Production method for transesterified oil / fat

Abstract

Provided is a method for producing a transesterified oil / fat having a high diacylglycerol purity while carrying out a glycerolysis reaction at a low temperature.　Specifically provided is a production method for a transesterified oil / fat, said method including a step in which an oil / fat and glycerin are reacted at a ratio [FA / GLY] of the number of moles of the fatty acid group to the number of moles of the glycerin group of 0.30-1.7 in the presence of a calcium-based catalyst at a reaction temperature of 90-165°C.

Description

Method for producing interesterified oils and fats

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

[0002] Diacylglycerol is used in various industrial fields, such as food and cosmetics. Diacylglycerol is generally produced by an esterification reaction between glycerin and a fatty acid or a glycerolysis reaction between glycerin and a fat or oil. These production methods are broadly divided into chemical methods using chemical catalysts such as hydroxides or 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.

[0003] (Patent Document 1) JP 2010-59406 A

[0004] The present invention provides a method for producing interesterified fats and oils, which includes 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. Detailed Description of the Invention

[0005] However, in the glycerolysis method, 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 materials. However, it is common technical knowledge that increasing this ratio results in the production of a large amount of monoacylglycerol when the equilibrium composition is reached. Since monoacylglycerol is easily emulsified, requires a high purification load, and has a unique flavor, it is desirable to reduce the amount of monoacylglycerol. Therefore, in conventional glycerolysis methods, the ratio of glycerin to fats and oils is reduced, thereby suppressing the production of monoacylglycerol while sacrificing some of the purity of diacylglycerol. Therefore, the present invention relates to a method for producing transesterified fats and oils rich in diacylglycerol at a high reaction rate while suppressing the production of monoacylglycerol.

[0006] The present inventors have found that when the ratio of glycerin to fats and oils is high, which has traditionally been thought to result in the production of a large amount of monoacylglycerol, the production of monoacylglycerol is suppressed by carrying out the reaction at a 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.

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

[0008] In the present invention, "transesterified fats and oils" refers to fats and oils obtained by reacting raw fats and oils with glycerin, then removing the catalyst by neutralization, filtration, etc., and removing unreacted phase-separated glycerin, and "reacted oil" refers to fats and oils obtained by reacting raw fats and oils with glycerin, but before removing the catalyst and unreacted phase-separated glycerin. Furthermore, in the present invention, the "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 fats and oils of the present invention includes 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. In this specification, "fat and oil" and "oil" are synonymous. Furthermore, 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, Job's tears 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 suitable oils include vegetable oils 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, cocoa butter, monkey fat, shea butter, and algae oil; animal oils such as fish oil, seal oil, whale oil, lard, beef tallow, and butter fat; microbial oils such as oils derived from polyunsaturated fatty acid-producing microorganisms such as Zygomycetes; and interesterified oils, hydrogenated oils, and fractionated oils thereof. These oils and fats can be used alone or in combination of two or more. Among these, liquid oils and fats are preferred in terms of the emulsification properties and ease of handling of interesterified oils and fats. Liquid oils and fats refer to oils and fats that are liquid at 20°C when subjected to a cooling test according to Standard Fats, Oils, and Fat Analysis Test Method 2.3.8-27. Furthermore, in the present invention, unlike a typical glycerolysis reaction, the reaction is carried out at a low temperature, which suppresses the production of trans fatty acids. Therefore, 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 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 that produce polyunsaturated fatty acids.

