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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Plant Polymer Research » Research » Publications at this Location » Publication #236461

Title: Synthesis of an amine-oleate derivative using an ionic catalyst

item Biswas, Atanu
item Doll, Kenneth - Ken
item Willett, Julious
item Erhan, Sevim
item Vermillion, Karl

Submitted to: Journal of Agricultural and Food Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 7/29/2009
Publication Date: 9/23/2009
Citation: Biswas, A., Sharma, B.K., Doll, K.M., Willett, J.L., Erhan, S.Z., Vermillion, K., Cheng, H. 2009. Synthesis of an amine-oleate derivative using an ionic catalyst. Journal of Agricultural and Food Chemistry. 57(1):8136-8141.

Interpretive Summary: In this research, we discovered a new, environmentally-friendly, fast method to make amino vegetable oil. Amino oils have possible applications as ingredients in lubricants, coatings, cosmetics, biodiesel fuel, agricultural chemicals, spandex fibers, antioxidants and pharmaceuticals. This method produced no byproducts and the catalyst ionic liquid was recovered and recycled. This discovery will benefit industrial chemical manufacturers, among others.

Technical Abstract: A facile (and environmentally friendly) reaction, between epoxidized methyl oleate and aniline to produce an oleate-aniline adduct, without the formation of fatty amide, was discovered. This reaction was carried out neat, with a catalytic amount of an ionic liquid. No solvent or byproducts were produced, and the ionic liquid could be recovered and recycled. The reaction product has been fully characterized by NMR and GC/MS.