Biolubricant basestocks from chemically modified plant oils: Ricinoleic acid based-tetraesters

Nadia Salih, Jumat Salimon, Emad Yousif, Bashar Mudhaffar Abdullah

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

Background: Plant oils have been investigated as a potential source of environmentally favorable biolubricants because of their biodegradability, renewability and excellent lubrication performance. Low oxidation and thermal stability, poor low-temperature properties and a narrow range of available viscosities, however, limit their potential application as industrial lubricants. The inherent problems of plant oils can be improved by attaching functional groups at the sites of unsaturation through chemical modifications. In this article, we will demonstrate how functionalization helps overcome these disadvantages.Results: In this work, mono-, tri- and tetra-esters have been synthesized, including 10,12-dihydroxy-9-(stearoyloxy)octadecanoic acid 3; 9,10,12-tris(stearoyloxy)octadecanoic acid 4; and 18-(4-ethylhexyloxy)-18-oxooctadecane-7,9,10-triyl tristearate 5. Pour-point and cloud-point measurements have shown that these derivatives have improved low-temperature properties as compared to the precursor. The tetra ester compound, 18-(4-ethylhexyloxy)-18-oxooctadecane-7,9,10-triyl tristearate 5, had the lowest pour point (PP) (-44.37°C) and the lowest cloud point (CP) (-41.25°C). This derivatization also improved the compound's thermo-oxidative stability, measured using pressurized differential scanning calorimetry (PDSC) and thin-film micro-oxidation (TFMO) testing. 18-(4-Ethylhexyloxy)-18-oxooctadecane-7,9,10-triyl tristearate 5 also had the highest onset temperature (OT) (282.10°C) and the lowest volatile loss and insoluble deposit (37.39% and 50.87%, respectively). Furthermore, the compounds' tribological behaviors were evaluated using the four-ball method. 18-(4-Ethylhexyloxy)-18-oxooctadecane-7,9,10-triyl tristearate 5 also had the lowest coefficient of friction (μ) (0.44).Conclusions: The results showed that, in general, these derivatives have good anti-wear and friction-reducing properties at relatively low concentrations under all of the test loads. Overall, the data indicates that these derivatives have significant potential to be used as biolubricant basestocks.

Original languageEnglish
Article number128
JournalChemistry Central Journal
Volume7
Issue number1
DOIs
Publication statusPublished - 25 Jul 2013

Fingerprint

Plant Oils
Low temperature properties
Esters
Derivatives
Friction
Oxidation
Biodegradability
Chemical modification
Functional groups
Lubrication
Lubricants
Differential scanning calorimetry
Thermodynamic stability
Deposits
Wear of materials
Viscosity
Thin films
Testing
ricinoleic acid
Temperature

Keywords

  • Biolubricant basestock
  • Chemical modification
  • Pressurized differential scanning calorimetry (PDSC)
  • Ricinoleic acid-based tetraesters
  • Thin-film micro-oxidation (TFMO)

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Biolubricant basestocks from chemically modified plant oils : Ricinoleic acid based-tetraesters. / Salih, Nadia; Salimon, Jumat; Yousif, Emad; Abdullah, Bashar Mudhaffar.

In: Chemistry Central Journal, Vol. 7, No. 1, 128, 25.07.2013.

Research output: Contribution to journalArticle

@article{83e7d5c977434f328a4bbe9e4ada4033,
title = "Biolubricant basestocks from chemically modified plant oils: Ricinoleic acid based-tetraesters",
abstract = "Background: Plant oils have been investigated as a potential source of environmentally favorable biolubricants because of their biodegradability, renewability and excellent lubrication performance. Low oxidation and thermal stability, poor low-temperature properties and a narrow range of available viscosities, however, limit their potential application as industrial lubricants. The inherent problems of plant oils can be improved by attaching functional groups at the sites of unsaturation through chemical modifications. In this article, we will demonstrate how functionalization helps overcome these disadvantages.Results: In this work, mono-, tri- and tetra-esters have been synthesized, including 10,12-dihydroxy-9-(stearoyloxy)octadecanoic acid 3; 9,10,12-tris(stearoyloxy)octadecanoic acid 4; and 18-(4-ethylhexyloxy)-18-oxooctadecane-7,9,10-triyl tristearate 5. Pour-point and cloud-point measurements have shown that these derivatives have improved low-temperature properties as compared to the precursor. The tetra ester compound, 18-(4-ethylhexyloxy)-18-oxooctadecane-7,9,10-triyl tristearate 5, had the lowest pour point (PP) (-44.37°C) and the lowest cloud point (CP) (-41.25°C). This derivatization also improved the compound's thermo-oxidative stability, measured using pressurized differential scanning calorimetry (PDSC) and thin-film micro-oxidation (TFMO) testing. 18-(4-Ethylhexyloxy)-18-oxooctadecane-7,9,10-triyl tristearate 5 also had the highest onset temperature (OT) (282.10°C) and the lowest volatile loss and insoluble deposit (37.39{\%} and 50.87{\%}, respectively). Furthermore, the compounds' tribological behaviors were evaluated using the four-ball method. 18-(4-Ethylhexyloxy)-18-oxooctadecane-7,9,10-triyl tristearate 5 also had the lowest coefficient of friction (μ) (0.44).Conclusions: The results showed that, in general, these derivatives have good anti-wear and friction-reducing properties at relatively low concentrations under all of the test loads. Overall, the data indicates that these derivatives have significant potential to be used as biolubricant basestocks.",
keywords = "Biolubricant basestock, Chemical modification, Pressurized differential scanning calorimetry (PDSC), Ricinoleic acid-based tetraesters, Thin-film micro-oxidation (TFMO)",
author = "Nadia Salih and Jumat Salimon and Emad Yousif and Abdullah, {Bashar Mudhaffar}",
year = "2013",
month = "7",
day = "25",
doi = "10.1186/1752-153X-7-128",
language = "English",
volume = "7",
journal = "Chemistry Central Journal",
issn = "1752-153X",
publisher = "Chemistry Central",
number = "1",