[0011] Fish oil can be extracted from raw materials such as sardines, herring, saury, mackerel, bonito, tuna, squid, and cod liver. Algae oil can be extracted from algae belonging to the Chlorophyceae, Bacillariophyceae, etc. These are preferably subjected to known separation and purification methods such as liquid-liquid separation, filtration, and centrifugation to remove impurities before the reaction. Alternatively, so-called concentrated oils can be used, which are obtained by selectively hydrolyzing fish oils or the like using lipase to increase the proportion 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 or fat may be 100% by mass, but in order to facilitate the concentration of highly unsaturated fatty acids, particularly eicosapentaenoic acid and docosahexaenoic acid, in the transesterified oil or fat, it is preferably 95% by mass or less, more preferably 92% by mass or less, and even more preferably 89% by mass or less. From the viewpoint of production efficiency, it is preferably 70% by mass or more, more preferably 75% by mass or more, and even more preferably 80% by mass or more. To reduce the triacylglycerol content in the oil or fat to be reacted with glycerin to less than 100% by mass, it is preferable to partially hydrolyze the oil or fat with lipase and then remove the resulting fatty acids by distillation. This operation allows selective removal of saturated fatty acids with 16 and 18 carbon atoms from the constituent fatty acids, thereby allowing the highly unsaturated fatty acids to be further concentrated in the oil or fat to be reacted with glycerin. Furthermore, 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, from the viewpoint 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, from the viewpoint of production efficiency.

[0013] The constituent fatty acids constituting the oils and fats are not particularly limited and may be either saturated or unsaturated fatty acids. From the viewpoint of handleability and industrial productivity of the oils and fats, the content of unsaturated fatty acids in the fatty acids constituting the oils and fats 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 in the unsaturated fatty acids is preferably 14 to 24, more preferably 16 to 22, and even more preferably 18 to 22. The amount of fatty acid in this specification is the amount converted to free fatty acid.

