WO2008053838A1 - Fractional modifier for fat - Google Patents

Abstract

A novel fractional modifier for fats which is to be added to and mixed with a fat, e.g., palm oil, in the step of separating the fat into a liquid fraction and a solid fraction, in order to obtain a higher-quality fractionated oil in a short cooling time. The fractional modifier for fats is characterized by comprising a glycerol/fatty acid polyester including a C8-22 fatty acid as a main constituent fatty acid.

Description

 Specification

 Oil / fat separation modifier

 Technical field

 [0001] In the process of separating oil and fat such as palm oil into its liquid part and solid part, the present invention reduces the time required for separation and improves the quality and yield of the separated oil and fat. The present invention relates to an oil / fat fractionation modifier to be added.

 Background art

 Oils and fats such as palm oil are a mixture of a component that is liquid at normal temperature (liquid portion) and a component that is solid at normal temperature (solid portion). Such fats and oils may be used as they are, but they are divided into a liquid part and a solid part. Depending on the intended application, each part (hereinafter, each part obtained by separation is classified as `` separated ''. "Oil" is sometimes used.)

[0003] The operation of dividing oil and fat into its liquid part and solid part is said to be fractionation (or fractionation). As this fractionation method, a natural fractionation method (dry method), a surfactant fractionation method, and a solvent fractionation method are known. Here, since the surfactant fractionation method uses a surfactant such as sodium dodecyl sulfate, there are problems in food hygiene, and the solvent fractionation method tends to cause problems such as a decrease in production efficiency. Therefore, oil and fats such as palm oil are usually separated by a natural separation method.

 [0004] In the natural fractionation method, oil and fat are heated and melted, and then gradually cooled to precipitate crystals, followed by filtration with a filter press or the like, and the produced crystal parts are separated from the liquid oil part to form a liquid. This is a method of separating into a solid part and a low-cost method with low equipment and running costs.

[0005] In this fractionation method, in order to obtain high-quality fractionated fats and oils, it is necessary to slowly cool the melted fats and oils over a long period of time to gradually precipitate crystals. If the cooling rate is increased and the cooling time is shortened, the mixing of the solid part of the liquid part and the mixing of the liquid part of the solid part will increase, and the quality of the fractionated oil will deteriorate. Furthermore, the amount of the liquid part in the crystal phase (solid part) increases, resulting in a decrease in the yield of the liquid part. [0006] On the other hand, in order to improve the production efficiency of fractionation, it is desired to shorten the cooling time. Therefore, it is desired to develop a separation method capable of obtaining a high-quality fractionated fat with a short cooling time and a high yield. In Patent Document 1 and Patent Document 2, as this method, oil and fat fractionation (emulsification for use) mainly comprising sucrose fatty acid ester whose main constituent fatty acid is stearic acid (Patent Document 1) or palmitic acid (Patent Document 2). ) Agent is added to and mixed with fats and oils, and a method for fractionating fats and oils is disclosed. According to this method, it is stated that high-quality fractionated fats and oils can be obtained in high yield in a short cooling time. .

 Patent Document 1: Japanese Patent Laid-Open No. 5-125389

 Patent Document 2: JP-A-6-181686

 Disclosure of the invention

 Problems to be solved by the invention

[0007] The present invention provides an oil / fat separation / modification agent that is added to and mixed with fats and oils in order to obtain high-quality separated oils and fats in a short cooling time in the step of separating the oils and fats into a liquid part and a solid part. Therefore, an object is to provide a novel fractionation modifier.

 Means for solving the problem

 [0008] As a result of extensive research, the present inventor has a process of fractionating fats and oils by adding a polyglycerin ester power of a specific saturated fatty acid, and a separation modifier such as palm oil to fats and oils. In order to complete the present invention, it was found that high-quality fractionated fats and oils (that is, a solid part with little liquid part mixing and a liquid part with little solid part mixing) can be obtained even with a short cooling time. It came.

 That is, the present invention, as a means for solving the above-mentioned problems, comprises a polyglycerin fatty acid ester containing a fatty acid having 8 to 22 carbon atoms as a main constituent fatty acid. (Claim 1) is provided.

[0010] The polyglycerol fatty acid ester constituting the oil / fat separation modifier of the present invention is characterized in that a fatty acid having 8 to 22 carbon atoms is a main constituent fatty acid. Here, “to be a main constituent fatty acid” means that all or most of the fatty acids constituting the polyglycerol fatty acid ester are composed of the fatty acids. However, other fatty acids may be used as long as the object and effect of the present invention are achieved (for example, the content is less than 10% by weight). [0011] The main constituent fatty acid is composed of one or two or more fatty acids whose fatty acid power of 8 to 22 carbon atoms is also selected. When the number of carbon atoms of the fatty acid is less than 8, the effect of promoting crystallization of the solid part, for example, palm stearin, is reduced. When the number of carbon atoms of the fatty acid exceeds 22, the crystallization of the solid part, for example, palm stearin, is promoted, but the promoting effect is too great, so that a high-quality fractionated oil cannot be obtained.

 [0012] Examples of the fatty acids having 8 to 22 carbon atoms include saturated prillic acid, strong puric acid, lauric acid, myristic acid, palmitic acid, stearic acid, and behenic acid, and other saturated fatty acids, palmitoleic acid, and olein. Mention may be made of unsaturated fatty acids such as acids, linoleic acid, linolenic acid and L-force acid.

