Osage Orange (Maclura pomifera L.) Seed Oil Poly(α-hydroxydibutylamine) Triglycerides: Synthesis and Characterization

• Published in: Journal of agricultural and food chemistry Vol. 63; no. 29; pp. 6588 - 6595
• Main Authors: Harry-O’kuru, Rogers E, Tisserat, Brent, Gordon, Sherald H, Gravett, Alan
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 29.07.2015; American Chemical Society, Books and Journals Division; Amer Chemical Soc
• Subjects: activated carbon; Agriculture; Agriculture, Multidisciplinary; ammonium hydroxide; Butylamines - chemistry; centrifugation; Chemistry; Chemistry, Applied; ethylene oxide; Ethylene Oxide - chemical synthesis; evaporation; fatty acid composition; Food Science & Technology; free fatty acids; hexane; Hydrogen Peroxide; Life Sciences & Biomedicine; lipid content; Maclura - chemistry; Maclura pomifera; Physical Sciences; Plant Oils - chemistry; Science & Technology; seed oils; seeds; Seeds - chemistry; solvents; Spectroscopy, Fourier Transform Infrared; temperature; trees; triacylglycerols; Triglycerides - chemical synthesis; amination; epoxidation; Osage orange; seed oil; poly(α-hydroxydibutylamine) triglyceride; poly(alpha-hydroxydibutylamine) triglyceride
• DOI: 10.1021/acs.jafc.5b01625
• ISSN: 0021-8561

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.