WO2012169457A1 - Method for fractionating oil and fat - Google Patents

Method for fractionating oil and fat Download PDF

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Publication number
WO2012169457A1
WO2012169457A1 PCT/JP2012/064363 JP2012064363W WO2012169457A1 WO 2012169457 A1 WO2012169457 A1 WO 2012169457A1 JP 2012064363 W JP2012064363 W JP 2012064363W WO 2012169457 A1 WO2012169457 A1 WO 2012169457A1
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Prior art keywords
triglyceride
mass
content
fatty acid
xxx
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PCT/JP2012/064363
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French (fr)
Japanese (ja)
Inventor
雅人 高場
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日清オイリオグループ株式会社
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Publication of WO2012169457A1 publication Critical patent/WO2012169457A1/en

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    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/02Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
    • A23D9/04Working-up
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B7/00Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
    • C11B7/0075Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of melting or solidifying points
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B7/00Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
    • C11B7/0083Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils with addition of auxiliary substances, e.g. cristallisation promotors, filter aids, melting point depressors

Definitions

  • the present invention relates to a triglyceride having two saturated fatty acid residues and one unsaturated fatty acid residue (X2U type triglyceride, wherein X represents a saturated fatty acid residue, U represents an unsaturated fatty acid residue, and the same applies hereinafter).
  • the present invention relates to a method for fractionated production of fats and oils to obtain rich oils and fats.
  • Hard butter including cocoa butter is widely used in foods such as chocolate, pharmaceuticals and cosmetics. These hard butters are mainly composed of triglycerides (X2U type triglycerides) having two saturated fatty acid residues and one unsaturated fatty acid residue.
  • triglycerides X2U type triglycerides
  • cocoa butter is 1,3-dipalmitoyl-2-oleoylglycerin (POP), triglyceride (POS) having an oleoyl group at the 2-position, one palmitoyl group and one stearoyl group, and 1,3- It is mainly composed of symmetric disaturated monounsaturated triglycerides having one unsaturated bond in the molecule, such as distearoyl-2-oleoylglycerin (SOS).
  • POP 1,3-dipalmitoyl-2-oleoylglycerin
  • POS triglyceride having an oleoyl group at the 2-position
  • palmitoyl group and one stearoyl group
  • 1,3- It is mainly composed of symmetric disaturated monounsaturated triglycerides having one unsaturated bond in the molecule, such as distearoyl-2-oleoylglycerin (SOS).
  • such triglycerides can be obtained as natural fats and oils containing this component, for example, fats and oils such as palm oil, shea fat, monkey fat, and lippe fat, or fractionated oils thereof.
  • fats and oils such as palm oil, shea fat, monkey fat, and lippe fat, or fractionated oils thereof.
  • a 1,3-selective lipase is allowed to act on specific fats and oils, not as oil fractions such as palm oils, shea fats, monkey fats, lippe fats, etc. It has been proposed (Patent Documents 1 to 3).
  • any of the above methods adversely affects the rapid melting characteristics in the mouth, which is a characteristic of confectionery fats and oils, so a high melting point fraction mainly composed of triglycerides (XXX type triglycerides) consisting of three saturated fatty acid residues. Fractionation to remove is essential. At present, this process is often carried out by dry fractionation, but due to the characteristics of dry fractionation, if the raw material fat contains a large amount of XXX type triglyceride, it is required for the high melting point fraction to be removed. Since the X2U type triglyceride remains, it is a cause of the poor yield of the X2U type triglyceride.
  • An object of the present invention is to provide a XXX type from an oil containing a saturated mono-unsaturated triglyceride (X2U type triglyceride or X2U) and containing only a saturated fatty acid residue (XXX type triglyceride or XXX). It is to provide a more efficient and industrially suitable fractionation method for recovering oils with low triglyceride content and rich in X2U type triglycerides.
  • the present inventor heated and melted oil containing a specific amount of XXX and X2U in the presence of a specific amount of fatty acid lower alkyl ester, and then cooled. It was found that the crystallization of the X2U triglyceride can be sufficiently delayed with respect to the crystallization of the XXX triglyceride as compared with the absence of the fatty acid alkyl ester.