 [0013] Incidentally, JP-A-3-31397 describes a fat and oil fractionation accelerator comprising polyglycerin fatty acid ester as an essential component. However, this fractionation accelerator is used to promote the filtration of fats and oils in the wintering process and to stabilize the filtration speed (line 4 to 2 from the lower left column on the first page of the same publication). The ring process is a method for removing only a wax component and a small amount of a high melting point component in fats and oils, and is different from the fractionation in the present invention for the purpose of separating a liquid part and a solid part to obtain both. .

 [0014] Further, the polyglycerin fatty acid ester constituting this fractionation accelerator has an esterification rate of 80% or more, the constituent fatty acid is 45% or less of fatty acid having 18 carbon atoms, and has 20 to 24 carbon atoms. It is described that it is desirable to remove saturated fatty acids and unsaturated fatty acids having a fatty acid content of 55% or more and having 16 or less carbon atoms as much as possible in view of the effect (see page 7, upper left column of the same publication). ~; Line 13).

 [0015] As a result of the study, the inventor found that the fractionation in the present invention includes a fatty acid having a small number of carbon atoms and a low esterification rate, unlike the case of the wintering as described above. Even so, they have found that it is an excellent fractionation modifier that gives high-quality fractionated fats and oils in a short cooling time.

[0016] The esterification rate of the polyglycerin fatty acid ester is usually 15 to 100%. That is, even when the esterification rate is less than 80%, the effect of the present invention (the effect of improving the quality of the separated oil and fat in a short cooling time in the separation of the oil and fat) can be obtained. Here, the esterification rate is the average degree of polymerization of polyglycerin calculated from the hydroxyl value (n) When the number of moles of fatty acid added to polyglycerin (M), (M / (n + 2)) X 100 = value calculated by esterification rate (%).

 [0017] The invention according to claim 2 is an oil / fat separation modifier characterized by comprising a polyglycerin fatty acid ester having a fatty acid having 8 to 18 carbon atoms as a main constituent fatty acid. When the cooling time for fractionation is shortened, for example, when it is shorter than about 10 hours, a polyglycerin fatty acid ester containing a fatty acid having 8 to 18 carbon atoms as a main constituent fatty acid is used as a fractionation modifier. Is preferable because a higher-quality fractionated fat is obtained. In particular, when the esterification rate is high, for example, when it exceeds 70%, by using a fatty acid having 8 to 18 carbon atoms as the main constituent fatty acid, a fatty acid having 19 to 22 carbon atoms is used as the main constituent fatty acid. Excellent effect can be obtained. In particular, when the esterification rate exceeds 90%, the effect of using a fatty acid having 8 to 18 carbon atoms as the main constituent fatty acid is more effective than the effect of using a fatty acid having 19 to 22 carbon atoms as the main constituent fatty acid. Remarkably superior. Among fatty acids having 8 to 18 carbon atoms, fatty acids having 14 to 18 carbon atoms are more preferable.

 [0018] The main constituent fatty acid in claim 2 has the same meaning as described above, but among them, those containing 90% by weight or more of one or more selected from fatty acids having 8 to 18 carbon atoms are preferable. More preferably, it is a case containing 90% by weight or more of one or more selected from fatty acids having 14 to 18 carbon atoms.

 [0019] The invention according to claim 3 is an oil or fat characterized by comprising a polyglycerin fatty acid ester having a fatty acid having 19 to 22 carbon atoms as a main constituent fatty acid and an esterification rate in the range of 15 to 85%. This is a fractionation modifier. Even when a fatty acid having 19 to 22 carbon atoms is used as the main constituent fatty acid, high-quality fractionated fats and oils can be obtained by setting the esterification rate of the polyglycerol fatty acid ester in the range of 15 to 85%. In particular, by setting the content within the range of 50 to 70%, it is possible to obtain higher quality fractionated fats and oils.

 [0020] As the fatty acid having 19 to 22 carbon atoms, one or a mixture of two or more selected from fatty acids having a carbon number in this range is used, among which behenic acid having 22 carbon atoms is preferably used. .

[0021] Even when a mixed fatty acid having a fatty acid having 19 to 22 carbon atoms and a fatty acid having 8 to 18 carbon atoms is used, the mixing ratio, the type of the fatty acid, etc. can be further increased Like Therefore, it is preferable to use this because a higher quality fractionated fat is obtained. As a preferred embodiment of the present invention, the oil / fat fractionation modifier according to claims 4 and 5 shown below is provided.

That is, the invention of claim 4 is

 15 to 70% by weight of saturated fatty acid having 19 to 22 carbon atoms, and

 Containing 30 to 85% by weight of saturated fatty acids having 8 to 18 carbon atoms;

 The average carbon number of the saturated fatty acid having 8 to 18 carbon atoms is 12 to 17

 An oil and fat separation modifier characterized by comprising a polyglycerol fatty acid ester having a mixed fatty acid as a constituent fatty acid.

[0023] The invention according to claim 5 provides:

 15 to 70% by weight of saturated fatty acid having 19 to 22 carbon atoms,

 0 to 60% by weight of saturated fatty acids having 12 to 18 carbon atoms; and 18

 15 to 70% by weight of unsaturated fatty acid having 18 to 22 carbon atoms,

 It comprises a polyglycerin fatty acid ester comprising a mixed fatty acid containing glycerin as a constituent fatty acid.

