Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer reviewed journal
Publication Acceptance Date: 3/8/2005
Publication Date: 4/10/2005
Citation: Harry-O'Kuru, R.E., Gordon, S.H., Biswas, A. 2005. A facile synthesis of aminohydroxy triglycerides from new crop oils. Journal of the American Oil Chemists' Society. 82:207-212. Interpretive Summary: This work reports the chemical bonding of amines to milkweed and salicornia oils in order to develop new useful compounds. Naturally aminated vegetable oils are rare or unknown. And introducing nitrogen as a structural component of the oil gives it novel desirable characteristics such as improved lubricity and moisture scavenging abilities. This is part of a continuing effort in the mission to develop new industrial products from agricultural materials under a congressionally funded National Program for Rural America. Together with earlier products from these oils, the new materials will further diversify and enhance demand for these oils and thus improve the rural farmer's economy.
Technical Abstract: Vegetable oils as the main source of plant lipids are currently generating much interest as renewable industrial feed stock for non-food industrial applications both as biobased-lubricants and biodiesel fuels; but of particular interest for us is use of new crop oils in novel industrial applications. These oils, in general, are glyceryl esters with olefinic bonds which are readily functionalizable. Aminated lipids are important intermediates in many applications including pharmaceutical formulations as they have a modifying effect on cell membranes. We have exploited the nucleophilic property of the carbon-carbon double bonds in our seed oils to generate the oxirane derivatives of the lipids. Ring opening of the epoxy intermediates with amines under anhydrous ZnCl2 catalysis is facile and the reaction proceeds smoothly at moderate temperatures to give the amino hydroxytriglycerides of milkweed and salicornia oils.