  • the present invention heats and melts oil containing a specific amount of XXX and X2U in the presence of a specific amount of fatty acid lower alkyl ester, then crystallizes XXX-rich crystals by cooling, and separates the liquid part ( The olein part rich in X2U) is collected based on the knowledge that the above problem can be solved.
  • one aspect of the present invention is an oil and fat containing a triglyceride content of 60% by mass or more, 10 to 70% by mass of XXX triglyceride and 10 to 50% by mass of X2U triglyceride in all triglycerides,
  • a lower alkyl ester is mixed to prepare a crystallization raw material having a triglyceride content of 10 to 50% by mass and a fatty acid lower alkyl ester content of 50 to 80% by mass.
  • the crystallization raw material is heated and melted, and then cooled. This is a method for fractionating fats and oils to obtain a liquid part (olein part) rich in X2U type triglycerides by crystallization and then fractionation.
  • the fat or oil having a triglyceride content of 60% by mass or more and containing 10 to 70% by mass of XXX type triglyceride and 10 to 50% by mass of X2U type triglyceride in total triglyceride is palm stearin. It is a method for fractionating certain fats and oils, and a method for fractionating fats and oils that are fractionated high melting point fractions of transesterified oil.
  • a method for fractionating fats and oils in which the content of XXX type triglyceride in the total triglyceride in the liquid part (olein part) rich in X2U type triglyceride is less than 10% by mass.
  • XXX which has an adverse effect on mouthfeel as fats and oils for chocolate is eliminated, and at the same time, useful X2U type triglycerides are efficiently produced. Since the fraction can be concentrated, the recovery rate of X2U in the production of X2U type triglyceride can be significantly increased, and the production cost can be reduced and the quality can be improved.
  • the fats and oils used in the fractionation method of the present invention are fats and oils having a triglyceride content of 60% by mass or more and containing 10 to 70% by mass of XXX type triglycerides and 10 to 50% by mass of X2U type triglycerides in the total triglycerides.
  • X represents a saturated fatty acid residue of triglyceride
  • U represents an unsaturated fatty acid residue.
  • the XXX type triglyceride (XXX) represents a triglyceride composed of three saturated fatty acid residues
  • the X2U type triglyceride (X2U) represents a triglyceride having two saturated fatty acid residues and one unsaturated fatty acid residue.
  • the saturated fatty acid residue X is preferably a saturated fatty acid residue having 16 to 22 carbon atoms because it is useful for confectionery and bakery purposes.
  • a stearoyl group (S), a palmitoyl group (P), a behenoyl group ( B) is preferred.
  • the unsaturated fatty acid residue U is preferably an oleyl group (O), a linoloyl group (L), or a linoleyl group (Ln).
  • mold triglyceride what has the same saturated fatty acid residue is preferable.
  • the fats and oils used for the fractionation method of the present invention refer to glycerides (a mixture of monoglyceride, diglyceride and triglyceride).
  • the oil and fat used in the fractionation method of the present invention preferably has a triglyceride content of 70% by mass or more, and the total triglyceride contains 20 to 50% by mass of XXX type triglyceride and 20 to 50% by mass of X2U type triglyceride. preferable.
  • the total content of XXX type triglyceride and X2U type triglyceride in the total triglyceride is preferably 60% by mass or more, more preferably 65% by mass or more, and further preferably 70 to 90% by mass. .
  • the triglyceride content of fats and oils used in the fractionation method of the present invention is in the above ranges, because XXX type triglyceride and X2U type triglyceride can be efficiently separated.
  • the triglyceride content is 90% by mass or more
  • the XXX content in the total triglycerides is 20 to 70% by mass
  • the X2U content is 20 to 50% by mass.
  • Another preferred embodiment of the fat used in the fractionation method of the present invention is, for example, a triglyceride having an oleoyl group of 50% by mass or more at the 2-position with a fatty acid lower alkyl ester cocoon (including the case where the fatty acid itself is used) and a transesterification reaction. Then, a high melting point fraction obtained by dry fractionation of a distillation residue obtained by distillation and then distillation may be used.
  • trioleoyl glycerin such as trioleoyl glycerin, shea butter low melting point rice cake (for example, iodine value 70-80), high oleic sunflower oil, high oleic lorinolen rapeseed oil, high oleic safflower oil, palm oil, palm fraction oil, etc.
