Method for producing interesterified fat

Abstract

To provide a method for producing interesterified fat with a high diacylglycerol purity while performing a glycerolysis reaction at a low temperature.SOLUTION: A method for producing interesterified fat includes a step of reacting fat with glycerol in the presence of a calcium-based catalyst at a reaction temperature of 90°C or higher and 165°C or lower, wherein the molar ratio of fatty acid groups to glycerol groups [FA / GLY] is 0.30 or more to 1.7 or less.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a method for producing interesterified fats and oils rich in diacylglycerol. [Background technology]

[0002] Diacylglycerol is used in various industrial fields such as food and cosmetics. Generally, diacylglycerol is produced by an esterification reaction between glycerin and fatty acids, or a glycerolysis reaction between glycerin and fats and oils. These production methods are roughly divided into chemical methods using chemical catalysts such as hydroxides and alkoxides of alkali metals or alkaline earth metals, and enzymatic methods using enzymes such as lipase. For example, Patent Document 1 describes a method for producing fats and oils with a high diacylglycerol content by adding calcium hydroxide as a catalyst to undeodorized rapeseed oil and glycerin and carrying out a glycerolysis reaction at a temperature of 210°C. The glycerolysis method can produce diacylglycerol with fewer steps than the esterification method. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] JP 2010-59406 A Summary of the Invention [Problem to be solved by the invention]

[0004] However, in the glycerolysis method, in order to increase the purity of diacylglycerol [diacylglycerol / (diacylglycerol+triacylglycerol)×100], it is necessary to increase the ratio of glycerin to fats and oils in the reaction raw material, but it is common technical knowledge that if the ratio is increased, a large amount of monoacylglycerol will be produced when the equilibrium composition is reached. Since monoacylglycerol is easily emulsified and requires a high purification load, and has a unique flavor, it is desirable to reduce the amount of monoacylglycerol. Therefore, in the conventional glycerolysis method, the ratio of glycerin to fats and oils is reduced to suppress the production of monoacylglycerol while sacrificing the purity of diacylglycerol to a certain extent. Therefore, the present invention relates to providing a method for producing interesterified fats and oils rich in diacylglycerol at a high reaction rate while suppressing the production of monoacylglycerol. [Means for solving the problem]

[0005] The present inventors have found that when the ratio of glycerin to fats and oils is high, which was previously thought to result in a large amount of monoacylglycerol being produced, the production of monoacylglycerol is suppressed by carrying out the reaction at low temperature in the presence of a calcium-based catalyst, and transesterified fats and oils rich in diacylglycerol can be obtained at a high reaction rate.

[0006] That is, the present invention provides a method for producing transesterified fats and oils, comprising a step of reacting fats and oils with glycerin in the presence of a calcium-based catalyst at a reaction temperature of 90°C or higher and 165°C or lower, with the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] being 0.30 or higher and 1.7 or lower. Effect of the Invention

[0007] According to the present invention, the production of monoacylglycerol can be suppressed by the glycerolysis reaction at a low temperature, and transesterified fats and oils rich in diacylglycerol can be obtained at a high reaction rate. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] In the present invention, "transesterified fats and oils" refers to fats and oils obtained by reacting a raw material fat and oil with glycerin, removing the catalyst by neutralization, filtration, etc., and removing unreacted phase-separated glycerin, and "reacted oil" refers to fats and oils obtained by reacting a raw material fat and oil with glycerin, but before removing the catalyst and unreacted phase-separated glycerin. In addition, in the present invention, "reacting step" refers to the step after the reaction temperature is reached, and does not include the step of raising the temperature to the reaction temperature.

[0009] The method for producing interesterified oils and fats of the present invention includes a step of reacting an oil and fat with glycerin in the presence of a calcium-based catalyst at a reaction temperature of 90°C or more and 165°C or less, with the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] being 0.30 or more and 1.7 or less. In this specification, "fat" and "oil" are synonymous. In addition, substances constituting fats and oils (oils) include not only triacylglycerols but also monoacylglycerols and diacylglycerols. In other words, fats and oils (oils) contain at least one of monoacylglycerols, diacylglycerols, and triacylglycerols.

[0010] In the present invention, the fats and oils to be reacted with glycerin are generally those mainly composed of triacylglycerol, and examples thereof include soybean oil, rapeseed oil, safflower oil, rice oil, corn oil, sunflower oil, cottonseed oil, olive oil, sesame oil, peanut oil, pearl barley oil, wheat germ oil, perilla oil, linseed oil, perilla oil, chia seed oil, sacha inchi oil, walnut oil, kiwi seed oil, salvia seed oil, grape seed oil, macadamia nut oil, and hazelnut oil. Examples of the oils and fats include vegetable oils and fats such as tallow oil, pumpkin seed oil, camellia oil, tea seed oil, borage oil, palm oil, palm olein, palm stearin, coconut oil, palm kernel oil, cacao butter, monkey fat, shea butter, and algae oil; animal oils and fats such as fish oil, seal oil, whale oil, lard, beef tallow, and butter fat; microbial oils such as oils and fats derived from microorganisms producing polyunsaturated fatty acids such as zygomycetes; and oils and fats such as transesterified oils, hydrogenated oils, and fractionated oils of these. The oils and fats can be used alone or in combination of two or more. Among them, the oil and fat is preferably a liquid oil and fat from the viewpoint of the emulsification characteristics of the transesterified oil and fat and ease of handling. Note that the liquid oil and fat refers to an oil and fat that is liquid at 20°C when a cooling test according to the Standard Fats and Oils Analysis Test Method 2.3.8-27 is carried out. In addition, in the present invention, since the production of trans acids is suppressed by the reaction at a low temperature, unlike a normal glycerolysis reaction, it is preferable to use fatty acids with a carbon chain length of 18 or more and the number of double bonds of 3 or more, which are expected to have various physiological functions. In particular, it is preferable to use one or more types of oils and fats selected from oils and fats rich in ω3 unsaturated fatty acids, such as perilla oil, linseed oil, perilla oil, chia seed oil, sacha inchi oil, algae oil, fish oil, seal oil, whale oil, and oils and fats derived from microorganisms producing polyunsaturated fatty acids.