[0024] In Claims 4 and 5, the saturated fatty acid having 19 to 22 carbon atoms is a force S in which one or a mixture of two or more selected from fatty acids having this range of carbon atoms is used. 22 behenic acids are preferably used.

[0025] When the mixed fatty acid is composed only of a saturated fatty acid (that is, in the case of claim 4), the saturated fatty acid having 8 to 18 carbon atoms mixed with the saturated fatty acid having 19 to 22 carbon atoms is The average carbon number is 12 to 17; When the average carbon number exceeds 17, the effectiveness as a fractionation modifier is reduced. Here, the average carbon number is obtained by multiplying the carbon number of each fatty acid constituting the saturated fatty acid having 8 to 18 carbon atoms by the composition ratio and averaging.

[0026] When the mixed fatty acid contains 15 to 70% by weight of saturated fatty acid having 19 to 22 carbon atoms and 15 to 70% by weight of unsaturated fatty acid having 18 to 22 carbon atoms, 12 to 18 carbon atoms; Fatty acids may be mixed up to 60% by weight V (ie in the case of claim 5). The saturated fatty acid having 12 to 18 carbon atoms may be composed of only a saturated fatty acid having 18 carbon atoms, that is, stearic acid. [0027] The polyglycerin constituting the polyglycerin fatty acid ester is not particularly limited, and those having a 1S average polymerization degree (n) of 2 to 15 are preferred (claim 6). More preferably, the average degree of polymerization (n) is 2 to 10; Here, the average degree of polymerization (n) is a value calculated from the hydroxyl value obtained by terminal analysis. Specifically, the average degree of polymerization (n) is calculated from the following formulas (Formula 1) and (Formula 2). Is done.

 [Formula 1] Molecular weight = 74n + 18

 (Formula 2) hydroxyl value = 56110 (n + 2) / molecular weight

 [0029] The hydroxyl value in the above (formula 2) is a numerical value that is an index of the number of hydroxyl groups contained in the esterified product. In order to acetylate the free hydroxyl group contained in the esterified product in lg. The number of milligrams of potassium hydroxide required to neutralize the required acetic acid. The number of milligrams of potassium hydroxide is calculated according to the Japan Oil Chemists 'Society edited by “The Japan Oil Chemists' Society, Standard Oil Analysis Test Method (1), 2003 version”.

 [0030] The polyglycerin fatty acid ester constituting the oil / fat separation modifier of the present invention is, for example, by heating and esterifying a mixed solution of the fatty acid, the polyglycerin, and sodium hydroxide. The ability to synthesize is possible. Also, the force S obtained by synthesizing the ester by a known method is controlled.

 [0031] The fat to which the oil / fat separation modifier of the present invention is applied is a mixture of a liquid part and a solid part, and many of them are so-called semi-solid fats that are semi-solid and semi-liquid at room temperature. is there. A typical example of such fats and oils is palm oil (Claim 7). Besides, palm kernel oil, monkey fat, cottonseed oil, rapeseed oil, soybean oil, corn oil, coconut oil, power Examples thereof include vegetable oils and fats such as fat, animal fats and oils such as beef fat, pork fat, fish oil and milk fat, mixtures thereof, and those obtained by hydrogenating these fats and oils.

[0032] The amount of use of the oil / fat separation modifier of the present invention is usually 0.0; When the amount is less than 01% by weight, the intended effect of the present invention may not be sufficiently exhibited. On the other hand, when the amount exceeds 5% by weight, the effect corresponding to the increase in the amount used is not improved, and the amount of the separation modifier mixed in the separation fat increases, resulting in a quality problem. There is a case. In order to prevent such a problem and exhibit a sufficient effect, the range of 0.05 to 0.5% by weight is preferable. [0033] The desired amount of the fractionation modifier of the present invention is added to the oil or fat to be classified. Oils and fats to be separated are oils and fats composed of a mixture of a liquid part and a solid part, and many of them, for example, palm oil is a so-called semi-solid oil and fat that is semi-solid and semi-liquid at room temperature. In the fractionation step, the oil is first heated and completely melted and mixed uniformly, and then gradually cooled in the same manner as in the normal natural fractionation method.

 [0034] Upon cooling, crystals of a solid portion (palm stearin in the case of palm oil) are produced.

 Thus, by separating the crystal part, a liquid part (palm olein in the case of palm oil) and a solid part can be obtained. This separation can be done using force S, using conventional means such as filtration.

 [0035] The appropriate cooling time (cooling rate) varies depending on the required quality (IV, etc.) of the fractionated oil and fat, and is not particularly limited. The shorter the cooling time, the higher the productivity, but the quality of the fractionated fat tends to decrease (the IV of the liquid part decreases and the IV of the solid part increases), so depending on the required quality of the fractionated fat To determine an appropriate cooling rate. This determination can be easily made by a simple preliminary experiment.

 [0036] The preferred range of the crystallization temperature, that is, the final cooling temperature, varies depending on the type of oil.

 [0037] As described above, the higher the cooling rate (the shorter the cooling time), the lower the quality of the fractionated fats and oils. However, when the fractionation modifier of the present invention is added, compared to the case where it is not added. Thus, fractionated fats and oils of the same quality can be obtained at a much higher cooling rate. Therefore, the time for the separation process can be shortened and productivity can be improved. On the other hand, when the same cooling time is adopted, a much higher quality fractionated fat can be obtained in a high yield.

