Continuous process of oxidative cleavage of vegetable oils
US-9790160-B2 · Oct 17, 2017 · US
US9296977B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9296977-B2 |
| Application number | US-201314382204-A |
| Country | US |
| Kind code | B2 |
| Filing date | Feb 28, 2013 |
| Priority date | Feb 29, 2012 |
| Publication date | Mar 29, 2016 |
| Grant date | Mar 29, 2016 |
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Provided is a method for producing a fatty acid composition having a low content of saturated fatty acid easily and with a high yield from a decomposed fatty acid composition containing monoacylglycerol. The method for producing a fatty acid composition having the content of saturated fatty acid of 8% by mass or less, comprising the following steps (1) to (3): (1) obtaining a fatty acid mixture by adjusting the component ratio of a decomposed fatty acid composition obtained by hydrolyzing a fat or oil so that the content of fatty acid is from 80 to 96% by mass, the content of monoacylglycerol is from 0.3 to 8% by mass, the content of diacylglycerol is from 1 to 12% by mass, and the mass ratio of diacylglycerol to monoacylglycerol [ (DAG)/(MAG)] is from 0.5 to 40; (2) cooling the fatty acid mixture obtained in step (1) to a temperature within the range from the temperature 2° C. lower than the cloud point of the fatty acid mixture to the temperature 13° C. lower than the cloud point, then mixing an aqueous wetting agent solution therewith, and maintaining the temperature of the mixture within the above-mentioned range; and (3) separating the solid phase precipitated in step (2) and the aqueous phase from the liquid oil phase, thereby obtaining the fatty acid composition in the form of a liquid oil phase.
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The invention claimed is: 1. A method for producing a fatty acid composition having a content of saturated fatty acid of 8% by mass or less, comprising: (1) providing a fatty acid mixture by adjusting the component ratio of a decomposed fatty acid composition, wherein said decomposed fatty acid composition is obtained by hydrolyzing a fat or oil without performing distillation of the decomposed fatty acid composition, so that in said fatty acid mixture the content of fatty acid is from 80 to 96% by mass, the content of monoacylglycerol is from 0.3 to 8% by mass, the content of diacylglycerol is from 1 to 12% by mass, and the mass ratio of diacylglycerol to monoacylglycerol [(DAG)/(MAG)] is from 0.5 to 40; (2) cooling the fatty acid mixture from (1) to a temperature within the range from a temperature that is 4° C. lower than the cloud point of the fatty acid mixture to a temperature that is 10° C. lower than the cloud point of the fatty acid mixture, then mixing an aqueous wetting agent solution therewith, and maintaining the temperature of the mixture within the above-mentioned range thereby providing a final fatty acid mixture comprising a precipitated solid phase, an aqueous phase, and a liquid oil phase; and (3) separating the solid phase from the final fatty acid mixture (2) and the aqueous phase from the liquid oil phase, thereby obtaining the fatty acid composition in the form of a liquid oil phase. 2. The method for producing a fatty acid composition of claim 1 , wherein the content of monoacylglycerol in the fatty acid mixture of said (1) providing is from 0.4 to 5.5% by mass. 3. The method for producing a fatty acid composition of claim 1 , wherein the content of monoacylglycerol in the fatty acid mixture of said (1) providing is from 0.6 to 4% by mass. 4. The method for producing a fatty acid composition of claim 1 , wherein the content of diacylglycerol in the fatty acid mixture of said (1) providing is from 2.5 to 10% by mass. 5. The method for producing a fatty acid composition of claim 1 , wherein the content of diacylglycerol in the fatty acid mixture of said (1) providing is from 3 to 9% by mass. 6. The method for producing a fatty acid composition of claim 1 , wherein the mass ratio of diacylglycerol to monoacylglycerol [(DAG)/(MAG)] is from 1 to 9. 7. The method for producing a fatty acid composition of claim 1 , wherein the mass ratio of diacylglycerol to monoacylglycerol [(DAG)/(MAG)] is from 1.1 to 7. 8. The method for producing a fatty acid composition of claim 1 , wherein saturated fatty acid accounts for 20% by mass or less of fatty acids constituting the fat or oil. 9. The method for producing a fatty acid composition of claim 1 , wherein the fat or oil is an undeodorized fat or oil. 10. The method for producing a fatty acid composition of claim 1 , wherein the amount of the aqueous wetting agent solution of said (2) cooling is from 50 to 400 parts by mass relative to 100 parts by mass of the fatty acid mixture. 