[0011] Fish oil can be extracted from raw materials such as sardines, herring, pacific saury, mackerel, bonito, tuna, squid, cod liver, etc. Algal oil can be extracted from algae belonging to the Chlorophyceae, Bacillariophyceae, etc. It is preferable to appropriately carry out known separation and purification means such as liquid-liquid separation, filtration, and centrifugation to remove impurities before the reaction. In addition, so-called concentrated oils may be used, which are produced by selectively hydrolyzing fish oil or the like using lipase to increase the ratio of unsaturated fatty acids such as eicosapentaenoic acid (C20:5, EPA) and docosahexaenoic acid (C22:6, DHA) in the fatty acids that make up the oil.

[0012] The triacylglycerol content in the oil may be 100% by mass, but is preferably 95% by mass or less, more preferably 92% by mass or less, and even more preferably 89% by mass or less in order to easily concentrate highly unsaturated fatty acids such as eicosapentaenoic acid and docosahexaenoic acid in the transesterified oil, and is preferably 70% by mass or more, more preferably 75% by mass or more, and even more preferably 80% by mass or more in terms of production efficiency. In order to make the triacylglycerol content in the oil to be reacted with glycerin less than 100% by mass, it is preferable to partially hydrolyze the oil by acting lipase on the oil, and then remove the resulting fatty acid by distillation. By this operation, it is possible to selectively remove saturated fatty acids with carbon numbers of 16 and 18 in the constituent fatty acids, and it is possible to further concentrate highly unsaturated fatty acids in the oil to be reacted with glycerin. In addition, the content of free fatty acids or salts thereof in the fats and oils is preferably 10% by mass or less, more preferably 7% by mass or less, even more preferably 4% by mass or less, and even more preferably 1% by mass or less in terms of preventing catalyst deactivation, and is preferably 0.01% by mass or more, more preferably 0.02% by mass or more, and even more preferably 0.03% by mass or more in terms of production efficiency.

[0013] The constituent fatty acids constituting the oil or fat are not particularly limited, and may be either saturated fatty acids or unsaturated fatty acids. From the viewpoints of handling properties and industrial productivity of the oil, the content of unsaturated fatty acids in the fatty acids constituting the oil is preferably 60 to 100% by mass, more preferably 70 to 98% by mass, and even more preferably 80 to 96% by mass. From the viewpoint of physiological effects, the number of carbon atoms of the unsaturated fatty acids is preferably 14 to 24, more preferably 16 to 22, and even more preferably 18 to 22. In this specification, the amount of fatty acid is calculated as the amount of free fatty acid.

[0014] In view of their physiological activity, it is preferable that the fatty acids constituting the oils and fats contain a large amount of fatty acids having a carbon chain length of 18 or more and a double bond number of 3 or more. Furthermore, according to the method of the present invention, it is possible to obtain an interesterified oil and fat having a high ratio of fatty acids having a carbon chain length of 18 or more and a double bond number of 3 or more in the reacted oil, while preventing the ratio of the fatty acids in the reacted oil from being lower than the ratio of the fatty acids having a carbon chain length of 18 or more and a double bond number of 3 or more in the reacting raw material oil and fat. The total content of fatty acids having a carbon chain length of 18 or more and a double bond number of 3 or more in the fatty acids constituting the oil is preferably 15% by mass or more, more preferably 20% by mass or more, even more preferably 25% by mass or more, and even more preferably 30% by mass or more from the viewpoint of physiological activity, and is preferably 99% by mass or less, more preferably 90% by mass or less, and even more preferably 80% by mass or less from the viewpoint of suppressing by-production of trans fatty acids. The total content of fatty acids having a carbon chain length of 18 or more and a double bond number of 3 or more in the fatty acids constituting the oil is preferably 15 to 99% by mass, more preferably 20 to 90% by mass, even more preferably 25 to 80% by mass, and even more preferably 30 to 80% by mass. Examples of fatty acids that have a carbon chain length of 18 or more and a double bond number of 3 or more in the fatty acids that compose the oils and fats include α-linolenic acid (C18:3), γ-linolenic acid (C18:3), arachidonic acid (C20:4), eicosapentaenoic acid (C20:5, EPA), docosapentaenoic acid (C22:5), docosahexaenoic acid (C22:6, DHA), etc. Among them, ω3 unsaturated fatty acids having a double bond at the third position counting from the methyl end of the carbon chain are preferred in terms of physiological activity and ease of enjoying the effects of the present invention.

[0015] The glycerin used in the present invention preferably has a purity of 95% by mass or more in terms of improving reactivity.

[0016] In the present invention, the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] during the reaction of fats and oils with glycerin is 0.30 or more and 1.7 or less. The ratio of the number of moles of fatty acid groups to the number of moles of glycerol groups [FA / GLY] is expressed by the following formula. FA / GLY = (moles of fatty acids + moles of monoacylglycerol + moles of diacylglycerol x 2 + moles of triacylglycerol x 3) / (moles of glycerin + moles of monoacylglycerol + moles of diacylglycerol + moles of triacylglycerol) The ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] is 0.30 or more, preferably 0.35 or more, more preferably 0.40 or more, from the viewpoint of reducing the amount of glycerin that does not dissolve in the oil phase, and is 1.7 or less, preferably 1.6 or less, more preferably 1.5 or less, from the viewpoint of increasing the ratio of diacylglycerol to monoacylglycerol in the reaction oil and increasing the reaction rate. The ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] is 0.30 to 1.7, preferably 0.35 to 1.6, more preferably 0.40 to 1.5.

