Triester derivatives of oleic acid: The effect of chemical structure on low temperature, thermo-oxidation and tribological properties

Jumat Salimon, Nadia Salih, Emad Yousif

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Due to the strict regulations imposed on mineral oil-based lubricants because of their non-biodegradable wastes, the development and applications of biolubricants are increasing daily. Plant oils are being investigated as a potential source of environmentally favorable lubricants because of their biodegradability, renewability, viscosity-temperature relationship, low volatility and excellent lubrication performance. However, the use of plant oils has some restriction, the most critical being oxidative stability and low-temperature problems. This paper presents systematic modifications to improve the physicochemical and tribological properties of plant oil derivatives. Thin-film micro-oxidation testing and pressure differential scanning calorimetry were used to compare the thermo-oxidative stabilities. The results showed that among the oleic acid-based triester compounds, 2-ethylhexyl 9-(myristoxy)-10-(heptanoyloxy)octadecanoate (9) had the lowest pour point (-47.19 °C) while 2-ethylhexyl 9-(caprooxy)-10-(heptanoyloxy)octadecanoate (5) had the highest onset temperature (103.10 °C) and the lowest amount of volatile loss and insoluble deposits at 89.17% and 78.51%, respectively. Overall, the data indicate that the biolubricant basestocks based on this chemical modification offer great potential for the development of industrial products.

Original languageEnglish
Pages (from-to)107-114
Number of pages8
JournalIndustrial Crops and Products
Volume38
Issue number1
DOIs
Publication statusPublished - Jul 2012

Fingerprint

plant fats and oils
biolubricants
chemical structure
oleic acid
lubricants
chemical derivatives
oxidation
oxidative stability
pour point
temperature
biodegradability
mineral oil
industrialization
differential scanning calorimetry
viscosity
testing

Keywords

  • Biolubricant basestocks
  • Boundary lubrication
  • Plant oils
  • Pour point
  • Thermo-oxidative stability

ASJC Scopus subject areas

  • Agronomy and Crop Science

Cite this

Triester derivatives of oleic acid : The effect of chemical structure on low temperature, thermo-oxidation and tribological properties. / Salimon, Jumat; Salih, Nadia; Yousif, Emad.

In: Industrial Crops and Products, Vol. 38, No. 1, 07.2012, p. 107-114.

Research output: Contribution to journalArticle

@article{fe2791c092e14fa79ccc7e3275d392c5,
title = "Triester derivatives of oleic acid: The effect of chemical structure on low temperature, thermo-oxidation and tribological properties",
abstract = "Due to the strict regulations imposed on mineral oil-based lubricants because of their non-biodegradable wastes, the development and applications of biolubricants are increasing daily. Plant oils are being investigated as a potential source of environmentally favorable lubricants because of their biodegradability, renewability, viscosity-temperature relationship, low volatility and excellent lubrication performance. However, the use of plant oils has some restriction, the most critical being oxidative stability and low-temperature problems. This paper presents systematic modifications to improve the physicochemical and tribological properties of plant oil derivatives. Thin-film micro-oxidation testing and pressure differential scanning calorimetry were used to compare the thermo-oxidative stabilities. The results showed that among the oleic acid-based triester compounds, 2-ethylhexyl 9-(myristoxy)-10-(heptanoyloxy)octadecanoate (9) had the lowest pour point (-47.19 °C) while 2-ethylhexyl 9-(caprooxy)-10-(heptanoyloxy)octadecanoate (5) had the highest onset temperature (103.10 °C) and the lowest amount of volatile loss and insoluble deposits at 89.17{\%} and 78.51{\%}, respectively. Overall, the data indicate that the biolubricant basestocks based on this chemical modification offer great potential for the development of industrial products.",
keywords = "Biolubricant basestocks, Boundary lubrication, Plant oils, Pour point, Thermo-oxidative stability",
author = "Jumat Salimon and Nadia Salih and Emad Yousif",
year = "2012",
month = "7",
doi = "10.1016/j.indcrop.2012.01.019",
language = "English",
volume = "38",
pages = "107--114",
journal = "Industrial Crops and Products",
issn = "0926-6690",
publisher = "Elsevier",
number = "1",

}

TY - JOUR

T1 - Triester derivatives of oleic acid

T2 - The effect of chemical structure on low temperature, thermo-oxidation and tribological properties

AU - Salimon, Jumat

AU - Salih, Nadia

AU - Yousif, Emad

PY - 2012/7

Y1 - 2012/7

N2 - Due to the strict regulations imposed on mineral oil-based lubricants because of their non-biodegradable wastes, the development and applications of biolubricants are increasing daily. Plant oils are being investigated as a potential source of environmentally favorable lubricants because of their biodegradability, renewability, viscosity-temperature relationship, low volatility and excellent lubrication performance. However, the use of plant oils has some restriction, the most critical being oxidative stability and low-temperature problems. This paper presents systematic modifications to improve the physicochemical and tribological properties of plant oil derivatives. Thin-film micro-oxidation testing and pressure differential scanning calorimetry were used to compare the thermo-oxidative stabilities. The results showed that among the oleic acid-based triester compounds, 2-ethylhexyl 9-(myristoxy)-10-(heptanoyloxy)octadecanoate (9) had the lowest pour point (-47.19 °C) while 2-ethylhexyl 9-(caprooxy)-10-(heptanoyloxy)octadecanoate (5) had the highest onset temperature (103.10 °C) and the lowest amount of volatile loss and insoluble deposits at 89.17% and 78.51%, respectively. Overall, the data indicate that the biolubricant basestocks based on this chemical modification offer great potential for the development of industrial products.

AB - Due to the strict regulations imposed on mineral oil-based lubricants because of their non-biodegradable wastes, the development and applications of biolubricants are increasing daily. Plant oils are being investigated as a potential source of environmentally favorable lubricants because of their biodegradability, renewability, viscosity-temperature relationship, low volatility and excellent lubrication performance. However, the use of plant oils has some restriction, the most critical being oxidative stability and low-temperature problems. This paper presents systematic modifications to improve the physicochemical and tribological properties of plant oil derivatives. Thin-film micro-oxidation testing and pressure differential scanning calorimetry were used to compare the thermo-oxidative stabilities. The results showed that among the oleic acid-based triester compounds, 2-ethylhexyl 9-(myristoxy)-10-(heptanoyloxy)octadecanoate (9) had the lowest pour point (-47.19 °C) while 2-ethylhexyl 9-(caprooxy)-10-(heptanoyloxy)octadecanoate (5) had the highest onset temperature (103.10 °C) and the lowest amount of volatile loss and insoluble deposits at 89.17% and 78.51%, respectively. Overall, the data indicate that the biolubricant basestocks based on this chemical modification offer great potential for the development of industrial products.

KW - Biolubricant basestocks

KW - Boundary lubrication

KW - Plant oils

KW - Pour point

KW - Thermo-oxidative stability

UR - http://www.scopus.com/inward/record.url?scp=84857005259&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84857005259&partnerID=8YFLogxK

U2 - 10.1016/j.indcrop.2012.01.019

DO - 10.1016/j.indcrop.2012.01.019

M3 - Article

AN - SCOPUS:84857005259

VL - 38

SP - 107

EP - 114

JO - Industrial Crops and Products

JF - Industrial Crops and Products

SN - 0926-6690

IS - 1

ER -