Isolation of tocopherol and sterol concentrate from sunflower oil deodorizer distillate
01 Oct 1996-Journal of the American Oil Chemists' Society (Springer-Verlag)-Vol. 73, Iss: 10, pp 1271-1274
TL;DR: In this paper, the isolation of tocopherols and sterols together as a concentrate from sunflower oil deodorizer distillate was investigated, which included process steps such as biohydrolysis, bioesterification and fractional distillation.
Abstract: The isolation of tocopherols and sterols together as a concentrate from sunflower oil deodorizer distillate was investigated. The sunflower oil deodorizer distillate was composed of 24.9% unsaponifiable matter with 4.8% tocopherols and 9.7% sterols, 28.8% free fatty acid (FFA) and 46.3% neutral glycerides. The isolation technology included process steps such as biohydrolysis, bioesterification and fractional distillation. The neutral glycerides of the deodorizer distillates were hydrolyzed byCandida cylindracea lipase. The total fatty acids (initial FFA plus FFA from neutral glycerides) were converted into butyl esters withMucor miehei lipase. The esterified product was then fractionally distilled in a Claisen-vigreux flask. The first fraction, which was collected at 180–230°C at 1.00 mm of Hg for 45 min, contained mainly butyl esters, hydrocarbons, oxidized products and some amount of free fatty acids. The fraction collected at 230–260°C at 1.00 mm Hg for 15 min was rich in tocopherols (about 30%) and sterols (about 36%). The overall recovery of tocopherols and sterols after hydrolysis, esterification and distillation were around 70% and 42%, respectively, of the original content in sunflower oil deodorizer distillate.
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TL;DR: In this article, a second order polynomial response surface equation was developed indicating the effect of variables on ester yield, which showed that all the experimental variables significantly affected the yield of fatty acid butyl esters (FABE).
Abstract: Supercritical carbon dioxide (SC-CO2) as a medium for esterification of free fatty acids (FFA) of hydrolyzed soy deodorizer distillate (DOD) with butanol, has been studied using Mucor miehei lipase as a biocatalyst. Process conditions (pressure, temperature, butanol and enzyme
concentration and incubation time) were optimized by conducting experiments at five different levels using a central composite rotatable design (CCRD) method. A second order polynomial response surface equation was developed indicating the effect of variables on ester yield.
Contour maps generated using the response surface equation, showed that all the experimental variables significantly affected the yield of fatty acid butyl esters (FABE). The reaction variables influenced the yield of esters both independently and in combination. A pressure of 122 bar, temperature 36 ◦C, butanol concentration 1.2 M, enzyme concentration 15% (w/w) and incubation time of 3 h were predicted to be the optimal for the maximum yield of 100% FABE, which was validated by an experiment to yield 95% of FABE. SC-CO2 is a potential
medium for the biomodification of soy DOD by esterification of free fatty acids with butanol.
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Abstract: The heat capacities in the liquid phase of the fatty acids hexadecanoic acid, octadecanoic acid, and cis-9-octadecenoic acid were measured, as well as those of their binary and ternary mixtures from temperatures close to solidification to 528 K. The measurements were correlated and contrasted with equations, methods, and values for the pure fatty acids, Ruzicka and Domalski's method providing better results for most of the temperature range studied. For binary and ternary mixtures, molar fraction average and corresponding states methods were used. The convenience of the former with respect to the latter was demonstrated; it is easier to apply and provides suitable results. Furthermore, in the case of the mixtures, only slight variations in heat capacity with composition were experienced. All the measurements were carried out using a DSC differential scanning calorimeter.
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TL;DR: In this article, the optimal conditions for maximum degree of triglyceride hydrolysis (94%) were found to be: pressure of 180 bar, temperature of 43 °C and moisture content of 40% to the triglyceride content.
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References
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01 Jan 1990
5,013 citations
TL;DR: In this article, a model mixture of pure oleic acid and dl-α-tocopherol was used to study any potential side reactions that may lower the tocopherol content during the esterification reaction.
