WO2013099830A1 - 油脂組成物の製造方法 - Google Patents
油脂組成物の製造方法 Download PDFInfo
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- WO2013099830A1 WO2013099830A1 PCT/JP2012/083385 JP2012083385W WO2013099830A1 WO 2013099830 A1 WO2013099830 A1 WO 2013099830A1 JP 2012083385 W JP2012083385 W JP 2012083385W WO 2013099830 A1 WO2013099830 A1 WO 2013099830A1
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Classifications
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
- A23D9/013—Other fatty acid esters, e.g. phosphatides
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
- A23D9/04—Working-up
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0075—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of melting or solidifying points
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0083—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils with addition of auxiliary substances, e.g. cristallisation promotors, filter aids, melting point depressors
Definitions
- the present invention relates to a method for producing an oil / fat composition, and a solid-liquid fractionation method for the oil / fat composition.
- Japanese Unexamined Patent Publication No. 4-300826 Japanese Patent Laid-Open No. 10-176181 Japanese Patent Laid-Open No. 2002-20882
- the present invention includes the following steps (1) and (2): (1) A step of adding a polyglycerin fatty acid ester having an average degree of polymerization of glycerin of 20 or more to an oil and fat composition containing 40% by mass or more of diacylglycerol, followed by cooling. (2) A step of separating the crystals precipitated in the step from the liquid part, The manufacturing method of the refined fats and oils composition containing this is provided.
- the present invention also includes the following steps (1) and (2): (1) A step of adding a polyglycerin fatty acid ester having an average degree of polymerization of glycerin of 20 or more to an oil and fat composition containing 40% by mass or more of diacylglycerol, followed by cooling. (2) A step of separating the crystal precipitated from the step and the liquid part, The solid-liquid fractionation method of the oil-fat composition containing this is provided.
- Patent Document 3 has a problem in that the yield after fractionation is low, and a large amount of emulsifier is required, so that the flavor of fats and oils tends to decrease. Therefore, this invention relates to providing the method which can manufacture efficiently the fats and oils composition with the high diacylglycerol content with the favorable external appearance in normal temperature.
- the present inventors have found that if a polyglycerin fatty acid ester having a high degree of polymerization is added to an oil containing a high amount of diacylglycerol, the precipitated crystals can be easily and efficiently separated. Moreover, even if the fats and oils which passed through such a process precipitate a crystal
- an oil and fat composition having a high diacylglycerol content which can easily fractionate high melting point components of fats and oils and has a good appearance at room temperature with a high yield, can be produced.
- the method of this invention can reduce the usage-amount of an emulsifier.
- the oil and fat composition of the present invention contains 40% by mass (hereinafter referred to as “%”) or more of diacylglycerol, but from the viewpoint of physiological effects, it further contains 50% or more, further 55% or more, and further 60% or more. From the viewpoint of industrial productivity, it is preferably 98% or less, more preferably 95% or less, further 93% or less, and further preferably 92% or less. Further, it is preferably contained in an amount of 50 to 98%, further 55 to 95%, further 55 to 93%, and more preferably 60 to 92%.
- the “oil / fat” includes one or more of triacylglycerol, diacylglycerol, and monoacylglycerol.
- the fatty acid constituting the diacylglycerol is not particularly limited, and may be either a saturated fatty acid or an unsaturated fatty acid. However, from the point that the effect of the present invention is effectively exhibited, 0 to 20% is a saturated fatty acid. preferable.
- the content of the saturated fatty acid in the constituent fatty acid is preferably 1% or more, more preferably 2% or more from the viewpoint of appearance, and further 15% or less, and further 10% or less from the viewpoint of physiological effects. preferable. Further, it is preferably 0 to 15%, more preferably 2 to 10%.
- Saturated fatty acids having 14 to 24 carbon atoms, more preferably 16 to 22 carbon atoms are preferred.
- the content of unsaturated fatty acids in the fatty acids constituting diacylglycerol is preferably 80% or more, more preferably 85% or more, and more preferably 90% or more from the viewpoint of appearance and physiological effect. From the viewpoint of properties, it is preferably 100% or less, more preferably 99% or less, and further 98% or less. Further, it is preferably 80 to 100%, further 85 to 99%, and more preferably 90 to 98%.
- the number of carbon atoms of the unsaturated fatty acid is preferably 14 to 24, more preferably 16 to 22, from the viewpoint of physiological effects.
- the content of the trans unsaturated fatty acid is preferably 0.01 to 5%, more preferably 0.01 to 3.5%, and further 0.01 to 3%. It is preferable from the viewpoint of physiological effect and appearance.
- the content of triacylglycerol is preferably 0.1 to 60%, more preferably 1 to 60%, and further preferably 5 to 60% from the viewpoint of industrial productivity of fats and oils.
- the content of monoacylglycerol is preferably 5% or less, more preferably 0 to 2%, and further preferably 0.1 to 1.5% from the viewpoint of improving the flavor.
- the content of free fatty acid (salt) is preferably 3.5% or less, more preferably 0.01 to 1.5%, from the viewpoint of flavor and the like.
- An oil and fat composition containing a high amount of diacylglycerol can be obtained by an esterification reaction between a fatty acid derived from fat and oil and glycerin, a glycerolysis reaction between fat and oil and glycerin, or the like.
- These reactions are carried out by a chemical method using a chemical catalyst such as an alkali metal or an alloy thereof, an alkali metal or alkaline earth metal oxide, a hydroxide or an alkoxide having 1 to 3 carbon atoms, and an enzymatic method using an enzyme such as lipase. It is divided roughly into. Of these, it is preferable in terms of flavor and the like that the reaction is performed enzymatically using lipase or the like as a catalyst under mild conditions.
