Method for producing vitamin E-enriched, especially tocotrienol-enriched, compositions from natural oils

Patent metadata

Field	Value
Publication number	US-10017712-B2
Application number	US-201515118021-A
Country	US
Kind code	B2
Filing date	Feb 6, 2015
Priority date	Feb 11, 2014
Publication date	Jul 10, 2018
Grant date	Jul 10, 2018

Abstract

The present disclosure relates generally to a process for manufacturing products enriched in the content of at least one vitamin E component, preferably tocotrienol, using solvent extraction and membrane filtration.

First claim

The invention claimed is:

1. A process, comprising:
(a) mixing a fatty acid oil mixture, comprising vitamin E components, with an immiscible organic solvent to form a heterogeneous, two-phase mixture;
(b) separating the resulting two-phase mixture to provide a first phase comprising a vitamin E depleted fatty acid oil mixture and a second phase comprising the organic solvent, vitamin E components and optionally at least one impurity;
(c) passing the second phase obtained in step (b) across at least one selective membrane, wherein a retentate forms comprising greater than 50% of the desired vitamin E components present in the second phase, and a permeate forms comprising the solvent and any component that is not retained by the membrane;
(d) removing the organic solvent from the retentate obtained in step (c) to provide as product 1 a composition enriched in at least one vitamin E component compared to the fatty acid oil mixture,
(e) optionally removing the organic solvent from the permeate obtained in step (c) to form as product 3 an impurity composition, and
(f) optionally separating the solvent from the first phase obtained in step (b) to obtain as product 2 a fatty acid oil mixture depleted in vitamin E components compared to the raw material;
wherein the fatty acid oil mixture comprises triglyceride oils, phospholipid oils, or any combination thereof; and
wherein the membrane used in step (c) is characterized by a rejection R Vit of the target vitamin E components which is greater than the membrane rejection of the at least one impurity species R imp .

2. The process according to claim 1 ,
characterized in that the process comprises a solvent selection step and a solvent screening step,
wherein in the solvent screening step partition coefficients PC for organic solvents or mixtures thereof are determined, optionally for different mixing ratios of organic solvent to fatty acid oil mixture, by a process comprising the following steps:
Extracting a sample of a fatty acid oil mixture with an organic solvent or mixture of organic solvents to obtain a bottom fraction and an extract fraction,
Measuring the concentration of at least one tocopherol and at least one tocotrienol in the bottom fraction as well as in the extract fraction, and
Calculating partition coefficients PCTocotrienol=concentration of a tocotrienol in the extract/concentration of the same tocotrienol in the bottom fraction and PCTocopherol=concentration of a tocopherol in the extract/concentration of the same tocopherol in the bottom fraction, for at least one tocotrienol and at least one tocopherol comprised in the fatty acid oil mixture,

and
wherein in the solvent selection step an organic solvent is selected for use in step (a) which has a PCTocotrienol that is higher than the PCTocopherol for at least one mixing ratio of organic solvent to fatty acid oil mixture.

3. The process according to claim 2 ,
characterized in that an organic solvent is selected for step (a) having a ratio of the PCTocotrienol to PCTocopherol for at least one mixing ratio of organic solvent to fatty acid oil mixture of from >1 to about 1000.

4. The process according to claim 1 , further comprising at least one of the following:
wherein the process in step a) comprises a solvent extraction process selected from the group consisting of a counter-current equilibrium stage extraction processes, a crosscurrent equilibrium stage extraction process a co-current equilibrium stage extraction process and a combination of at least two of these processes;
wherein step (a) of the process is performed at a pressure of (i) 1-10 atm absolute when organic solvents are used other than liquefied gases or supercritical gases, (ii) 1-80 atm absolute when an organic solvent system containing or consisting of liquefied gases is used, and (iii) 1-400 atm absolute when an organic solvent system containing or consisting of supercritical gases is used; and
wherein the process in step (a) is performed at a temperature in the range −20° C. to 200° C.

5. The process according to claim 1 , further comprising at least one of the following:
wherein the passing of the second phase obtained in step (b) across the at least one selective membrane in step (c) comprises diafiltration, cross-flow filtration, or a combination of diafiltration and cross-flow filtration;
wherein process step (c) is performed at a temperature ranging from about −10° C. to about 60° C. and
wherein the filtration pressure in step (c) ranges from about 5 bar to about 70 bar.

6. The process according to claim 1 ,
further comprising passing the retentate obtained in step (c) or product 1 obtained after step (d) across at least one second selective membrane to form a second retentate comprising enriched content of vitamin E components, and a second permeate comprising at least one impurity compound, wherein the at least one second selective membrane may be the same as, or different from, the at least one selective membrane.

7. The process according to claim 2 ,
further comprising passing the retentate obtained in step (c) or product 1 obtained after step (d) across at least one second selective membrane to form a second retentate comprising enriched content of vitamin E components, and a second permeate comprising at least one impurity compound, wherein the at least one second selective membrane may be the same as, or different from, the at least one selective membrane.

8. The process according to claim 1 , further comprising at least one of the following:
treating the vitamin E enriched composition obtained after step (c) or (d) with at least one adsorption process comprising at least one absorbent or adsorbent, at least one solvent extraction process, at least one distillation or evaporation process or at least one chromatography process;
recovering any solvent in steps (e) and/or (f) for re-use in step (a); and
repeating the individual process steps (a) to (d) for a period of time ranging from about 10 minutes to about twenty hours.

9. The process according to claim 2 , further comprising at least one of the following:
treating the vitamin E enriched composition obtained after step (c) or (d) with at least one adsorption process comprising at least one absorbent or adsorbent, at least one solvent extraction process, at least one distillation or evaporation process or at least one chromatography process;
recovering any solvent in steps (e) and/or (f) for re-use in step (a); and
repeating the individual process steps (a) to (d) for a period of time ranging from about 10 minutes to about twenty hours.

10. The process according to claim 1 , comprising at least one of the following:
wherein the initial fatty acid oil mixture has an acid value in the range 0.2 to 25 mg KOH/g;
wherein the initial fatty acid oil mixture comprises greater than 20%, triglycerides and/or phospholipid oils; and
wherein the initial fatty acid oil mixture comprises greater than 100 ppm total tocopherols and tocotrienols.

11. The process according to claim 1 , comprising at least one of the following:
wherein the initial fatty acid oil mixture comprises at least from about 10% to about 30% by weight of omega-3 fatty acids; and
wherein the initial fatty acid oil mixture comprises vegetable oil, oil derived from marine sources, oil derived from algae, oil derived from microbes, animal fat, or animal oil.

12. The process according to claim 1 , comprising at least one of the following:
wherein the at least one impurity is selected from the group consisting of free cholesterol, esterified cholesterol, sterols, esterified sterols, phenolic compounds, free fatty acids, monoglycerides,

Assignees

• Evonik Degussa Gmbh

Inventors

• Boam Andrew
• Bouwhuis Yuri
• Koleva Velichka Yordanova
• Rocha Maria Ines Fontes
• Schwarm Michael

Classifications

• C11B3/008

  by filtration, e.g. including ultra filtration, dialysis (C11B3/005 takes precedence) · CPC title

• C11B11/00 Primary

  Recovery or refining of other fatty substances, e.g. lanolin or waxes · CPC title

• C11B1/10 Primary

  by extracting · CPC title

• C11B3/006

  by extraction · CPC title

• C07D311/72

  3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols · CPC title