[0014] In view of physiological activity, the fatty acids constituting the oils and fats preferably contain a large amount of fatty acids having a carbon chain length of 18 or more and three or more double bonds. Furthermore, according to the method of the present invention, it is possible to obtain interesterified oils and fats in which the proportion of fatty acids having a carbon chain length of 18 or more and three or more double bonds in the reactant oil is high, while preventing the proportion of such fatty acids in the reactant oil from becoming lower than the proportion of fatty acids having a carbon chain length of 18 or more and three or more double bonds in the reactant oil. In view of physiological activity, the total content of fatty acids having a carbon chain length of 18 or more and three or more double bonds in the fatty acids constituting the oils and fats 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. Furthermore, in view of suppressing the by-production of trans fatty acids, it is preferably 99% by mass or less, more preferably 90% by mass or less, and even more preferably 80% by mass or less. The total content of fatty acids having a carbon chain length of 18 or more and three or more double bonds in the fatty acids constituting the oil or fat 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 having a carbon chain length of 18 or more and three or more double bonds in the fatty acids constituting the oil or fat include α-linolenic acid (C18:3), γ-linolenic acid (C18:3), arachidonic acid (C20:4), eicosapentaenoic acid (C20:5, EPA), docosapentaenoic acid (C22:5), and docosahexaenoic acid (C22:6, DHA). Among these, ω3 unsaturated fatty acids having a double bond at the third position 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 order to improve 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] when reacting 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 glycerin groups [FA / GLY] is expressed by the following formula. FA / GLY=(moles of fatty acid+moles of monoacylglycerol+moles of diacylglycerol×2+moles of triacylglycerol×3) / (moles of glycerin+moles of monoacylglycerol+moles of diacylglycerol+moles of triacylglycerol) The ratio of the moles of fatty acid groups to the moles of glycerin groups [FA / GLY] is 0.30 or more, preferably 0.35 or more, and more preferably 0.40 or more, from the viewpoint of being able to reduce the amount of glycerin that does not dissolve in the oil phase, and is 1.7 or less, preferably 1.6 or less, and more preferably 1.5 or less, from the viewpoint of being able to increase the ratio of diacylglycerol to monoacylglycerol in the reaction oil and to increase 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, and 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 a catalyst, it is possible to increase the reaction rate while suppressing the production of monoacylglycerol. The calcium-based catalyst used in the present invention may be any catalyst that catalyzes the glycerolysis reaction. Examples of calcium-based catalysts include calcium hydroxide, calcium carbonate, calcium oxide, calcium silicate, and calcium alkoxides such as calcium methoxide. These catalysts may be used alone or in combination of two or more. Of these, calcium hydroxide, calcium oxide, and calcium silicate are preferred because they can improve the diacylglycerol purity of 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 reaction raw materials (total of oils and fats 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, from the viewpoint of reducing the amount of neutralizing agent. When the calcium catalyst is calcium hydroxide or calcium oxide, the amount 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 reaction raw materials. Similarly, when the calcium-based catalyst is calcium silicate, the amount 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 reaction raw materials (total of oils and fats 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, from the viewpoint of reducing the amount of neutralizing agent. When the calcium-based catalyst is calcium silicate, the amount 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 reaction raw materials.Furthermore, when the calcium-based catalyst is calcium hydroxide and calcium oxide, the molar amount of the calcium-based catalyst relative to the molar amount of glycerin [mmol-calcium-based catalyst / mol-glycerin] is preferably 0.2 or more, more preferably 0.5 or more, even more preferably 1.2 or more, still more preferably 3.0 or more, still more preferably 10.0 or more, and still more preferably 15.0 or more from the viewpoint of improving reactivity, and is preferably 340 or less, more preferably 170 or less, and still more preferably 80 or less from the viewpoint of being able to reduce the amount of neutralizing agent. In the case of calcium hydroxide and calcium oxide, the ratio of the molar amount of the calcium-based catalyst to the molar amount of glycerin [mmol-calcium-based catalyst / mol-glycerin] is preferably 0.2 to 340, more preferably 0.5 to 340, even more preferably 1.2 to 170, still more preferably 3.0 to 170, still more preferably 10.0 to 80, and still more preferably 15.0 to 80. Similarly, when the calcium-based catalyst is calcium silicate, the molar amount of the calcium-based catalyst relative to the molar amount of glycerin [mmol-calcium-based catalyst / mol-glycerin] is preferably 30 or more, more preferably 60 or more, even more preferably 90 or more, still more preferably 120 or more, still more preferably 150 or more, and still more preferably 180 or more from the viewpoint of improving reactivity, and is preferably 900 or less, more preferably 700 or less, and still more preferably 500 or less from the viewpoint of being able to reduce the amount of neutralizing agent. In the case of calcium silicate, the ratio of the molar amount of the calcium-based catalyst to the molar amount of glycerin [mmol-calcium-based catalyst / mol-glycerin] is preferably 30 to 900, more preferably 60 to 900, even more preferably 90 to 700, still more preferably 120 to 700, still more preferably 150 to 500, and still 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 is preferably carried out at 50°C or higher when raising the temperature to the reaction temperature from the viewpoints of suppressing catalyst deactivation and improving the diacylglycerol purity of the reaction oil. Here, "50°C or higher" does not mean that no calcium-based catalyst is added to the reaction raw material at temperatures below 50°C, but rather means that the amount required to catalyze the reaction is added at 50°C or higher. The temperature at which the calcium-based 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 viewpoints of suppressing catalyst deactivation and improving the diacylglycerol purity of the reaction oil. Furthermore, from the viewpoint of improving quality, the temperature is preferably 165°C or lower, more preferably 160°C or lower, and even more preferably 155°C or lower. The temperature at which the calcium-based 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 the reaction temperature as needed to carry out the glycerolysis reaction with the fats and oils and glycerin.

[0019] In the present invention, the reaction temperature is 90°C or higher and 165°C or lower. It is unclear why the effects of the present invention are achieved when the reaction is carried out at such a low temperature compared to a typical glycerolysis reaction, but it is believed to be due to the following mechanism. When the glycerolysis reaction of fats and oils with glycerin is carried out at a high temperature, the solubility of glycerin in fats and oils is high, making it easier for monoacylglycerol to be stabilized in the reaction oil, and the reaction equilibrium leans toward 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, making it difficult for monoacylglycerol to be stabilized in the reaction oil. This inhibits the equilibrium and suppresses the production of monoacylglycerol, which is thought to increase the ratio of diacylglycerol to monoacylglycerol in the reaction oil while increasing the reaction rate. The reaction temperature is 90°C or higher, preferably 95°C or higher, and more preferably 100°C or higher, from the viewpoint of improving the reaction rate. Furthermore, from the viewpoint of increasing the ratio of diacylglycerol to monoacylglycerol in the reaction oil, it is 165°C or lower, preferably 160°C or lower, and more preferably 155°C or lower. The reaction temperature is 90 to 165°C, preferably 95 to 160°C, and more preferably 100 to 155°C. Furthermore, from the viewpoint of increasing the ratio of diacylglycerol to monoacylglycerol in the reaction oil, it is preferable that a step of reacting at above 165°C is not substantially included. "Substantially not included" preferably means 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%. Furthermore, "substantially not included," in terms of specific time, 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.

