Oil or fat composition production method

Abstract

[Problem] To provide an oil or fat composition production method that can efficiently separate a liquid fraction containing an XOX-type triglyceride by efficiently removing an XXX-type triglyceride from a material oil or fat. [Solution] An oil or fat composition production method according to the present invention is for producing an oil or fat composition containing an XOX-type triglyceride having saturated fatty acid residues at positions 1 and 3 and an oleyl group at position 2. The method is characterized by comprising a step for, while lowering the temperature of a molten-state material oil or fat containing the XOX-type triglyceride and an XXX-type triglyceride having saturated fatty acid residues at positions 1, 2, and 3, adding a seed agent containing the XXX-type triglyceride and crystallizing the XXX-type triglyceride, and a step for obtaining a liquid fraction containing the XOX-type triglyceride by removing a crystal fraction that contains the XXX-type triglyceride crystallized from the material oil or fat. The method is characterized in that the amount of the XXX-type triglyceride contained in the liquid fraction is 75% or less with respect to the amount of the XXX-type triglyceride contained in the material oil or fat.

Description

Method for producing oil and fat composition

[0001] The present invention relates to a method for producing an oil or fat composition, and more particularly to a method for producing an oil or fat composition rich in XOX triglycerides by dry fractionation.

[0002] Hard butters, including cocoa butter, are widely used in foods such as chocolate-based confectionery and bread, as well as in pharmaceuticals and cosmetics. These hard butters are primarily composed of triglycerides having one unsaturated bond in the molecule, such as XOX triglycerides having saturated fatty acid residues at positions 1 and 3 and an oleoyl group at position 2. Generally, such triglycerides can be obtained from natural fats and oils containing this component, such as palm oil, shea butter, monkey fat, and illipe fat, or fractionated oils thereof.

[0003] As a method for obtaining fats and oils containing the above-mentioned triglycerides, fat and oil fractionation methods such as solvent fractionation and dry fractionation have been widely used. The above-mentioned solvent fractionation method has long been used effectively for fractionation into crystalline fraction and liquid fraction, but since it requires the use of large amounts of organic solvents such as hexane and acetone, it is necessary to handle them with great care from the viewpoint of safety and hygiene. In addition, it is necessary to remove the solvent from each fraction after fractionation, which consumes a large amount of energy, resulting in an increase in production costs. Therefore, in recent years, dry fractionation methods, which are highly safe and cost-effective, have been widely studied.

[0004] Dry fractionation is a method in which raw oils and fats that have been completely melted by heating without using an organic solvent are cooled while being stirred in a crystallization tank to precipitate crystals (crystallization), and then the resulting mixture is fractionated into a crystalline fraction and a liquid fraction by squeezing or filtration. Dry fractionation is preferable to solvent fractionation from the standpoint of safety, but has problems such as lower solid-liquid separability between the crystalline fraction and the liquid fraction than solvent fractionation, making it difficult to remove the liquid fraction entrapped in the crystalline fraction.

[0005] In response to the above problems, Patent Document 1 proposes a dry fractionation of fats and oils to obtain SUS-rich fats and oils with an SUS content of 60% by weight or more from SUS-containing fats and oils with an SUS content of 30% by weight or more by stirring crystallization and squeeze filtration. This involves adding 5 to 200 ppm by weight of crystalline S3 components to the SUS-containing fat and oil at a temperature 0 to 2°C higher than the cloud point of the SUS-containing fat and oil, mixing, and stirring to crystallize (SUS: 2-unsaturated, 1,3-disaturated glyceride; S3: 3-saturated triglyceride; S: saturated fatty acid with 16 to 22 carbon atoms; U: unsaturated fatty acid with 18 carbon atoms). Furthermore, Patent Document 2 proposes a method for producing triglycerides rich in XOX fats and oils, which comprises heating and dissolving triglycerides containing 20 to 60 mass% of triglycerides having saturated fatty acid residues at the 1- and 3-positions and an oleoyl group at the 2-position (XOX fat and oil) in the presence of 1 to 30 mass% of a fatty acid lower alkyl ester, followed by cooling to crystallize and performing solid-liquid separation. Furthermore, Patent Document 3 proposes a dry fractionation method using fractionated palm oil or its interesterified oil as a raw material oil and fat, the dry fractionation method comprising the steps of blending and dissolving an oil and fat composition containing the raw material oil and fat so that the ratio of trisaturated triglycerides to triglycerides in the oil and fat composition is 1.5% by weight or more and 3.5% by weight or less and the ratio of dipalmitin monostearin to the trisaturated triglycerides contained in the oil and fat composition is 20% by weight or more, and subsequently crystallizing the dissolved oil and fat composition and separating it into a crystalline fraction and a liquid fraction, thereby obtaining the liquid fraction having an iodine value of 66 or more.

[0006] International Publication No. 2018 / 097118 International Publication No. 2009 / 031680 Patent No. 4091099

[0007] However, there remains a need for the development of a method for producing an oil and fat composition rich in XOX triglycerides, from which XXX triglycerides have been sufficiently removed by dry fractionation.

[0008] Therefore, an object of the present invention is to provide a method for producing an oil or fat composition that can efficiently remove XXX triglycerides from raw oil or fat and efficiently separate a liquid fraction containing XOX triglycerides.

[0009] The present inventors have conducted extensive research to solve the above problems. As a result, they have found that the above problems can be solved by adding a specific seed agent to a raw material fat or oil during a temperature-lowering process from a molten state. This has led to the completion of the present invention.