 [0038] In addition, when the fractionation modifier of the present invention is used, fine crystals are formed in a short time, so that the solid part and the liquid part can be easily separated by filtration. Improve

[0039] The fractionated fats and oils thus obtained can be used for various applications. For example, the solid fat portion is used as a raw oil for fats such as shortening and chocolate. The liquid part is used as a raw oil for frying oil and mayonnaise.

The invention's effect [0040] In the step of separating oil and fat such as palm oil into its liquid part and solid part, when the separation modifier of the present invention is added to and mixed with the oil and fat, high quality separated oil and fat can be obtained even in a short cooling time. You can power to get. Since the cooling time in the separation process is short, the time of the separation process can be shortened and productivity is improved.

 [0041] Here, the high-quality fractionated fats and oils mean a solid part in which the liquid part is hardly mixed, a liquid part in which the solid part is hardly mixed! The liquid part is composed mainly of unsaturated fatty acid triacyl glyceride, and the solid part is composed mainly of saturated fatty acid triacylglycerol. It means a liquid part with a high IV) and a solid part with a low IV.

 [0042] When the fat is palm oil, palmolein (liquid part) and palm stearin (solid part) are obtained by fractionation, but the addition of the fractionation modifier of the present invention promotes crystallization of palm stearin. Therefore, the time required for separation can be shortened, and high IV permolein and low IV palm stearin can be obtained in high yield.

 [0043] Further, when polyglycerin fatty acid ester is added to fats and oils such as palm oil, the crystals produced by cooling are very fine and hard, so that the crystals are not destroyed during filtration. It is possible to reduce clogging of the filter and shorten the filtration time. From this point of view, productivity can be improved.

 BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the best mode for carrying out the present invention will be described based on examples, but the scope of the present invention is not limited to these examples, as long as the gist of the present invention is not impaired. Further, a mode in which changes are made also belongs to the present invention.

 Example

 <0045> <Synthesis of polyglycerol fatty acid ester>

 The polyglycerin fatty acid ester used in the examples was synthesized by the method shown below.

[0046] <Synthesis example; >

First, equimolar palmitic acid, stearic acid and oleic acid were mixed to obtain a mixed fatty acid. Next, 12: 1 of this mixed fatty acid and decaglycerin (Sakamoto Pharmaceutical Co., Ltd.) A (molar ratio) mixture was prepared. Sodium hydroxide (0.1% by weight with respect to the mixture) was added to this mixture, and then the temperature was raised to 240 to 250 ° C. to carry out the esterification reaction, and the polyglycerol fatty acid ester used in the examples. 1 was prepared. The esterification reaction was carried out with stirring under a nitrogen stream until the acid value became 1 or less. Further, since the molar ratio is 12: 1, the esterification rate is about 100% ({12 / (10 + 2)} × 100%).

 [0047] <Synthesis Example 2>

 Instead of using mixed fatty acids consisting of equimolar palmitic acid, stearic acid and oleic acid, palmitic acid was used alone, and a mixture of decaglycerin (Sakamoto Yakuhin Kogyo Co., Ltd.) 12: 1 (molar ratio) was prepared. Prepared polyglycerin fatty acid ester 2 in the same manner as in Synthesis Example 1. (Esterification rate: approx. 100%)

 <Synthesis Example 3>

 Instead of the mixed fatty acid consisting of equimolar palmitic acid, stearic acid and oleic acid, mixed fatty acid consisting of equimolar palmitic acid and stearic acid was used, and 10: 1 (moles) of decaglycerin (manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.) was used. The polyglycerin fatty acid ester 3 was prepared in the same manner as in Synthesis Example 1 except that the mixture of the ratio was prepared. (Esterification rate: about 83%)

 <Synthesis Example 4>

 Instead of using a mixed fatty acid consisting of equimolar palmitic acid, stearic acid, and oleic acid, stearic acid was used alone, and a 11: 1 (molar ratio) mixture of decaglycerin (Sakamoto Yakuhin Kogyo Co., Ltd.) was prepared. Prepared polyglycerin fatty acid ester 4 in the same manner as in Synthesis Example 1. (Esterification rate: about 92%)

 [0050] <Synthesis Example 5>

 Instead of a mixed fatty acid consisting of equimolar palmitic acid, stearic acid and oleic acid, behenic acid was used alone to prepare a 12: 1 (molar ratio) mixture of decaglycerin (manufactured by Sakamoto Pharmaceutical Co., Ltd.). Except for the above, polyglycerin fatty acid ester 5 was prepared in the same manner as in Synthesis Example 1. (Esterification rate: approx. 100%)

[0051] <Synthesis Example 6> Polyglycerol fatty acid ester 6 was prepared in the same manner as in Synthesis Example 5 except that the molar ratio of behenic acid to decaglycerol was 7: 1. (Esterification rate: about 58%)

 [0052] <Synthesis Example 7>

 Instead of mixed fatty acid consisting of equimolar palmitic acid, stearic acid and oleic acid, mixed fatty acid consisting of equimolar stearic acid, oleic acid and behenic acid was used. Polyglycerin fatty acid ester 7 was prepared in the same manner as in Synthesis Example 1, except that a mixture of 12: 1 (molar ratio) was prepared. (Esterification rate: approx. 100%)