- any of vegetable oils and animal fats may be used.
- Specific raw materials include rapeseed oil (canola oil), sunflower oil, corn oil, soybean oil, sesame oil, rice oil, safflower oil, cottonseed oil, palm oil, palm oil, olive oil, grape oil, avocado oil, sesame oil Peanut oil, macadamia nut oil, hazelnut oil, walnut oil, lard, beef tallow, chicken oil, butter oil, fish oil and the like.
- rapeseed oil sunflower oil
- corn oil soybean oil
- sesame oil rice oil
- safflower oil cottonseed oil
- palm oil palm oil
- olive oil grape oil
- avocado oil, sesame oil Peanut oil, macadamia nut oil, hazelnut oil, walnut oil, lard, beef tallow, chicken oil, butter oil, fish oil and the like.
- those obtained by separating and mixing these oils and fats, and those prepared by adjusting the fatty acid composition by hydrogenation or transesterification can be used
- the polyglycerin fatty acid ester used in the present invention is obtained by esterifying polyglycerin and a fatty acid.
- the average polymerization degree of glycerin of the polyglycerin fatty acid ester is 20 or more, but it is preferably 22 or more from the viewpoint that the high melting point component of the oil can be efficiently separated, and from the same point, 50 or less, and further It is preferable that it is 45 or less. Further, it is preferably 20 to 50, more preferably 20 to 45, and still more preferably 22 to 45.
- the “average degree of polymerization of glycerin” refers to a value obtained by measuring the degree of polymerization of the polyglycerol part of the polyglycerol fatty acid ester by GPC.
- the fatty acid constituting the polyglycerol fatty acid ester is not particularly limited, and may be either a saturated fatty acid or an unsaturated fatty acid.
- the content of saturated fatty acid is preferably 20% or more, more preferably 20 to 100%, further 30 to 100%, further 40 to 100%, still more 50 to It is preferable that it is 100% from the point that the high melting-point component of fats and oils can be fractionated efficiently.
- Saturated fatty acids include those having 10 to 22 carbon atoms, preferably those having 12 to 18 carbon atoms, and more preferably those having 16 to 18 carbon atoms.
- the fatty acid constituting the polyglycerol fatty acid ester is more preferably a saturated fatty acid having 16 to 18 carbon atoms of 30 to 100%, and further preferably 50 to 100% from the same point as described above.
- the content of unsaturated fatty acid is preferably 80% or less, more preferably 0 to 75%, further 0 to 60%, still more 0 to 40%. It is preferable from the point that the high melting point component of fats and oils can be fractionated efficiently.
- unsaturated fatty acids include those having 14 to 24 carbon atoms, and those having 16 to 22 carbon atoms are preferred.
- the hydroxyl value of the polyglycerin fatty acid ester is preferably 80 mg-KOH / g or less, and more preferably 3 to 80 mg-KOH / g from the viewpoint of maintaining a good appearance.
- the hydroxyl value in the present invention refers to a value measured by the standard fat and oil test analysis method described in Examples.
- the amount of polyglycerin fatty acid ester used is preferably 1 ppm or more, more preferably 2 ppm or more, and further 5 ppm or more based on the fat or oil composition from the viewpoint of suppressing crystallization of diacylglycerol. Therefore, it is preferable to add at a ratio of 1,000 ppm or less, further 100 ppm or less, further 80 ppm or less, and further 60 ppm or less. Further, it is preferably added at a ratio of 1 to 1,000 ppm, further 1 to 100 ppm, further 2 to 80 ppm, and further 5 to 60 ppm. Two or more polyglycerol fatty acid esters may be used in combination.
- the amount of polyglycerol fatty acid ester used is 0.0001 parts by mass or more, further 0.0002 parts by mass or more, and further 0.0005 parts by mass with respect to 100 parts by mass of the oil or fat composition from the viewpoint of suppressing crystallization of diacylglycerol.
- it is preferably 10 parts by mass or less, further 0.1 parts by mass or less, further 0.01 parts by mass or less, further 0.008 parts by mass or less, and further 0.006 parts by mass. Part or less.
- the cooling temperature of the oil / fat composition may be any temperature at which the high melting point component crystallizes and precipitates, but is preferably ⁇ 3 ° C. or more, more preferably 0 ° C. preferable. Further, it is preferably in the range of -3 ° C to 20 ° C, more preferably 0 to 15 ° C. By cooling to such a temperature range, the high melting point component crystals can be grown to a size suitable for fractionation.
- the cooling time varies depending on the amount of raw material, cooling capacity, and the like, and may be appropriately selected depending on the composition of the oil and fat composition. In general, the cooling time is about 0.5 to 100 hours, preferably about 0.8 to 90 hours, and more preferably 1 to 80 hours.
- the method for separating the precipitated crystals from the liquid part after cooling is not particularly limited, and examples thereof include filtration, centrifugation, and sedimentation separation. It is preferable that the temperature at the time of fractionation is the same as that at the time of cooling the oil and fat composition.
- a high-melting-point component is separated and removed from the oil / fat composition, and a purified oil / fat composition containing a high concentration of diacylglycerol having a good appearance at room temperature is obtained.
- fats and oils having saturated fatty acids as constituent fatty acids can be preferably separated and removed as high melting point components, and fats and oils having saturated fatty acids having 14 to 24 carbon atoms are more preferably separated and removed. be able to.