[0010] That is, the present invention provides the following: [1] A method for producing an oil or fat composition containing an XOX triglyceride having saturated fatty acid residues at positions 1 and 3 and an oleoyl group at position 2, comprising the steps of: adding a seed agent containing an XXX triglyceride while cooling a raw oil or fat containing an XOX triglyceride and an XXX triglyceride having saturated fatty acid residues at positions 1, 2, and 3 from a molten state to crystallize the XXX triglyceride; and removing a crystalline fraction containing the XXX triglyceride crystallized from the raw oil or fat to obtain a liquid fraction containing an XOX triglyceride, wherein the content of the XXX triglyceride in the liquid fraction is 75% or less of the content of the XXX triglyceride in the raw oil or fat. [2] The production method according to [1], wherein the amount of XXX triglycerides supplied by the addition of the seed agent is 0.0005% by mass or more and 1.0% by mass or less relative to the raw oil / fat. [3] The production method according to [1] or [2], wherein the amount of the seed agent added is 0.001% by mass or more and 2.0% by mass or less relative to the raw oil / fat, and the content of XXX triglycerides in the seed agent is 10% by mass or more and 99% by mass or less. [4] The production method according to any of [1] to [3], wherein the temperature when the seed agent is added is lower than the melting temperature of XXX triglycerides and higher than the melting temperature of XOX triglycerides. [5] The production method according to any of [1] to [4], wherein the temperature when the seed agent is added is 3.0 to 20°C higher than the cloud point of the raw oil / fat. [6] The production method according to any one of [1] to [5], wherein the content of XOX triglycerides in the raw oil or fat is 40% by mass or more and 90% by mass or less, and the content of XXX triglycerides in the raw oil or fat is 1.0% by mass or more and 10% by mass or less. [7] The production method according to any one of [1] to [6], wherein the content of XOX triglycerides in the liquid fraction is 40% by mass or more and 95% by mass or less, and the content of XXX triglycerides in the liquid fraction is 0.1% by mass or more and 7.5% by mass or less.[8] The production method according to any one of [1] to [7], wherein the XOX triglycerides in the raw oil or fat comprise SOS triglycerides having stearoyl groups at positions 1 and 3 and an oleoyl group at position 2. [9] The production method according to any one of [1] to [8], wherein the XXX triglycerides in the raw oil or fat comprise SSS triglycerides having stearoyl groups at positions 1, 2, and 3.

[10] The production method according to any one of [1] to [9], wherein the XXX triglycerides in the seed agent comprise SSS triglycerides having stearoyl groups at positions 1, 2, and 3.

[11] The production method according to

[10] , wherein the SSS triglycerides in the seed agent have β-type crystalline polymorphism.

[12] The production method according to any one of [1] to

[11] , wherein the mass ratio of the liquid fraction to the raw oil or fat is 90.0% or more when the content of XXX triglycerides in the raw oil or fat is 1.0% by mass or more but less than 3.0% by mass, and 80.0% or more when the content of XXX triglycerides in the raw oil or fat is 3.0% by mass or more but less than 10% by mass.

[13] The production method according to any one of [1] to

[12] , wherein the temperature-lowering treatment is carried out under conditions of 0.5°C / hour or more and 60°C / hour or less.

[0011] According to the present invention, it is possible to provide a method for producing an oil or fat composition, which can efficiently remove XXX triglycerides from raw oil or fat and efficiently separate a liquid fraction containing XOX triglycerides.

[0012] [Definition] In the present invention, a triglyceride in an oil or fat has a structure in which one molecule of glycerol is linked to three molecules of fatty acid residues via ester bonds. The 1st, 2nd, and 3rd positions of a triglyceride refer to the positions where the fatty acid residues are bonded.

[0013] In the present invention, the saturated fatty acid residue (X) has 16 or more carbon atoms, preferably 16 to 24, more preferably 16 to 22, even more preferably 16 to 20, and even more preferably 16 to 18. In the case of XXX triglycerides having saturated fatty acid residues at positions 1, 2, and 3 and XOX triglycerides having saturated fatty acid residues at positions 1 and 3 and an oleoyl group at position 2, X may be the same saturated fatty acid residue or different saturated fatty acid residues. Specific examples of saturated fatty acid residue X include palmitic acid (P, 16), stearic acid (S, 18), arachidic acid (20), behenic acid (22), and lignoceric acid (24). The above numerical notations refer to the number of carbon atoms of the fatty acid residue.

[0014] [Method for producing an oil / fat composition] The method for producing an oil / fat composition of the present invention is a method for producing an oil / fat composition containing XOX triglycerides, and comprises the steps of: a step of adding a seed agent containing XXX triglycerides to a raw oil / fat containing XOX triglycerides and XXX triglycerides while cooling the raw oil / fat from a molten state to crystallize the XXX triglycerides (crystallization step); and a step of removing a crystalline fraction containing the XXX triglycerides crystallized from the raw oil / fat to obtain a liquid fraction containing XOX triglycerides (solid-liquid separation step).

[0015] (Raw material oil and fat) The raw material oil and fat used in the crystallization step contains XOX triglycerides and XXX triglycerides. The content of XOX triglycerides in the raw material oil and fat is preferably 40% by mass or more, more preferably 45% by mass or more, even more preferably 50% by mass or more, and preferably 90% by mass or less, more preferably 85% by mass or less, and even more preferably 80% by mass or less. In a preferred embodiment of the present invention, the content of XOX triglycerides in the raw material oil and fat is preferably 40% by mass or more and 90% by mass or less, more preferably 45% by mass or more and 85% by mass or less, and even more preferably 50% by mass or more and 80% by mass or less. If the content of XOX triglycerides in the raw material oil and fat is within the above numerical range, an oil and fat composition rich in XOX triglycerides can be easily obtained.

[0016] The content of XXX triglycerides in the raw oil or fat is preferably 1.0% by mass or more, more preferably 1.5% by mass or more, even more preferably 2.0% by mass or more, and preferably 10% by mass or less, more preferably 9.5% by mass or less, and even more preferably 9.0% by mass or less. In a preferred embodiment of the present invention, the content of XXX triglycerides in the raw oil or fat is preferably 1.0% by mass or more and 10% by mass or less, more preferably 1.5% by mass or more and 9.5% by mass or less, and even more preferably 2.0% by mass or more and 9.0% by mass or less. If the content of XXX triglycerides in the raw oil or fat is within the above numerical range, the addition of a seed agent makes it easier to crystallize the XXX triglycerides, and therefore makes it easier to remove the crystalline fraction containing XXX triglycerides.

[0017] In a preferred embodiment of the present invention, the XOX triglycerides in the raw oil and fat preferably include an SOS triglyceride having stearoyl groups at positions 1 and 3 and an oleoyl group at position 2. The content of SOS triglycerides in the raw oil and fat is preferably 30% by mass or more, more preferably 35% by mass or more, even more preferably 40% by mass or more, and preferably 80% by mass or less, more preferably 75% by mass or less, and even more preferably 70% by mass or less. In a preferred embodiment of the present invention, the content of SOS triglycerides in the raw oil and fat is preferably 30% by mass or more and 80% by mass or less, more preferably 35% by mass or more and 75% by mass or less, and even more preferably 40% by mass or more and 70% by mass or less. If the content of SOS triglycerides in the raw oil and fat is within the above numerical range, an oil and fat composition rich in SOS triglycerides can be easily obtained.