[0017] In the present invention, the reaction between fats and oils and glycerin is carried out in the presence of a calcium-based catalyst. By using a calcium-based catalyst as the catalyst, it is possible to increase the reaction rate while suppressing the production of monoacylglycerol. The calcium catalyst used in the present invention may be any catalyst that catalyzes the glycerolysis reaction. Examples of calcium catalysts include calcium hydroxide, calcium carbonate, calcium oxide, calcium silicate, calcium alkoxides such as calcium methoxide, etc. These may be used alone or in combination of two or more. Among them, calcium hydroxide, calcium oxide, and calcium silicate are preferred because they can improve the purity of diacylglycerol in the reaction oil. In the case of calcium hydroxide and calcium oxide, the amount of calcium catalyst added is preferably 0.01% by mass or more, more preferably 0.02% by mass or more, even more preferably 0.03% by mass or more, and even more preferably 0.04% by mass or more, based on the raw materials for reaction (total of fats and oils and glycerin), from the viewpoint of improving reactivity, and is preferably 2.0% by mass or less, more preferably 1.5% by mass or less, and even more preferably 1.0% by mass or less, based on the viewpoint of reducing the amount of neutralizing agent. In the case of calcium hydroxide and calcium oxide, the amount of calcium catalyst added is preferably 0.01 to 2.0% by mass, more preferably 0.02 to 1.5% by mass, even more preferably 0.03 to 1.5% by mass, and even more preferably 0.04 to 1.0% by mass, based on the raw materials for reaction. Similarly, when the calcium-based catalyst is calcium silicate, the amount of calcium silicate added 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 even more preferably 2.0% by mass or more, based on the raw materials (total of fats and oils and glycerin) from the viewpoint of improving reactivity, and is preferably 20.0% by mass or less, more preferably 15.0% by mass or less, and even more preferably 10.0% by mass or less, based on the viewpoint of reducing the amount of neutralizer. When the calcium-based catalyst is calcium silicate, the amount of calcium silicate added is preferably 0.5 to 20.0% by mass, more preferably 1.0 to 15.0% by mass, even more preferably 1.5 to 15.0% by mass, and even more preferably 2.0 to 10.0% by mass, based on the raw materials. In addition, when the calcium catalyst is calcium hydroxide and calcium oxide, the molar amount of the calcium catalyst relative to the molar amount of glycerin [mmol-calcium catalyst / mol-glycerin] is preferably 0.2 or more, more preferably 0.5 or more, even more preferably 1.2 or more, even more preferably 3.0 or more, even more preferably 10.0 or more, even more preferably 15.0 or more from the viewpoint of improving reactivity, and from the viewpoint of reducing the amount of neutralizing agent, it is preferably 340 or less, more preferably 170 or less, even more preferably 80 or less. In the case of calcium hydroxide and calcium oxide, the ratio of the molar amount of the calcium catalyst relative to the molar amount of glycerin [mmol-calcium catalyst / mol-glycerin] is preferably 0.2 to 340, more preferably 0.5 to 340, even more preferably 1.2 to 170, even more preferably 3.0 to 170, even more preferably 10.0 to 80, even more preferably 15.0 to 80. Similarly, the molar amount of the calcium catalyst relative to the molar amount of glycerin when the calcium catalyst is calcium silicate [mmol-calcium catalyst / mol-glycerin] is preferably 30 or more, more preferably 60 or more, even more preferably 90 or more, even more preferably 120 or more, even more preferably 150 or more, even more preferably 180 or more, from the viewpoint of improving reactivity, and from the viewpoint of reducing the amount of neutralizing agent, it is preferably 900 or less, more preferably 700 or less, even more preferably 500 or less. The ratio of the molar amount of the calcium catalyst relative to the molar amount of glycerin when calcium silicate is calcium silicate [mmol-calcium catalyst / mol-glycerin] is preferably 30 to 900, more preferably 60 to 900, even more preferably 90 to 700, even more preferably 120 to 700, even more preferably 150 to 500, even more preferably 180 to 500.

[0018] In the present invention, the timing of adding the calcium-based catalyst to the reaction raw material is not particularly limited, but it is preferable to raise the temperature to the reaction temperature at 50° C. or higher in order to suppress deactivation of the catalyst and to improve the purity of diacylglycerol in the reaction oil. Here, "at 50° C. or higher" does not mean that no calcium-based catalyst is added to the reaction raw material at a temperature below 50° C., but means that the amount required to catalyze the reaction is added at 50° C. or higher. The temperature at which the calcium catalyst is added to the reaction raw material is preferably 60° C. or higher, more preferably 75° C. or higher, and even more preferably 90° C. or higher, from the viewpoint of suppressing deactivation of the catalyst and improving the diacylglycerol purity of the reaction oil, and is preferably 165° C. or lower, more preferably 160° C. or lower, and even more preferably 155° C. or lower, from the viewpoint of improving quality. The temperature at which the calcium catalyst is added to the reaction raw material is preferably 60 to 165° C., more preferably 75 to 160° C., and even more preferably 90 to 155° C. After adding a calcium-based catalyst to the reaction raw materials, the temperature is raised to a reaction temperature as necessary to carry out a glycerolysis reaction with the oils and fats and glycerin.

[0019] In the present invention, the reaction temperature is 90° C. or higher and 165° C. or lower. The reason why the effect of the present invention is exhibited when the reaction is carried out at such a low temperature condition compared to the normal glycerolysis reaction is not clear, but it is believed to be due to the following mechanism. When the glycerolysis reaction between fats and oils and glycerin is carried out at a high temperature, the solubility of glycerin in fats and oils is high, and monoacylglycerol is easily stabilized in the reaction oil, so the reaction equilibrium leans towards the production of monoacylglycerol. On the other hand, when the glycerolysis reaction is carried out at a low reaction temperature of 165°C or lower, the solubility of glycerin in fats and oils is low, and monoacylglycerol is difficult to stabilize in the reaction oil, so the equilibrium is inhibited and the production of monoacylglycerol is suppressed, and it is considered that the ratio of diacylglycerol to monoacylglycerol in the reaction oil can be increased while increasing the reaction rate. The reaction temperature is 90°C or higher, preferably 95°C or higher, more preferably 100°C or higher, from the viewpoint of improving the reaction rate, and 165°C or lower, preferably 160°C or lower, more preferably 155°C or lower, from the viewpoint of increasing the ratio of diacylglycerol to monoacylglycerol in the reaction oil. The reaction temperature is 90 to 165°C, preferably 95 to 160°C, more preferably 100 to 155°C. In addition, it is preferable that the step of reacting at more than 165°C is not substantially included, from the viewpoint of increasing the ratio of diacylglycerol to monoacylglycerol in the reaction oil. "Substantially not included" is preferably 10% or less of the time required for the reaction step, more preferably 5% or less, even more preferably 2.5% or less, and even more preferably 0%. In addition, "substantially not included" is preferably 24 minutes or less, more preferably 12 minutes or less, even more preferably 6 minutes or less, and even more preferably 0 minutes, in terms of specific time.

