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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 #310632

Title: Osage orange (Maclura pomifera L) seed oil poly(alpha-hydroxydibutylamine) triglycerides: Synthesis and characterization

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

Submitted to: Journal of Agricultural and Food Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 6/1/2015
Publication Date: 8/21/2015
Publication URL:
Citation: Harry-O'kuru, R.E., Tisserat, B., Gordon, S.H., Gravett, A. 2015. Osage orange (Maclura pomifera L) seed oil poly(alpha-hydroxydibutylamine) triglycerides: Synthesis and characterization. Journal of Agricultural and Food Chemistry. 63(29):6588-6595.

Interpretive Summary: This paper explores the recovery of Osage orange oil from the seed. This process would bring to use a tree oil that is new and not in competition with edible oils like soybean, corn, and other food grade oils. The dry Osage orange seeds were cooled in dry ice before milling to a dry powder, which was then extracted with hexane. The extracted crude oil was cleaned before treating with formic acid and hydrogen peroxide. The obtained product was shown to be the epoxide of the oil, and it has several uses. One use of the epoxide was to treat it with dibutylamine to form a novel compound, hydroxy butylamine of Osage orange oil. This is being tested for use in industry.

Technical Abstract: Milled Osage orange seeds (Maclura pomifera (Raf.) Schneid) were Soxhlet extracted with hexane, and portions of the extract were treated with activated carbon before solvent removal. The crude oil was winterized and degummed by centrifugation at low temperature. Decantation of the centrifuge gave an admixture of the triglycerides and free fatty acids. The free fatty acid content of the oil was removed when portions of the admixture were diluted with hexane and shaken with cold aqueous ammonium hydroxide (0.1M) solution. The desiccant-dried organic phase was concentrated under reduced pressure to give the cleaned Osage orange triglyceride after solvent removal by rotary evaporation at 67o C. Epoxidation of the resulting cleaned triglyceride 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. The purpose of this work was to derivatize and thereby stabilize this highly unsaturated tree oil for its eventual use in lubrication applications.