[0018] The XXX triglycerides in the raw oil / fat preferably include SSS triglycerides having stearoyl groups at positions 1, 2, and 3. The content of SSS triglycerides in the raw oil / fat is preferably 0.5% by mass or more, more preferably 1.0% by mass or more, even more preferably 1.5% by mass or more, and preferably 9.0% by mass or less, more preferably 8.5% by mass or less, and even more preferably 8.0% by mass or less. In a preferred embodiment of the present invention, the content of SSS triglycerides in the raw oil / fat is preferably 0.5% by mass or more and 9.0% by mass or less, more preferably 1.0% by mass or more and 8.5% by mass or less, and even more preferably 1.5% by mass or more and 8.0% by mass or less. If the content of SSS triglycerides in the raw oil or fat is within the above numerical range, the addition of a seed agent makes it easier to crystallize the SSS triglycerides, making it easier to remove the crystalline fraction containing SSS triglycerides.

[0019] The method for producing the above-mentioned raw oil and fat is not particularly limited, and can be produced by a conventionally known method. For example, it can be produced by the following method. (1) A fatty acid lower alkyl ester (including the case where the fatty acid itself is used) is added to an oil and fat containing a triglyceride having an oleoyl group at the 2-position, and a transesterification reaction is carried out. Examples of oils and fats containing a triglyceride having an oleoyl group at the 2-position include trioleoylglycerin, a low-melting point fraction of shea butter, high oleic sunflower oil, high oleic low-linolenic rapeseed oil, high oleic safflower oil, palm oil, and palm fractionated oil. As the fatty acid lower alkyl ester, a lower alcohol ester of a saturated fatty acid having 16 to 24 carbon atoms is preferred, a lower alcohol ester of a saturated fatty acid having 16 to 22 carbon atoms is more preferred, a lower alcohol ester of a saturated fatty acid having 16 to 20 carbon atoms is even more preferred, and a lower alcohol ester of a saturated fatty acid having 16 to 18 carbon atoms is even more preferred. As the lower alcohol, an alcohol having 1 to 6 carbon atoms is preferred, with methanol, ethanol, and isopropyl alcohol being more preferred, and ethanol being even more preferred. The transesterification reaction is preferably an enzymatic transesterification reaction catalyzed by a conventionally known 1,3-selective lipase. Examples of 1,3-selective lipases include Rhizopus lipase, Aspergillus lipase, Mucor lipase, pancreatic lipase, and rice bran lipase. As the 1,3-selective lipase, commercially available formulated products can also be used. For example, Amano Enzyme's Lipase DF "Amano" 15-K (also known as Lipase D), Novozymes' Lipozyme RMIM, and Lipozyme TLIM can be used to carry out the 1,3-selective transesterification reaction. In the transesterification reaction, the molar ratio of the triglyceride having an oleoyl group at position 2 to the fatty acid lower alkyl ester is preferably 1 / 2 or less, and particularly preferably 1 / 2 to 1 / 30. In the transesterification reaction, either a continuous reaction system or a batch reaction system can be used.For example, in a batch reaction system, the amount of lipase added is preferably 0.01 to 10 parts by mass, more preferably 0.01 to 2 parts by mass, and even more preferably 0.1 to 1.5 parts by mass per 100 parts by mass of fat or oil. Conventional known conditions can be used for the esterification reaction. For example, the reaction temperature is preferably 35°C to 100°C, more preferably 35°C to 80°C, and even more preferably 40°C to 60°C, and the reaction time is preferably 0.1 to 50 hours, more preferably 0.5 to 30 hours, and even more preferably 1 to 20 hours. (2) The transesterified oil obtained by the transesterification reaction is filtered to remove the lipase, thereby obtaining a reacted oil. The conditions for the filtration are not particularly limited, and conventionally known filtration methods can be used. (3) The reacted oil is distilled to remove unreacted raw materials and by-products such as oleic acid and their lower alkyl esters, thereby obtaining a raw material fat or oil. The distillation conditions are not particularly limited, and any conventionally known distillation method can be used. For example, the distillation temperature is preferably 100° C. or higher and 300° C. or lower, more preferably 120° C. or higher and 250° C. or lower.

[0020] (Seed Agent) The seed agent used in the crystallization step contains XXX triglycerides. The amount of XXX triglycerides supplied by the addition of the seed agent is preferably 0.0005% by mass or more, more preferably 0.001% by mass or more, even more preferably 0.002% by mass or more, still more preferably 0.004% by mass or more, and preferably 1.0% by mass or less, more preferably 0.7% by mass or less, even more preferably 0.6% by mass or less, and even more preferably 0.5% by mass or less, relative to the raw oil or fat. In a preferred embodiment of the present invention, the amount of XXX triglycerides supplied by the addition of the seed agent is preferably 0.0005% by mass or more and 1.0% by mass or less, more preferably 0.001% by mass or more and 0.7% by mass or less, even more preferably 0.002% by mass or more and 0.6% by mass or less, and even more preferably 0.004% by mass or more and 0.5% by mass or less, relative to the raw oil or fat. If the amount of XXX triglyceride supplied by adding a seed agent is within the above numerical range, the addition of the seed agent will cause nuclei of XXX triglycerides to form in the raw oil or fat, making it easier to crystallize the XXX triglycerides, and therefore making it easier to remove the crystalline fraction containing the XXX triglycerides.

[0021] The amount of seed agent added is preferably 0.001% by mass or more, more preferably 0.002% by mass or more, even more preferably 0.005% by mass or more, still more preferably 0.01% by mass or more, and preferably 2.0% by mass or less, more preferably 1.0% by mass or less, even more preferably 0.7% by mass or less, and still more preferably 0.5% by mass or less, relative to the raw oil or fat. In a preferred embodiment of the present invention, the amount of seed agent added is preferably 0.001% by mass or more and 2.0% by mass or less, more preferably 0.002% by mass or more and 1.0% by mass or less, even more preferably 0.005% by mass or more and 0.7% by mass or less, and still more preferably 0.01% by mass or more and 0.5% by mass or less, relative to the raw oil or fat. If the amount of seed agent added is within the above numerical range, the addition of the seed agent will cause nuclei of XXX triglycerides to form in the raw oil or fat, making it easier to crystallize the XXX triglycerides, and therefore making it easier to remove the crystalline fraction containing the XXX triglycerides.

