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Process for the extraction of squalene, sterols and vitamin e contained in condensates of physical refining and/or in distillates of deodorization of plant oils

A technology of deodorization distillate and physical refining, applied in the fields of sterols, vitamin E and squalene

Inactive Publication Date: 2011-06-08
SOPHIM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, tocopherols or sterols that have been in contact with hexane and methanol or other solvents derived from petroleum at one point or another in the extraction process cannot claim the label as a natural product capable of being used in "green" formulations, even with the IP mark

Method used

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  • Process for the extraction of squalene, sterols and vitamin e contained in condensates of physical refining and/or in distillates of deodorization of plant oils
  • Process for the extraction of squalene, sterols and vitamin e contained in condensates of physical refining and/or in distillates of deodorization of plant oils
  • Process for the extraction of squalene, sterols and vitamin e contained in condensates of physical refining and/or in distillates of deodorization of plant oils

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] Example 1 - Esterification of a deodorized distillate of sunflower oil with bioethanol - step a).

[0107] In a 5 liter round bottom flask, DD 1.000 g of oleic sunflower oil (tournesol oléique) is introduced, which has the following composition:

[0108] Saponifiable fraction: free fatty acid: 38%, triglyceride: 25.8%, fatty acid ester: 7%;

[0109] • Unsaponifiable fraction: 29.2%. The unsaponifiable fraction consisted of 38.6% sterols and triterpene alcohols, 19.9% ​​squalene, 6.5% vitamin E, 29.8% non-squalene hydrocarbons, 5.2% unidentified products and impurities.

[0110]The condensate was mixed with 620 g of absolute ethanol, ie ethanol in a 10-fold molar excess relative to the fatty acid. 1 g of concentrated sulfuric acid was added, ie 0.1% relative to the mass of the condensate added. The stirred round bottom flask was purged several times with nitrogen and then heated to 90°C. The reaction was carried out under reflux of ethanol for 4 hours. After cooling...

Embodiment 2

[0111] Example 2 - Esterification of sunflower oil DD with bioethanol - step a).

[0112] The same sunflower oil DD 500 g as in Example 1 was introduced into a 1 liter autoclave. The condensate was mixed with 154.9 g of anhydrous bioethanol, ie a 5-fold molar excess of ethanol / fatty acid. 0.5 g of concentrated sulfuric acid was added, ie 0.1% relative to the mass of the condensate added. After purging several times with nitrogen, the reactor was gradually heated to 90° C. with stirring within 1 hour, a pressure of 2.5 bar was achieved. After cooling the reactor, the reaction medium is neutralized with 0.5 N sodium ethoxide solution by stirring for 30 minutes. The ethanol was then distilled at atmospheric pressure and then at the end of the distillation at a vacuum of 50 mbar and a temperature of 100° C. to remove the water of esterification. An anhydrous product with an acid number of 0.8 is obtained without isomerization of the squalene.

Embodiment 3

[0113] Example 3 - Ethanolysis of sunflower oil DD esterified with bioethanol - step a).

[0114] In a 5-liter round-bottomed flask, 1.000 g of the esterification product of Example 1, containing 25.8% of triglycerides and 11.2% of sterols in esterified form, corresponding to 1 mole of ester, were introduced. Add 20 moles of anhydrous bioethanol (20-fold molar excess), that is, 920 grams of bioethanol, in which 1% by weight of sodium is pre-dissolved, so as to generate sodium alkoxide in situ. The round bottom flask was then heated at 80° C. for 2 hours under reflux of ethanol with stirring. The sodium present in the form of sodium ethoxide was then neutralized by 0.5N sulfuric acid solution. The ethanol was distilled first at atmospheric pressure and then at a reduced pressure of 50 mbar. Sodium sulfate formed during neutralization was removed by washing with water. All glycerides, as well as pre-existing steroids, have been converted to ethyl esters, which results in effi...

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Abstract

The invention describes an overall process for the extraction of sterols, vitamin E, squalene and other plant-based hydrocarbons from deodorization distillates of plant oils. After an esterification of the free fatty acids, then a transesterification of the combined fatty acids (glycerides and sterides) by the same short alcohol, three successive distillations make it possible to successively recover a first fraction of hydrocarbons, the main fraction of alkyl esters, then the heaviest alkyl esters with squalene. The third distillate will be used for the production of squalene and a second fraction of hydrocarbons. The residue of the third distillation will be used for the production of sterols and vitamin E. By using bioethanol, plant-based glycerol and the plant-based hydrocarbons of the process, the process makes it possible to extract each of the four unsaponifiable substances without any solvent of oil-based origin and to claim the seals of approval for products obtained by natural physical and chemical processes.

Description

technical field [0001] The present invention relates to a method capable of simultaneously extracting squalene, sterols and vitamin E (tocopherols and tocotrienols) contained in deodorized distillates and / or physical refining condensates of vegetable oils. It belongs to the technical field of the treatment of lipids. Background technique [0002] Vegetable oils contain 0.5% to 2% unsaponifiable fractions, commonly referred to as "unsaponifiables". The qualitative and quantitative composition of this unsaponifiable varies with the vegetable oil, but with some exceptions sterols make up its major part, of which β-sitosterol is always the most abundant. In addition to sterols, there are four classes of products with lower proportions: tocopherols and tocotrienols, triterpene alcohols, aliphatic alcohols and hydrocarbons. [0003] Tocopherols (alpha, beta, gamma, delta) and tocotrienols (alpha, beta, gamma, delta) are specific phenols collectively known as vitamin E, which are...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C11/21C07J9/00C11B3/12C11C3/00
CPCC11C3/02C11C3/003C07J9/00C07C11/21C11B3/12A61P3/02
Inventor J·马格纳特G·塞克基O·古伊隆
Owner SOPHIM
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