- the yield (yield) of the purified fat composition from the fat composition is preferably 60% or more, more preferably 70% or more, and further 75% or more from the viewpoint of production efficiency.
- the content of diacylglycerol in the refined oil / fat composition is preferably 40% or more, more preferably 45% or more, and still more preferably 50% or more from the viewpoint of physiological effects and industrial productivity of the oil / fat.
- the upper limit is not particularly defined, but is preferably 99% or less, more preferably 98% or less, and still more preferably 97% or less, from the viewpoint of industrial productivity of fats and oils. Further, 40 to 99%, further 45 to 98%, and further 50 to 97% are preferable.
- the refined fat composition obtained by the production method of the present invention and the solid-liquid fractionation method is useful as a liquid fat because of its good appearance at room temperature.
- the liquid oil means an oil that is liquid at 20 ° C. when a cooling test is conducted according to the standard oil analysis test method 2.3.8-27.
- the refined fat composition of the present invention can be used in the same manner as general edible fats and oils, and can be widely applied to various foods and drinks using fats and oils.
- the present invention further discloses the following method.
- Next steps (1) and (2) (1) A step of adding a polyglycerin fatty acid ester having an average degree of polymerization of glycerin of 20 or more to an oil and fat composition containing 40% by mass or more of diacylglycerol, followed by cooling. (2) A step of separating the crystals precipitated in the step from the liquid part, The manufacturing method of the refined fats and oils composition containing this.
- the content of diacylglycerol in the oil and fat composition is preferably 50% by mass or more, more preferably 55% by mass or more, still more preferably 60% by mass or more, and preferably 98% by mass or less. Preferably it is 95% by mass or less, more preferably 93% by mass or less, still more preferably 92% by mass or less, more preferably 50 to 98% by mass, still more preferably 55 to 95% by mass, and still more preferably 55 to 95% by mass.
- the content of saturated fatty acid in the fatty acid constituting diacylglycerol is preferably 1% by mass or more, more preferably 2% by mass or more, and preferably 15% by mass or less, more preferably 10% by mass.
- the average degree of polymerization of glycerin in the polyglycerin fatty acid ester is preferably 22 or more, preferably 50 or less, more preferably 45 or less, and further preferably 20 to 50, still more preferably 20 45. More preferably, the method for producing a purified fat composition according to any one of ⁇ 1> to ⁇ 4>, which is 22 to 45.
- the content of saturated fatty acids is preferably 20% by mass or more, more preferably 20 to 100% by mass, still more preferably 30 to 100% by mass, and still more preferably 40%.
- the fatty acid constituting the polyglycerol fatty acid ester is preferably 30 to 100% by mass of a saturated fatty acid having 16 to 18 carbon atoms, more preferably 50 to 100% by mass of a saturated fatty acid having 16 to 18 carbon atoms.
- the addition amount of ⁇ 10> polyglycerol fatty acid ester is preferably 1 ppm or more, more preferably 2 ppm or more, still more preferably 5 ppm or more, and 1,000 ppm or less, preferably 100 ppm or less, based on the oil or fat composition.
- Preferably it is 80 ppm or less, more preferably 60 ppm or less, more preferably 1 to 1,000 ppm, more preferably 1 to 100 ppm, further preferably 2 to 80 ppm, and further preferably 5 to 60 ppm.
- the manufacturing method of the refined fats and oils composition in any one of ⁇ 9>.
- the amount of polyglycerin fatty acid ester added is preferably 0.0001 parts by mass or more, more preferably 0.0002 parts by mass or more, and still more preferably 0.0005 parts by mass or more with respect to 100 parts by mass of the oil or fat composition.
- preferably 10 parts by mass or less preferably 0.1 parts by mass or less, still more preferably 0.01 parts by mass or less, still more preferably 0.008 parts by mass or less, still more preferably 0.006 parts by mass.
- more preferably 0.0001 to 0.1 parts by mass still more preferably 0.0001 to 0.01 parts by mass, still more preferably 0.0002 to 0.008 parts by mass, and still more preferably 0.00.
- the method for producing a purified fat / oil composition according to any one of ⁇ 1> to ⁇ 9>, wherein the amount is from 0005 to 0.006 parts by mass.
- the cooling temperature of the ⁇ 12> fat composition is preferably ⁇ 3 ° C. or higher, more preferably 0 ° C.
- the method for producing a purified fat / oil composition according to any one of ⁇ 1> to ⁇ 11>, which is 20 ° C., more preferably 0 to 15 ° C. ⁇ 13>
- the content of diacylglycerol in the refined fat composition is preferably 40% by mass or more, more preferably 45% by mass or more, still more preferably 50% by mass or more, and preferably 99% by mass or less.
- Next steps (1) and (2) (1) A step of adding a polyglycerin fatty acid ester having an average degree of polymerization of glycerin of 20 or more to an oil and fat composition containing 40% by mass or more of diacylglycerol, followed by cooling. (2) A step of separating the crystal precipitated from the step and the liquid part, The solid-liquid fractionation method of fats and oils composition containing this.
- the content of diacylglycerol in the oil / fat composition is preferably 50% by mass or more, more preferably 55% by mass or more, still more preferably 60% by mass or more, and preferably 98% by mass or less.
- the solid-liquid fractionation method for an oil and fat composition according to ⁇ 14>, which is 93% by mass, more preferably 60 to 92% by mass.
- the content of the saturated fatty acid in the fatty acid constituting the diacylglycerol is preferably 1% by mass or more, more preferably 2% by mass or more, and preferably 15% by mass or less, more preferably 10% by mass.
