Purification of 1,2-diacylglycerols from vegetable oils: Comparison of molecular distillation and liquid CO2 extraction

Industrial Crops and Products

Volumn 28, Issue 2, 2008, Pages 113-121

  Compton, David L ^a   Laszlo, Joseph A ^a   Eller, Fred J ^a   Taylor, Scott L ^a  

^a AGRICULTURAL RESEARCH SERVICE   (United States)

Author keywords

1,2 Diacylglycerols; Acyl migration; Alcoholysis; Fatty acid propyl esters; Liquid CO2 extraction; Molecular distillation

Indexed keywords

BYPRODUCTS; ESTERS; FATTY ACIDS; FOOD ADDITIVES; FOOD PROCESSING; GLYCEROL; LUBRICATING OILS; ORGANIC COMPOUNDS; PURIFICATION; TIN ALLOYS; VEGETABLE OILS;

ACYL MIGRATION; ACYLGLYCEROL; LIPOZYME TL IM; MOLECULAR DISTILLATION (MD); OLEIC SUNFLOWER; PURIFICATION TECHNIQUES; REGIOSPECIFIC; SOYBEAN OIL (SBO); STRUCTURED LIPIDS; VISCOSITY VALUES;

DISTILLATION;

CARBON DIOXIDE; CATALYSIS; COMPARATIVE STUDY; DICOTYLEDON; DISTILLATION; ENZYME ACTIVITY; ESTER; EXTRACTION METHOD; FATTY ACID; LIPID; NUCLEAR MAGNETIC RESONANCE; PHYSICAL PROPERTY; SOYBEAN; VEGETABLE OIL; VISCOSITY;

GLYCINE MAX; HELIANTHUS;

CARBON DIOXIDE; ENZYME; PURIFICATION; REMOVAL;

EID: 47549113286     PISSN: 09266690     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.indcrop.2008.01.010     Document Type: Article

References (27)