[0020] The rate of temperature rise of the reaction raw materials to the reaction temperature is preferably 0.1° C. / min or more, more preferably 0.15° C. / min or more, and even more preferably 0.2° C. / min or more, from the viewpoint of suppressing deactivation of the catalyst and industrial productivity, and is preferably 20° C. / min or less, more preferably 10° C. / min or less, and even more preferably 3° C. / min or less, from the viewpoint of reducing the heating load of the equipment. The rate of temperature rise of the reaction raw materials to the reaction temperature is preferably 0.1 to 20° C. / min, more preferably 0.15 to 10° C. / min, and even more preferably 0.2 to 3° C. / min.

[0021] The reaction time is preferably 0.1 hours or more, more preferably 0.25 hours or more, and even more preferably 0.5 hours or more, from the viewpoint of increasing the ratio of diacylglycerol to monoacylglycerol in the reaction oil and suppressing the reverse reaction upon cooling by decreasing the catalytic activity, and from the viewpoint of industrial productivity, it is preferably within 15 hours, more preferably within 12 hours, and even more preferably within 9 hours. The reaction time is preferably 0.1 hours or more and 15 hours or less, more preferably 0.25 hours or more and 12 hours or less, and even more preferably 0.5 hours or more and 9 hours or less.

[0022] In order to improve the reactivity and to prevent a decrease in catalytic performance, it is preferable to carry out the reaction between fats and oils and glycerin after removing water contained in the reaction raw materials by reducing pressure, bubbling with nitrogen, or the like. The water concentration of the reaction raw material before the addition of the calcium-based catalyst is preferably 0.01 to 0.5 mass%, more preferably 0.03 to 0.4 mass%, and even more preferably 0.05 to 0.3 mass%, from the standpoint of industrial productivity and preventing a decrease in catalytic performance.

[0023] The reaction may be carried out under reduced pressure or normal pressure. When the reaction is carried out under reduced pressure, the pressure is not particularly limited, but is preferably 13,000 Pa or less in order to reduce the moisture content in the reaction system. When the reaction is carried out under normal pressure, the reaction is preferably carried out under a nitrogen atmosphere in which nitrogen is circulated in order to suppress oxidation of the resulting transesterified oil or fat.

[0024] After the glycerolysis reaction is completed, the calcium-based catalyst used as a catalyst is still present in the reaction oil, so it is preferable to neutralize the calcium-based catalyst and remove it by filtration or the like after the glycerolysis reaction is completed. The neutralizing agent is not particularly limited, but since the neutralized product is insoluble in water or oils and can be easily removed by filtration, an acid such as sulfuric acid, hydrochloric acid, or phosphoric acid is preferred, and phosphoric acid is more preferred.

[0025] In the present invention, the neutralization of the calcium catalyst is carried out by adding a neutralizing agent to the calcium catalyst in an amount preferably 1.2 times by mol or more, more preferably 1.25 times by mol or more, and even more preferably 1.3 times by mol or more, from the viewpoint of suppressing the decrease in the diacylglycerol concentration due to ester exchange in the case of performing a distillation treatment thereafter. The upper limit of the molar ratio is not particularly limited, but is preferably 3.0 times by mol or less, more preferably 2.6 times by mol or less, and even more preferably 2.2 times by mol or less, from the viewpoint of suppressing the increase in the acid value of the neutralized oil. The amount of the neutralizing agent to the calcium catalyst is preferably 1.2 to 3.0 times by mol, more preferably 1.25 to 2.6 times by mol, and even more preferably 1.3 to 2.2 times by mol.

[0026] The temperature of the neutralization step, that is, the step from adding the neutralizing agent to the reaction oil containing the calcium catalyst until the stirring is finished (hereinafter the same), is preferably 40° C. or higher, more preferably 70° C. or higher, and even more preferably 100° C. or higher, from the viewpoint of sufficiently generating the neutralized product. Also, from the viewpoint of suppressing the reverse reaction and the oxidation, it is preferably 165° C. or lower, more preferably 160° C. or lower, and even more preferably 150° C. or lower.

[0027] The time for the neutralization step is preferably from 1 to 240 minutes, more preferably from 3 to 180 minutes, and even more preferably from 10 to 120 minutes, in terms of sufficiently producing the neutralized product.

[0028] In the neutralization step, in order to sufficiently produce the neutralized product, it is preferable to carry out the neutralization with stirring. The means for stirring is not particularly limited.

[0029] In the present invention, after the glycerolysis reaction, diacylglycerol may be concentrated or a purification process for ordinary fats and oils may be carried out. Specifically, steps such as distillation, acid treatment, water washing, decolorization, and deodorization may be included. In the present invention, after the glycerolysis reaction, an enzymatic esterification reaction may be further carried out, but from the viewpoint of increasing the ratio of highly unsaturated fatty acids in the reaction oil, it is preferable to carry out a distillation treatment without carrying out an esterification reaction.