- the solid-liquid fractionation method for oil and fat compositions according to ⁇ 14> or ⁇ 15> which is more preferably 0 to 15% by mass, and more preferably 2 to 10% by mass.
- the average degree of polymerization of glycerin in the polyglycerin fatty acid ester is preferably 22 or more, 50 or less, preferably 45 or less, more preferably 20 to 50, still more preferably 20 to 45, More preferably, the solid-liquid fractionation method of the oil and fat composition according to any one of ⁇ 14> to ⁇ 17>, which is 22 to 45.
- the content of saturated fatty acid is preferably 20% by mass or more, more preferably 20 to 100% by mass, still more preferably 30 to 100% by mass, and still more preferably 40%.
- the fatty acid constituting the polyglycerol fatty acid ester is preferably 30 to 100% by mass of a saturated fatty acid having 16 to 18 carbon atoms, more preferably 50 to 100% by mass of a saturated fatty acid having 16 to 18 carbon atoms. 14.
- ⁇ 22> The fat and oil composition according to any one of ⁇ 14> to ⁇ 21>, wherein the hydroxyl group value of the polyglycerol fatty acid ester is preferably 80 mg-KOH / g or less, more preferably 3 to 80 mg-KOH / g.
- the addition amount of ⁇ 23> polyglycerin fatty acid ester is preferably 1 ppm or more, more preferably 2 ppm or more, still more preferably 5 ppm or more, and 1,000 ppm or less, preferably 100 ppm or less, based on the oil or fat composition.
- the oil-and-fat composition is 80 ppm or less, more preferably 60 ppm or less, more preferably 1 to 1,000 ppm, further preferably 1 to 100 ppm, more preferably 2 to 80 ppm, and further preferably 5 to 60 ppm.
- the solid-liquid fractionation method of the oil-and-fat composition in any one.
- the addition amount of ⁇ 24> polyglycerin fatty acid ester is preferably 0.0001 parts by mass or more, more preferably 0.0002 parts by mass or more, and further preferably 0.0005 parts by mass or more with respect to 100 parts by mass of the oil or fat composition.
- preferably 10 parts by mass or less preferably 0.1 parts by mass or less, still more preferably 0.01 parts by mass or less, still more preferably 0.008 parts by mass or less, still more preferably 0.006 parts by mass.
- more preferably 0.0001 to 0.1 parts by mass still more preferably 0.0001 to 0.01 parts by mass, still more preferably 0.0002 to 0.008 parts by mass, and still more preferably 0.00.
- the method for solid-liquid fractionation of an oil or fat composition according to any one of ⁇ 14> to ⁇ 23>, wherein the content is 0005 to 0.006 parts by mass.
- the cooling temperature of the ⁇ 25> fat composition is preferably ⁇ 3 ° C. or higher, more preferably 0 ° C.
- (Ii) Fatty Acid Fatty Acid Composition About 10 mg of an oil and fat sample and 0.5 mL of a trimethylsilylating agent (“silylating agent TH”, manufactured by Kanto Chemical) were added to a glass sample bottle, sealed, and heated at 70 ° C. for 15 minutes. To this, 1.0 mL of water and 1.5 mL of hexane were added and shaken. After standing, the upper layer was analyzed by gas chromatography (GLC).
- silating agent TH a trimethylsilylating agent
- Acid value 5.611 ⁇ D ⁇ F2 / E (D: 0.1 mol / L potassium hydroxide-ethanol standard solution usage (ml), E: sampling amount (g), F2: 0.1 mol / L potassium hydroxide-ethanol standard solution factor)
- Fat and oil composition A 3000 g of fatty acid obtained by hydrolyzing rapeseed oil and 480 g of glycerin were mixed, and an esterification reaction was carried out using immobilized 1,3-position selective lipase (manufactured by Novoldisk Industries) as a catalyst. After the lipase preparation was filtered off, the reaction-finished product was subjected to molecular distillation, further decolorized and washed with water, and then deodorized at 235 ° C. for 1 hour to obtain a fat composition A containing a high amount of diacylglycerol (DAG).
- DAG diacylglycerol
- Fat and oil composition B 1000 g of fatty acid obtained by hydrolyzing sunflower oil and 155 g of glycerin were mixed, and an esterification reaction was carried out using immobilized 1,3-position selective lipase (manufactured by Novoldisk Industry) as a catalyst. After the lipase preparation was filtered off, the reaction-finished product was subjected to molecular distillation, further decolorized and washed with water, and then deodorized at 235 ° C. for 1 hour to obtain a fat composition B containing a high amount of diacylglycerol (DAG).
- Polyglycerin fatty acid ester As polyglycerin fatty acid esters, PGE1 to PGE5 (manufactured by Taiyo Kagaku Co., Ltd.) and decaglycerin fatty acid ester THL-15 (manufactured by Sakamoto Pharmaceutical Co., Ltd.) were used. The respective glycerin average polymerization degree, hydroxyl value, and fatty acid composition are shown in Table 2.
- Examples 1 to 9 and Comparative Examples 1 to 14 Polyglycerin fatty acid ester was added to the oil and fat composition A or B prepared above at the ratio shown in Table 3, and the whole was heated to 70 ° C. to make a uniform liquid state. Dispense 100 g into a centrifuge tube, leave it in a thermostatic bath at 3 ° C., 5 ° C., 8 ° C., or 10 ° C. for 3 days to cool, then precipitate the crystals at the same temperature and centrifuge at 3000 rpm for 20 minutes. The liquid part was collected respectively. The yield of the liquid part is shown in Table 3.
