title: Osage Orange (Maclura pomifera L.) Seed Oil Poly(α-hydroxydibutylamine) Triglycerides: Synthesis and Characterization.
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 centrifugate 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 (0.1 M) 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 67 °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(α-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.
authors.forename: Rogers E
authors.initials: RE
authors.lastname: Harry-O'kuru
authors.forename: Brent
authors.initials: B
authors.lastname: Tisserat
authors.forename: Sherald H
authors.initials: SH
authors.lastname: Gordon
authors.affiliation: §Hedge Apple Biotech, 211 Woodrig Road, Bloomington, Illinois 61704, United States.
authors.forename: Alan
authors.initials: A
authors.lastname: Gravett
mesh_terms: D002082:Butylamines / Q000737:chemistry*; D005027:Ethylene Oxide / Q000138:chemical synthesis; D006861:Hydrogen Peroxide; D031624:Maclura / Q000737:chemistry*; D010938:Plant Oils / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D014280:Triglycerides / Q000138:chemical synthesis*
chemical_list: D002082:Butylamines; D010938:Plant Oils; D014280:Triglycerides; C045274:dibutylamine; D006861:Hydrogen Peroxide; D005027:Ethylene Oxide
keywords: Osage orange; amination; epoxidation; poly(α-hydroxydibutylamine) triglyceride; seed oil