[0030] The interesterified oil obtained by the method of the present invention contains, in addition to diacylglycerol, triacylglycerol, monoacylglycerol, and dissolved unreacted glycerin, with the ratio of diacylglycerol to monoacylglycerol being higher. In the interesterified oil obtained by the method of the present invention, the ratio of diacylglycerol to monoacylglycerol [diacylglycerol / monoacylglycerol mass ratio] is preferably 1.08 or more, more preferably 1.10 or more, even more preferably 1.12 or more, and is preferably 2.2 or less, more preferably 2.0 or less, even more preferably 1.8 or less, from the viewpoint of suppressing emulsification and reducing the purification load. The ratio of diacylglycerol to monoacylglycerol [diacylglycerol / monoacylglycerol mass ratio] is preferably 1.08 to 2.2, more preferably 1.10 to 2.0, even more preferably 1.12 to 1.8.

[0031] The transesterified oil obtained by the method of the present invention is rich in diacylglycerol, and the diacylglycerol content is preferably 38 to 56 mass%, more preferably 40 to 54 mass%, and even more preferably 42 to 52 mass%, from the viewpoint of improving physiologically active functions. The content of monoacylglycerol in the interesterified oil is preferably 22 to 45% by mass, more preferably 23 to 43.5% by mass, and even more preferably 24 to 42% by mass, from the viewpoint of improving physiological activity. The interesterified oil obtained by the method of the present invention can be used in the same manner as general edible oils and fats, by removing monoacylglycerol by distillation or the like, as necessary.

[0032] In the transesterified oil obtained by the method of the present invention, the free fatty acid content is preferably 5% by mass or less, more preferably 4% by mass or less, even more preferably 3% by mass or less, and even more preferably 2% by mass or less, from the viewpoints of reducing the load of the refining process and industrial productivity. Also, from the viewpoint of efficient reaction, the free fatty acid content is preferably 0.1% by mass or more, more preferably 0.3% by mass or more, and even more preferably 0.5% by mass or more.

[0033] In the transesterified oils and fats, the reaction rate (diacylglycerol + monoacylglycerol content) is preferably 72 to 96 mass%, more preferably 75 to 94 mass%, and even more preferably 77 to 92 mass%, from the viewpoints of suppressing emulsification and reducing the purification load.

[0034] In the interesterified oil obtained by the method of the present invention, the purity of diacylglycerol is preferably 55% by mass or more, more preferably 60 to 90% by mass, even more preferably 65 to 90% by mass, and still more preferably 69 to 90% by mass, from the viewpoints of physiological effects and industrial productivity. Here, the purity of diacylglycerol is [diacylglycerol / (diacylglycerol+triacylglycerol)×100].