 <Example;! To 7, Comparative Example 1>

 0.5 g of the polyglycerol fatty acid ester obtained in Synthesis Examples 1 to 7 was added to 100 g of palm oil (IV56), and then heated to 80 ° C. to completely dissolve the palm oil. While stirring at 25 rpm, the mixture was gradually cooled over the cooling time (crystallization time) shown in Table 1 until the palm oil reached the crystallization temperature shown in Table 1. Thereafter, Nutsche suction filtration was performed to obtain a liquid part and a solid part. In addition, IV of the liquid part was measured. This experiment was taken as an example, and the results are shown in Table 1. Moreover, the polyglycerol fatty acid ester obtained in Synthesis Examples 1 to 7 was not added, and other conditions were the same as those in Examples. This is referred to as Comparative Example 1, and the results are also shown in Table 1.

 [0054] The IV measurement was conducted in 2003 version, established by the Japan Oil Chemists' Society.

.4 1 Iodine number (Wiis-cyclohexane method)

[0055] [Table 1]

Fractionation-modified fatty acid Estenol Crystallization Cooling time Liquid part type Carbon number conversion% Temperature ° chr. IV Example 1 C 16 / C 18/9 6 64. 4 Example 1 b Synthesis example 1 C18: 1 1 00 1 1 6 6 1. 0 Example 1 c 1 3 24 6 5. 0 Example 2 Synthesis Example 2 C 16 1 00 9 6 6 3. 4 Example 3 Synthesis Example 3 CI 6 / C18 1 00 9 6 6 1. 4 Example 4 Synthesis Example 4 C18 9 2 9 6 6 3.2 Example 5 Synthesis Example 5 C22 1 00 9 6 5 9.2 Example 6 Synthesis Example 6 C22 5 8 9 6 64. 9 Example 6 b 1 3 24 6 6. 9 Example 7 Synthesis Example 7 C 18 / C 22/1 00 9 6 6 5. 2 Example 7 b C 18: 1 1 3 24 6 6. 3 Comparative Example 1 9 6 5 9.0 Comparative Example 1 b Blank 1 1 6 5 8. 7 Comparative Example 1 c 1 3 24 5 9. 8

[0056] From the results of Table 1, an example in which the oil / fat separation modifier of the present invention was added to separate the oil / fat;

 In the case of (7), the same crystallization temperature and cooling time can give a high-quality fractionated fat with a higher IV in the liquid part than in the comparative example in which the fractionation modifier was not added. It is shown.

[0057] In Examples:! To 4, a high-quality fractionated fat with a high IV in the liquid part was obtained compared to Example 5 in which behenic acid (22 carbon atoms) was used as the fatty acid. Yes. Here, the polyglycerol fatty acid ester used in Examples;! To 4 has a fatty acid having 8 to 18 carbon atoms (particularly a fatty acid having 14 to 18 carbon atoms) as a main constituent fatty acid. That is, the results in Table 1 Oil / fat fractionation reformer comprising a polyglycerin fatty acid ester having a primary fatty acid of 8 to 18 as a main constituent fatty acid (particularly a polyglycerol fatty acid ester having a fatty acid of 14 to 18 as a main constituent fatty acid) (claim) (Corresponding to the invention described in 2) shows that it is particularly excellent among the oil and fat fractionation modifiers of the present invention.

[0058] Further, when Example 5 and Example 6 are compared, the example in which the esterification rate is 58% is higher than that in Example 5 in which the esterification rate is 100% at the same cooling time (6 hours). In the case of 6, high-quality fractionated fats and oils with higher liquid part IV were obtained. Examples 5 and 6 are both examples using behenic acid (22 carbon atoms) as a fatty acid, but in Example 6, it is as high as or higher than in Examples 1 to 4 above. IV (liquid part), high-quality fractionated fats and oils are obtained.

 [0059] That is, from this result, even when using a polyglycerin fatty acid ester whose main constituent fatty acid is a fatty acid having a large carbon number (fatty acid having 19 to 22 carbon atoms) such as behenic acid, the esterification rate is 58%. When the degree is small, it is shown that a particularly excellent fractionation modifier can be obtained among the oil and fat fractionation modifiers of the present invention (as in Examples 1 to 4 above). From this result and the results shown in Table 7 below, it is clear that a particularly excellent fractionation modifier can be obtained in the range of the esterification rate of 50 to 70%. (Invention of Claim 3)

 [0060] Example 7 is an example using a mixed fatty acid composed of oleic acid, which is an unsaturated fatty acid, together with behenic acid and stearic acid, and is the same as or similar to those in Examples 1 to 4 and Example 6 above. The above high IV (liquid part), high quality fractionated fats are obtained. That is, from this result, even when a fatty acid having a large carbon number such as behenic acid (fatty acid having 19 to 22 carbon atoms) is used, the fatty acid has a saturated fatty acid such as stearic acid and an unsaturated fatty acid such as oleic acid. It has been shown that by using a polyglyceryl fatty acid ester having a mixed fatty acid as a main constituent fatty acid, a particularly excellent fractionation modifier can be obtained among the oil and fat fractionation modifiers of the present invention.