}

TY - JOUR

T1 - Biolubricant basestocks from chemically modified plant oils

T2 - Ricinoleic acid based-tetraesters

AU - Salih, Nadia

AU - Salimon, Jumat

AU - Yousif, Emad

AU - Abdullah, Bashar Mudhaffar

PY - 2013/7/25

Y1 - 2013/7/25

N2 - Background: Plant oils have been investigated as a potential source of environmentally favorable biolubricants because of their biodegradability, renewability and excellent lubrication performance. Low oxidation and thermal stability, poor low-temperature properties and a narrow range of available viscosities, however, limit their potential application as industrial lubricants. The inherent problems of plant oils can be improved by attaching functional groups at the sites of unsaturation through chemical modifications. In this article, we will demonstrate how functionalization helps overcome these disadvantages.Results: In this work, mono-, tri- and tetra-esters have been synthesized, including 10,12-dihydroxy-9-(stearoyloxy)octadecanoic acid 3; 9,10,12-tris(stearoyloxy)octadecanoic acid 4; and 18-(4-ethylhexyloxy)-18-oxooctadecane-7,9,10-triyl tristearate 5. Pour-point and cloud-point measurements have shown that these derivatives have improved low-temperature properties as compared to the precursor. The tetra ester compound, 18-(4-ethylhexyloxy)-18-oxooctadecane-7,9,10-triyl tristearate 5, had the lowest pour point (PP) (-44.37°C) and the lowest cloud point (CP) (-41.25°C). This derivatization also improved the compound's thermo-oxidative stability, measured using pressurized differential scanning calorimetry (PDSC) and thin-film micro-oxidation (TFMO) testing. 18-(4-Ethylhexyloxy)-18-oxooctadecane-7,9,10-triyl tristearate 5 also had the highest onset temperature (OT) (282.10°C) and the lowest volatile loss and insoluble deposit (37.39% and 50.87%, respectively). Furthermore, the compounds' tribological behaviors were evaluated using the four-ball method. 18-(4-Ethylhexyloxy)-18-oxooctadecane-7,9,10-triyl tristearate 5 also had the lowest coefficient of friction (μ) (0.44).Conclusions: The results showed that, in general, these derivatives have good anti-wear and friction-reducing properties at relatively low concentrations under all of the test loads. Overall, the data indicates that these derivatives have significant potential to be used as biolubricant basestocks.

AB - Background: Plant oils have been investigated as a potential source of environmentally favorable biolubricants because of their biodegradability, renewability and excellent lubrication performance. Low oxidation and thermal stability, poor low-temperature properties and a narrow range of available viscosities, however, limit their potential application as industrial lubricants. The inherent problems of plant oils can be improved by attaching functional groups at the sites of unsaturation through chemical modifications. In this article, we will demonstrate how functionalization helps overcome these disadvantages.Results: In this work, mono-, tri- and tetra-esters have been synthesized, including 10,12-dihydroxy-9-(stearoyloxy)octadecanoic acid 3; 9,10,12-tris(stearoyloxy)octadecanoic acid 4; and 18-(4-ethylhexyloxy)-18-oxooctadecane-7,9,10-triyl tristearate 5. Pour-point and cloud-point measurements have shown that these derivatives have improved low-temperature properties as compared to the precursor. The tetra ester compound, 18-(4-ethylhexyloxy)-18-oxooctadecane-7,9,10-triyl tristearate 5, had the lowest pour point (PP) (-44.37°C) and the lowest cloud point (CP) (-41.25°C). This derivatization also improved the compound's thermo-oxidative stability, measured using pressurized differential scanning calorimetry (PDSC) and thin-film micro-oxidation (TFMO) testing. 18-(4-Ethylhexyloxy)-18-oxooctadecane-7,9,10-triyl tristearate 5 also had the highest onset temperature (OT) (282.10°C) and the lowest volatile loss and insoluble deposit (37.39% and 50.87%, respectively). Furthermore, the compounds' tribological behaviors were evaluated using the four-ball method. 18-(4-Ethylhexyloxy)-18-oxooctadecane-7,9,10-triyl tristearate 5 also had the lowest coefficient of friction (μ) (0.44).Conclusions: The results showed that, in general, these derivatives have good anti-wear and friction-reducing properties at relatively low concentrations under all of the test loads. Overall, the data indicates that these derivatives have significant potential to be used as biolubricant basestocks.

KW - Biolubricant basestock

KW - Chemical modification

KW - Pressurized differential scanning calorimetry (PDSC)

KW - Ricinoleic acid-based tetraesters

KW - Thin-film micro-oxidation (TFMO)

UR - http://www.scopus.com/inward/record.url?scp=84880915149&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84880915149&partnerID=8YFLogxK

U2 - 10.1186/1752-153X-7-128

DO - 10.1186/1752-153X-7-128

M3 - Article

C2 - 23885790

AN - SCOPUS:84880915149

VL - 7

JO - Chemistry Central Journal

JF - Chemistry Central Journal

SN - 1752-153X

IS - 1

M1 - 128

ER -