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Abstract
Description
(1)ジアシルグリセロールを40質量%以上含有する油脂組成物に、グリセリンの平均重合度が20以上であるポリグリセリン脂肪酸エステルを添加し、次いで冷却する工程、
(2)前記工程により析出した結晶を液体部より分離する工程、
を含む、精製油脂組成物の製造方法を提供するものである。
また、本発明は、次の工程(1)及び(2):
(1)ジアシルグリセロールを40質量%以上含有する油脂組成物に、グリセリンの平均重合度が20以上であるポリグリセリン脂肪酸エステルを添加し、次いで冷却する工程、
(2)前記工程により析出した結晶と液体部とを分離する工程、
を含む、油脂組成物の固液分別法を提供するものである。
したがって、本発明は、常温での外観が良好なジアシルグリセロール含有量の高い油脂組成物を、効率良く製造することのできる方法を提供することに関する。
ポリグリセリン脂肪酸エステルを構成する脂肪酸のうち、飽和脂肪酸の含有量は20%以上であることが好ましく、より好ましくは20~100%、更に30~100%、更に40~100%、より更に50~100%であることが、油脂の高融点成分を効率的に分別できるという点から好ましい。飽和脂肪酸としては、炭素数10~22のものが挙げられ、炭素数12~18のものが好ましく、炭素数16~18のものがより好ましい。ポリグリセリン脂肪酸エステルを構成する脂肪酸は、炭素数16~18の飽和脂肪酸が30~100%であることが更に好ましく、より更に50~100%であることが、上記と同様の点から好ましい。
冷却時間は、原料の量、冷却能力などによって異なり、油脂組成物の組成により適宜選択すればよい。一般的には、冷却時間は0.5~100時間、好ましくは0.8~90時間程度であり、より好ましくは1~80時間である。
本発明の精製油脂組成物は、一般の食用油脂と同様に使用でき、油脂を用いた各種飲食物に広範に適用することができる。
(1)ジアシルグリセロールを40質量%以上含有する油脂組成物に、グリセリンの平均重合度が20以上であるポリグリセリン脂肪酸エステルを添加し、次いで冷却する工程、
(2)前記工程により析出した結晶を液体部より分離する工程、
を含む、精製油脂組成物の製造方法。
<3>ジアシルグリセロールを構成する脂肪酸中の飽和脂肪酸の含有量が、好ましくは1質量%以上、より好ましくは2質量%以上であり、また、好ましくは15質量%以下、より好ましくは10質量%以下であり、また、更に好ましくは0~15質量%、更に好ましくは2~10質量%である<1>又は<2>に記載の精製油脂組成物の製造方法。
<4>飽和脂肪酸が、好ましくは炭素数14~24、より好ましくは炭素数16~22の飽和脂肪酸である<3>に記載の精製油脂組成物の製造方法。
<5>ポリグリセリン脂肪酸エステルのグリセリンの平均重合度が、好ましくは22以上であり、また、好ましくは50以下、より好ましくは45以下であり、また、更に好ましくは20~50、更に好ましくは20~45、更に好ましくは22~45である<1>~<4>のいずれかに記載の精製油脂組成物の製造方法。
<6>ポリグリセリン脂肪酸エステルを構成する脂肪酸のうち、飽和脂肪酸の含有量が、好ましくは20質量%以上、より好ましくは20~100質量%、更に好ましくは30~100質量%、更に好ましくは40~100質量%、更に好ましくは50~100質量%である<1>~<5>のいずれかに記載の精製油脂組成物の製造方法。
<7>飽和脂肪酸が、好ましくは炭素数10~22、より好ましくは炭素数12~18、更に好ましくは炭素数16~18の飽和脂肪酸である<6>に記載の精製油脂組成物の製造方法。
<8>ポリグリセリン脂肪酸エステルを構成する脂肪酸が、好ましくは炭素数16~18の飽和脂肪酸が30~100質量%、より好ましくは炭素数16~18の飽和脂肪酸が50~100質量%である<1>~<7>のいずれかに記載の精製油脂組成物の製造方法。
<9>ポリグリセリン脂肪酸エステルの水酸基価が、好ましくは80mg-KOH/g以下、より好ましくは3~80mg-KOH/gである<1>~<8>のいずれかに記載の精製油脂組成物の製造方法。
<10>ポリグリセリン脂肪酸エステルの添加量が、油脂組成物に対して好ましくは1ppm以上、より好ましくは2ppm以上、更に好ましくは5ppm以上であり、また、1,000ppm以下、好ましくは100ppm以下、より好ましくは80ppm以下、更に好ましくは60ppm以下であり、また、更に好ましくは1~1,000ppm、更に好ましくは1~100ppm、更に好ましくは2~80ppm、更に好ましくは5~60ppmである<1>~<9>のいずれかに記載の精製油脂組成物の製造方法。
<11>ポリグリセリン脂肪酸エステルの添加量が、油脂組成物100質量部に対して、好ましくは0.0001質量部以上、より好ましくは0.0002質量部以上、更に好ましくは0.0005質量部以上であり、また、好ましくは10質量部以下、より好ましくは0.1質量部以下、更に好ましくは0.01質量部以下、更に好ましくは0.008質量部以下、更に好ましくは0.006質量部以下であり、また、更に好ましくは0.0001~0.1質量部、更に好ましくは0.0001~0.01質量部、更に好ましくは0.0002~0.008質量部、更に好ましくは0.0005~0.006質量部である<1>~<9>のいずれかに記載の精製油脂組成物の製造方法。
<12>油脂組成物の冷却温度が、好ましくは-3℃以上、より好ましくは0℃以上であり、また、20℃以下、好ましくは15℃以下であり、また、更に好ましくは-3℃~20℃、更に好ましくは0~15℃である<1>~<11>のいずれかに記載の精製油脂組成物の製造方法。
