Synthesis, Characterization and Physicochemical Properties of Oleic Acid Ether Derivatives as Biolubricant Basestocks

Salimon, Jumat; Salih, Nadia; Yousif, Emad

doi:10.5650/jos.60.613

Cited by 32 publications

(24 citation statements)

References 18 publications

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“…Due to the increasing market relevance of environmentally labeled products, the ecological properties of plant oil biolubricants have been intensively studied over the last few years [18,19]. In general, their aquatic toxicity is very low or almost negligible, and they are readily biodegradable in most cases.…”

Section: Resultsmentioning

confidence: 99%

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

Salih

Salimon

Yousif

et al. 2013

Chemistry Central Journal

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BackgroundPlant 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.ResultsIn 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).ConclusionsThe 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.

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Section: Resultsmentioning

confidence: 99%

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

Salih

Salimon

Yousif

et al. 2013

Chemistry Central Journal

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“…The results of the study depict that CO epoxide viscosity (249.84 cSt) has been improved over the unmodified CO, and this signifies that the synthesized CO epoxide can serve as an acceptable lubricant base stock with enhanced viscosity to reduce friction. The ability of substance to resist free flow is one of the highly significant attributes for many heavy duty and industrial materials such as fuels, lubricants, and surfactants [58]. Therefore, it is desirable that the viscosity must be high enough all the time to keep good oil film between the moving parts to reduce friction [58].…”

Section: Viscosity and Viscosity Indexmentioning

confidence: 99%

“…Therefore, it is desirable that the viscosity must be high enough all the time to keep good oil film between the moving parts to reduce friction [58]. Otherwise, due to loss in the lubricant, there is a tendency to increase the friction thereby resulting in power loss and rapid wear on the machine parts [58]. Viscosity is one of the crucial parameters while selecting a lubricant for a specific application, and failure to use the right lubricant with the required viscosity results in extreme temperature that may result in poor lubrication, equipment failure, and damage [59].…”

Section: Viscosity and Viscosity Indexmentioning

confidence: 99%

“…The ability of substance to resist free flow is one of the highly significant attributes for many heavy duty and industrial materials such as fuels, lubricants, and surfactants [58]. Therefore, it is desirable that the viscosity must be high enough all the time to keep good oil film between the moving parts to reduce friction [58]. Otherwise, due to loss in the lubricant, there is a tendency to increase the friction thereby resulting in power loss and rapid wear on the machine parts [58].…”

Section: Viscosity and Viscosity Indexmentioning

confidence: 99%

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Response surface methodology for optimization of bio‐lubricant basestock synthesis from high free fatty acids castor oil

Borugadda

Goud

2015

Energy Science & Engineering

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In this paper, an eco-friendly single-step process for the synthesis of biolubricant basestock from high free fatty acid (FFA) castor oil (CO) via epoxidation reaction was investigated. Influence of various process parameters on the structural modification of CO and their interaction with the maximum oxirane oxygen content (OOC) was optimized. Central composite design (CCD) as one of the tools in response surface methodology (RSM) was used to evaluate the effects of process variables on maximum OOC. Iodine value (IV) and OOC was used to monitor the progress of epoxidation. From the RSM study, the optimal condition inferred was H 2 O 2 , 1.65 mol; catalyst loading, 15.14 wt%; temperature, 52.81°C; and reaction time, 2.81 h. At this optimum condition, OOC was found to be 3.85 mass%. Further, the epoxide product was confirmed by 1 H, 13 C NMR spectral technique and OOC was determined by the standard HBr method. Finally, the significant physico-chemical properties for the prepared epoxide were determined and compared with the castor oil. 372

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“…Environmentally friendly synthetic polyol esters constitute alternatives to mineral and vegetable oil based cold rolling lubricants. These Synthetic polyol esters are much more flexible in their application usage compared with natural esters because of their much wider viscosity range, higher oxidative and thermal stability and better low temperature flow characteristics with high degree of biodegradability and low aquatic toxicity [1][2][3][4][5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Tribological Evaluation of New Generation Materials for Aluminum Cold Rolling Oils

2016

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Abstract:The present concept of being globally "green" puts additional demands on lubricants. They are to be biodegradable and ecofriendly. Therefore, in a search for alternate lubricants meeting the above demands, we have synthesized biodegradable new generation esters using alcohols such as 2,2-dimethyl-1,3-propane diol and 2,2-diethyl-1,3-propane diol and fatty acids like caproic and 2-ethyl caproic in presence of indigenous ion exchange resin catalyst. The synthesized esters were analyzed and characterized for their physico chemical properties. In addition, with a view to finding out the possibility of using these esters as aluminum cold rolling oils, their lubricity characteristics, biodegradability and toxicity were also investigated. The products were found to have good potential for use in biodegradable aluminum cold rolling oils meeting IS: 14385-2002 specification.

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Synthesis, Characterization and Physicochemical Properties of Oleic Acid Ether Derivatives as Biolubricant Basestocks

Cited by 32 publications

References 18 publications

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

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

Response surface methodology for optimization of bio‐lubricant basestock synthesis from high free fatty acids castor oil

Synthesis, Characterization and Tribological Evaluation of New Generation Materials for Aluminum Cold Rolling Oils

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