[0035] In relation to the above-mentioned embodiment, the present invention further discloses the following method for producing interesterified oils and fats. <1> A method for producing transesterified oils and fats, comprising a step of reacting an oil and fat with glycerin in the presence of a calcium-based catalyst at a reaction temperature of 95°C or higher and 160°C or lower, with the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] being 0.35 or higher and 1.6 or lower. <2> A method for producing transesterified oils and fats, comprising a step of reacting oils and fats with glycerin in the presence of calcium hydroxide or calcium oxide as a calcium-based catalyst, at a reaction temperature of 90°C or more and 165°C or less, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] of 0.35 to 1.6 and a molar amount of calcium-based catalyst to the molar amount of glycerin [mmol-calcium-based catalyst / mol-glycerin] of 3.0 to 170. <3> A method for producing transesterified oils and fats, comprising a step of reacting oils and fats with glycerin in the presence of calcium silicate as a calcium-based catalyst, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] of 0.35 to 1.6 and a molar amount of calcium-based catalyst to the molar amount of glycerin [mmol-calcium-based catalyst / mol-glycerin] of 90 to 700, at a reaction temperature of 90°C to 165°C. <4> A method for producing transesterified fats and oils, comprising the step of reacting fats and oils with glycerin in the presence of a calcium catalyst at a reaction temperature of 90°C or higher and 165°C or lower, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] set to 0.35 or higher and 1.6 or lower, wherein the total content of fatty acids having a carbon chain length of 18 or longer and three or more double bonds in the fatty acids constituting the fats and oils reacted with glycerin is 15 to 99 mass%. <5> A method for producing transesterified fats and oils, comprising the step of reacting fats and oils with glycerin in the presence of a calcium catalyst at a reaction temperature of 90°C or higher and 165°C or lower, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] being 0.35 or higher and 1.6 or lower, wherein the mass ratio of diacylglycerol to monoacylglycerol in the obtained transesterified fats and oils is 1.10 or higher and 2.2 or lower. <6> A method for producing transesterified fats and oils, comprising the step of reacting fats and oils with glycerin in the presence of a calcium catalyst at a reaction temperature of 90°C or higher and 165°C or lower, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] being 0.35 or higher and 1.6 or lower, wherein the resulting transesterified fats and oils have a reaction rate (diacylglycerol + monoacylglycerol content) of 72 to 96 mass%. <7> A method for producing transesterified oils and fats, comprising a step of reacting oils and fats with glycerin in the presence of calcium hydroxide or calcium oxide as a calcium-based catalyst, at a reaction temperature of 95°C or more and 160°C or less, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] of 0.30 or more and 1.7 or less, and a molar amount of calcium-based catalyst to the molar amount of glycerin [mmol-calcium-based catalyst / mol-glycerin] of 3.0 or more and 170 or less. <8> A method for producing transesterified oils and fats, comprising a step of reacting oils and fats with glycerin in the presence of calcium silicate as a calcium-based catalyst, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] of 0.30 or more and 1.7 or less, and a molar amount of calcium-based catalyst to the molar amount of glycerin [mmol-calcium-based catalyst / mol-glycerin] of 90 or more and 700 or less, at a reaction temperature of 95°C or more and 160°C or less. <9> A method for producing transesterified fats and oils, comprising the step of reacting fats and oils with glycerin in the presence of a calcium catalyst at a reaction temperature of 95°C or higher and 160°C or lower, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] set to 0.30 or higher and 1.7 or lower, wherein the total content of fatty acids having a carbon chain length of 18 or longer and having three or more double bonds in the fatty acids constituting the fats and oils reacted with glycerin is 15 to 99 mass%. <10> A method for producing transesterified fats and oils, comprising the step of reacting fats and oils with glycerin in the presence of a calcium catalyst at a reaction temperature of 95°C or higher and 160°C or lower, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] being 0.30 or higher and 1.7 or lower, wherein the mass ratio of diacylglycerol to monoacylglycerol in the obtained transesterified fats and oils is 1.10 or higher and 2.2 or lower. <11> A method for producing transesterified oils and fats, comprising a step of reacting an oil or fat with glycerin in the presence of a calcium catalyst at a reaction temperature of 95°C or higher and 160°C or lower, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] being 0.30 or higher and 1.7 or lower, wherein the reaction rate (diacylglycerol + monoacylglycerol content) of the obtained transesterified oil or fat is 72 to 96 mass%. <12> A method for producing transesterified fats and oils, comprising a step of reacting fats and oils with glycerin in the presence of calcium hydroxide or calcium oxide as a calcium-based catalyst at a reaction temperature of 90°C or higher and 165°C or lower, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] of 0.30 to 1.7 and a molar amount of calcium-based catalyst to the molar amount of glycerin [mmol-calcium-based catalyst / mol-glycerin] of 3.0 to 170, wherein the total content of fatty acids having a carbon chain length of 18 or longer and having 3 or more double bonds in the fatty acids constituting the fats and oils reacted with glycerin is 15 to 99 mass%. <13> A method for producing transesterified fats and oils, comprising the step of reacting fats and oils with glycerin in the presence of calcium silicate as a calcium catalyst, at a reaction temperature of 90°C or higher and 165°C or lower, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] of 0.30 or higher and 1.7 or lower, and a molar amount of calcium catalyst to the molar amount of glycerin [mmol-calcium catalyst / mol-glycerin] of 90 or higher and 700 or lower, wherein the total content of fatty acids having a carbon chain length of 18 or longer and having 3 or more double bonds in the fatty acids constituting the fats and oils reacted with glycerin is 15 to 99 mass%. <14> A method for producing transesterified oils and fats, comprising a step of reacting an oil or fat with glycerin in the presence of calcium hydroxide or calcium oxide as a calcium-based catalyst, at a reaction temperature of 90°C or higher and 165°C or lower, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] of 0.30 or higher and 1.7 or lower, and a molar amount of the calcium-based catalyst to the molar amount of glycerin [mmol-calcium-based catalyst / mol-glycerin] of 3.0 or higher and 170 or lower, wherein the mass ratio of diacylglycerol to monoacylglycerol in the obtained transesterified oil or fat is 1.10 or higher and 2.2 or lower. <15> A method for producing transesterified oils and fats, comprising a step of reacting an oil or fat with glycerin in the presence of calcium silicate as a calcium-based catalyst, at a reaction temperature of 90°C or higher and 165°C or lower, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] of 0.30 or higher and 1.7 or lower, and a molar amount of calcium-based catalyst to the molar amount of glycerin [mmol-calcium-based catalyst / mol-glycerin] of 90 or higher and 700 or lower, wherein the mass ratio of diacylglycerol to monoacylglycerol in the obtained transesterified oil or fat is 1.10 or higher and 2.2 or lower. <16> A method for producing transesterified oils and fats, comprising a step of reacting an oil or fat with glycerin in the presence of calcium hydroxide or calcium oxide as a calcium-based catalyst, at a reaction temperature of 90°C or higher and 165°C or lower, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] of 0.30 or higher and 1.7 or lower, and a molar amount of the calcium-based catalyst to the molar amount of glycerin [mmol-calcium-based catalyst / mol-glycerin] of 3.0 or higher and 170 or lower, wherein the reaction rate (diacylglycerol + monoacylglycerol content) in the obtained transesterified oil or fats is 72 to 96 mass%. <17> A method for producing transesterified oils and fats, comprising a step of reacting an oil or fat with glycerin in the presence of calcium silicate as a calcium-based catalyst, at a reaction temperature of 90°C or higher and 165°C or lower, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] of 0.30 or higher and 1.7 or lower, and a molar amount of the calcium-based catalyst to the molar amount of glycerin [mmol-calcium-based catalyst / mol-glycerin] of 90 or higher and 700 or lower, wherein the reaction rate (diacylglycerol + monoacylglycerol content) of the obtained transesterified oil or fat is 72 to 96 mass%. <18> A method for producing transesterified fats and oils, comprising the step of reacting fats and oils with glycerin in the presence of a calcium catalyst at a reaction temperature of 90°C or higher and 165°C or lower, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] of 0.30 or higher and 1.7 or lower, wherein the total content of fatty acids having a carbon chain length of 18 or higher and three or more double bonds in the fatty acids constituting the fats and oils reacted with glycerin is 15 to 99 mass%, and the mass ratio of diacylglycerol to monoacylglycerol in the obtained transesterified fats and oils is 1.10 or higher and 2.2 or lower. <19> A method for producing transesterified fats and oils, comprising the step of reacting fats and oils with glycerin in the presence of a calcium catalyst at a reaction temperature of 90°C or higher and 165°C or lower, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] of 0.30 to 1.7, wherein the total content of fatty acids having a carbon chain length of 18 or longer and three or more double bonds in the fatty acids constituting the fats and oils reacted with glycerin is 15 to 99 mass%, and the reaction rate (diacylglycerol + monoacylglycerol content) in the obtained transesterified fats and oils is 72 to 96 mass%. <20> A method for producing transesterified fats and oils, comprising the step of reacting fats and oils with glycerin in the presence of a calcium-based catalyst at a reaction temperature of 90°C or higher and 165°C or lower, with a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] of 0.30 or higher and 1.7 or lower, wherein the resulting transesterified fats and oils have a mass ratio of diacylglycerol to monoacylglycerol of 1.10 or higher and 2.2 or lower, and the resulting transesterified fats and oils have a reaction rate (diacylglycerol + monoacylglycerol content) of 72 to 96 mass%. EXAMPLES

[0036] In the following examples, "%" means "% by mass."

