Submitted to: Meeting Abstract
Publication Type: Abstract only
Publication Acceptance Date: 8/15/2004
Publication Date: 10/18/2004
Citation: Blair, N.M., Biswas, A., Adhvaryu, A., Gordon, S.H., Erhan, S.Z., Willett, J.L. 2004. Amine functionalized soybean oil [abstract]. American Chemical Society. p.108. Interpretive Summary:
Technical Abstract: Specialty chemicals based on renewable resources are desirable commodities due to their eco-friendly nature and "green" product characteristics. These chemicals can demonstrate comparable physical and chemical properties to conventional petroleum based products. Suitably functionalized amines in the triacylglycerol structure can function as an antioxidant, as well as an anti wear/anti friction agent. In additon, the amphiphilic nature of seed oils makes them an excellent candidate as base fluid. The reaction of amine and epoxidized seed oils in presence of catalyst almost always lead to different intra/inter molecular cross linked products. In most cases, the triacyglycerol structure is lost due to the disruption of ester linkage. Currently, there is no reported literature describing effective aminolysis of vegetable oil without cross linking. Thus, our goal was to selectively react the epoxy group of the epoxidized soybean oil with amines to give amine-functionalized soybean oil. The optimization procedure involved various amines and catalysts for maximum aminolysis, without crosslinking and disruption of the ester linkage. Diethyl amine and ZnCl2 were found to be the best. NMR and IR were used to characterize the products. These amine derivatives will serve the dual function of antioxidant and antiwear specialty chemical in automotive and industrial applications.