<13>精製油脂組成物中のジアシルグリセロールの含有量が、好ましくは40質量%以上、より好ましくは45質量%以上、更に好ましくは50質量%以上であり、また、好ましくは99質量%以下、より好ましくは98質量%以下、より好ましくは97質量%以下であり、また、更に好ましくは40~99質量%、更に好ましくは45~98質量%、更に好ましくは50~97質量%である<1>~<12>のいずれかに記載の精製油脂組成物の製造方法。
(1)ジアシルグリセロールを40質量%以上含有する油脂組成物に、グリセリンの平均重合度が20以上であるポリグリセリン脂肪酸エステルを添加し、次いで冷却する工程、
(2)前記工程により析出した結晶と液体部とを分離する工程、
を含む、油脂組成物の固液分別法。
<15>油脂組成物中のジアシルグリセロールの含有量が、好ましくは50質量%以上、より好ましくは55質量%以上、更に好ましくは60質量%以上であり、また、好ましくは98質量%以下、より好ましくは95質量%以下、より好ましくは93質量%以下、更に好ましくは92質量%以下であり、また、更に好ましくは50~98質量%、更に好ましくは55~95質量%、更に好ましくは55~93質量%、更に好ましくは60~92質量%である<14>に記載の油脂組成物の固液分別法。
<16>ジアシルグリセロールを構成する脂肪酸中の飽和脂肪酸の含有量が、好ましくは1質量%以上、より好ましくは2質量%以上であり、また、好ましくは15質量%以下、より好ましくは10質量%以下であり、また、更に好ましくは0~15質量%、更に好ましくは2~10質量%である<14>又は<15>に記載の油脂組成物の固液分別法。
<17>飽和脂肪酸が、好ましくは炭素数14~24、より好ましくは炭素数16~22の飽和脂肪酸である<16>に記載の油脂組成物の固液分別法。
<18>ポリグリセリン脂肪酸エステルのグリセリンの平均重合度が、好ましくは22以上であり、また、50以下、好ましくは45以下であり、また、更に好ましくは20~50、更に好ましくは20~45、更に好ましくは22~45である<14>~<17>のいずれかに記載の油脂組成物の固液分別法。
<19>ポリグリセリン脂肪酸エステルを構成する脂肪酸のうち、飽和脂肪酸の含有量が、好ましくは20質量%以上、より好ましくは20~100質量%、更に好ましくは30~100質量%、更に好ましくは40~100質量%、更に好ましくは50~100質量%である<14>~<18>のいずれかに記載の油脂組成物の固液分別法。
<20>飽和脂肪酸が、好ましくは炭素数10~22、より好ましくは炭素数12~18、更に好ましくは炭素数16~18の飽和脂肪酸である<19>に記載の油脂組成物の固液分別法。
<21>ポリグリセリン脂肪酸エステルを構成する脂肪酸が、好ましくは炭素数16~18の飽和脂肪酸が30~100質量%、より好ましくは炭素数16~18の飽和脂肪酸が50~100質量%である<14>~<20>のいずれかに記載の油脂組成物の固液分別法。
<22>ポリグリセリン脂肪酸エステルの水酸基価が、好ましくは80mg-KOH/g以下、より好ましくは3~80mg-KOH/gである<14>~<21>のいずれかに記載の油脂組成物の固液分別法。
<23>ポリグリセリン脂肪酸エステルの添加量が、油脂組成物に対して好ましくは1ppm以上、より好ましくは2ppm以上、更に好ましくは5ppm以上であり、また、1,000ppm以下、好ましくは100ppm以下、より好ましくは80ppm以下、更に好ましくは60ppm以下であり、また、更に好ましくは1~1,000ppm、更に好ましくは1~100ppm、更に好ましくは2~80ppm、更に好ましくは5~60ppmである<14>~<22>のいずれかに記載の油脂組成物の固液分別法。
<24>ポリグリセリン脂肪酸エステルの添加量が、油脂組成物100質量部に対して、好ましくは0.0001質量部以上、より好ましくは0.0002質量部以上、更に好ましくは0.0005質量部以上であり、また、好ましくは10質量部以下、より好ましくは0.1質量部以下、更に好ましくは0.01質量部以下、更に好ましくは0.008質量部以下、更に好ましくは0.006質量部以下であり、また、更に好ましくは0.0001~0.1質量部、更に好ましくは0.0001~0.01質量部、更に好ましくは0.0002~0.008質量部、更に好ましくは0.0005~0.006質量部である<14>~<23>のいずれかに記載の油脂組成物の固液分別法。
<25>油脂組成物の冷却温度が、好ましくは-3℃以上、より好ましくは0℃以上であり、また、20℃以下、好ましくは15℃以下であり、また、更に好ましくは-3℃~20℃、更に好ましくは0~15℃である<14>~<24>のいずれかに記載の油脂組成物の固液分別法。
(i)油脂の構成脂肪酸組成
日本油化学会編「基準油脂分析試験法」中の「脂肪酸メチルエステルの調製法(2.4.1.-1996)」に従って脂肪酸メチルエステルを調製し、得られたサンプルを、American Oil Chemists. Society Official Method Ce 1f-96(GLC法)により測定した。
ガラス製サンプル瓶に、油脂サンプル約10mgとトリメチルシリル化剤(「シリル化剤TH」、関東化学製)0.5mLを加え、密栓し、70℃で15分間加熱した。これに水1.0mLとヘキサン1.5mLを加え、振とうした。静置後、上層をガスクロマトグラフィー(GLC)に供して分析した。
<GLC条件>
(条件)
装置:アジレント6890シリーズ(アジレントテクノジー社製)
インテグレーター:ケミステーションB 02.01 SR2(アジレントテクノジー社製)
カラム:DB-1ht(Agilent J&W社製)
キャリアガス:1.0mL He/min
