Granted Patent
B2
US 12,331,015 · App. 18/164,765 · Granted Jun 17, 2025
Highly unsaturated fatty acid or highly unsaturated fatty acid ethyl ester with reduced environmental pollutants, and method for producing same
Inventors:
Nobushige Doisaki (Tokyo, JP); Kazuhiko Hata (Ibaraki, JP); Shinji Tokiwa (Ibaraki, JP); Kazunori Matsushima (Tokyo, JP)
Assignee:
NISSUI CORPORATION
C07C51/44B01D3/143C07C51/47C07C57/03C07C67/03C07C67/54C07C67/56C07C69/587C11B3/12C11C1/04C11C3/003A23D9/02A23L33/115A61K31/20A61K31/202A61K31/232B01D15/325C11B3/16
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Abstract
A highly unsaturated fatty acid or a highly unsaturated fatty acid ethyl ester that has been produced using as a feedstock oil a fat or oil that contains highly unsaturated fatty acids as constituent fatty acids and which has been reduced in the contents of environmental pollutants, wherein among the dioxins contained, polychlorinated dibenzoparadioxins (PCDDs) and polychlorinated dibenzofurans (PCDFs) are contained in amounts of less than 0.05 pg-TEQ/g and coplanar PCBs (Co-PCBs) in amounts of less than 0.03 pg-TEQ/g. Also disclosed is a method for producing the highly unsaturated fatty acid or highly unsaturated fatty acid ethyl ester by the steps of removing free fatty acids and environmental pollutants by thin-film distillation from a feedstock oil, ethyl esterifying the resulting fat or oil, and refining the same by rectification and column chromatography.
Claims (21)
1. A method of producing a highly unsaturated fatty acid ethyl ester with reduced contents of polychlorinated dibenzoparadioxins (PCDDs), polychlorinated dibenzofurans (PCDFs) and coplanar PCB (Co-PCBs), the method comprising the steps of:
a) removing free fatty acids and environmental pollutants by thin-film distillation from a feedstock oil derived from a marine product, the feedstock oil containing highly unsaturated fatty acids as constituent fatty acids, and the highly unsaturated fatty acids containing at least 18 carbon atoms and at least 3 double bonds;
b) ethyl esterifying the highly unsaturated fatty acids present as constituent of fat or oil contained in the product of step (a);
c) refining the product of step (b) by rectification and column chromatography, wherein a concentration of the highly unsaturated fatty acid ethyl ester in the sum of fatty acid ethyl esters is at least 80area %.
2. The method according to claim 1 , wherein amount of a brominated flame retardant in the highly unsaturated fatty acid or the highly unsaturated fatty acid ethyl ester is also reduced.
3. The method according to claim 1 , wherein the concentration of the highly unsaturated fatty acid ethyl ester in the sum of fatty acid ethyl esters is at least 85area %.
4. The method according to claim 1 , wherein the feedstock oil containing highly unsaturated fatty acids as constituent fatty acids is fish oil, krill oil, marine mammal oil or microorganism oil.
5. The method according to claim 1 , wherein the thin-film distillation is carried out at a temperature of 200-270° C.
6. The method according to claim 1 , wherein the thin-film distillation is carried out at a pressure of 5 Pa or lower.
7. The method according to claim 1 , wherein the thin-film distillation is carried out at a flow rate of 20-200 (kg/h)/m 2 .
8. The method according to claim 1 , wherein the thin-film distillation is molecular distillation or short path distillation.
9. The method according to claim 1 , wherein rectification is performed in three or more distillation columns.
10. The method according to claim 1 , wherein refining by column chromatography uses column chromatography of reverse-phase distribution type.
11. The method according to claim 1 , wherein in step (c) the concentration of the highly unsaturated fatty acid ethyl ester in the sum of fatty acid ethyl esters is at least 90 area %.
12. The method according to claim 1 , wherein in step (c) the concentration of the highly unsaturated fatty acid ethyl ester in the sum of fatty acid ethyl esters is at least 95 area %.
13. The method according to claim 1 , wherein in step (c) the concentration of the highly unsaturated fatty acid ethyl ester in the sum of fatty acid ethyl esters is at least 80 area % and at most 97 area %.
14. A method of producing a highly unsaturated fatty acid with reduced contents of polychlorinated dibenzoparadioxins (PCDDs), polychlorinated dibenzofurans (PCDFs) and coplanar PCB (Co-PCBs), the method comprising the steps of:
a) removing free fatty acids and environmental pollutants by thin-film distillation from a feedstock oil derived from a marine product, the feedstock oil containing highly unsaturated fatty acids as constituent fatty acids, and the highly unsaturated fatty acids containing at least 18 carbon atoms and at least 3 double bonds;
b) ethyl esterifying the highly unsaturated fatty acids present as constituent of fat or oil contained in the product of step (a);
c) refining the product of step (b) by rectification and column chromatography, wherein a concentration of the highly unsaturated fatty acid ethyl ester in the sum of fatty acid ethyl esters is at least 80area %; and
d) producing the highly unsaturated fatty acid by hydrolyzing the highly unsaturated fatty acid ethyl ester of step (c).
Assignments (2)
CHANGE OF NAME
Recorded Aug 22, 2023
From: NIPPON SUISAN KAISHA, LTD.
To: NISSUI CORPORATION
Reel/Frame 064664/0323 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Feb 6, 2023
From: DOISAKI, NOBUSHIGE; HATA, KAZUHIKO; TOKIWA, SHINJI; MATSUSHIMA, KAZUNORI
To: NIPPON SUISAN KAISHA, LTD.
Reel/Frame 062600/0149 →
Priority Claims (1)
JP 2012-110809
· May 14, 2012
· national
Continuity (5)
Division
14400652
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