[0037] [Analysis method] (i) Determination of fatty acid composition The samples were converted into fatty acid methyl esters according to the "Methyl Esterification Method (Boron Trifluoride Methanol Method) (2.4.1.2-1996)" in the "Standard Methods for the Analysis of Fats, Oils and Related Materials, 2003 Edition" compiled by the Japan Oil Chemists' Society, and the obtained samples were subjected to gas chromatography (GC).

[0038] (ii) Measurement of the glyceride composition (MAG, DAG and TAG composition) of the total glyceride of interesterified oils and fats when using linseed oil Approximately 10 mg of transesterified oil and 0.5 mL of trimethylsilylation agent ("Silylation Agent TH", Kanto Chemical) were added to a glass sample bottle, sealed, and heated at 70°C for 15 minutes. 1.5 mL of water and 1.5 mL of hexane were added to the bottle and shaken. After standing, the upper layer was subjected to gas chromatography (GC) to analyze the glyceride composition.

[0039] (iii) Measurement of the glyceride composition (MAG, DAG and TAG composition) of the total glyceride of interesterified oils using algae oil Because the detection sensitivity of gas chromatography (GC) decreases when EPA or DHA is included, a thin-layer chromatography detector was used for the analysis. After TLC development using a mixed solvent of 70 vol% hexane and 30 vol% ethyl acetate, the analysis was performed using an Iatroscan (manufactured by LSI Medience).

[0040] Example 1 263.1 g of decolorized linseed oil (ADM) and 136.9 g of glycerin were placed in a 1000 mL 4-neck flask equipped with a stirring blade (75 mm x 20 mm). The ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] was 0.50. The mixture was dehydrated under reduced pressure at 70°C and 400 Pa for 30 minutes while stirring at 400 r / min. After that, the mixture was heated to the reaction temperature of 140°C at a temperature increase rate of 4°C / min while circulating nitrogen at normal pressure. Next, 0.6 g of calcium hydroxide was added as a catalyst, and the glycerolysis reaction was carried out at 140°C and normal pressure while circulating nitrogen. After 4 hours from the start of the reaction, the mixture was cooled to 95°C, phosphoric acid was added, and the mixture was stirred for 30 minutes to obtain a neutralized oil. The neutralized oil was collected in a test tube capable of centrifugation, and centrifuged at 3000 r / min for 10 minutes to remove the precipitated glycerin and catalyst to obtain an interesterified oil.

[0041] Example 2 The glycerolysis reaction was carried out in the same manner as in Example 1, except that the raw material oils for the glycerolysis reaction, 304.8 g of decolorized linseed oil (manufactured by ADM) and 95.2 g of glycerin, were used, and the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] was set to 0.75, to obtain an interesterified oil.

[0042] Example 3 The glycerolysis reaction was carried out in the same manner as in Example 1, except that the raw material oils for the glycerolysis reaction, 331.1 g of decolorized linseed oil (manufactured by ADM) and 68.9 g of glycerin, were used, and the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] was set to 1.00, to obtain an interesterified oil.

[0043] Example 4 The glycerolysis reaction was carried out in the same manner as in Example 1, except that the raw material oils for the glycerolysis reaction, 349.1 g of decolorized linseed oil (manufactured by ADM) and 50.9 g of glycerin, were used, and the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] was set to 1.25, to obtain an interesterified oil.

[0044] Example 5 The glycerolysis reaction was carried out in the same manner as in Example 1, except that the raw material oils for the glycerolysis reaction, 362.3 g of decolorized linseed oil (manufactured by ADM) and 37.7 g of glycerin, were used, and the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] was set to 1.50, to obtain an interesterified oil.

[0045] Comparative Example 1 The glycerolysis reaction was carried out in the same manner as in Example 1, except that the raw material oils for the glycerolysis reaction, 372.3 g of decolorized linseed oil (manufactured by ADM) and 27.7 g of glycerin, were used, and the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] was set to 1.75, to obtain an interesterified oil.

[0046] Example 6 The glycerolysis reaction was carried out in the same manner as in Example 1, except that the raw material oil for the glycerolysis reaction was 302.6 g of algae oil (product name: Life'somega 60 manufactured by DSM), 97.4 g of glycerin, the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] was 0.70, and the catalyst addition temperature and reaction temperature were 150°C, to obtain an interesterified oil.

[0047] Example 7 The glycerolysis reaction was carried out in the same manner as in Example 6, except that the raw material oil for the glycerolysis reaction was 334.5 g of algae oil (product name: Life'somega 60 manufactured by DSM), 65.5 g of glycerin, and the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] was 1.00, to obtain an interesterified oil.

[0048] Example 8 The glycerolysis reaction was carried out in the same manner as in Example 6, except that the raw material oil for the glycerolysis reaction was 351.7 g of algae oil (product name: Life'somega 60 manufactured by DSM), 48.3 g of glycerin, and the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] was 1.25, to obtain an interesterified oil.

[0049] Example 9 The raw material oil for the glycerolysis reaction was 364.3 g of algae oil (trade name: Life'somega 60 manufactured by DSM) and 35.7 g of glycerin. The glycerolysis reaction was carried out in the same manner as in Example 6, except that the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] was set to 1.50, to obtain an interesterified oil.

[0050] Comparative Example 2 The glycerolysis reaction was carried out in the same manner as in Example 6, except that the raw material oil for the glycerolysis reaction was 373.8 g of algae oil (product name: Life'somega 60 manufactured by DSM), 26.2 g of glycerin, and the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] was 1.75, to obtain an interesterified oil.

[0051] Example 10 The catalyst calcium hydroxide was added after the reduced pressure dehydration of the raw material, the pressure was reduced to 9300 Pa, and the temperature was increased to the reaction temperature of 140°C at a heating rate of 1°C / min. Except for this, the ester-exchanged oil was obtained under the same conditions as in Example 1.

[0052] Example 11 The timing of adding the catalyst calcium hydroxide was after the reduced pressure dehydration of the raw material, the pressure was reduced to 9300 Pa, and the temperature was increased to the reaction temperature of 140°C at a heating rate of 1°C / min. Except for this, the ester-exchanged oil was obtained under the same conditions as in Example 2.