  • Saturated fatty acid lower alkyl ester is added to raw oil and fat, and 1,3-selective lipase such as lysops lipase, Aspergillus lipase, mucor lipase, pancreatic lipase, rice nuclei lipase, etc. is allowed to act on the transesterification reaction. .
  • the high melting point fraction is a by-product produced when X2U type triglyceride (XOX) is produced, the triglyceride content in fats and oils (glycerides) is 60% by mass or more, and the XXX content in all triglycerides is 10 to 10%. 70% by mass and X2U content is 10-50% by mass.
  • Rhizopus delemar and Rhizopus oryzae belonging to the genus Rhizopus are preferable.
  • these lipases include Robin's product: Picantase R8000 and Amano Enzyme's product: Lipase F-AP15.
  • the most suitable lipase is derived from Rhizopus oryzae, Amano Enzyme's product: Lipase DF ( Amano) 15-K (also referred to as lipase D). This is a powder lipase.
  • the lipase DF (Amano) 15-K has conventionally been derived from Rhizopus delemar.
  • the lipase used may be obtained by drying a lipase-containing aqueous solution containing a lipase medium component or the like.
  • the powder lipase is preferably spherical and has a water content of 10% by mass or less. In particular, 90% by mass or more of the lipase powder preferably has a particle size of 1 to 100 ⁇ m.
  • the powder lipase is preferably produced by spray-drying a lipase-containing aqueous solution whose pH is adjusted to 6 to 7.5.
  • granulated powder lipase obtained by granulating the lipase with soybean powder and then pulverizing it.
  • immobilized lipase can also be used suitably.
  • trade names such as Lipozyme®RM®IM, Lipozyme®TL®IM manufactured by Novozymes, and the like can be mentioned.
  • a fat / oil (triglyceride having an oleoyl group at 50% by mass or more at the 2-position) and a fatty acid lower alkyl ester are in a mass ratio of 20:80 to 50:50, preferably 25:75 to 45:55.
  • the 1,3-selective lipase can be added to the reaction raw material mixed at a ratio of 1, and the transesterification reaction can be carried out by a conventional method. In this case, 0.01 to 10 parts by mass (preferably 0.01 to 2 parts by mass, more preferably 0.1 to 1.5 parts by mass) of lipase is added per 100 parts by mass of the reaction raw material, and 35 to 100 ° C.
  • the transesterification reaction is carried out at a temperature (preferably 35 to 80 ° C., more preferably 40 to 60 ° C.) for 0.1 to 50 hours (preferably 0.5 to 30 hours, more preferably 1 to 20 hours). Is preferred.
  • the reaction is preferably carried out batchwise.
  • the reaction temperature may be any number of times as long as it is a temperature at which fats and oils as reaction substrates dissolve and has enzyme activity.
  • the optimal reaction time varies depending on the amount of enzyme added, reaction temperature, etc., and may be adjusted as appropriate.
  • distillation is carried out to remove unreacted raw materials, by-product fatty acids and fatty acid lower alkyl esters to 50% by mass or less, and dry fractionation at 18 to 38 ° C., preferably 22 to 34 ° C.
  • a high melting point fraction containing oils and fats used in the fractionation method of the present invention is obtained.
  • the fatty acid lower alkyl ester used in the fractionation method of the present invention is preferably a lower alcohol ester of a fatty acid having 16 to 22 carbon atoms, and may be a saturated fatty acid lower alkyl ester, an unsaturated fatty acid lower alkyl ester, or a mixture thereof.
  • an ester with an alcohol having 1 to 6 carbon atoms is preferable, and an ester with methanol, ethanol or isopropyl alcohol is preferable.
  • an ester with ethanol is preferable from the viewpoint of processing of edible fats and oils.
  • the crystallization raw material used in the fractionation method of the present invention has an oil and fat having a triglyceride content of 60% by mass or more, 10 to 70% by mass of XXX type triglyceride and 10 to 50% by mass of X2U type triglyceride in all triglycerides, , A mixture having a triglyceride content of 10 to 50% by mass and a fatty acid lower alkyl ester content of 50 to 80% by mass obtained by mixing with a fatty acid lower alkyl ester.
