DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Tertiary and Quaternary Ammonium-Phosphate Ionic Liquids as Lubricant Additives

Abstract

In this work we investigated the feasibility of five quaternary (aprotic) and four tertiary (protic) ammonium ionic liquids (ILs) with an identical organophosphate anion as lubricant antiwear additives. Viscosity, oil solubility, thermal stability, and corrosivity of the candidate ILs were characterized and correlated to the molecular structure. The protic group exhibits higher oil solubility than the aprotic group, and longer alkyl chains seem to provide better oil solubility and higher thermal stability. Selected ILs were applied as oil additives in steel-cast iron tribological tests and demonstrated promising anti-scuffing and anti-wear functionality. The thickness, nanostructure, coverage and composition of the tribofilm formed by the besting performing IL were revealed by surface characterization for mechanistic understanding of the tribochemical interactions between the IL and metal surface. Results provide fundamental insights of the correlations among the molecular structure, physiochemical properties and lubricating performance for ammonium-phosphate ILs.

Authors:
 [1];  [1];  [1];  [1];  [1];  [2];  [1]
  1. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
  2. Shell Global Solutions, Houston, TX (United States)
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Sciences (CNMS)
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE)
OSTI Identifier:
1324065
Grant/Contract Number:  
AC05-00OR22725
Resource Type:
Accepted Manuscript
Journal Name:
Tribology Letters
Additional Journal Information:
Journal Volume: 63; Journal Issue: 22; Journal ID: ISSN 1023-8883
Publisher:
Springer
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Ionic liquid; Ammonium; Lubricant additive; Oil-soluble; Organophosphate

Citation Formats

Barnhill, William C., Luo, Huimin, Meyer, III, Harry M, Ma, Cheng, Chi, Miaofang, Papke, Brian L., and Qu, Jun. Tertiary and Quaternary Ammonium-Phosphate Ionic Liquids as Lubricant Additives. United States: N. p., 2016. Web. doi:10.1007/s11249-016-0707-6.
Barnhill, William C., Luo, Huimin, Meyer, III, Harry M, Ma, Cheng, Chi, Miaofang, Papke, Brian L., & Qu, Jun. Tertiary and Quaternary Ammonium-Phosphate Ionic Liquids as Lubricant Additives. United States. https://doi.org/10.1007/s11249-016-0707-6
Barnhill, William C., Luo, Huimin, Meyer, III, Harry M, Ma, Cheng, Chi, Miaofang, Papke, Brian L., and Qu, Jun. Thu . "Tertiary and Quaternary Ammonium-Phosphate Ionic Liquids as Lubricant Additives". United States. https://doi.org/10.1007/s11249-016-0707-6. https://www.osti.gov/servlets/purl/1324065.
@article{osti_1324065,
title = {Tertiary and Quaternary Ammonium-Phosphate Ionic Liquids as Lubricant Additives},
author = {Barnhill, William C. and Luo, Huimin and Meyer, III, Harry M and Ma, Cheng and Chi, Miaofang and Papke, Brian L. and Qu, Jun},
abstractNote = {In this work we investigated the feasibility of five quaternary (aprotic) and four tertiary (protic) ammonium ionic liquids (ILs) with an identical organophosphate anion as lubricant antiwear additives. Viscosity, oil solubility, thermal stability, and corrosivity of the candidate ILs were characterized and correlated to the molecular structure. The protic group exhibits higher oil solubility than the aprotic group, and longer alkyl chains seem to provide better oil solubility and higher thermal stability. Selected ILs were applied as oil additives in steel-cast iron tribological tests and demonstrated promising anti-scuffing and anti-wear functionality. The thickness, nanostructure, coverage and composition of the tribofilm formed by the besting performing IL were revealed by surface characterization for mechanistic understanding of the tribochemical interactions between the IL and metal surface. Results provide fundamental insights of the correlations among the molecular structure, physiochemical properties and lubricating performance for ammonium-phosphate ILs.},
doi = {10.1007/s11249-016-0707-6},
journal = {Tribology Letters},
number = 22,
volume = 63,
place = {United States},
year = {2016},
month = {6}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 10 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

A structural analysis of vehicle design responses to Corporate Average Fuel Economy policy
journal, November 2009

  • Shiau, Ching-Shin Norman; Michalek, Jeremy J.; Hendrickson, Chris T.
  • Transportation Research Part A: Policy and Practice, Vol. 43, Issue 9-10
  • DOI: 10.1016/j.tra.2009.08.002

