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Title: Synthesis of lubrication fluids and surfactant precursors from soybean oil

item Doll, Kenneth - Ken
item Erhan, Sevim

Submitted to: United States-Japan Cooperative Program in Natural Resources
Publication Type: Abstract Only
Publication Acceptance Date: 7/2/2008
Publication Date: 8/24/2008
Citation: Doll, K.M., Sharma, B.K., Erhan, S.Z. 2008. Synthesis of lubrication fluids and surfactant precursors from soybean oil [abstract]. United States-Japan Cooperative Program in Natural Resources. p. 124-125.

Interpretive Summary:

Technical Abstract: Starting with soybean oil or soybean oil derived methyl oleate, a variety of compounds have been synthesized. The epoxidation of oleochemicals is a simple way to use the unsaturation naturally available in the vegetable oil and convert it into a variety of other useful chemicals. Epoxidized methyl oleate (EMO) can be reacted with simple carboxylic acids under relatively mild conditions, without the use of a catalyst. The reaction parameters of this reaction have been studied and an Arrhenius activation energy of 66.7 kJ mol-1 has been calculated. The resultant fluids have physical properties which make them useful in the lubrication industry. For example, the cloud point and pour point of a material made from EMO and octanoic acid are -33 and -31 deg C respectively. They have also been shown to reduce the measured coefficient of friction in a testing system from 0.4, all the way down to 0.1. The fluids are effective, even at a concentration of only 0.01M. A similar reaction of EMO can be undertaken using a ketone and phosphoric acid catalyst. The resultant acetal (ketal) is of interest as a pH degradable surfactant where calculations show a molar volume change of 75 cm3 is possible upon hydrolysis. These are a couple of areas in which oleochemicals can have a positive impact in the replacement of petroleum in the future.