Abstract
1-Alkyl-3-methylimidazolium ibuprofen ionic liquids (ILs, L-Ibu104, L-Ibu106 and L-Ibu108) were synthesized from an anti-inflammatory drug, sodium ibuprofen. The physicochemical and tribological properties of these ILs as neat lubricants for steel/steel and steel/copper contacts were measured. The results of hydrolysis stability evaluation and copper strip corrosion test show that these kinds of ILs are hydrolysis stable and have no corrosion to the metal contacts because of stability of anion. The friction and wear test results exhibit that these ibuprofen ILs have more effective friction-reducing and anti-wear properties than poly-alpha-olefin (PAO40) and 1-hexyl-3-methylimidazolium bis(trifluoromethylsulphonyl)imide (L-F106) at 100 °C. According to the X-ray photoelectron spectrometer analytical results, we speculated that physical adsorption films can easily formed on the metal worn surfaces during the rubbing process because of the high adsorption ability of Ibu− anion, which play an important role in the good lubricating behaviours of ibuprofen ILs.
Graphical Abstract
Similar content being viewed by others
References
Sheldon, R.A.: Green solvents for sustainable organic synthesis: state of the art. Green Chem. 7, 267–278 (2005)
Kulacki, K.J., Lamberti, G.A.: Toxicity of imidazolium ionic liquids to freshwater algae. Green Chem. 10, 104–110 (2008)
Payne, S.M., Kerton, F.M.: Solubility of bio-sourced feedstocks in ‘green’ solvents. Green Chem. 12, 1648–1653 (2010)
El Abedin, S.Z., Pölleth, M., Meiss, S.A., Janek, J., Endres, F.: Ionic liquids as green electrolytes for the electrodeposition of nanomaterials. Green Chem. 9, 549–553 (2007)
Hagiwara, R., Ito, Y.: Room temperature ionic liquids of alkylimidazolium cations and fluoroanions. J. Fluor. Chem. 105, 221–227 (2000)
Torimoto, T., Tsuda, T., Okazaki, K., Kuwabata, S.: New frontiers in materials science opened by ionic liquids. Adv. Mater. 22, 1196–1221 (2010)
Predel, T., Pohrer, B., Schlücker, E.: Ionic liquids as alternative lubricants for special applications. Chem. Eng. Technol. 33, 132–136 (2010)
Zhou, F., Liang, Y., Liu, W.: Ionic liquid lubricants: designed chemistry for engineering applications. Chem. Soc. Rev. 38, 2590–2599 (2009)
Liu, Q., Hou, X., Li, N., Zong, M.: Ionic liquids from renewable biomaterials: synthesis, characterization and application in the pretreatment of biomass. Green Chem. 14, 304–307 (2012)
Harjani, J.R., Singer, R.D., Garcia, M.T., Scammells, P.J.: Biodegradable pyridinium ionic liquids: design, synthesis and evaluation. Green Chem. 11, 83–90 (2009)
Morrissey, S., Pegot, B., Coleman, D., Garcia, M.T., Ferguson, D., Quilty, B., Gathergood, N.: Biodegradable, non-bactericidal oxygen-functionalised imidazolium esters: a step towards ‘greener’ ionic liquids. Green Chem. 11, 475–483 (2009)
Ye, C., Liu, W., Chen, Y., Yu, L.: Room-temperature ionic liquids: a novel versatile lubricant. Chem. Commun. 21, 2244–2245 (2001)
Qu, J., Blau, P.J., Dai, S., Luo, H., Meyer, H.M.: Ionic liquids as novel lubricants and additives for diesel engine applications. Tribol. Lett. 35, 181–189 (2009)
Bermúdez, M.-D., Jiménez, A.-E., Sanes, J., Carrión, F.-J.: Ionic liquids as advanced lubricant fluids. Molecules 14, 2888–2908 (2009)
Jiménez, A.E., Bermúdez, M.D., Iglesias, P., Carrión, F.J., Martínez-Nicolás, G.: 1-N-alkyl-3-methylimidazolium ionic liquids as neat lubricants and lubricant additives in steel–aluminium contacts. Wear 260, 766–782 (2006)
Cai, M., Zhao, Z., Liang, Y., Zhou, F., Liu, W.: Alkyl imidazolium ionic liquids as friction reduction and anti-wear additive in polyurea grease for steel/steel contacts. Tribol. Lett. 40, 215–224 (2010)
Fan, M., Liang, Y., Zhou, F., Liu, W.: Dramatically improved friction reduction and wear resistance by in situ formed ionic liquids. RSC Adv. 2, 6824–6830 (2012)
Swatloski, R.P., Holbrey, J.D., Rogers, R.D.: Ionic liquids are not always green: hydrolysis of 1-butyl-3-methylimidazolium hexafluorophosphate. Green Chem. 5, 361–363 (2003)