[0020] The rate at which the reaction raw materials are heated 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 preventing catalyst deactivation 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 on the equipment. The rate at which the reaction raw materials are heated 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 that extending the reaction time can increase the ratio of diacylglycerol to monoacylglycerol in the reaction oil and can reduce catalytic activity and suppress reverse reactions upon cooling, and from the viewpoint that extending the reaction time can reduce catalytic activity and suppress reverse reactions upon cooling, the reaction time is preferably 15 hours or less, more preferably 12 hours or less, and even more preferably 9 hours or less, from the viewpoint of industrial productivity. 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 reactivity and prevent a decrease in catalytic performance, the reaction between fats and oils and glycerin is preferably carried out after removing water contained in the reaction raw materials by reducing pressure, bubbling with nitrogen, etc. The water concentration of the reaction raw materials before the addition of the calcium-based catalyst is preferably 0.01 to 0.5% by mass, more preferably 0.03 to 0.4% by mass, and even more preferably 0.05 to 0.3% by mass, in terms of industrial productivity and preventing a decrease in catalytic performance.

[0023] The reaction may usually 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 water content in the reaction system. When the reaction is carried out under normal pressure, it is preferable to carry out the reaction under a nitrogen atmosphere in which nitrogen is circulated in order to suppress oxidation of the resulting interesterified oil or fat.

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

[0025] In the present invention, the neutralization of the calcium-based catalyst is carried out by adding a neutralizing agent in an amount preferably 1.2 times by mole or more, more preferably 1.25 times by mole or more, and even more preferably 1.3 times by mole or more relative to the calcium-based catalyst, in order to prevent a decrease in the diacylglycerol concentration due to transesterification during subsequent distillation treatment. The upper limit of the molar ratio is not particularly limited, but is preferably 3.0 times by mole or less, more preferably 2.6 times by mole or less, and even more preferably 2.2 times by mole or less, in order to prevent an increase in the acid value of the neutralized oil. The amount of neutralizing agent relative to the calcium-based catalyst is preferably 1.2 to 3.0 times by mole, more preferably 1.25 to 2.6 times by mole, and even more preferably 1.3 to 2.2 times by mole.

[0026] The temperature in the neutralization step, i.e., the step from adding a neutralizing agent to the reaction oil containing the calcium-based catalyst until the stirring is completed (the same applies hereinafter), 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 producing a neutralized product. Moreover, from the viewpoint of being able to suppress reverse reactions and oxidation, the temperature 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, from the viewpoint of sufficiently producing the neutralized product.

[0028] In the neutralization step, it is preferable to carry out the neutralization while stirring in order to sufficiently produce the neutralized product. 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 similar to that used for ordinary fats and oils may be carried out. Specific examples include distillation, acid treatment, water washing, bleaching, and deodorization. In the present invention, an enzymatic esterification reaction may be further carried out after the glycerolysis reaction. However, from the viewpoint of increasing the proportion 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 oils and fats obtained by the method of the present invention contain, in addition to diacylglycerol, triacylglycerol, monoacylglycerol, and dissolved unreacted glycerin, but the ratio of diacylglycerol to monoacylglycerol is high. In the interesterified oils and fats 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, from the viewpoint of suppressing emulsification and reducing the purification load, and is also preferably 2.2 or less, more preferably 2.0 or less, even more preferably 1.8 or less. 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 interesterified oils and fats obtained by the method of the present invention are rich in diacylglycerol, and the diacylglycerol content is preferably 38 to 56% by mass, more preferably 40 to 54% by mass, and even more preferably 42 to 52% by mass, from the viewpoint of improving physiologically active functions. Furthermore, the monoacylglycerol content in the interesterified oils and fats 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 physiologically active functions. The interesterified oils and fats obtained by the method of the present invention can be used in the same way as general edible oils and fats, by removing the monoacylglycerol, if necessary, by distillation or the like.