 [0061] <Examples 8 to 22>

First, fatty acids having carbon numbers shown in Table 2 were mixed at a mixing ratio shown in Table 2 to obtain mixed fatty acids. Next, a 12: 1 (molar ratio) mixture of this mixed fatty acid and decaglycerin (manufactured by Sakamoto Pharmaceutical Co., Ltd.) was prepared. Then, in the same manner as in Synthesis Example 1, polyglycerin fatty acid Esters were prepared. The esterification rate is about 100%.

 [0062] 0.5 g of the polyglycerol fatty acid ester thus obtained was added to palm oil (IV56U00 g, and then heated to 60 ° C to dissolve the palm oil. The solution was gradually cooled over 6 hours until it reached ° C (crystallization temperature), followed by Nutsche suction filtration to obtain a liquid part and a solid part. This was carried out in the same manner as in Example 1. In addition, the liquid part was allowed to stand at 5 ° C., and the time until the crystals were precipitated (crystal precipitation time) was determined.

[0063] [Table 2]

Carbon number of fatty acids [Mixing ratio] Carbon number average C22 mixed part Crystal precipitation average * Combined ratio IV (Hr) Difficult 8 C10 / C18 / C22 [1: 3: 1] 1 6 20% 62.6 6 Difficult example 9 C12 / C14 / C22 [1: 1: 3] 1? ) 60% 63. 0 10 Cat example 10 C12 / C16 / C22 [1: 1: 3] 14 60% 63. 8 6 Difficult example 11 C12 / C18 / C22 [1: 3: 1] 16. 5 20% 63 9 6 Male 12 C12 / C22 [1: 2] 1 2 6 7% 62. 6 6

* ¾Example 13 C14 / C16 / C22 [1: 1: 3] 1 5 60% 64. 3 15 Example 14 C14 / C16 / C22 [1: 1: 1] 1 5 33% 63. 0 10 Difficult 15 C14 / C18 / C22 [1: 1: 1] 1 6 33% 64. 0 15 Example 16 C14 / C18 / C22 [1: 1: 3] 1 6 60% 64. 2 11 Difficult 17 C14 / C18 / C22 [3: 1: 1] 1 6 20% 62. 0 9 Difficult 18 C14 / C22 [1: 1] 14 50% 62. 6 12

¾¾ Example 19 C14 / C22 [1: 2] 14 6 7% 63.4 4 15 None 20 C14 / C22 [2: 1] 14 33% 62. 6 11 None 21 C16 / C18 / C22 [1: 1: 3] 1 7 60% 63. 4 15 Example 22 C18 / C22 [1: 1] 1 8 60% 63. 4 13 & b ― ―-% 58. 7 1

* Average carbon number of saturated fatty acids with 8 to 18 carbon atoms

* * Weight of all fatty acids of saturated fatty acids with 19 to 22 carbon atoms. / ₀ Example 8 to 22 fractional modifier used in the fractionation modifier according to claim 4, Chi words, 15 to 70 wt% of saturated fatty acids of 19-22 carbon atoms, and

 Containing 30 to 85% by weight of saturated fatty acids having 8 to 18 carbon atoms;

 The average carbon number of the saturated fatty acid having 8 to 18 carbon atoms is 12 to 17

It is contained in a fat and oil fractionation modifier characterized by comprising a polyglycerin fatty acid ester having a mixed fatty acid as a constituent fatty acid. As can be seen from the results in Table 2, this fractionation Compared to the comparative example lb with the same crystallization temperature and cooling time and no fractionation modifier added, the quality is much higher (additional IV in the liquid part) It is shown that a fractionated oil is obtained. Furthermore, the IV values (Table 2) of the liquid parts in Examples 8 to 22 are the same crystallization temperature and crystallization time (11 ° C, 6 hours, respectively), and polydariserin used for the synthesis of polydariserin fatty acid ester. Is much higher than IV ^ t (Table 1) of the liquid part in Example lb. From this result, it can be said that the fractionation modifier according to claim 4 has a more excellent effect than the fractionation modifier according to claim 2.

 <Examples 23 to 25>

 First, fatty acids having the number of carbon atoms shown in Table 3 were mixed at the mixing ratio shown in Table 3 to obtain mixed fatty acids. Next, a 6: 1 (molar ratio) mixture of this mixed fatty acid and tetraglycerin (manufactured by Sakamoto Pharmaceutical Co., Ltd.) was prepared. Thereafter, a polyglycerol fatty acid ester was prepared in the same manner as in Synthesis Example 1. The esterification rate is about 100%.

 [0066] 0.5 g of the polyglycerin fatty acid ester thus obtained was added to palm oil (IV56U00 g and then heated to 60 ° C to dissolve the palm oil. The solution was gradually cooled over 6 hours until it reached ° C (crystallization temperature), followed by Nutsche suction filtration to obtain a liquid part and a solid part. This was carried out in the same manner as in Example 1. In addition, the liquid portion was allowed to stand at 5 ° C., and the time until crystals were precipitated (crystal precipitation time) was determined.