[0022] The content of XXX triglycerides in the seed agent is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 20% by mass or more, still more preferably 25% by mass or more, and preferably 99% by mass or less, more preferably 98% by mass or less, even more preferably 97% by mass or less, and even more preferably 95% by mass or less. In a preferred embodiment of the present invention, the content of XXX triglycerides in the seed agent is preferably 10% by mass or more and 99% by mass or less, more preferably 15% by mass or more and 98% by mass or less, even more preferably 20% by mass or more and 97% by mass or less, and even more preferably 25% by mass or more and 95% by mass or less. If the content of XXX triglycerides in the seed agent is within the above-mentioned numerical range, the addition of the seed agent produces XXX triglyceride nuclei in the raw oil or fat, facilitating crystallization of XXX triglycerides, and thus facilitating removal of the crystalline fraction containing XXX triglycerides.

[0023] The XXX triglycerides in the seed agent preferably contain SSS triglycerides having stearoyl groups at the 1st, 2nd, and 3rd positions. In particular, in order to facilitate the formation of SSS triglyceride nuclei in the raw oil or fat, the SSS triglycerides in the seed agent preferably have a β-type crystalline polymorph. The content of SSS triglycerides in the XXX triglycerides is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, still more preferably 80% by mass or more, and preferably 99% by mass or less, more preferably 95% by mass or less, even more preferably 92% by mass or less, and still more preferably 90% by mass or less. In a preferred embodiment of the present invention, the content of SSS triglycerides in the XXX triglycerides in the seed agent is preferably 50% by mass or more and 99% by mass or less, more preferably 60% by mass or more and 95% by mass or less, even more preferably 70% by mass or more and 92% by mass or less, and even more preferably 80% by mass or more and 90% by mass or less.

[0024] (Crystallization step) In the crystallization step, the raw material oil or fat is first heated to a molten state. The heating temperature is preferably 50°C or higher and 90°C or lower, more preferably 55°C or higher and 85°C or lower, and even more preferably 60°C or higher and 80°C or lower.

[0025] Next, the molten raw oil and fat is subjected to a temperature-lowering treatment. The temperature after the temperature-lowering may be any temperature at which the XXX triglycerides in the raw oil and fat crystallize. The temperature after the temperature-lowering is preferably lower than the cloud point of the raw oil and fat, and is preferably 0.1 to 10°C lower than the cloud point of the raw oil and fat, more preferably 0.1 to 8.0°C lower, more preferably 0.1 to 7.0°C lower, and even more preferably 0.1 to 6.0°C lower. If the temperature after the temperature-lowering is within the above numerical range, the XXX triglycerides in the raw oil and fat can be efficiently crystallized.

[0026] The temperature-lowering rate is not particularly limited, but is preferably 0.5° C. / hour to 60° C. / hour, more preferably 1.0° C. / hour to 50° C. / hour, and even more preferably 2.0° C. / hour to 40° C. / hour. If the temperature-lowering rate is within the above range, the time required for the crystallization step can be shortened, and the productivity of the oil or fat composition can be improved.

[0027] The seed agent is added during the temperature-lowering treatment of the raw oil or fat. The temperature-lowering treatment may be continued or interrupted when the seed agent is added. The temperature when the seed agent is added is preferably lower than the melting temperature of the XXX triglycerides and higher than the melting temperature of the XOX triglycerides. A temperature lower than the melting temperature of the XXX triglycerides prevents the seed agent containing the XXX triglycerides from melting, making it easier for it to function as a nucleus for crystallization. Furthermore, a temperature higher than the melting temperature of the XOX triglycerides allows the seed agent to be added before the crystallization of the XOX triglycerides, making it easier for it to function as a nucleus for crystallization.

[0028] When adding a seed agent to a raw fat or oil in the crystallization process, it can be added as is, or a seed dispersion in which the seed agent is dispersed in the raw fat or oil can be used. For example, the seed dispersion can be prepared by adding 0.5 to 20 mass% of the seed agent to a raw fat or oil whose temperature has been adjusted to the temperature at which the seed agent is added, and then performing high-speed stirring for 5 minutes using a high-speed disperser. Note that the preparation procedure for the seed dispersion is not limited to the above example.

[0029] The temperature at the time of addition of the seed agent is preferably 3.0 to 20° C. higher than the cloud point of the raw oil or fat, more preferably 3.5 to 18° C. higher, more preferably 4.0 to 16° C. higher, and even more preferably 4.5 to 15° C. higher. When the temperature at the time of addition of the seed agent is higher than the cloud point of the raw oil or fat by the above-mentioned numerical value, the seed agent can be added before the crystallization of triglycerides in the raw oil or fat, and the seed agent can easily function as a crystallization nucleus.

[0030] The crystallization time from the start of the temperature-lowering treatment to the start of the solid-liquid separation step is not particularly limited, as long as it is a time that allows sufficient crystallization of the XXX triglycerides in the raw oil and fat. The crystallization time is preferably 0.5 hours or more and 24 hours or less, more preferably 1.0 hours or more and 12 hours or less, even more preferably 1.5 hours or more and 10 hours or less, and even more preferably 2.0 hours or more and 8.0 hours or less. If the crystallization time is within the above numerical range, the XXX triglycerides in the raw oil and fat can be efficiently crystallized, thereby improving the productivity of the oil and fat composition. The retention time after reaching the final temperature after temperature reduction is not particularly limited, as long as it is a time that allows sufficient crystallization of the XXX triglycerides in the raw oil and fat. The retention time is preferably 0.1 hours or more and 24 hours or less, more preferably 0.2 hours or more and 10 hours or less, even more preferably 0.3 hours or more and 5 hours or less, and even more preferably 0.5 hours or more and 3.0 hours or less. If the retention time is within the above range, the XXX triglycerides in the raw material oil and fat can be efficiently crystallized, thereby improving the productivity of the oil and fat composition.

[0031] (Solid-liquid separation step) The solid-liquid separation step is a step of removing a crystalline fraction containing XXX triglycerides crystallized from the raw oil or fat to obtain a liquid fraction containing XOX triglycerides. The separation method for removing the crystalline fraction from the raw oil or fat to obtain the liquid fraction is not particularly limited, and a conventionally known solid-liquid separation method can be used.