11. The method for producing a fatty acid composition of claim 1 , wherein the aqueous wetting agent solution is an aqueous solution comprising a surfactant and an inorganic electrolyte. 12. The method for producing a fatty acid composition of claim 11 , wherein the surfactant is an anionic surfactant. 13. The method for producing a fatty acid composition of claim 11 , wherein the inorganic electrolyte is selected from the group consisting of sodium chloride, sodium sulfate, magnesium sulfate, and aluminum sulfate. 14. The method for producing a fatty acid composition of claim 1 , wherein the aqueous wetting agent solution of said cooling comprises a freezing-point depressant selected from the group consisting of glycerol and ethylene glycol. 15. The method for producing a fatty acid composition of claim 1 , wherein the temperature of the fatty acid mixture is maintained within the range from the temperature 4° C. lower than the cloud point of the fatty acid mixture to the temperature 10° C. lower than the cloud point for 5 to 180 minutes during said (2) cooling. 16. The method for producing a fatty acid composition of claim 1 , wherein the viscosity of the final fatty acid mixture of said (2) cooling is from 30 to 3000 mPa·s. 17. The method for producing a fatty acid composition of claim 1 , wherein the viscosity of the final fatty acid mixture of said (2) cooling is from 50 to 2000 mPa·s. 18. The method for producing a fatty acid composition of claim 1 , wherein the fatty acid composition obtained of said (3) separating comprises a total content of diacylglycerol and monoacylglycerol of from 1.5% by mass to 19% by mass. 19. The method for producing a fatty acid composition of claim 1 , wherein the fatty acid composition obtained of said (3) separating comprises a total content of diacylglycerol and monoacylglycerol of from 4% by mass to 12% by mass. 20. A method for reducing the amount of saturated fatty acid in a fatty acid composition comprising: (1) providing a fatty acid mixture by adjusting the component ratio of a decomposed fatty acid composition, wherein said decomposed fatty acid composition is obtained by hydrolyzing a fat or oil without performing distillation of the decomposed fatty acid composition, so that in said fatty acid mixture the content of fatty acid is from 80 to 96% by mass, the content of monoacylglycerol is from 0.3 to 8% by mass, the content of diacylglycerol is from 1 to 12% by mass, and the mass ratio of diacylglycerol to monoacylglycerol [(DAG)/(MAG)] is from 0.5 to 40; (2) cooling the fatty acid mixture obtained from (1) to a temperature within the range from a temperature that is 4° C. lower than the cloud point of the fatty acid mixture to a temperature that is 10° C. lower than the cloud point of the fatty acid mixture, then mixing an aqueous wetting agent solution therewith, and maintaining the temperature of the mixture within the above-mentioned range thereby providing a final fatty acid mixture comprising a precipitated solid phase, an aqueous phase, and a liquid oil phase; and (3) separating the solid phase from the final fatty acid mixture (2) and the aqueous phase from the liquid oil phase, thereby obtaining the fatty acid composition in the form of a liquid oil phase. 21. The method for reducing the amount of saturated fatty acid in the fatty acid composition of claim 20 , wherein the content of diacylglycerol in the fatty acid mixture of said (1) providing is from 2.5 to 10% by mass. 22. The method for reducing the amount of saturated fatty acid in the fatty acid composition of claim 20 , wherein the content of diacylglycerol in the fatty acid mixture of said (1) providing is from 3 to 9% by mass. 23. The method for producing a fatty acid composition of claim 1 , wherein said (2) cooling the fatty acid mixture from (1) is to a temperature within the range from a temperature that is 4° C. lower than the cloud point of the fatty acid mixture to a temperature that is 8° C. lower than the cloud point of the fatty acid mixture. 24. The method for reducing the amount of saturated fatty acid in the fatty acid composition of claim 20 , wherein said (2) cooling the fatty acid mixture from (1) is to a temperature within the range from a temperature that is 4° C. lower than the cloud point of the fatty acid mixture to a temperature that is 8° C. lower than the cloud point of the fatty acid mixture.
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