: 01 August 2021

Accepted: 20 November 2021

Published: 25 April 2022

Issue date: January 2023

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Acknowledgements

The authors acknowledge the supports from the National Natural Science Foundation of China (No. 51805455), Sichuan Science and Technology Program (Nos. 2019YFG0306 and 2019YFSY0012), and the Fundamental Research Funds for the Central Universities (No. 2682020CX04). We also thank the technical support provided by "Ceshigo Research Service Agency for DSC analysis, www.ceshigo.com" and Analytical and Testing Center of Southwest Jiaotong University for supporting the SEM measurements.

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