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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Bio-oils Research » Research » Publications at this Location » Publication #311288
Title: Osage orange (Maclura pomifera L) seed oil poly-(-a-hydroxy dibutylamine) triglycerides: Synthesis and characterization

Author
item Harry O Kuru, Rogers
item Tisserat, Brent
item Gordon, Sherald
item GRAVETT, ALAN - Hedge Apple Biotech

Submitted to: Society of Tribologists and Lubrication Engineers
Publication Type: Abstract Only
Publication Acceptance Date: 12/18/2014
Publication Date: 5/8/2015
Citation: Harry O Kuru, R.E., Tisserat, B., Gordon, S.H., Gravett, A. 2015. Osage orange (Maclura pomifera L) seed oil poly-(-a-hydroxy dibutylamine) triglycerides: Synthesis and characterization [abstract]. Society of Tribologists and Lubrication Engineers Annual Meeting & Exhibition. p. 54.

Interpretive Summary:

Technical Abstract: In exploring alternative vegetable oils for non-food industrial applications, especially in temperate climates, tree seed oils that are not commonly seen as competitors to soybean, peanut, and corn oils can become valuable sources of new oils. Many trees produce edible fruits and seeds while others produce fruit and pods containing seeds not considered edible for human consumption in terms of the “Food vs. Fuel” debate. In this context, we milled Osage orange seeds and solvent extracted the meal using a Soxhlet extractor. Portions of the extracted oil were treated with activated carbon before solvent removal. The obtained crude oil was chilled and degummed by centrifugation. Free fatty acid content of the crude oil was removed when portions of it were diluted with hexane and shaken with a cold aqueous ammonium hydroxide (0.1M) solution. The desiccant dried organic phase was concentrated to yield the cleaned Osage orange triglyceride after solvent removal by rotary evaporation at 67 deg C. Epoxidation of the resulting cleaned oil was effected by reaction with in situ generated peroxy performic acid in H2O2. The oxirane rings of the derivatized oil were then opened using N,N-dibutylamine catalyzed by anhydrous ZnCl2 to afford the poly-(-a-hydroxydibutylamine) triglyceride. Characterization of the hydroxy dibutylamine triglyceride and its precursors were determined by TLC, FT-IR, 1H- and 13C-NMR. Lubricity characteristics of the hydroxy dibutylamine triglyceride will be discussed.