  • the crystallization raw material used in the fractionation method of the present invention preferably has a triglyceride content of 15 to 50% by mass and a fatty acid lower alkyl ester content of 50 to 75% by mass, a triglyceride content of 20 to 45% by mass, More preferably, the alkyl ester content is 55 to 70% by mass. Moreover, it is preferable that the total content of the triglyceride and the fatty acid lower alkyl ester in the crystallization raw material used in the fractionation method of the present invention is 80% by mass or more.
  • the triglyceride content and the fatty acid lower alkyl ester content in the crystallization raw material used in the fractionation method of the present invention are in the above ranges, it is preferable because the XXX triglyceride and the X2U triglyceride can be efficiently separated.
  • the triglyceride content is 60% by mass or more, and 10 to 70% by mass of XXX type triglyceride and 10 to 50% by mass of X2U type triglyceride in all triglycerides.
  • % Fat and fatty acid lower alkyl ester are preferably mixed at a mass ratio of 20:80 to 50:50, more preferably mixed at a mass ratio of 25:75 to 50:50, It is more preferable to mix at a mass ratio of 30:70 to 45:55.
  • the triglyceride content in the oil and fat is 90% by mass or more
  • the XXX content in the total triglyceride is 20 to 70% by mass
  • the X2U content is 20 to 50%.
  • examples thereof include a mixture in which palm stearin which is mass% and a fatty acid lower alkyl ester are mixed at a mass ratio of 30:70 to 45:55.
  • the triglyceride content in fats and oils (glycerides) is 60% by mass or more, and the XXX content in all triglycerides is 10 to 70% by mass.
  • the fractionation method of the present invention can be carried out in the same manner as usual dry fractionation of fats and oils, except that the crystallization raw material contains 50 to 80% by mass of a fatty acid lower alkyl ester.
  • the crystallization raw material heated and melted is generally cooled while stirring in a tank to precipitate crystals, and then a high melting point fraction (solid part) and a low melting point fraction are obtained by pressing and / or filtration. This can be done by obtaining a minute (liquid part).
  • the heat melting may be a temperature at which both the crystallization raw material and the fatty acid lower alkyl ester can be dissolved to form a liquid and varies depending on the content and composition of the triglyceride and the fatty acid lower alkyl ester contained in the crystallization raw material, For example, the temperature is 60 to 100 ° C., preferably 70 to 90 ° C.
  • the fractionation temperature varies depending on the content and composition of the triglyceride and fatty acid lower alkyl ester contained in the crystallization raw material, but can be carried out at 10 to 40 ° C., more preferably 15 to 35 ° C.
  • a liquid part (olein part) rich in X2U triglyceride can be obtained from a crystallization raw material having a triglyceride content of 10 to 50% by mass and a fatty acid lower alkyl ester content of 50 to 80% by mass.
  • the liquid part (olein part) rich in X2U type triglyceride obtained by the fractionation method of the present invention preferably has a XXX content in all triglycerides of less than 10% by mass, more preferably 5% by mass or less. Moreover, it is preferable that the X2U content in all the triglycerides exceeds 50 mass%, and it is still more preferable that it is 60 mass% or more.
  • the liquid part (olein part) rich in X2U type triglyceride obtained by the fractionation method of the present invention can be used, for example, alone or mixed with other fats and oils for confectionery bread applications. Moreover, it can use as raw material fats and oils which manufacture the high purity X2U type
  • the method for fractionating fats and oils of the present invention is also preferably used by being incorporated into a process for producing X2U type triglycerides in combination with transesterification. That is, by transesterifying only a fat or oil, or a mixture of fat and fatty acid and / or fatty acid lower alkyl ester, a transesterified oil containing X2U type triglyceride is obtained, and the transesterified oil is fractionated to obtain a low melting point.
  • an oil and fat rich in X2U type triglyceride is obtained in the middle melting point fraction, and the remaining high melting point fraction is subjected to the fractionation method of the present invention, so that the low melting point fraction low in XXX content and rich in X2U type triglyceride (liquid part) Is recovered, and the low-melting-point fraction is returned to, for example, transesterified oil containing X2U triglyceride before fractionation, whereby a production process for increasing the recovery rate of X2U triglyceride can be achieved.
