Osage Orange (Maclura pomifera L.) Seed Oil Poly(α-hydroxydibutylamine) Triglycerides: Synthesis and Characterization
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...
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Published in | Journal of agricultural and food chemistry Vol. 63; no. 29; pp. 6588 - 6595 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
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WASHINGTON
American Chemical Society
29.07.2015
American Chemical Society, Books and Journals Division Amer Chemical Soc |
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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. |
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AbstractList | 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. 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 degrees 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(alpha-hydtotydibutylamine) triglyceride. The purpose of this work was to derivatize and thereby stabilize this highly unsaturated tree oil for its eventual use in lubrication applications: 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. |
Author | Harry-O’kuru, Rogers E Tisserat, Brent Gordon, Sherald H Gravett, Alan |
AuthorAffiliation | Functional Food Research Unit Bio-Oils Research Unit Plant Polymer Research Unit National Center for Agricultural Utilization Research, Agricultural Research Service, U.S. Department of Agriculture |
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Keywords | amination epoxidation Osage orange seed oil poly(α-hydroxydibutylamine) triglyceride poly(alpha-hydroxydibutylamine) triglyceride |
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References | Harry-O'kuru, RE (WOS:000292841900014) 2011; 88 Harry-O'kuru, RE (WOS:000228808300010) 2005; 82 Collingwood, G. H. (000358896200011.10) 1939; 45 ALIEV, R. K. (BCI:BCI19634200015511) 1961; 3 Bonner, F. T. (000358896200011.8) 1974; 450 HART, JH (WOS:A1968B789100017) 1968; 14 Wolfrom, M. L. (000358896200011.20) 1941; 63 Betts, H. S. (000358896200011.7) 1929; 46 Baumgardt, J. P. (000358896200011.6) 1972; 50 Tsao, R (WOS:000185990500012) 2003; 51 (000358896200011.1) 1967 Wolfrom, M. L. (000358896200011.19) 1939; 61 WAGNER, JG (WOS:A1952YG69900012) 1952; 41 BARNES, RA (WOS:A1955WB85900032) 1955; 77 Moser, BR (WOS:000289697700059) 2011; 25 SMITH, JL (WOS:A1981LE99000003) 1981; 35 CLOPTON, JR (WOS:A1953UJ31500007) 1953; 30 Harry-O'kuru, RE (WOS:000300644100013) 2012; 60 (000358896200011.2) 2013 Alchmedkhodzhaeva, N. M. (000358896200011.3) 1972 Akhmedkhodzhaeva N. M. (ref2/cit2) 1972 Hart J. H. (ref10/cit10) 1968; 14 ref17/cit17 ref18/cit18 ref19/cit19 ref21/cit21 ref11/cit11 ref12/cit12 ref15/cit15 ref16/cit16 Baumgardt J. P. (ref5/cit5) 1972; 50 Bonner F. T. (ref7/cit7) 1974 ref13/cit13 ref14/cit14 ref8/cit8 ref4/cit4 Collingwood G. H. (ref9/cit9) 1939; 45 ref1/cit1 Aliev R. K. (ref3/cit3) 1961; 3 ref20/cit20 Betts H. S. (ref6/cit6) 1929 |
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Snippet | Milled Osage orange seeds (Maclura pomifera (Raf.) Schneid) were Soxhlet extracted with hexane, and portions of the extract were treated with activated carbon... Milled Osage orange seeds (Maclura pomifera (Raf.) Schneid) were Soxhlet extracted:with hexane, and portions of the extract were treated with activated carbon... |
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SubjectTerms | 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 |
Title | Osage Orange (Maclura pomifera L.) Seed Oil Poly(α-hydroxydibutylamine) Triglycerides: Synthesis and Characterization |
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