Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 3/21/2003
Publication Date: 8/22/2003
Citation: Hwang, H.-S., Adhvaryu, A., Erhan, S.Z. 2003. Preparation and properties of lubricant basestocks from epoxidized soybean oil and 2-ethylhexanol. Journal of the American Oil Chemists' Society. 80:811-815.
Interpretive Summary: Lubricants are usually derived from petroleum sources and are toxic to environment in case of accidental spillage and during waste disposal. An alternative is to develop vegetable oil based synthetic lubricant that can meet most of the performance characteristics of existing petroleum based lubricants. Various approaches were made to convert soybean oil into synthetic lube by reacting with other compounds. The current work demonstrates the method and step in preparing these synthetic fluids. These products have good low temperature fluidity, oxidatively stable and high viscosity indices. The products are biodegradable and non-toxic. These products will find application in agricultural, forestry, marine and certain industrial equipment.
Technical Abstract: Synthetic lubricant basestocks were prepared from epoxidized soybean oil (ESO) and 2-ethylhexanol (2-EH) to be used alone or with polyalphaolefin (PAO). Sulfuric acid-catalyzed reaction of ESO with 2-EH involves ring-opening reaction at the epoxy group followed by transesterification at the ester group. Reaction with other catalysts including p-toluenesufonic acid, Dowex 50W-8X, boron trifluoride, and sodium methoxide were also examined. Pour points of the products were observed as low as -21C and -30C without and with 1% of PPD (pour point depressant), respectively. When the hydroxy groups in the products were esterified with an acid anhydride, lower pour points were observed. Pour point depression of the product by adding PAO has been tested. Oxidative stability of the product has been examined using PDSC (pressurized differential scanning calorimetry) and compared with those of synthetic lubricant basestocks, PAO and a synthetic ester.