Functional Room-temperature Ionic Liquids as Lubricants for an Aluminum-on-Steel System
journal, May 2004

  • Mu, Zonggang; Liu, Weimin; Zhang, Shuxiang
  • Chemistry Letters, Vol. 33, Issue 5
  • DOI: 10.1246/cl.2004.524

Ionic Liquid Lubrication Effects on Ceramics in a Water Environment
journal, October 2004


The tribological performance of BCN films under ionic liquids lubrication
journal, January 2009


Lubrication of TiN, CrN and DLC PVD Coatings with 1-Butyl-1-Methylpyrrolidinium tris(pentafluoroethyl)trifluorophosphate
journal, July 2010


Ionic Liquids as Advanced Lubricant Fluids
journal, August 2009


Ionic Liquids in Tribology
journal, June 2009


A Review of Ionic Liquids for Green Molecular Lubrication in Nanotechnology
journal, July 2010


1-N-alkyl -3-methylimidazolium ionic liquids as neat lubricants and lubricant additives in steel–aluminium contacts
journal, April 2006


Imidazolium ionic liquids as additives of the synthetic ester propylene glycol dioleate in aluminium–steel lubrication
journal, August 2008


Bisimidazolium Ionic Liquids as the High-Performance Antiwear Additives in Poly(ethylene glycol) for Steel−Steel Contacts
journal, January 2009

  • Yao, Meihuan; Liang, Yongmin; Xia, Yanqiu
  • ACS Applied Materials & Interfaces, Vol. 1, Issue 2
  • DOI: 10.1021/am800132z

Imidazolium Ionic Liquids As Antiwear and Antioxidant Additive in Poly(ethylene glycol) for Steel/Steel Contacts
journal, March 2010

  • Cai, Meirong; Liang, Yongmin; Yao, Meihuan
  • ACS Applied Materials & Interfaces, Vol. 2, Issue 3
  • DOI: 10.1021/am900847j

Ionic liquids with ammonium cations as lubricants or additives
journal, July 2006


Lubrication of an electroplated nickel matrix silicon carbide coated eutectic aluminium—silicon alloy automotive cylinder bore with an ionic liquid as a lubricant additive
journal, March 2009

  • Mistry, K.; Fox, M. F.; Priest, M.
  • Proceedings of the Institution of Mechanical Engineers, Part J: Journal of Engineering Tribology, Vol. 223, Issue 3
  • DOI: 10.1243/13506501JET562

Ionic Liquids as Novel Lubricants and Additives for Diesel Engine Applications
journal, April 2009


Capacity of selected ionic liquids as alternative EP/AW additive
journal, April 2010

  • Schneider, Ameneh; Brenner, Josef; Tomastik, Christian
  • Lubrication Science, Vol. 22, Issue 6-7
  • DOI: 10.1002/ls.120

Antiwear Performance and Mechanism of an Oil-Miscible Ionic Liquid as a Lubricant Additive
journal, February 2012

  • Qu, Jun; Bansal, Dinesh G.; Yu, Bo
  • ACS Applied Materials & Interfaces, Vol. 4, Issue 2, p. 997-1002
  • DOI: 10.1021/am201646k

Comparison of an oil-miscible ionic liquid and ZDDP as a lubricant anti-wear additive
journal, March 2014


Phosphonium-Organophosphate Ionic Liquids as Lubricant Additives: Effects of Cation Structure on Physicochemical and Tribological Characteristics
journal, December 2014

  • Barnhill, William C.; Qu, Jun; Luo, Huimin
  • ACS Applied Materials & Interfaces, Vol. 6, Issue 24
  • DOI: 10.1021/am506702u

Synergistic Effects Between Phosphonium-Alkylphosphate Ionic Liquids and Zinc Dialkyldithiophosphate (ZDDP) as Lubricant Additives
journal, July 2015

  • Qu, Jun; Barnhill, William C.; Luo, Huimin
  • Advanced Materials, Vol. 27, Issue 32
  • DOI: 10.1002/adma.201502037

Tribological Bench and Engine Dynamometer Tests of a Low Viscosity SAE 0W-16 Engine Oil Using a Combination of Ionic Liquid and ZDDP as Anti-Wear Additives
journal, September 2015