[0032] In the present invention, the content of XXX triglycerides in the liquid fraction is 75% or less, preferably 60% or less, and more preferably 50% or less, of the content of XXX triglycerides in the raw oil or fat. If the content of XXX triglycerides in the liquid fraction is 75% or less of the content of XXX triglycerides in the raw oil or fat, the object of the present invention, which is to efficiently remove XXX triglycerides from the raw oil or fat, can be achieved.

[0033] The content of XOX triglycerides in the liquid fraction is preferably 40% by mass or more, more preferably 45% by mass or more, even more preferably 50% by mass or more, and preferably 95% by mass or less, more preferably 90% by mass or less, and even more preferably 85% by mass or less. In a preferred embodiment of the present invention, the content of XOX triglycerides in the liquid fraction is preferably 40% by mass or more and 95% by mass or less, more preferably 45% by mass or more and 90% by mass or less, and even more preferably 50% by mass or more and 85% by mass or less. The content of XOX triglycerides in the liquid fraction is preferably 0.97 to 1.1 times the content of XOX triglycerides in the raw oil or fat. If the content of XOX triglycerides in the liquid fraction is within the above numerical range, a liquid fraction rich in XOX triglycerides can be obtained.

[0034] The content of XXX triglycerides in the liquid fraction is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, even more preferably 0.3% by mass or more, even more preferably 0.5% by mass or more, and preferably 7.5% by mass or less, more preferably 5.0% by mass or less, even more preferably 4.0% by mass or less, and even more preferably 3.0% by mass or less. In a preferred embodiment of the present invention, the content of XXX triglycerides in the liquid fraction is preferably 0.1% by mass or more and 7.5% by mass or less, more preferably 0.2% by mass or more and 5.0% by mass or less, even more preferably 0.3% by mass or more and 4.0% by mass or less, and even more preferably 0.5% by mass or more and 3.0% by mass or less. If the content of XXX triglycerides in the liquid fraction is within the above numerical range, the XXX triglycerides can be removed from the raw oil or fat by adding a seed agent, thereby obtaining a liquid fraction with a reduced XXX triglyceride content.

[0035] The mass ratio (yield) of the liquid fraction to the raw oil / fat is preferably 90.0% or more, more preferably 91.0% or more, and even more preferably 92.0% or more when the content of XXX triglycerides in the raw oil / fat is 1.0% by mass or more and less than 3.0% by mass. Furthermore, the yield is preferably 80.0% or more, more preferably 81.0% or more, and even more preferably 82.0% or more when the content of XXX triglycerides in the raw oil / fat is 3.0% by mass or more and 10% by mass or less. If the yield is within the above numerical range, the object of the present invention of efficiently removing XXX triglycerides from the raw oil / fat and efficiently separating a liquid fraction containing XOX triglycerides can be achieved.

[0036] The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to the contents of the following examples. In the examples and comparative examples, "%" is based on mass unless otherwise specified.

[0037] <Analysis> (Triglyceride content) The content of each triglyceride in the raw oil / fat, seed agent, and fractionated fractions was measured by gas chromatography (in accordance with AOCS Ce5-86). The content of each triglyceride is shown in Tables 1 and 2. (XOX triglyceride content) The XOX / X2O ratio was analyzed using a silver ion column-HPLC method (in accordance with J. High Resol. Chromatogr., 18, 105-107 (1995)). The contents of XOX and SOS triglycerides were calculated based on the following formula. The calculation results are shown in Table 2. XOX triglyceride content = X2O triglyceride content × (XOX / X2O ratio) SOS triglyceride content = S2O triglyceride content × (XOX / X2O ratio) (Fatty acid ethyl ester content) The fatty acid ethyl ester content in the raw material oil or fat was measured by gas chromatography. The fatty acid ethyl ester content indicates the mass % of fatty acid ethyl esters in all components. The content of each fatty acid ethyl ester is shown in Table 1. (Cloud point) The cloud point of the raw oils and fats was measured in accordance with Standard Testing Methods for Analysis of Fats, Oils and Related Materials (2.2.7-2013), compiled by the Japan Oil Chemists' Society. The cloud point of each raw oil and fat is shown in Table 1. (Iodine value: Wiess-cyclohexane method) The iodine value (Wiess-cyclohexane method) of the raw oil and fats was measured in accordance with Standard Testing Methods for Analysis of Fats, Oils and Related Materials (2.3.4.1-2013), compiled by the Japan Oil Chemists' Society. (Yield) The yield of the liquid fraction was calculated based on the following formula. The calculation results are shown in Table 2. Yield (%) = (Iodine value of raw oil and fat - Iodine value of crystalline fraction) / (Iodine value of liquid fraction - Iodine value of crystalline fraction) x 100 (Residual liquid rate) The residual liquid rate was calculated based on the following formula. The calculation results are shown in Table 2. Residual liquid rate (%) = SO2 content of crystalline fraction / SO2 content of liquid fraction x 100 When the same raw material is used, a lower residual liquid ratio indicates that the crystal fraction and the filtrate fraction are separated more efficiently.

[0038] <Production of Raw Oil 1> High oleic sunflower oil was mixed with stearic acid ethyl ester, and a transesterification reaction was carried out using a lipase preparation with 1,3-position specificity as a catalyst. Subsequently, distillation was carried out to completely remove the fatty acid ethyl esters, yielding Raw Oil 1 (XXX triglyceride content: 2.1%, SSS triglyceride content: 1.6%, XOX triglyceride content: 52.7%, SOS triglyceride content: 41.5%, SO2 triglyceride content: 27.0%, fatty acid ethyl ester content: 0%).

[0039] <Production of Raw Oil 2> A transesterification reaction was carried out in the same manner as in the production of Raw Oil 1. Then, distillation was carried out to obtain Raw Oil 2 (XXX triglyceride content: 2.2%, SSS triglyceride content: 1.6%, XOX triglyceride content: 53.1%, SOS triglyceride content: 41.9%, SO2 triglyceride content: 26.6%, fatty acid ethyl ester content: 6%).

[0040] <Production of Raw Oil 3> A transesterification reaction was carried out in the same manner as in the production of Raw Oil 1. Then, distillation was carried out to obtain Raw Oil 3 (XXX triglyceride content: 2.4%, SSS triglyceride content: 1.8%, XOX triglyceride content: 52.6%, SOS triglyceride content: 41.5%, SO2 triglyceride content: 26.0%, fatty acid ethyl ester content: 10%).