インジェクター:Split(1:50)、T=340℃
ディテクター:FID、T=350℃
オーブン温度:80℃から10℃/分で340℃まで昇温、15分間保持
日本油化学会編「基準油脂分析試験法2003年版」中の「ヒドロキシル価(ピリジン無水酢酸法 2.3.6.2-1996)」に従い、水酸基価を分析した。25gの無水酢酸を100mLのメスフラスコに入れ、ピリジンを標線まで加えて混合し、アセチル化試薬とした。首長の丸底フラスコにサンプル約5gを計量し、アセチル化試薬5mlを加え、フラスコの首に小さな漏斗をのせ、フラスコの底部を加熱浴に約1cmの深さに沈めて95~100℃に加熱した。1時間後、加熱浴からフラスコを取り出し冷却し、漏斗から1mlの蒸留水を加え、再度加熱浴に入れ10分間加熱した。再び常温まで冷却し、漏斗やフラスコの首に凝縮した液を5mlの中性エタノールでフラスコ内に洗い流し、0.5mol/L水酸化カリウム-エタノール標準液でフェノールフタレイン指示薬を用いて未反応のアセチル化試薬の加水分解産物を滴定した。なお、本試験と並行して空試験を行い、滴定結果から下記の式をもとに算出した値を「水酸基価(mg-KOH/g)」(OHV)とした。
水酸基価=(A-B)×28.05×F1/C+酸価
(A:空試験の0.5mol/L水酸化カリウム-エタノール標準液使用量(ml)、B:本試験の0.5mol/L水酸化カリウム-エタノール標準液使用量(ml)、F1:0.5mol/L水酸化カリウム-エタノール標準液のファクター、C:試料採取量(g))
酸価については、日本油化学会編「基準油脂分析試験法2003年版」中の「酸価(2.3.1-1996)」に従い、三角フラスコにサンプル約5gを計量し、エタノール:酢酸エチル=1:1の溶媒を100mL加え溶解した。0.1mol/L水酸化カリウム-エタノール標準液でフェノールフタレイン指示薬を用いて滴定し、滴定結果から下記の式をもとに算出した値を「酸価(mg-KOH/g)」とした。
酸価=5.611×D×F2/E
(D:0.1mol/L水酸化カリウム-エタノール標準液使用量(ml)、E:試料採取量(g)、F2:0.1mol/L水酸化カリウム-エタノール標準液のファクター)
阪本薬品工業株式会社発行「ポリグリセリンエステル(P75)」記載の方法にて、ポリグリセリン脂肪酸エステルをKOH-エタノールでケン化分解し、希硫酸でpHを4に調整した後、ヘキサンで脂肪酸部を抽出した。水層はpHを7に調整した後、メタノールで脱塩処理をし、ポリグリセリン部を得た。得られたポリグリセリン部はグリセリン平均重合度の分析に、脂肪酸部は構成脂肪酸の分析に供した。
ポリグリセリンを、カラムはTSK2500PWXL(東ソー(株))、溶媒は蒸留水(トリフルオロ酢酸を0.1%添加)、流量は1mL/min、検出器はRID、温度40℃、注入量50μLの条件でGPCにより分析した。ポリエチレングリコールで検量線を作成し、ポリエチレングリコール換算のポリグリセリンの重量平均分子量(Mw2)、グリセリンの重量平均分子量(Mw1)を測定した。次にグリセリンの換算係数(F)を次式(1)により算出した。
F=92/Mw1 (1)
(式中、F=グリセリンの換算係数、Mw1=グリセリンの重量平均分子量)
ポリグリセリンの「グリセリン平均重合度」は、上記で求めた重量平均分子量(Mw2)から、次式(2)により求めた。
n=(Mw2×F-18)/74 (2)
(式中、n=グリセリン重量平均重合度、F=グリセリンの換算係数、Mw2=ポリグリセリン重量平均分子量)
油脂の構成脂肪酸組成と同様の方法により測定した。
次式により、本発明の製造方法、並びに固液分別法により得られた精製油脂組成物の収率(%)を算出した。
精製油脂組成物の質量/油脂組成物の質量×100 (%)
油脂組成物A:菜種油を加水分解して得た脂肪酸3000gとグリセリン480gとを混合し、固定化1,3位選択リパーゼ(ノボルディスクインダストリー社製)を触媒としてエステル化反応を行った。リパーゼ製剤を濾別した後、反応終了品を分子蒸留し、更に脱色、水洗した後、235℃にて1時間脱臭してジアシルグリセロール(DAG)高含有の油脂組成物Aを得た。
表1に油脂組成物A及びBのグリセリド組成、脂肪酸組成を示す。
ポリグリセリン脂肪酸エステルとして、PGE1~PGE5(太陽化学(株)製)、デカグリセリン脂肪酸エステルTHL―15(阪本薬品工業(株)製)を用いた。それぞれのグリセリン平均重合度、水酸基価、脂肪酸組成を表2に示す。
上記で調製した油脂組成物A又はBに、表3に示す割合でポリグリセリン脂肪酸エステルを添加し、70℃まで加熱し全体を均一な液状とした。遠心管に100g分注し、3℃,5℃,8℃又は10℃の恒温槽に3日間静置し冷却した後、析出した結晶を同じ温度で回転数3000r/min、20分間遠心分離し、それぞれ液体部を回収した。液体部の収率を表3に示す。
〔結晶の有無の評価基準〕
3:完全に溶解し、清澄
2:僅かな結晶の残存
1:溶け残りが目立つ
これに対し、比較例では、析出した結晶を分別できないか、或いは分別できてもその収率は低いものであった。
Claims (7)
- 次の工程(1)及び(2):
(1)ジアシルグリセロールを40質量%以上含有する油脂組成物に、グリセリンの平均重合度が20以上であるポリグリセリン脂肪酸エステルを添加し、次いで冷却する工程、
(2)前記工程により析出した結晶を液体部より分離する工程、
を含む、精製油脂組成物の製造方法。 - グリセリンの平均重合度が20以上であるポリグリセリン脂肪酸エステルの添加量が、油脂組成物に対し1~1,000ppmである、請求項1記載の精製油脂組成物の製造方法。
- グリセリンの平均重合度が20以上であるポリグリセリン脂肪酸エステルの添加量が、油脂組成物に対し1~100ppmである、請求項1記載の精製油脂組成物の製造方法。
