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EP-4737545-A1 - COMPOSITION CONTAINING POLYUNSATURATED FATTY ACID OR ESTER DERIVATIVE THEREOF, AND METHOD FOR PRODUCING SAME

EP4737545A1EP 4737545 A1EP4737545 A1EP 4737545A1EP-4737545-A1

Abstract

The present process is a method for producing a fatty acid composition containing a polyunsaturated fatty acid (hereinafter referred to as PUFA) or an ester derivative thereof, and is provided, wherein the method includes: storing a solvent in Container A to obtain an eluent under an inert gas atmosphere in Container A; purifying a fatty acid mixture containing PUFA or an ester derivative thereof by chromatography using the eluent as a mobile phase to obtain a fraction containing PUFA or an ester derivative thereof; and concentrating the fraction containing the PUFA or an ester derivative thereof to obtain a fatty acid composition containing the PUFA or an ester derivative thereof.

Inventors

  • KAWANO, TAKAAKI
  • TOUSAKA, Shunsuke
  • EBI, TAKESHI
  • TATEISHI, YUUSUKE
  • HAYASHI, KATSUTOSHI
  • MATSUDA, HIROYUKI
  • SATO, SEIZO
  • FURIHATA, KIYOMI
  • YAMAGUCHI, HIDEAKI

Assignees

  • Nissui Corporation

Dates

Publication Date
20260506
Application Date
20240627

Claims (20)

  1. A process for producing a fatty acid composition containing a polyunsaturated fatty acid (hereinafter also referred to as PUFA) or an ester derivative thereof, comprising: (1) storing a solvent in Container A to obtain an eluent under an inert gas atmosphere in Container A; (2) purifying a fatty acid mixture containing a PUFA or an ester derivative thereof by chromatography using the eluent as a mobile phase to obtain a fraction containing the PUFA or an ester derivative thereof; and (3) concentrating the fraction containing the PUFA or an ester derivative thereof to obtain a fatty acid composition containing the PUFA or an ester derivative thereof.
  2. The process according to claim 1, wherein concentrating the fraction comprises recovering, as a solvent, the eluent present in the fraction containing the PUFA or an ester derivative thereof by distillation under reduced pressure and/or heating.
  3. The process according to claim 1 or 2, wherein the solvent contains a solvent obtained by distillation.
  4. The process according to any one of claims 1 to 3, wherein the solvent contains a solvent recovered from the fraction containing the PUFA or an ester derivative thereof in concentrating the fraction.
  5. The process according to any one of claims 1 to 4, wherein the dissolved oxygen concentration of the eluent in Container A is 20 mg/L or less, 15 mg/L or less, or 11 mg/L or less.
  6. The process according to any one of claims 1 to 5, wherein the headspace oxygen concentration in Container A is 10 vol% or less, 5 vol% or less, 4 vol% or less, 3 vol% or less, 2 vol% or less, 1 vol% or less, 0.5 vol% or less, or 0.1 vol% or less.
  7. The process according to any one of claims 1 to 6, wherein the fraction containing the PUFA or an ester derivative thereof is stored under an inert gas atmosphere in Container C.
  8. The process according to any one of claims 1 to 7, wherein the fraction containing the PUFA or an ester derivative thereof is stored under an inert gas atmosphere in Container C and the headspace oxygen concentration in Container C after the fraction is stored is 1.5 vol% or less, 1.0 vol% or less, 0.7 vol% or less, 0.5 vol% or less, 0.3 vol% or less, or 0.1 vol% or less.
  9. The process according to any one of claims 1 to 8, wherein the fatty acid mixture containing the PUFA or an ester derivative thereof is stored under an inert gas atmosphere in Container B before the fatty acid mixture is purified.
  10. The process according to claim 9, wherein the headspace oxygen concentration in Container B is 1.5 vol% or less, 1.0 vol% or less, 0.7 vol% or less, 0.5 vol% or less, 0.3 vol% or less, or 0.1 vol% or less.
  11. The process according to any one of claims 1 to 10, wherein the fatty acid composition containing the PUFA or an ester derivative thereof is stored under an inert gas atmosphere in Container D.
  12. The process according to claim 11, wherein the headspace oxygen concentration in Container D is 0.7 vol% or less, 0.5 vol% or less, 0.3 vol% or less, or 0.1 vol% or less.
  13. The process according to any one of claims 1 to 12, wherein the inert gas in Container A, the inert gas in Container B, the inert gas in Container C, and the inert gas in Container D are each independently nitrogen, argon, or carbon dioxide gas.
  14. The process according to any one of claims 1 to 13, wherein the inert gas in Container A, the inert gas in Container B, the inert gas in Container C, and the inert gas in Container D are each nitrogen.
  15. The process according to any one of claims 1 to 14, wherein the proportion of the PUFA or an ester derivative thereof in all fatty acids or their ester derivatives in the fatty acid composition containing the PUFA or an ester derivative thereof is 97% or more, 96% or more, 90% or more, 80% or more, 70% or more, or 50% or more.
  16. The process according to any one of claims 1 to 15, wherein the color b value of the fatty acid composition containing the PUFA or an ester derivative thereof is 3.2 or less, 3 or less, 2.8 or less, 2.5 or less, 2 or less, 1.5 or less, 1 or less, or 0.7 or less.
  17. The process according to any one of claims 1 to 16, wherein the anisidine value of the fatty acid composition containing the PUFA or an ester derivative thereof is 15 or less, 10 or less, 5 or less, 1 or less, 0.7 or less, 0.5 or less, 0.3 or less, or 0.25 or less.
  18. The process according to any one of claims 1 to 17, wherein the residual amount of eluent in the fatty acid composition containing the PUFA or an ester derivative thereof is 100 ppm or less, 50 ppm or less, 10 ppm or less, 5 ppm or less, 1 ppm or less, 0.5 ppm or less, or 0.16 ppm or less.
  19. The process according to any one of claims 1 to 18, wherein the heating temperature for concentrating the fraction is a maximum temperature of 190°C or lower, 160°C or lower, 140°C or lower, 135°C or lower, 130°C or lower, 120°C or lower, or 100°C or lower, and/or 40°C or higher, 60°C or higher, 80°C or higher, 100°C or higher, 120°C or higher, 130°C or higher, 135°C or higher, 140°C or higher, or 160°C or higher.
  20. The process according to any one of claims 1 to 19, wherein the minimum pressure under reduced pressure when the fraction is concentrated is 100 Pa or less, 50 Pa or less, 20 Pa or less, 10 Pa or less, 5 Pa or less, 2 Pa or less, or 1 Pa or less, and/or 0.1 Pa or more, 0.2 Pa or more, 0.5 Pa or more, 1 Pa or more, 2 Pa or more, 5 Pa or more, or 10 Pa or more.