[0041] <Production of Raw Oil 4> Raw oil 4 (XXX triglyceride content: 2.6%, SSS triglyceride content: 1.9%, XOX triglyceride content: 54.5%, SOS triglyceride content: 43.0%, SO2 triglyceride content: 24.8%, fatty acid ethyl ester content: 0%) was obtained in the same manner as in the production of Raw Oil 1.

[0042] <Production of Raw Oil 5> Raw oil 1 was mixed with stearic acid ethyl ester and subjected to transesterification using a lipase preparation having 1,3-position specificity as a catalyst. Subsequently, distillation was carried out to completely remove the fatty acid ethyl esters, yielding Raw Oil 5 (XXX triglyceride content: 8.9%, SSS triglyceride content: 7.1%, XOX triglyceride content: 75.9%, SOS triglyceride content: 64.1%, SO2 triglyceride content: 6.8%, fatty acid ethyl ester content: 0%).

[0043] <Production of Raw Oil 6> Raw oil 6 (XXX triglyceride content: 2.7%, SSS triglyceride content: 2.0%, XOX triglyceride content: 53.8%, SOS triglyceride content: 43.1%, SO2 triglyceride content: 26.1%, fatty acid ethyl ester content: 4%) was obtained in the same manner as in the production of Raw Oil 1.

[0044] <Production of Raw Oil 7> Raw oil 7 (XXX triglyceride content: 4.2%, SSS triglyceride content: 3.2%, XOX triglyceride content: 82.7%, SOS triglyceride content: 69.5%, SO2 triglyceride content: 5.8%, fatty acid ethyl ester content: 0%) was obtained in the same manner as in the production of Raw Oil 5.

[0045] <Production of Seed Agent A> Solid part A was obtained in the same manner as in Example 2 of Patent Document 2, in which solid part 2-1 was obtained. The obtained solid part A was then distilled to completely remove fatty acid ethyl esters, thereby obtaining oil A (XXX triglyceride content: 38.8%, SSS triglyceride: 32.0%). Oil A was completely melted at 80°C, solidified at 20°C, and then kept overnight in a 43°C incubator to obtain seed agent A (XXX triglyceride content: 38.8%, SSS triglyceride: 32.0%, β-crystals).

[0046] <Production of Seed Agent B> Flake-shaped extremely hardened rapeseed oil was placed in a thermostatic chamber and allowed to stand at 62°C for 64 hours to obtain flaky oil. The obtained flaky oil was pulverized by collision of the raw materials with each other in an airflow pulverizer to obtain seed agent B (XXX triglyceride content: 92.2%, SSS triglyceride content: 79.2%, β-crystals) which is a powdered oil composition.

[0047] <Production of Seed Agent C> A solid part B was obtained in the same manner as in Example 2 of Patent Document 2, in which solid part 2-1 was obtained. The obtained solid part B was then completely melted at 80°C, solidified at 20°C, and then kept overnight in a 43°C incubator to obtain seed agent C (XXX triglyceride content: 19.5%, SSS triglyceride content: 16.3%, fatty acid ethyl ester content: 17%, β-type crystals).

[0048] [Example 1-1] 800 g of raw oil and fat 1 was heated to 65°C and melted, then cooled at a temperature-lowering rate of 25°C / hour, and cooled to 43°C, which was 8°C higher than the cloud point of raw oil and fat 1. A seed dispersion prepared using seed agent A was added, and 0.05% of seed agent A (0.019% as XXX triglycerides) was supplied to the raw oil and fat. Subsequently, the temperature was lowered from 43°C to 34°C at a temperature-lowering rate of 12°C / hour, and the mixture was held at 34°C for 2.5 hours to precipitate XXX triglycerides. The mixture was then transferred to a press filter, the pressure was increased from 0.5 MPa to 3.0 MPa, and the mixture was pressurized and filtered. The crystalline fraction containing XXX triglycerides was separated by compression filtration, and a liquid fraction containing XOX triglycerides (XXX triglyceride content: 1.0%, SSS triglyceride content: 0.7%, XOX triglyceride content: 52.8%, SOS triglyceride content: 41.4%, SO2 triglyceride content: 27.7%) was obtained in a yield of 95.3%.

[0049] Comparative Example 1-1 The same procedure as in Example 1 was conducted, except that seed agent A was not added to raw material oil / fat 1, the temperature was lowered from 43°C to 30°C, and the raw material oil / fat 1 was maintained at 30°C for 2.5 hours, and the crystalline fraction was removed to obtain a liquid fraction (XXX triglyceride content: 0.7%, SSS triglyceride content: 0.5%, XOX triglyceride content: 52.9%, SOS triglyceride content: 41.5%, SO2 triglyceride content: 28.2%) in a yield of 89.6%.

[0050] [Example 2-1] 800 g of raw oil and fat 2 was heated to 65 ° C. and melted, and then cooled to 43 ° C., 8.5 ° C. higher than the cloud point of raw oil and fat 2, while cooling at a temperature decrease rate of 25 ° C. / hour. A seed dispersion prepared using seed agent A was added, and 0.2% of seed agent A (0.078% as XXX triglycerides) was supplied to the raw oil and fat. Subsequently, the temperature was decreased from 43 ° C. to 34 ° C. at a temperature decrease rate of 12 ° C. / hour, and the mixture was held at 34 ° C. for 1.5 hours to precipitate XXX triglycerides. The mixture was then transferred to a press filter, the pressure was increased from 0.5 MPa to 3.0 MPa, and the mixture was subjected to press filtration. The crystalline fraction containing XXX triglycerides was separated by compression filtration, and a liquid fraction containing XOX triglycerides (XXX triglyceride content: 1.0%, SSS triglyceride content: 0.6%, XOX triglyceride content: 52.8%, SOS triglyceride content: 41.7%, SO2 triglyceride content: 27.7%) was obtained in a yield of 92.7%.

[0051] Example 2-2 The same procedure as in Example 2-1 was repeated, except that the amount of seed agent A added relative to the raw oil / fat was changed to 0.05% (XXX triglyceride supply amount: 0.019%) and the mixture was maintained at 34°C for 2 hours. The crystalline fraction was removed, and a liquid fraction (XXX triglyceride content: 1.0%, SSS triglyceride content: 0.7%, XOX triglyceride content: 52.9%, SOS triglyceride content: 41.8%, SO2 triglyceride content: 27.8%) was obtained in a yield of 94.2%.

