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 paper, tocopherol succinates from sterol-removed, succinated deodorizer distillate (DOD) mixture by crystallization was investigated. But, the results showed that the recovery of succinates was poor with all solvents tested, with less than 10% of original succinates in the raw material being crystallized under conditions employed.
Abstract: Isolation of tocopherol succinates from sterol-removed, succinated deodorizer distillate (DOD) mixture by crystallization was investigated. Membrane technology was also evaluated for its effectiveness to separate tocopherol succinates from mixtures containing sterols and tocopherols. Crystallization was conducted at −20C for 24 h with different solvents, including hexane, petroleum ether, and a mixture of acetone and methanol (4:1, v/v). The crystallization results showed that recovery of tocopherol succinates from the cake fraction was poor with all solvents tested, with less than 10% of original tocopherol succinates in the raw material being crystallized under conditions employed. Among the solvents tested, hexane was better for the recovery of non-α-tocopherol succinates in the cake fraction. Furthermore, a high properties of free fatty acids (FFA) was co-crystallized along with tocopherol succinates for all solvents used, leading to tocopherol succinates contents in the cake fractions lower than that in the raw material. Two nanofiltration membranes (DS-7 and AP01) were also examined using hexane or petroleum ether as a solvent. The recovery of tocopherol succinates was over 60%. However, their concentration was increased only by 6%. A combined process was then evaluated that included crystallization before succinylation, succinylation, first stage membrane separation, and second stage membrane separation. The final tocopherols concentration derived from this combined process was mice as much as that of the original DOD.
6 citations
Dissertation•
03 Jun 2003
TL;DR: In this article, the authors presented a method to transform two products of the agriculture tropicale traditionnelle, the noix du Bresil Berthalletia excelsa and le fruit of Noni Marinda Citrifalia, into anti-oxydants and anti-radicalaires.
Abstract: L'objectif de cette these est de transformer deux produits issus de l'agriculture tropicale traditionnelle la noix du Bresil Berthalletia excelsa et le fruit de Noni Marinda Citrifalia en aliments sante. Ces produits naturels ont des teneurs importantes en molecules a proprietes medicinales dont certaines comme les anti-oxydants, les lipides insatures, les mineraux ont ete analyses. L'huile de la noix du Bresil a ete extraite et analysee finement (acides gras, sterols, tocopherols, phospholipides). Le tourteau issus de cette extraction est particulierement riche en selenium (126 ppm) qui est repute pour ses pouvoirs anti-oxydants et anti-radicalaires. Les proteines ont ete fractionnees en 4 fractions. L'analyse par HPLC-SM de ces quatre fractions a prouve que le selenium est lie par une liaison covalente a deux acides amines la selenomethionine et selenocysteine. Le facteur de conversion azote/proteine a ete recalcule a 6,97 en fonction de la composition en acides amines de la proteine. Un lait de noix du Bresil particulierement riche en selenium a ete produit par extraction directe sur les noix. Le haut contenu en selenium de la noix du Bresil et de ses derives font de ces produits une base pour la creation d'aliments sante anti-radicalaire. Un procede d'extraction du jus de Noni a ete optimise a partir des fruits frais provenant du Cambodge. La composition biochimique et minerale des graines et du tourteau a ete etudiee. Les acides gras, phospholipides, tocopherols et sterols ont ete analyses dans toutes les fractions lipidiques. Le facteur de conversion azote/proteine a ete recalcule a 7,05 en fonction de la composition en acides amines de la proteine. Le jus a ete traite par micro-filtration tangentielle et osmose inverse afin de le stabiliser micro biologiquement et physiquement. Le jus pasteurise de couleur jaune est stable durant au moins 4 semaines a temperature ambiante. La composition biochimique du jus qui a montre la forte presence de molecules a proprietes anti-oxydantes n'explique pas a elle seule les effets medicinaux reputes du jus de Noni. Certaines molecules et en particulier les alcaloides meriteraient d'etre etudies. Les travaux issus de cette these ont deja permit a ces deux produits tropicaux de trouver des applications industrielles en para-pharmacie dans les pays developpes.
6 citations
TL;DR: In this article, a reverse osmosis polyamide membrane was used to test the feasibility of concentrating triacylglycerol (TAG) and α-tocopherol/β-sitosterol from model mixtures (Oleic acid (OA)/TAG and OA/α-tochemophylacetyl/β-) solubilized in SC-CO2 using cross-flow filtration regime.
6 citations
16 Aug 2013
2 citations
References
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Book•
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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