Description

TECHNICAL FIELD This disclosure relates to a fatty acid composition containing a polyunsaturated fatty acid (hereinafter also referred to as PUFA) or an ester derivative thereof, and a method for producing the same. BACKGROUND ART Polyunsaturated fatty acids or their ester derivatives are used as raw materials for pharmaceuticals, health foods, and cosmetics. Methods such as precision distillation, a silver nitrate complex method, and chromatography are known as processes for production to obtain high-purity polyunsaturated fatty acids or their ester derivatives for use in pharmaceuticals, health foods, and cosmetics from natural fats and oils (see, for example, PTL 1 to 4). On the other hand, there is a problem of alteration and/or deterioration of compositions containing polyunsaturated fatty acids or their ester derivatives. For example, PTL 1 describes the provision of a composition of PUFA or an ester derivative thereof having a dissolved oxygen amount, a peroxide value, an acid value, and an anisidine value that equal to or below certain values in order to solve the problem of preventing and/or delaying the progress of oxidation during the manufacturing process and during the storage period of the product. PTL 2 points out a risk that dissolved oxygen in an eluent can lead to alteration and/or deterioration of PUFA and the like when separating and purifying PUFAs or their ester derivatives by chromatography using an adsorption resin as a carrier, and describes that in order to prevent this risk, the eluent can be used through heating and refluxing or blowing of nitrogen or carbon dioxide gas into the eluent. Furthermore, PTL 3 describes the use of a channel-type agitator as a reaction vessel in a process for producing an ester derivative of PUFA using a silver salt solution, and describes carrying out the process under low-oxygen conditions to suppress the deterioration of the silver salt solution. PTL4 relates to an ester derivative purification of PUFA by chromatography, including simulated moving bed chromatography and the example describes "All chromatography operations are performed under an inert gas atmosphere while protected from light". CITATION LIST PATENT LITERATURE PTL 1: Japanese Patent Laid-Open No. 2017-114776PTL 2: Japanese Patent Laid-Open No. 61-291540PTL 3: Japanese Patent Laid-Open No. 2019-135307PTL 4: Japanese Translation of PCT International Application Publication No. 2017-502130 SUMMARY OF INVENTION TECHNICAL PROBLEM The present inventors have discovered a problem such that in the production of a fatty acid composition containing a polyunsaturated fatty acid or an ester derivative thereof, unless the dissolved oxygen in a mobile phase is suppressed, the oxygen concentration cannot be sufficiently reduced even when a fraction containing a polyunsaturated fatty acid or an ester derivative thereof obtained by chromatography is stored under an inert gas atmosphere in a container, resulting in alteration of the polyunsaturated fatty acid or an ester derivative thereof during solvent removal, particularly a problem of coloring. SOLUTION TO PROBLEM The present disclosure relates to providing a fatty acid composition containing a polyunsaturated fatty acid or an ester derivative thereof, in which alteration such as coloring is suppressed by the use of an eluent as a mobile phase obtained by placing it under an inert gas atmosphere in a container during chromatography for purifying the fatty acid mixture containing the polyunsaturated fatty acid or an ester derivative thereof. In one aspect of the present disclosure, the following method for producing a fatty acid composition containing a polyunsaturated fatty acid or an ester derivative thereof is provided. In one aspect of the present disclosure the following fatty acid composition containing a polyunsaturated fatty acid or an ester derivative thereof is provided. [1-1] A process for producing a fatty acid composition containing a polyunsaturated fatty acid (hereinafter also referred to as PUFA) or an ester derivative thereof, including: (1) storing a solvent in Container A to obtain an eluent under an inert gas atmosphere in Container A;(2) purifying a fatty acid mixture containing a PUFA or an ester derivative thereof by chromatography using the eluent as a mobile phase to obtain a fraction containing the PUFA or an ester derivative thereof; and(3) concentrating the fraction containing the PUFA or an ester derivative thereof to obtain a fatty acid composition containing the PUFA or an ester derivative thereof. [1-2] The process according to [1-1], wherein concentrating the fraction includes recovering, as a solvent, the eluent present in the fraction containing the PUFA or an ester derivative thereof by distillation under reduced pressure and/or heating. [1-3] The process according to [1-1] or [1-2], wherein the solvent contains a solvent obtained by distillation. [1-4] The process according to any one of [1-1] to [1-3], wherein th