  • a triglyceride having an oleoyl group at 50% by mass or more at the 2-position is saturated fatty acid lower alkyl ester (fatty acid (Including the case of using itself)
  • the triglyceride content in fats and oils (glycerides) obtained by dry fractionation of the distillation residue obtained by distillation is 60% by mass or more, and in all triglycerides
  • the high melting point fraction having a XXX content of 10 to 70% by mass and an X2U content of 10 to 50% by mass and a fatty acid lower alkyl ester are mixed to obtain a triglyceride content of 10 to 50% by mass and a fatty acid lower alkyl ester.
  • a crystallization raw material having a content of 50 to 80% by mass melting the crystallization raw material by heating, The mixture is cooled to crystallize the crystals, and then fractionated to obtain a liquid part (olein part) rich in X2U type triglyceride having an XXX content of less than 10% by mass and an X2U content of more than 50% by mass. ) And returning the liquid part to the transesterified oil before fractionation, thereby increasing the recovery rate of the X2U triglyceride.
  • Palm stearic acid (iodine value 30) 120.0 g was mixed with palmitic acid ethyl ester (trade name: ethyl palmitate, manufactured by Inoue Fragrance Co., Ltd.) 180.5 g, and the fatty acid ethyl ester content was 60.1% by mass. 300.5 g of crystallization raw material 1 was obtained. The obtained crystallization raw material 1 (300.5 g) was completely dissolved at 80 ° C. and then cooled at 15 ° C.
  • the liquid part 1 obtained by the fractionation method of the present invention has a significantly lower XXX content in all triglycerides (1.8% by mass) and a significant concentration of X2U (63.3% by mass). %).
  • Example 2 Preparation of powder lipase composition A
  • Amano Enzyme Co., Ltd . Enzyme solution (150,000 U / ml) of lipase DF (Amano) 15-K (also referred to as lipase D) was autoclaved (121 ° C., 15 minutes) in advance and cooled to room temperature.
  • Fat soy powder (fat content is 23% by mass, trade name: Alpha Plus HS-600, manufactured by Nisshin Cosmo Foods Co., Ltd.) 10% aqueous solution is added in 3 times amount with stirring, pH 7 with 0.5N NaOH solution After adjustment to 0.8, spray drying (Tokyo Science Instrument Co., Ltd., SD-1000 type) was performed to obtain a powder lipase composition A.
  • the obtained reaction product 2 (15808 g) was subjected to thin film distillation, and fatty acid ethyl was removed from the reaction product at a distillation temperature of 140 ° C., and the triglyceride content was 80.2% by mass and the fatty acid ethyl content was 18.2% by mass.
  • Residue 2-1 (8052 g) and distillation fraction 2 (7828 g) were obtained.
  • the obtained distillation residue 2-1 (8000 g) was completely dissolved at 50 ° C., then cooled at 27 ° C.
  • the liquid part 2-2 obtained by the fractionation method of the present invention has a significantly lower XXX content (2.9% by mass) in the total triglycerides than the crystallization raw material 2 and a significant concentration of X2U (63. 0 mass%).
  • Solid-liquid separation was performed to obtain a solid part 2-3 (66.9 g) and a liquid part 2-3 (64.7 g).
  • the distillation residue 2-2 before the press filtration had poor fluidity when being sent to the filter, and fine crystals leaked into the filtrate (liquid part), resulting in insufficient solid-liquid separation.
  • Table 3 shows the analysis value of each process oil.
  • the fatty acid ethyl ester content and triglyceride (TAG) content and composition were analyzed using the GLC method.
  • the fractionation method of the present invention can obtain a fractionation accuracy equal to or higher than that of solvent fractionation.

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Abstract

A method for fractionating oil and fat, characterized in that an oil/fat having a triglyceride content of 60 wt% or more and including, among all triglycerides, 10-70 wt% of an XXX triglyceride and 10-50 wt% of a X2U triglyceride, is mixed with a fatty acid lower-alkyl ester; a raw material for crystallization is prepared, the raw material having a 10-50 wt% triglyceride content and a 50-80 wt% fatty acid lower-alkyl ester content; the raw material for crystallization is heat-melted and subsequently cooled; a crystal precipitate is formed; and the precipitate is fractionated, resulting in a liquid part (olein part) having a high X2U triglyceride content. This fractionation method is more efficient and industrially suitable for recovering oils/fats having a low XXX triglyceride content but a high X2U triglyceride content from oils/fats containing X2U triglycerides (X is a saturated fatty-acid residue and U is an unsaturated fatty-acid residue) and having a high XXX triglyceride content (X is a saturated fatty-acid residue).

