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United States Department of Agriculture

Agricultural Research Service

Research Project: CHEMICAL SYSTEMS FOR SOYBEAN OIL CONVERSION TO INDUSTRIAL PRODUCTS

Location: Bio-oils Research Unit

Title: Production of phosphorous-containing oleochemicals through an epoxide route

Authors
item DOLL, KENNETH
item Sharma, Brajendra -
item Pereira, Mirian -
item Santos, Gabriel -
item Suarez, Paulo -
item ERHAN, SEVIM

Submitted to: International Journal of Sustainable Engineering
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: July 11, 2011
Publication Date: August 16, 2012
Citation: Doll, K.M., Sharma, B.K., Pereira, M.S., Santos, G.F., Suarez, P.A., Erhan, S.Z. 2012. Production of phosphorous-containing oleochemicals through an epoxide route. International Journal of Sustainable Engineering. 5:280-285.

Interpretive Summary: We have synthesized a new vegetable oil-based compound which has the potential to be a sulfur-free lubricant additive. Lubricants are used throughout most of our manufacturing industries. Extreme pressure (EP) additives must commonly be added to lubricants that are used in many high wear applications. A common additive used for this purpose is zinc dialkyldithiophosphate. Although it is effective, it is no longer allowed in some applications due to its high sulfur content. The compound reported here is a sulfur-free compound, which is also based on vegetable oil. It may find its way into many applications, such as flame resistant coatings, but will surely be an effective EP additive that will work well in bio-based lubricants and help increase their use, benefiting both lubricant producers and users.

Technical Abstract: Phosphorous was incorporated into the middle of the fatty chain on a methyl ester utilizing an epoxide route. Methyl oleate was epoxidized and then a catalyzed or uncatalyzed ring opening reaction was performed using dibutyl phosphate in order to synthesize a butyl dioxaphospholane-containing derivative of methyl octadecanoate. Utilizing a titanium and zirconium oxide catalyst, a yield of 37% is possible. A similar reaction is possible using bis-2-ethylhexyl phosphate. However, an aryl phosphate, diphenyl phosphate, was not active in these reactions. These compounds are likely to be useful extreme pressure lubricant additives which will be highly compatible with soybean oil-based lubricants, and is also sulfur and metal free.

Last Modified: 9/10/2014