- グリセリンの平均重合度が20以上であるポリグリセリン脂肪酸エステルの添加量が、油脂組成物100質量部に対し0.0001~0.1質量部である、請求項1記載の精製油脂組成物の製造方法。
- グリセリンの平均重合度が20以上であるポリグリセリン脂肪酸エステルの添加量が、油脂組成物100質量部に対し0.0001~0.01質量部である、請求項1記載の精製油脂組成物の製造方法。
- ポリグリセリン脂肪酸エステルを構成する脂肪酸のうち、飽和脂肪酸の含有量が20質量%以上である、請求項1~5のいずれか1項に記載の精製油脂組成物の製造方法。
- 次の工程(1)及び(2):
(1)ジアシルグリセロールを40質量%以上含有する油脂組成物に、グリセリンの平均重合度が20以上であるポリグリセリン脂肪酸エステルを添加し、次いで冷却する工程、
(2)前記工程により析出した結晶と液体部とを分離する工程、
を含む、油脂組成物の固液分別法。
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JP2004067998A (ja) * | 2002-06-14 | 2004-03-04 | Kao Corp | 脂肪酸の製造法 |
JP2004189965A (ja) * | 2002-12-13 | 2004-07-08 | Taiyo Kagaku Co Ltd | フライ用油脂組成物、フライ用油脂結晶成長抑制剤 |
JP2005146098A (ja) * | 2003-11-14 | 2005-06-09 | Kao Corp | 脂肪酸の製造方法 |
WO2008053838A1 (fr) * | 2006-10-31 | 2008-05-08 | Sakamoto Yakuhin Kogyo Co., Ltd. | Agent de modification du fractionnement pour la graisse |
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JP2995855B2 (ja) * | 1989-11-28 | 1999-12-27 | 三菱化学株式会社 | 油中水型乳化物および保水性改善剤 |
US6004611A (en) | 1996-10-18 | 1999-12-21 | Kao Corporation | General-purpose oils composition |
US20080069932A1 (en) * | 2004-04-28 | 2008-03-20 | Kao Corporation | Oil or Fat Composition |
JP4815427B2 (ja) | 2007-12-28 | 2011-11-16 | 花王株式会社 | 油脂組成物 |
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JPH04300826A (ja) | 1991-03-28 | 1992-10-23 | Kao Corp | 体重増加抑制剤 |
JPH10176181A (ja) | 1996-10-18 | 1998-06-30 | Kao Corp | 液状汎用型油脂組成物 |
JP2002020782A (ja) | 2000-07-13 | 2002-01-23 | Kao Corp | 油脂組成物の固液分別法 |
JP2004067998A (ja) * | 2002-06-14 | 2004-03-04 | Kao Corp | 脂肪酸の製造法 |
JP2004043702A (ja) * | 2002-07-15 | 2004-02-12 | Kao Corp | 油脂類の製造法 |
JP2004189965A (ja) * | 2002-12-13 | 2004-07-08 | Taiyo Kagaku Co Ltd | フライ用油脂組成物、フライ用油脂結晶成長抑制剤 |
JP2005146098A (ja) * | 2003-11-14 | 2005-06-09 | Kao Corp | 脂肪酸の製造方法 |
WO2008053838A1 (fr) * | 2006-10-31 | 2008-05-08 | Sakamoto Yakuhin Kogyo Co., Ltd. | Agent de modification du fractionnement pour la graisse |
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TW201332451A (zh) | 2013-08-16 |
JP5816075B2 (ja) | 2015-11-17 |
EP2799532B1 (en) | 2018-06-27 |
US20150030750A1 (en) | 2015-01-29 |
EP2799532A4 (en) | 2015-08-12 |
EP2799532A1 (en) | 2014-11-05 |
CN104053761A (zh) | 2014-09-17 |
JP2013136676A (ja) | 2013-07-11 |
TWI572289B (zh) | 2017-03-01 |
CN104053761B (zh) | 2017-02-22 |
US10231468B2 (en) | 2019-03-19 |
KR101946672B1 (ko) | 2019-02-11 |
KR20140116384A (ko) | 2014-10-02 |
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