[0067] [Table 3]

Carbon number of fatty acids [Mixing ratio] Ash 3 Number average C22 mixed liquid part Crystal precipitation B grade * Combined ratio * * IV (H r) Cat example 2 3 C14 / C16 / C22 [1: 1: 3] 1 5 6 0% 6 2. 0 1 0 Example 2 4 C14 / C16 / C22 [3: 1: 6] 1 4. 5 6 0% 6 2. 7 1 3 Difficult example 2 5 C14 / C22 [1: 2 ] 1 4 6 7% 6 2. 3 8 i: \ MffH b ― 1% 5 8. 7 1

* Average carbon number of saturated fatty acids with 8 to 18 carbon atoms

 * * Weight% of total fatty acids of saturated fatty acids with 19 to 22 carbon atoms

[0068] The fractionation modifier used in Examples 23 to 25 is also included in the fractionation modifier according to claim 4. As is clear from the results in Table 3, by adding this fractionation modifier, the same crystallization temperature and cooling time were used, compared to the comparative example lb that was fractionated without addition of the fractionation modifier. In addition, high-quality fractionated fats (high IV in the liquid part) were obtained, and Example lb (Table 1) with the same crystallization temperature and crystallization time (11 ° C, 6 hours, respectively) and Even when compared, an excellent effect (high liquid part, IV value) is obtained!

 [0069] In Examples 23 to 25, tetraglycerin was used for the synthesis of the polyglycerin fatty acid ester, but the same effects (Table 2) as in Examples 8 to 22 using decaglycerin were obtained.

 [0070] <Examples 26 to 33>

 First, fatty acids having carbon numbers shown in Table 4 were mixed at a mixing ratio shown in Table 4 to obtain mixed fatty acids. Next, a 12: 1 (molar ratio) mixture of this mixed fatty acid and decaglycerin (manufactured by Sakamoto Pharmaceutical Co., Ltd.) was prepared. Thereafter, a polyglycerol fatty acid ester was prepared in the same manner as in Synthesis Example 1. The esterification rate is about 100%.

[0071] 0.5 g of the polyglycerin fatty acid ester thus obtained was added to palm oil (IV56U00 g, and then heated to 60 ° C to dissolve the palm oil. The solution was gradually cooled over 6 hours until it reached ° C (crystallization temperature), followed by Nutsche suction filtration to obtain a liquid part and a solid part. This was carried out in the same manner as in Example 1. Also, the liquid part was allowed to stand at 5 ° C until crystals were precipitated. Time (crystal precipitation time) was determined. These results are shown in Table 4.

[Table 4]

実施例 26〜33で使用された分別改質剤は、請求項 5に記載の分別改質剤、すな わち、炭素数 19〜22の飽和脂肪酸を 15〜70重量％、

The fractionation modifier used in Examples 26 to 33 is the fractionation modifier according to claim 5, that is, 15 to 70% by weight of a saturated fatty acid having 19 to 22 carbon atoms,

 0 to 60% by weight of saturated fatty acids having 12 to 18 carbon atoms; and 18

 15 to 70% by weight of unsaturated fatty acid having 18 to 22 carbon atoms,

It comprises a polyglycerin fatty acid ester comprising a mixed fatty acid containing glycerin as a constituent fatty acid, and is contained in an oil / fat separation modifier. As is clear from the results in Table 4, by adding this fractionation modifier, the same crystallization temperature and cooling time were used, compared to the comparative example lb that was fractionated without the addition of the fractionation modifier. It is shown that high quality (high IV of liquid part) fractionated fats and oils can be obtained. Furthermore, the IV values (Table 4) of the liquid parts in Examples 26 to 33 are the same crystallization temperature and crystallization time (11 ° C. and 6 hours, respectively), and were used for the synthesis of polyglycerol fatty acid esters. Polyglycerin is also the same decaglycerin, much higher than the IV ^ t (Table 1) of the liquid portion in Example lb. From this result, the claims The fractionation modifier according to 5 is more effective than the fractionation modifier according to claim 2.

 <Examples 34 to 38>

 First, fatty acids having carbon numbers shown in Table 5 were mixed at a mixing ratio shown in Table 5 to obtain mixed fatty acids. Next, a 6: 1 (molar ratio) mixture of this mixed fatty acid and tetraglycerin (manufactured by Sakamoto Pharmaceutical Co., Ltd.) was prepared. Thereafter, a polyglycerol fatty acid ester was prepared in the same manner as in Synthesis Example 1. The esterification rate is about 100%.

 [0075] 0.5 g of the polyglycerin fatty acid ester thus obtained was added to palm oil (IV56U00 g and then heated to 60 ° C to dissolve the palm oil. The solution was gradually cooled over 6 hours until it reached ° C (crystallization temperature), followed by Nutsche suction filtration to obtain a liquid part and a solid part. This was carried out in the same manner as in Example 1. In addition, the liquid portion was allowed to stand at 5 ° C., and the time until the crystals were precipitated (crystal precipitation time) was determined.

 [0076] [Table 5]

[0077] The fractionation modifier used in Examples 34 to 38 is also included in the fractionation modifier according to claim 5. As is clear from the results in Table 5, by adding this fractionation modifier, the same crystallization temperature and cooling time were used, compared to the comparative example lb that was fractionated without addition of the fractionation modifier. In addition, high-quality (high IV of liquid part) fractionated fats and oils are obtained. In addition, even when compared with Example lb (Table 1) having the same crystallization temperature and crystallization time (11 ° C, 6 hours, respectively), excellent effects (high liquid part, IV value) were obtained. ! /

In Examples 34 to 38, tetraglycerin was used for the synthesis of polyglycerin fatty acid ester, but the same effects (Table 4) as in Examples 26 to 33 using decaglycerin were obtained.