[0032] The transesterified oil or fat obtained by the method of the present invention preferably has a free fatty acid content of 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 on the refining process and industrial productivity. Furthermore, from the viewpoint of carrying out the reaction efficiently, 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 interesterified oils and fats, the reaction rate (diacylglycerol + monoacylglycerol content) is preferably 72 to 96% by mass, more preferably 75 to 94% by mass, and even more preferably 77 to 92% by mass, from the viewpoint of suppressing emulsification and reducing the purification load.

[0034] Furthermore, in the interesterified oil or fat 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 diacylglycerol purity is [diacylglycerol / (diacylglycerol+triacylglycerol)×100].

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

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

[0037] [Analysis Method] (i) Measurement of Fatty Acid Composition A sample was subjected to fatty acid methyl esterification in accordance with "Methyl Esterification Method (Boron Trifluoride Methanol Method) (2.4.1.2-1996)" in "Standard Methods for the Analysis of Fats, Oils and Related Materials, 2003 Edition" compiled by the Japan Oil Chemists' Society, and the obtained sample was subjected to gas chromatography (GC).

[0038] (ii) Measurement of glyceride composition (each composition of MAG, DAG, and TAG) in total glycerides of interesterified oil when using linseed oil Approximately 10 mg of interesterified oil and 0.5 mL of trimethylsilylating agent ("Silylation Agent TH", manufactured by 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 (each composition of MAG, DAG, and TAG) of the total glycerides of interesterified oils and fats using algae oil. Since the detection sensitivity of gas chromatography (GC) decreases when EPA or DHA is included, analysis was performed using a thin-layer chromatography detector. After TLC development using a mixed solvent of 70 vol% hexane and 30 vol% ethyl acetate, analysis was performed using an Iatroscan (manufactured by LSI Medience).

[0040] Example 1: 263.1 g of bleached linseed oil (manufactured by ADM) and 136.9 g of glycerin, the raw material oils for the glycerolysis reaction, were placed in a 1000 mL four-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. While stirring at 400 r / min, the mixture was dehydrated under reduced pressure at 70°C and 400 Pa for 30 minutes. Then, while circulating nitrogen at atmospheric pressure, the mixture was heated to the reaction temperature of 140°C at a heating rate of 4°C / min. Next, 0.6 g of calcium hydroxide was added as a catalyst, and the glycerolysis reaction was carried out at 140°C under atmospheric pressure and nitrogen. After 4 hours from the start of the reaction, the mixture was cooled to 95°C, and phosphoric acid was added, followed by stirring for 30 minutes to obtain a neutralized oil. The neutralized oil was collected in a test tube suitable for centrifugation and centrifuged at 3000 rpm for 10 minutes to remove the precipitated glycerin and catalyst, thereby obtaining an interesterified oil.

[0041] Example 2 A glycerolysis reaction was carried out in the same manner as in Example 1, except that the raw materials for the glycerolysis reaction, 304.8 g of bleached 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 A glycerolysis reaction was carried out in the same manner as in Example 1, except that the raw materials for the glycerolysis reaction, 331.1 g of bleached 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 A glycerolysis reaction was carried out in the same manner as in Example 1, except that the raw materials for the glycerolysis reaction, 349.1 g of bleached 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 A glycerolysis reaction was carried out in the same manner as in Example 1, except that the raw materials for the glycerolysis reaction, 362.3 g of bleached 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 A 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 bleached 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 A glycerolysis reaction was carried out in the same manner as in Example 1, except that the feedstock oil for the glycerolysis reaction was 302.6 g of algae oil (trade name: Life'somega 60, manufactured by DSM) and 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 A 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 (trade name: Life'somega 60, manufactured by DSM) and 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 A 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 (trade name: Life'somega 60, manufactured by DSM) and 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 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 1.50, using 364.3 g of algae oil (trade name: Life'somega 60, manufactured by DSM) and 35.7 g of glycerin as raw material oils, to obtain an interesterified oil.