1. American Oil Chemists Society. Acid value. Official Methods and Recommended Practices of the American Oil Chemists' Society. 4th ed. (1994), AOCS, Champaign, IL pp. Cd 3d-63
2. American Oil Chemists Society. Lovibond method using colored glasses calibrated in accordance with the Lovibond tintometer color scale. Official Methods and Recommended Practices of the American Oil Chemists' Society. 4th ed. (1994), AOCS, Champaign, IL pp. Cd 3d-63
3. American Oil Chemists Society. Peroxide value acetic acid-isooctane method. Official Methods and Recommended Practices of the American Oil Chemists' Society. 4th ed. (1994), AOCS, Champaign, IL pp. Cd 8b-90
4. American Society for Testing Materials (ASTM). Standard Method of Test for Viscosity of Transparent and Opaque Liquids (Kinematic and Dynamic Viscosities) ASTM (D 445-65) (1991), ASTM, Philadelphia, PA pp. 184-190
5. American Society for Testing Materials. Standard Method for Calculating Viscosity Index from Kinematic Viscosity at 40 and 100 °C ASTM (D 2270-79) (1991), ASTM, Philadelphia, PA pp. 277-285
6. Boswinkel G.J., Derksen J.T.P., van't Riet K., and Cuperus F.P. Kinetics of acyl migration in monoglycerides and dependence on acyl chainlength. J. Am. Oil Chem. Soc. 73 (1996) 707-711
7. Cermak S.C., John A.L., and Evangelista R.L. Enrichment of decanoic acid in cuphea fatty acids by molecular distillation. Ind. Crops Prod. 26 (2007) 93-99
8. 1H NMR spectroscopy of fatty acids and their derivatives: quantification by NMR. In: The Lipid Library. http://www.lipidlibrary.co.uk/nmr/1NMRquan/index.htm.
9. 1H NMR spectroscopy of fatty acids and their derivatives: glycerol esters. In: The Lipid Library. http://www.lipidlibrary.co.uk/nmr/1NMRglyc/index.htm.
10. Compton, D.L., Laszlo, J.A., 2002. Novel sunscreens from vegetable oil and plant phenols. US Patent 6,346,236.
11. Compton D.L., Laszlo J.A., and Berhow M.A. Identification and quantification of feruloylated mono- and diacylglycerols from vegetable oils. J. Am. Oil Chem. Soc. 83 (2006) 753-758
12. 1H NMR. J. Am. Oil Chem. Soc. 84 (2007) 343-348
13. DeFilippi, L.J., Grall, S.G., Kinney, J.F., Laszlo, J.A., Compton, D.L., 2007. Formulations with feruloyl glycerides and methods of preparations. US Patent application 11,771,843.
14. Eller F.J., Taylor S.L., Compton D.L., Laszlo J.A., and Palmquist D.E. Counter-current liquid carbon dioxide purification of a model reaction mixture. J. Supercritic. Fluids 43 (2008) 510-514
15. Fureby A.M., Virto C., Adlercreutz P., and Mattiasson B. Acyl migration in 2-monoolein. Biocatal. Biotransf. 14 (1996) 89-111
16. Heisler A., Rabiller C., and Hublin L. Lipase catalyzed isomerization of 1,2-(2,3)-diacylglyceride into 1,3-diacylglyceride. The crucial role of water. Biotechnol. Lett. 13 (1991) 327-332
17. Isbell T.A., Edgecomb M.R., and Lowery B.A. Physical properties of estolides and their ester derivatives. Ind. Crop Prod. 13 (2001) 11-20
18. Kim I.-H., Ko S.-N., Lee S.-M., Chung S.-H., Kim H., Lee K.-T., and Ha T.-Y. Production of structured lipids by lipase-catalyzed acidolysis in supercritical carbon dioxide: effect on acyl migration. J. Am. Oil Chem. Soc. 81 (2004) 537-541
19. Kim H.-J., Lee K.-T., Lee M.-K., Jeon S.-M., and Choi M.-S. Diacylglycerol-enriched structured lipids containing CLA and capric acid alter body fat mass and lipid metabolism in rats. Ann. Nutr. Metab. 50 (2006) 219-228
20. Kodali D.R., Tercyak A., Fahey D., and Small D.M. Acyl migration in 1,2-dipalmitoyl-sn-glycerol. Chem. Phys. Lipids 52 (1990) 163-170
21. Laszlo J.A., and Compton D.L. Enzymatic glycerolysis and transesterification of soybean oil for enhanced production of feruloylated mono- and diacylglycerols. J. Am. Oil Chem. Soc. 83 (2006) 765-770
22. Laszlo J.A., Compton D.L., Eller F.J., Taylor S.L., and Isbell T.A. Packed-bed bioreactor synthesis of feruloylated monoacyl- and diacylglycerols: clean production of a "green" sunscreen. Green Chem. 5 (2003) 382-386
23. Mu H., and Høy C.-E. Intestinal absorption of specific structured triacylglycerols. J. Lipid Res. 42 (2001) 792-798
24. Nakajima Y., Fukasawa J., and Shimada A. Physiochemical properties of diacylglycerol. In: Katsuragi Y., Yasukawa T., Matsuo N., Flickinger B.D., Tokimitsu I., and Matlock M.G. (Eds). Diacylglycerol Oil (2004), AOCS Press, Champaign, IL 183-196
25. Privett O.S., Blank M.L., and Lundberg W.O. Determination of mono-, di-, and triglycerides by molecular distillation and thin layer chromatography. J. Am. Oil Chem. Soc. 38 (1961) 312-316
26. Serdarevich B. Glyceride isomerizations in lipid chemistry. J. Am. Oil Chem. Soc. 44 (1967) 381-393
27. Xu X., Skands A., and Adler-Nissen J. Purification of specific structured lipids by distillation: effects on acyl migration. J. Am. Oil Chem. Soc. 78 (2001) 715-718