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United States Department of Agriculture

Agricultural Research Service

Title: Chemically Modified Fatty Acid Methyl Esters: Potential as Lubricant and Surfactant

Authors
item Erhan, Sevim
item Sharma, Brajendra - PENN STATE UNIVERSITY
item Doll, Kenneth

Submitted to: International Symposium on Surfactants in Solution
Publication Type: Abstract Only
Publication Acceptance Date: January 1, 2008
Publication Date: August 27, 2008
Citation: Erhan, S.Z., Sharma, B.K., Doll, K.M. 2008. Chemically Modified Fatty Acid Methyl Esters: Potential as Lubricant and Surfactant [abstract]. International Symposium on Surfactants in Solution. p. 2.

Technical Abstract: Renewable raw materials are going to play a noteworthy role in the development of sustainable green chemistry because of their eco-friendly and non-toxic nature. A novel process was developed for the production of biodegradable lubricant base stocks from epoxidized fatty acid methyl esters and common organic acids without any catalyst. These branched esters were characterized as alpha-hydroxy ester derivatives of methyl oleate. The study shows how functionalization helps overcome some of the disadvantages of vegetable oils. These disadvantages are poor oxidation and low temperature properties, and can be improved by adding functional groups at the sites of unsaturation through chemical modification. These derivatives show improved low temperature properties and increased thermo-oxidative stability over olefinic compounds. Tribological behaviors were evaluated as additives, in soybean oil and polyalphaolefin, using four-ball and ball-on-disk configurations. These derivatives have good anti-wear and friction-reducing properties at relatively low concentrations under all test loads. Their surface tensions were also determined and a trend was observed. The materials with larger side chain branches had lower surface tension than those containing smaller side chain branches. An exception to this trend was found when studying the compound with the carbonyl containing levulinic acid side chain, which had the highest surface tension of the branched oleochemicals studied. Overall, the data indicate that some of these derivatives have significant potential to be used as lubricating base oils or additives.

Last Modified: 9/21/2014
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