Abstract: Separation of sterols and tocopherols from fatty acids in deodorizer distillate was facilitated through lipase-catalyzed modification of fatty acids in canola, mixed and soya deodorizer distillates. The fatty acid esterification with methanol catalyzed by SP-382 (an immobilized nonspecific lipase) proceeded rapidly, with conversion of fatty acid to methyl ester in 5 h being 96.5, 83.5 and 89.4%, respectively. A model mixture of pure oleic acid and dl-α-tocopherol was used to study any potential side reactions that may lower the tocopherol content during the esterification reaction. Under the conditions employed, the loss of tocopherol was less than 5%. Simple vacuum distillation (1–2 mm Hg) was employed to remove the volatile fraction (methyl esters of fatty acids, some fatty acids and other volatiles) of the esterified deodorizer distillate, leaving behind sterols, sterol esters and tocopherols. Sterols and tocopherols were almost completely retained in the residue fraction with recoveries in the range of 95%. Overall recoveries of sterols and tocopherols after esterification and distillation were over 90% for all the deodorizer distillate samples.
81 citations
"Isolation of tocopherol and sterol ..." refers background or methods in this paper
...This type of oxidation loss during esterification and distillation was reported by Ramamurthi and McCurdy ( 5 )....
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...Ramamurthi and McCurdy ( 5 ) esterifled the deodorizer distillate with methanol with a nonspecific SP 382 lipase, and about 4-10% fatty acids were retained in the reaction mixture....
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...Recently, Ramamurthi and Mc-Curdy ( 5 ) have tried to concentrate sterols and tocopherols from canola deodorizer distillate (which contained initially 1.00% w/w tocopherols and 1.58% w/w sterols) and soybean deodorizer distillate (initially containing tocopherols at 12.74% w/w and sterols at 11.39% w/w) by an enzymatic process....
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TL;DR: In this paper, the feasibility and technical merits of supercritical fluid extraction (SFE) as a potential alternative to molecular distillation for enriching tocopherols effectively from soybean sludge were examined.
Abstract: Supercritical fluid extraction (SFE) has been widely applied as a promising alternative to current extraction processes used in the food and pharmaceutical industries. SFE has some advantages over conventional separation processes such as liquid-liquid extraction, distillation, and adsorption. The most important advantage of utilizing SFE is the easy separation of the solvent from the extracted material without solvent residue. Further, supercritical fluids provide lower mass transfer resistance than those in conventional separation processes. A number of references dealing with the basic principles and applications of SFE are now available [1-3]. The objective of this study is therefore to examine the feasibility and technical merits of SFE as a potential alternative to molecular distillation for enriching tocopherols effectively from soybean sludge. In this regard, the solubilities of both sterol-removed soybean sludge and esterified soybean sludge in SC-CO2 were determined by a flow-through SFE system at temperature and pressure ranges f 35–70∘C and 200–400 bar, respectively. The tocopherol content in the extracts collected continously at equilibrium conditions up to the approximate 70 wt% extraction rate of the feed was checked by HPLC at each interval. The results of these initial feasibility experiments could provide fundamental information for the suitable application of a continous-type SFE for concentrating tocopherols.
70 citations
TL;DR: In this article, polyphenols were extracted from the rape of Israeli olive oil using hexane, acetone and ethanol in a simple sequential procedure yielding three fractions (A,B,C).
Abstract: Polyphenols were extracted from the rape of Israeli olive oil using hexane, acetone and ethanol in a simple sequential procedure yielding three fractions (A,B,C). Fraction A (extracted with hexane) contained few polyphenols (0.05%), while Fraction B (extracted with acetone) and Fraction C (extracted with ethanol) contained about 5% polyphenols each. Fractions B and C were also found to contain the highest ortho-di-phenol concentration (about 3%). The addition of purified Fraction B at a level of 100 ppm to refined olive or soybean oils partially inhibited the oxidative deterioration when the oils were stored in the dark at 100 C.
58 citations
"Isolation of tocopherol and sterol ..." refers methods in this paper
...Separation of sterols and tocopherols has also been tried by Sheabar and Neeman ( 3 ) with a combination of solvent extraction and chemical treatment....
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01 Apr 1992
55 citations
"Isolation of tocopherol and sterol ..." refers background in this paper
...Supercritical fluid extraction technology is promising, and attempts have been made to isolate tocopherols from soya sludge ( 4 ) by this process....
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