[0052] Example 2-3 The same procedure as in Example 2-1 was repeated, except that the amount of seed agent A added was changed to 0.01% (XXX triglyceride supply amount: 0.004%) and the mixture was kept at 34°C for 2.5 hours. The crystalline fraction was removed and a liquid fraction (XXX triglyceride content: 0.8%, SSS triglyceride content: 0.5%, XOX triglyceride content: 53.0%, SOS triglyceride content: 41.8%, SO2 triglyceride content: 27.5%) was obtained in a yield of 95.9%.

[0053] Example 2-4 The same procedure as in Example 2-2 was repeated, except that the temperature was lowered from 43°C to 34°C at a rate of 38°C / hour and then maintained at 34°C for 2.5 hours. The crystalline fraction was removed, and a liquid fraction (XXX triglyceride content: 0.9%, SSS triglyceride content: 0.6%, XOX triglyceride content: 53.1%, SOS triglyceride content: 41.9%, SO2 triglyceride content: 27.7%) was obtained in a yield of 94.4%.

[0054] [Example 3-1] 800 g of raw oil / fat 3 was heated to 65°C to a molten state, and then cooled to 43°C, which is 9.7°C higher than the cloud point of raw oil / fat 3, while cooling at a temperature decrease rate of 25°C / hour. A seed dispersion prepared using seed agent A was added, and 0.05% of seed agent A (0.019% as XXX triglycerides) was supplied to the raw oil / fat. Subsequently, the temperature was decreased from 43°C to 32°C at a temperature decrease rate of 12°C / hour, and the mixture was held at 32°C for 1.5 hours to crystallize XXX triglycerides. The mixture was then transferred to a press filter, the pressure was increased from 0.5 MPa to 3.0 MPa, and the mixture was subjected to press filtration. The crystalline fraction containing XXX triglycerides was separated by compression filtration, and a liquid fraction containing XOX triglycerides (XXX triglyceride content: 0.8%, SSS triglyceride content: 0.4%, XOX triglyceride content: 52.8%, SOS triglyceride content: 41.3%, SO2 triglyceride content: 26.8%) was obtained in a yield of 94.3%.

[0055] [Example 4-1] 2500 g of raw oil 4 was heated to 70°C to a molten state, and then cooled at a rate of 3°C / hour. When the temperature reached 50°C, which was 14.3°C higher than the cloud point of raw oil 4, 0.5% of seed agent B (XXX triglyceride supply amount: 0.461%) was added to raw oil 4. Subsequently, the temperature was lowered from 50°C to 30°C at a rate of 3°C / hour, and the mixture was held at 30°C for 0.5 hours to precipitate XXX triglycerides. The mixture was then transferred to a press filter, the pressure was increased from 0.5 MPa to 3.0 MPa, and the mixture was subjected to press filtration. The crystalline fraction containing XXX triglycerides was separated by compression filtration, and a liquid fraction containing XOX triglycerides (XXX triglyceride content: 1.0%, SSS triglyceride content: 0.5%, XOX triglyceride content: 54.3%, SOS triglyceride content: 42.5%, SO2 triglyceride content: 25.6%) was obtained in a yield of 95.6%.

[0056] [Example 5-1] 800 g of raw oil and fat 5 was heated to 70 ° C. to a molten state, and then cooled to 50 ° C., which is 5 ° C. higher than the cloud point of raw oil and fat 5, while cooling at a temperature decrease rate of 25 ° C. / hour. A seed dispersion prepared using seed agent A was added, and 0.05% of seed agent A (0.019% as XXX triglycerides) was supplied to the raw oil and fat. Subsequently, the temperature was decreased from 50 ° C. to 43 ° C. at a temperature decrease rate of 12 ° C. / hour, and the mixture was held at 43 ° C. for 2 hours to crystallize XXX triglycerides. The mixture was then transferred to a press filter, the pressure was increased from 0.5 MPa to 3.0 MPa, and the mixture was subjected to press filtration. The crystalline fraction containing XXX triglycerides was separated by compression filtration, and a liquid fraction containing XOX triglycerides (XXX triglyceride content: 2.1%, SSS triglyceride content: 1.2%, XOX triglyceride content: 81.3%, SOS triglyceride content: 68.2%, SO2 triglyceride content: 7.4%) was obtained in a yield of 84.3%.

[0057] Comparative Example 5-1 XXX triglycerides were crystallized in raw oil 5 in the same manner as in Example 5-1, except that seed agent A was not added to raw oil 5. However, in the solid-liquid separation step, the crystalline fraction containing the XXX triglycerides crystallized from raw oil 5 could not be sufficiently removed by filtration, and it was also found that some of the crystalline fraction escaped into the liquid fraction by filtration, making it impossible to satisfactorily separate the crystalline fraction from the liquid fraction.

[0058] [Example 6-1] Raw material fat 6: 4,600 kg was heated to 67 ° C. to a molten state, and then cooled to 43 ° C., 7.6 ° C. higher than the cloud point of raw material fat 6, while cooling at a temperature decreasing rate of 12 ° C. / hour. A seed dispersion prepared using seed agent C was added, and 0.02% of seed agent C (0.004% as XXX triglycerides) was supplied to the raw material fat. Subsequently, the temperature was decreased from 43 ° C. to 33 ° C. at a temperature decreasing rate of 6.7 ° C. / hour, and the mixture was held at 33 ° C. for 2.5 hours to crystallize XXX triglycerides. Thereafter, the mixture was transferred to a press filter, the pressure was increased from 0.5 MPa to 2.9 MPa, and the mixture was subjected to press filtration. The crystalline fraction containing XXX triglycerides was separated by compression filtration, and a liquid fraction containing XOX triglycerides (XXX triglyceride content: 1.1%, SSS triglyceride content: 0.7%, XOX triglyceride content: 54.2%, SOS triglyceride content: 43.4%, SO2 triglyceride content: 26.4%) was obtained in a yield of 95.1%.