  • Barnhill, William C.; Gao, Hong; Kheireddin, Bassem
  • Frontiers in Mechanical Engineering, Vol. 1
  • DOI: 10.3389/fmech.2015.00012

Use of esters of acids of phosphorus as lubricity additives for high-temperature synthetic lubricating oils (a review)
journal, May 1976

  • Barabanova, G. V.; Ivanov, V. I.; Kossova, L. V.
  • Chemistry and Technology of Fuels and Oils, Vol. 12, Issue 5
  • DOI: 10.1007/BF00717944

The effect of chemical structure on the load-carrying properties of amine phosphates
journal, October 1971


Anti-wear and friction reducing additives composed of ortho-phenylene phosphate-amine salts for polyether type base stocks
journal, June 1998


Protic Ionic Liquids with Ammonium Salts as Lubricants for Magnetic Thin Film Media
journal, August 2008


Protic ammonium carboxylate ionic liquid lubricants of OFHC copper
journal, June 2013


Surface interactions, corrosion processes and lubricating performance of protic and aprotic ionic liquids with OFHC copper
journal, May 2013


Ultra-Low Friction with a Protic Ionic Liquid Boundary Film at the Water-Lubricated Sapphire–Stainless Steel Interface
journal, October 2013


Halide-Free Synthesis and Tribological Performance of Oil-Miscible Ammonium and Phosphonium-Based Ionic Liquids
journal, April 2015

  • Westerholt, A.; Weschta, M.; Bösmann, A.
  • ACS Sustainable Chemistry & Engineering, Vol. 3, Issue 5
  • DOI: 10.1021/sc500517n

Protic Ionic Liquids:  Properties and Applications
journal, January 2008

  • Greaves, Tamar L.; Drummond, Calum J.
  • Chemical Reviews, Vol. 108, Issue 1, p. 206-237
  • DOI: 10.1021/cr068040u

Nanostructured Protic Ionic Liquids Retain Nanoscale Features in Aqueous Solution While Precursor Brønsted Acids and Bases Exhibit Different Behavior
journal, March 2011

  • Greaves, Tamar L.; Kennedy, Danielle F.; Weerawardena, Asoka
  • The Journal of Physical Chemistry B, Vol. 115, Issue 9
  • DOI: 10.1021/jp1112203

Density, viscosity and electrical conductivity of protic alkanolammonium ionic liquids
journal, January 2011

  • Pinkert, André; Ang, Keng L.; Marsh, Kenneth N.
  • Physical Chemistry Chemical Physics, Vol. 13, Issue 11
  • DOI: 10.1039/c0cp02222e

Protic ionic liquids based on phosphonium cations: comparison with ammonium analogues
journal, January 2011

  • Rana, Usman Ali; Vijayaraghavan, R.; Walther, Mareike
  • Chemical Communications, Vol. 47, Issue 42
  • DOI: 10.1039/c1cc14761g

Ionic Liquids: Past, present and future
journal, January 2012

  • Austen Angell, C.; Ansari, Younes; Zhao, Zuofeng
  • Faraday Discuss., Vol. 154
  • DOI: 10.1039/C1FD00112D

Hydrogen bonds in protic ionic liquids and their correlation with physicochemical properties
journal, January 2011

  • Miran, Muhammed Shah; Kinoshita, Hiroshi; Yasuda, Tomohiro
  • Chemical Communications, Vol. 47, Issue 47
  • DOI: 10.1039/c1cc14817f

Hydrogen bonding in ionic liquids
journal, January 2015

  • Hunt, Patricia A.; Ashworth, Claire R.; Matthews, Richard P.
  • Chemical Society Reviews, Vol. 44, Issue 5
  • DOI: 10.1039/C4CS00278D

Protic Ionic Liquids: Evolving Structure–Property Relationships and Expanding Applications
journal, September 2015


A multi-technique approach to the characterization of iron phosphide tribofilm
journal, December 2012


Works referencing / citing this record:

New dimensions in salt–solvent mixtures: a 4th evolution of ionic liquids
journal, January 2018

  • MacFarlane, Douglas R.; Chong, Alison L.; Forsyth, Maria
  • Faraday Discussions, Vol. 206
  • DOI: 10.1039/c7fd00189d

Tribological Improvement Using Ionic Liquids as Additives in Synthetic and Bio-Based Lubricants for Steel–Steel Contacts
journal, November 2019