[0050] Comparative Example 2 A 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 (trade name: Life'somega 60, manufactured by DSM) and 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 An interesterified oil was obtained under the same conditions as in Example 1, except that calcium hydroxide as a catalyst was added after the raw material was dehydrated under reduced pressure, the pressure was reduced to 9,300 Pa, and the temperature was increased to the reaction temperature of 140°C at a heating rate of 1°C / min.

[0052] Example 11 Interesterified fats and oils were obtained under the same conditions as in Example 2, except that calcium hydroxide as a catalyst was added after the raw material was dehydrated under reduced pressure, the pressure was reduced to 9,300 Pa, and the temperature was increased to the reaction temperature of 140°C at a heating rate of 1°C / min.

[0053] Example 12 An interesterified oil was obtained under the same conditions as in Example 3, except that calcium hydroxide as a catalyst was added after the raw material was dehydrated under reduced pressure, the pressure was reduced to 9,300 Pa, and the temperature was increased to the reaction temperature of 140°C at a heating rate of 1°C / min.

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

[0055] Comparative Example 4 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 An interesterified 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 raw material was dehydrated under reduced pressure, the raw material was heated to the reaction temperature of 210°C at a temperature increase rate of 1°C / min, and the glycerolysis reaction was carried out for 1 hour.

[0057] Example 13 A glycerolysis reaction was carried out in the same manner as in Example 6 to obtain an interesterified oil, except that 334.5 g of algae oil (trade name: Life'somega 60, manufactured by DSM) and 65.5 g of glycerin were used as raw oils for the glycerolysis reaction, 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, 4.0 g of calcium hydroxide was used as a catalyst, and the catalyst addition temperature and reaction temperature were set to 100°C.

[0058] Example 14 A glycerolysis reaction was carried out in the same manner as in Example 6 to obtain an interesterified oil, except that 334.5 g of algae oil (trade name: Life'somega 60, manufactured by DSM) and 65.5 g of glycerin were used as raw oil for the glycerolysis reaction, 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, 4.0 g of calcium hydroxide was used as a catalyst, and the catalyst addition temperature and reaction temperature were set to 110°C.

[0059] Example 15 A glycerolysis reaction was carried out in the same manner as in Example 6 to obtain an interesterified oil, except that 334.5 g of algae oil (trade name: Life'somega 60, manufactured by DSM) and 65.5 g of glycerin were used as raw oils for the glycerolysis reaction, 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, 0.16 g of calcium hydroxide was used as a catalyst, and the catalyst addition temperature and reaction temperature were set to 160°C.

[0060] Example 16 A glycerolysis reaction was carried out in the same manner as in Example 1, except that 331.1 g of bleached linseed oil (manufactured by ADM) and 68.9 g of glycerin were used as raw oils for the glycerolysis reaction, 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, 0.44 g of calcium oxide was used as a catalyst, and the catalyst addition temperature and reaction temperature were set to 150°C, to obtain an interesterified oil.

[0061] Example 17 A glycerolysis reaction was carried out in the same manner as in Example 1 to obtain an interesterified oil, except that the raw material oils for the glycerolysis reaction were 331.1 g of bleached 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 a catalyst addition temperature and a reaction temperature of 150°C.

[0062]

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

Claims

1. A method for producing transesterified oils and fats, comprising a step of reacting oils and fats 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. A 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 fats and oils and glycerin.

3. A 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 fats and oils and glycerin.

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

5. A method for producing an ester-exchanged oil or fat as described in 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 among the fatty acids constituting the oil or fat is 15% by mass or more.

6. A method for producing an interesterified oil or fat according to any one of claims 1 to 5, wherein the diacylglycerol / monoacylglycerol mass ratio in the oil or fat after the interesterification reaction is 1.08 or more, and the total of diacylglycerol and monoacylglycerol is 72 mass% or more.

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