[0059] [Example 7-1] 400 g of raw oil and fat 7 was heated to 70 ° C. and melted, and then cooled to 50 ° C., which is 9.6 ° C. higher than the cloud point of raw oil and fat 7, while cooling at a temperature decrease rate of 6 ° C. / hour. A seed dispersion prepared using seed agent C was added, and 0.02% of seed agent C (0.004% as XXX triglycerides) was supplied to the raw oil and fat. Subsequently, the temperature was decreased from 50 ° C. to 41 ° C. at a temperature decrease rate of 6 ° C. / hour, and the mixture was held at 41 ° C. for 3 hours to crystallize XXX triglycerides. The mixture was then transferred to a press filter, the pressure was increased from 0.5 MPa to 3.0 MPa, and the mixture was subjected to press filtration. The crystalline fraction containing XXX triglycerides was separated by compression filtration, and a liquid fraction containing XOX triglycerides (XXX triglyceride content: 1.5%, SSS triglyceride content: 0.9%, XOX triglyceride content: 84.3%, SOS triglyceride content: 70.7%, SO2 triglyceride content: 5.9%) was obtained in a yield of 90.5%.

[0060]

[0061]

[0062] As shown in Table 2, comparing Example 1-1 and Comparative Example 1-1, the addition of a seed agent improved the yield of the liquid fraction while reducing the XXX triglyceride content in the liquid fraction to 75% by mass or less relative to that in raw oil / fat 1. In Examples 2-1 to 2-4, when the raw oil / fat, the amount of seed agent added, and the temperature-lowering treatment conditions were changed, the liquid fraction was efficiently separated while reducing the XXX triglyceride content in the liquid fraction to 75% by mass or less relative to that in raw oil / fat 2. In Example 3-1, when the type of raw oil / fat was changed, the liquid fraction was efficiently separated while reducing the XXX triglyceride content in the liquid fraction to 75% by mass or less relative to that in raw oil / fat 3. In Example 4-1, when the type of raw oil / fat and seed agent was changed, the liquid fraction was efficiently separated while reducing the XXX triglyceride content in the liquid fraction to 75% by mass or less relative to that in raw oil / fat 4. Comparing Example 5-1 and Comparative Example 5-1, when the raw oil / fat was changed to raw oil / fat 5, which had a high content of XXX triglycerides, the liquid fraction could be efficiently separated while reducing the content of XXX triglycerides in the liquid fraction to 75% by mass or less relative to raw oil / fat 5. In Example 6-1, when the types of raw oil / fat and seed agent were changed, the liquid fraction could be efficiently separated while reducing the content of XXX triglycerides in the liquid fraction to 75% by mass or less relative to raw oil / fat 6. In Example 7-1, when the types of raw oil / fat and seed agent were changed, the liquid fraction could be efficiently separated while reducing the content of XXX triglycerides in the liquid fraction to 75% by mass or less relative to raw oil / fat 7. The "residual liquid rate" in Table 2 is the ratio of the SO2 triglyceride content in the liquid fraction to the SO2 triglyceride content in the crystalline fraction. The lower the residual liquid ratio, the less liquid fraction remains in the crystal fraction, and the better the separation of the crystal fraction and the liquid fraction. The lower the residual liquid ratio, the higher the yield tends to be, which is preferable. When the separation of the crystal fraction and the liquid fraction is good, the residual liquid ratio should be 55% or less.

Claims

1. A method for producing an oil or fat composition containing an XOX triglyceride having saturated fatty acid residues at the 1st and 3rd positions and an oleoyl group at the 2nd position, comprising the steps of: adding a seed agent containing an XXX triglyceride while cooling a raw oil or fat containing an XOX triglyceride and an XXX triglyceride having saturated fatty acid residues at the 1st, 2nd, and 3rd positions from a molten state, thereby crystallizing the XXX triglyceride; and removing a crystalline fraction containing the XXX triglyceride crystallized from the raw oil or fat, thereby obtaining a liquid fraction containing an XOX triglyceride, wherein the content of the XXX triglyceride in the liquid fraction is 75% or less of the content of the XXX triglyceride in the raw oil or fat.

2. The manufacturing method described in claim 1, wherein the amount of XXX triglyceride supplied by adding the seed agent is 0.0005% by mass or more and 1.0% by mass or less relative to the raw material oil or fat.

3. The manufacturing method described in claim 1, wherein the amount of the seed agent added is 0.001% by mass or more and 2.0% by mass or less relative to the raw oil and fat, and the content of XXX-type triglycerides in the seed agent is 10% by mass or more and 99% by mass or less.

4. The method according to claim 1, wherein the temperature at the time of adding the seed agent is lower than the melting temperature of the XXX triglyceride and higher than the melting temperature of the XOX triglyceride.

5. The manufacturing method according to claim 1, wherein the temperature at the time of adding the seed agent is 3.0 to 20°C higher than the cloud point of the raw material oil or fat.

6. The manufacturing method described in claim 1, wherein the content of XOX triglycerides in the raw oil is 40% by mass or more and 90% by mass or less, and the content of XXX triglycerides in the raw oil is 1.0% by mass or more and 10% by mass or less.

7. The method according to claim 1, wherein the content of XOX triglycerides in the liquid fraction is 40% by mass or more and 95% by mass or less, and the content of XXX triglycerides in the liquid fraction is 0.1% by mass or more and 7.5% by mass or less.

8. The method of claim 1, wherein the XOX triglycerides in the raw material oil include SOS triglycerides having stearoyl groups at the 1st and 3rd positions and an oleoyl group at the 2nd position.

9. The production method described in claim 1, wherein the XXX triglycerides in the raw material oil or fat include SSS triglycerides having stearoyl groups at the 1st, 2nd, and 3rd positions.

10. The method of claim 1, wherein the XXX triglycerides in the seed agent include SSS triglycerides having stearoyl groups at the 1st, 2nd, and 3rd positions.

11. The method of claim 10, wherein the SSS triglyceride in the seed agent has a β-type crystalline polymorphism.

12. A manufacturing method as described in claim 1, wherein the mass ratio of the liquid fraction to the raw oil or fat is 90.0% or more when the content of XXX triglycerides in the raw oil or fat is 1.0% by mass or more but less than 3.0% by mass, and is 80.0% or more when the content of XXX triglycerides in the raw oil or fat is 3.0% by mass or more but less than 10% by mass.

13. The manufacturing method according to claim 1, wherein the temperature-lowering treatment is carried out under conditions of 0.5°C / hour to 60°C / hour.

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