 <Examples 39 to 43, Comparative Example 2>

 The fatty acids having carbon numbers shown in Table 6 were mixed at the mixing ratio shown in Table 6 to obtain mixed fatty acids. Next, a 12: 1 (molar ratio) mixture of this mixed fatty acid and decaglycerin (manufactured by Sakamoto Pharmaceutical Co., Ltd.) was prepared. Thereafter, a polyglycerol fatty acid ester was prepared in the same manner as in Synthesis Example 1. The esterification rate is about 100%.

 [0080] 0.5 g of the polyglycerin fatty acid ester thus obtained was added to palm oil (IV52U00 g and then heated to 60 ° C to dissolve the palm oil. The solution was gradually cooled over 2 hours until it reached ° C (crystallization temperature), followed by Nutsche suction filtration to obtain a liquid part and a solid part. This was carried out in the same manner as in Example 1. Also, the time until the crystals were precipitated by leaving the liquid part at 20 ° C. (crystal precipitation time) was determined, and the results are shown in Table 6. The same experiment as in Example 39 was performed except that glyceryl fatty acid ester was not added, and this was taken as Comparative Example 2 and the results are also shown in Table 6.

[0081] [Table 6]

Fatty acid carbon number [mol. /. ] Liquid part

 IV (Hr) Row 39 C12 / C16 / C22 [20/20/60] 55. 0 4 Difficult Case 40 C12 / C18 / C22 [15/15/70] 55. 5 7 Row 41 C18 / C18: l / C22 [15/15/70] 56. 2 9 Example 42 C18 / C18: 1 / C22 [20/20/60] 55. 1 7 Example 43 C18 / C18: 1 / C22 [30/10 / 60] 55. 7 6 Row 2 ― 52. 7 0. 5

[0082] Examples 39 to 43 and Comparative Example 2 are fractionation modifiers included in the scope of claim 4 of the present invention.

 This is a case where the fractionation modifiers (Examples 41 to 43) included in the scope of Examples 39 and 40 and Claim 5 are applied to so-called single fractionation. From the results of Table 6, in Examples 39 to 43, the IV of the liquid part was higher than that in Comparative Example 2 where fractionation was performed without adding a fractionation modifier at the same crystallization temperature and cooling time. It has been shown that high-quality fractionated fats can be obtained.

 <Examples 44 to 47>

 Polyglycerol fatty acid esters with esterification rates of 45%, 53%, 68%, and 80% were prepared in the same manner as in Synthesis Example 5 except that the molar ratio of behenic acid and decaglycerol was changed.

Yes

 [0084] The same conditions (crystallization temperature) as in Example 6 except that one of these polyglycerin fatty acid esters was used instead of the polyglycerin fatty acid ester obtained in Synthesis Example 6. : Palm oil (IV56) was fractionated at 9 ° C and crystallization time: 6 hours to obtain a liquid part and a solid part, and IV of the liquid part was measured. The results are shown in Table 7.

[0085] [Table 7] Of fatty acid estenore liquid part

 Anthrax rate% I V

 Example 4 4 C22 5 3 6 3. 2

 Example 4 5 C22 6 8 6 3.4

 Example 4 6 C22 8 0 6 0. 2

 Example 4 7 C22 4 5 6 1.2 From the results shown in Table 7 and the results of Example 6 in Table 1 above, polyglycerin containing a fatty acid having a large number of carbon atoms such as benoic acid as a main constituent fatty acid. Even when fatty acid esters are used, it has been shown that particularly excellent fractionation modifiers can be obtained when the esterification rate is in the range of 50 to 70%. For example, so-called double fractionation In the case of a crystallization temperature of 10 ° C or less, it can be seen that a fractionated oil of palm oil having an IV (iodine value) of 62 to 3 or more can be obtained with a cooling time shorter than about 10 hours.

Claims

The scope of the claims  [1] A fat and oil separation modifier comprising a polyglycerin fatty acid ester having a fatty acid having 8 to 22 carbon atoms as a main constituent fatty acid. [2] A segregation modifier for fats and oils comprising a polyglycerin fatty acid ester having a fatty acid having 8 to 18 carbon atoms as a main constituent fatty acid. [3] A fat and oil separation modifier comprising a polyglycerin fatty acid ester having a fatty acid having 19 to 22 carbon atoms as a main constituent fatty acid and an esterification rate of 15 to 85%. [4] 15 to 70% by weight of saturated fatty acids having 19 to 22 carbon atoms, and  Containing 30 to 85% by weight of saturated fatty acids having 8 to 18 carbon atoms;  The average carbon number of the saturated fatty acid having 8 to 18 carbon atoms is 12 to 17  An oil and fat separation modifier characterized by comprising a polyglycerin fatty acid ester having a mixed fatty acid as a constituent fatty acid. [5] 15 to 70% by weight of saturated fatty acid having 19 to 22 carbon atoms,  0 to 60% by weight of saturated fatty acids having 12 to 18 carbon atoms; and 18  15 to 70% by weight of unsaturated fatty acid having 18 to 22 carbon atoms,  An oil / fat separation modifier characterized by comprising a polyglycerin fatty acid ester containing a mixed fatty acid containing a fatty acid as a constituent fatty acid. [6] The oil / fat separation modifier according to any one of claims 1 to 5, wherein the polyglycerin fatty acid ester constituting the polyglycerin fatty acid ester has a degree of polymerization of 2 to 15;  [7] The oil / fat separation modifier according to any one of claims 1 to 6, wherein the oil / fat is palm oil.