Palacio, M., Bhushan, B.: A review of ionic liquids for green molecular lubrication in nanotechnology. Tribol. Lett. 40, 247–268 (2010)
Minami, I., Inada, T., Okada, Y.: Tribological properties of halogen-free ionic liquids. Proc. Inst. Mech. Eng. Part J J. Eng. Tribol. 226, 891–902 (2012)
Kondo, Y., Yagi, S., Koyama, T., Tsuboi, R., Sasaki, S.: Lubricity and corrosiveness of ionic liquids for steel-on-steel sliding contacts. Proc. Inst. Mech. Eng. Part J J. Eng. Tribol. 226, 991–1006 (2012)
Kondo, Y., Koyama, T., Tsuboi, R., Nakano, M., Miyake, K., Sasaki, S.: Tribological performance of halogen-free ionic liquids as lubricants of hard coatings and ceramics. Tribol. Lett. 51, 243–249 (2013)
Santini, A.O., De Oliveira, J.E., Pezza, H.R., Pezza, L.: A new potentiometric ibuprofenate ion sensor immobilized in a graphite matrix for determination of ibuprofen in tablets. Microchem. J. 84, 44–49 (2006)
Yong, C.S., Oh, Y.K., Jung, S.H., Rhee, J.D., Kim, H.D., Kim, C.K., Choi, H.G.: Preparation of ibuprofen-loaded liquid suppository using eutectic mixture system with menthol. Eur. J. Pharm. Sci. 23, 347–353 (2004)
Pavliv, L., Voss, B., Rock, A.: Pharmacokinetics, safety, and tolerability of a rapid infusion of iv ibuprofen in healthy adults. Am. J. Health Syst. Pharm. 68, 47–51 (2011)
Viau, L., Tourné-Péteilh, C., Devoisselle, J.M., Vioux, A.: Ionogels as drug delivery system: one-step sol–gel synthesis using imidazolium ibuprofenate ionic liquid. Chem. Commun. 46, 228–230 (2010)
Tourné-Péteilh, C., Devoisselle, J.M., Vioux, A., Judeinstein, P., In, M., Viau, L.: Surfactant properties of ionic liquids containing short alkyl chain imidazolium cations and ibuprofenate anions. Phys. Chem. Chem. Phys. 13, 15523–15529 (2011)
Bonhôte, P., Dias, A.P., Papageorgiou, N., Kalyanasundaram, K., Grätzel, M.: Hydrophobic, highly conductive ambient-temperature molten salts. Inorg. Chem. 35, 1168–1178 (1996)
Wen, S., Huang, P.: Principles of Tribology, 4th edn, p. 10. Tsinghua University Press, Beijing (2010)
Pensado, A.S., Comuñas, M.J.P., Fernández, J.: The pressure–viscosity coefficient of several ionic liquids. Tribol. Lett. 31, 107–118 (2008)
Reddy, R.G., Zhang, Z.J., Arenas, M.F., Blake, D.M.: Thermal stability and corrosivity evaluations of ionic liquids as thermal energy storage media. High Temp. Mater. Process. 22, 87–93 (2003)
Wasserscheid, P., van Hal, R., Bösmann, A.: 1-n-Butyl-3-methylimidazolium ([bmim]) octylsulfate—an even ‘greener’ ionic liquid. Green Chem. 4, 400–404 (2002)
Minami, I., Mori, S.: Concept of molecular design towards additive technology for advanced lubricants. Lubr. Sci. 19, 127–149 (2007)
Minami, I.: Ionic liquids in tribology. Molecules 14, 2286–2305 (2009)
Liu, X., Zhou, F., Liang, Y., Liu, W.: Benzotriazole as the additive for ionic liquid lubricant: one pathway towards actual application of ionic liquids. Tribol. Lett. 23, 191–196 (2006)
National Institute of Standards and Technology. NIST X-Ray Photoelectron Spectroscopy Database, version 4.1. http://srdata.nist.gov/xps/ (2012)
Cai, M., Liang, Y., Yao, M., Xia, Y., Zhou, F., Liu, W.: Imidazolium ionic liquids as antiwear and antioxidant additive in poly(ethylene glycol) for steel/steel contacts. ACS Appl. Mater. Interfaces 2, 870–876 (2010)
Kajdas, C.: Importance of anionic reactive intermediates for lubricant component reactions with friction surfaces. Lubr. Sci. 6, 203–228 (1994)
Acknowledgments
The authors acknowledge the financial support from the NSFC (51305428, 21125316) and “973” programme (2013CB632301) and West Light Foundation of The Chinese Academy of Sciences.
Author information
Authors and Affiliations
Corresponding authors
Additional information
Zenghong Song and Qiangliang Yu have contributed equally to this work.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Song, Z., Yu, Q., Cai, M. et al. Green Ionic Liquid Lubricants Prepared from Anti-Inflammatory Drug. Tribol Lett 60, 38 (2015). https://doi.org/10.1007/s11249-015-0611-5
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s11249-015-0611-5