[0053] Example 12 The catalyst calcium hydroxide was added after the reduced pressure dehydration of the raw material, the pressure was reduced to 9300 Pa, and the temperature was increased to the reaction temperature of 140°C at a heating rate of 1°C / min. Except for this, the ester-exchanged oil was obtained under the same conditions as in Example 3.

[0054] Comparative Example 3 An interesterified oil was obtained under the same conditions as in Example 3, except that 0.882 g of sodium methylate was added as a catalyst at 70° C. and the glycerolysis reaction was carried out under conditions changed to 150° C. and 5 hours.

[0055] Comparative Example 4 An interesterified oil was obtained under the same conditions as in Comparative Example 3, except that 0.536 g of sodium hydroxide was added as a catalyst at 150°C.

[0056] Comparative Example 5 The ester-exchanged oil was obtained under the same conditions as in Example 3, except that 0.4 g of calcium hydroxide as a catalyst was added after the reduced pressure dehydration of the raw material, the temperature was raised to the reaction temperature of 210°C at a heating rate of 1°C / min, and the glycerolysis reaction was carried out for 1 hour.

[0057] Example 13 The glycerolysis reaction was carried out in the same manner as in Example 6, except that the raw material oil for the glycerolysis reaction was 334.5 g of algae oil (product name: Life'somega 60 manufactured by DSM), 65.5 g of glycerin, a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] of 1.00, 4.0 g of calcium hydroxide was used as a catalyst, and the catalyst addition temperature and reaction temperature were 100°C, to obtain an interesterified oil.

[0058] Example 14 The glycerolysis reaction was carried out in the same manner as in Example 6, except that the raw material oil for the glycerolysis reaction was 334.5 g of algae oil (product name: Life'somega 60 manufactured by DSM), 65.5 g of glycerin, the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] was 1.00, 4.0 g of calcium hydroxide was used as a catalyst, and the catalyst addition temperature and reaction temperature were 110°C, to obtain an interesterified oil.

[0059] Example 15 The glycerolysis reaction was carried out in the same manner as in Example 6, except that the raw material oil for the glycerolysis reaction was 334.5 g of algae oil (product name: Life'somega 60 manufactured by DSM), 65.5 g of glycerin, the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] was 1.00, 0.16 g of calcium hydroxide was used as a catalyst, and the catalyst addition temperature and reaction temperature were 160°C, to obtain an interesterified oil.

[0060] Example 16 The glycerolysis reaction was carried out in the same manner as in Example 1, except that the raw material oils for the glycerolysis reaction were 331.1 g of decolorized linseed oil (manufactured by ADM), 68.9 g of glycerin, a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] of 1.00, 0.44 g of calcium oxide as a catalyst, and a catalyst addition temperature and a reaction temperature of 150°C, to obtain an interesterified oil.

[0061] Example 17 The glycerolysis reaction was carried out in the same manner as in Example 1, except that the raw material oils for the glycerolysis reaction were 331.1 g of decolorized linseed oil (manufactured by ADM), 68.9 g of glycerin, a ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] of 1.00, 20.00 g of calcium silicate as a catalyst, and the catalyst addition temperature and reaction temperature were 150°C, to obtain an interesterified oil.

[0062] [Table 1]

[0063] As is clear from Table 1, when a calcium-based catalyst is used as the catalyst and the glycerolysis reaction is carried out at a low [FA / GLY] molar ratio and low reaction temperature, the diacylglycerol / monoacylglycerol ratio in the reaction oil is higher than in the case of a high reaction temperature, and the reaction rate, which indicates the total of diacylglycerol and monoacylglycerol, is higher than in the case of a high [FA / GLY] molar ratio, and it was confirmed that a large amount of triacylglycerol remains (Examples 1 to 17, Comparative Examples 1 and 2). Furthermore, when the catalyst was added before increasing the temperature of the reaction raw materials, a slightly larger amount of triacylglycerol remained, but the diacylglycerol / monoacylglycerol mass ratio was increased (Examples 10 to 12 and Examples 1 to 3). On the other hand, it was found that when a sodium-based catalyst was used, a large amount of monoacylglycerol was produced, and the diacylglycerol / monoacylglycerol ratio was low (Comparative Examples 3 to 4 and Example 3). Furthermore, it was found that when calcium hydroxide was used as a catalyst and the reaction was carried out at a high temperature with a low [FA / GLY] ratio, a large amount of monoacylglycerol was produced and the diacylglycerol / monoacylglycerol ratio was decreased (Comparative Example 5 and Example 3).

Claims

1. A method for producing transesterified fats and oils, comprising a step of reacting fats and oils with glycerin in the presence of a calcium-based catalyst at a reaction temperature of 90° C. or higher and 165° C. or lower, with the ratio of the number of moles of fatty acid groups to the number of moles of glycerin groups [FA / GLY] being 0.30 or higher and 1.7 or lower.

2. 2. The method for producing transesterified fats and oils according to claim 1, wherein the amount of calcium hydroxide or calcium oxide used as the calcium catalyst is 0.01 mass % or more based on the total amount of the fats and oils and glycerin.

3. 2. The method for producing transesterified fats and oils according to claim 1, wherein the amount of calcium silicate used as the calcium catalyst is 0.5 mass % or more based on the total amount of the fats and oils and glycerin.

4. The method for producing an interesterified oil or fat according to any one of claims 1 to 3, wherein the fatty acid constituting the oil or fat contains a fatty acid having a carbon chain length of 18 or more and a double bond number of 3 or more.

5. The method for producing an interesterified oil or fat according to claim 4, wherein the content of fatty acids having a carbon chain length of 18 or more and a double bond number of 3 or more in fatty acids constituting the oil or fat is 15% by mass or more.

6. The method for producing an interesterified oil or fat according to any one of claims 1 to 3, wherein the diacylglycerol / monoacylglycerol mass ratio in the oil or fat after the interesterification reaction is 1.08 or more, and the total amount of diacylglycerol and monoacylglycerol is 72% by mass or more.

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