Submitted to: Journal of Agriculture and Food Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 9/6/2005
Publication Date: 11/15/2005
Citation: Biswas, A., Adhvaryu, A., Gordon, S.H., Erhan, S.Z., Willett, J.L. 2005. Synthesis of diethylamine functionalized soybean oils. Journal of Agriculture and Food Chemistry. 53(24):9485-9490. Interpretive Summary: Growing public concern and strict government regulations over oil pollution have created a demand for environmentally friendly lubricants. Most lubricants originate from petroleum stock, which is toxic to the environment and difficult to dispose of. Therefore, lubricants prepared from renewable biodegradable resources such as soybean oil are of interest as natural alternatives to synthetic petroleum based lubricants. A novel chemical modification of soybean oil was developed to improve its oxidative and thermal stability. The soybean oil was epoxidized and the epoxy groups were reacted with amines to give amine derivatives. Various amines and catalysts were tried to achieve maximum conversion without crosslinking or decomposing the soybean oil. Diethylamine and ZnC12 were found to be the best amine and catalyst. These soybean oil amine derivatives have comparable physical and chemical properties to synthetic lubricants and also may serve the dual function of antioxidant and antiwear specialty chemicals in automotive and industrial applications. This work addresses growing concerns among lubricant manufacturers interested in natural environmentally friendly alternative to petroleum based lubricants.
Technical Abstract: We have developed a simple method to prepare amine functionalized soybean oil. The epoxy groups of the ESBO with amines were selectively reacted with amines to give amine-functionalized soybean oil from various amines and catalysts used for maximum aminolysis, without crosslinking and disruption of the ester linkage. Diethylamine and ZnC12 were found to be the best. Aggressive conditions or catalysts led to cleavage of the ester groups. Optimally, six molar equivalents of diethylamine with 20 mole % of ZnC12 opened up to 4 of the 5.5 epoxy groups of ESBO.