Description

油脂の分別方法Oil and fat separation method
 本発明は、2つの飽和脂肪酸残基と1つの不飽和脂肪酸残基を有するトリグリセリド(X2U型トリグリセリド:ここで、Xは飽和脂肪酸残基、Uは不飽和脂肪酸残基を示す。以下、同じ)に富んだ油脂を得るための、油脂の分別製造方法に関する。 The present invention relates to a triglyceride having two saturated fatty acid residues and one unsaturated fatty acid residue (X2U type triglyceride, wherein X represents a saturated fatty acid residue, U represents an unsaturated fatty acid residue, and the same applies hereinafter). The present invention relates to a method for fractionated production of fats and oils to obtain rich oils and fats.
 カカオ脂をはじめとするハードバターは、チョコレートを始めとした食品、医薬品及び化粧品などに広く用いられている。これらのハードバターは、2つの飽和脂肪酸残基と1つの不飽和脂肪酸残基を有するトリグリセリド(X2U型トリグリセリド)を主成分としている。例えばカカオ脂は、1,3-ジパルミトイル-2-オレオイルグリセリン(POP)、2位にオレオイル基を有しパルミトイル基とステアロイル基を各1基づつ有するトリグリセリド(POS)及び1,3-ジステアロイル-2-オレオイルグリセリン(SOS)などの、分子内に1つの不飽和結合を有する対称型の2飽和1不飽和型トリグリセリド類を主成分としている。 ハ ー ド Hard butter including cocoa butter is widely used in foods such as chocolate, pharmaceuticals and cosmetics. These hard butters are mainly composed of triglycerides (X2U type triglycerides) having two saturated fatty acid residues and one unsaturated fatty acid residue. For example, cocoa butter is 1,3-dipalmitoyl-2-oleoylglycerin (POP), triglyceride (POS) having an oleoyl group at the 2-position, one palmitoyl group and one stearoyl group, and 1,3- It is mainly composed of symmetric disaturated monounsaturated triglycerides having one unsaturated bond in the molecule, such as distearoyl-2-oleoylglycerin (SOS).
 一般的に、このようなトリグリセリドは、この成分を含む天然の油脂、例えばパーム油、シア脂、サル脂、イリッペ脂などの油脂またはその分画油として得ることができる。又、パーム油、シア脂、サル脂、イリッペ脂などの油脂の分画油としてではなくて、特定の油脂に1,3選択性リパーゼを作用させ、エステル交換反応を利用して製造する方法が提案されている(特許文献1~3)。 Generally, such triglycerides can be obtained as natural fats and oils containing this component, for example, fats and oils such as palm oil, shea fat, monkey fat, and lippe fat, or fractionated oils thereof. In addition, there is a method in which a 1,3-selective lipase is allowed to act on specific fats and oils, not as oil fractions such as palm oils, shea fats, monkey fats, lippe fats, etc. It has been proposed (Patent Documents 1 to 3).
 上記いずれの方法においても、製菓用油脂の特徴である口中での速やかな融解特性に悪影響を及ぼすので、3つの飽和脂肪酸残基からなるトリグリセリド(XXX型トリグリセリド)を主成分とする高融点画分を除去する分画操作は不可欠である。現在、この工程は乾式分別で行われることが多くなっているが、乾式分別の特性上、原料油脂中にXXX型トリグリセリドが多く含まれると、除去すべき高融点画分に、必要とされるX2U型トリグリセリドが残留するため、X2U型トリグリセリドの歩留まりが悪くなる一因となっている。歩留まりを向上させるためには溶剤分別が必要であったり、複雑な工程管理が必要であったりと、生産効率の面でなお満足のゆくものはなく、XXX型トリグリセリドを多く含む原料油脂からのX2U型トリグリセリドに富んだ油脂のより効率的で、より工業化に適した製造方法が望まれている。 Any of the above methods adversely affects the rapid melting characteristics in the mouth, which is a characteristic of confectionery fats and oils, so a high melting point fraction mainly composed of triglycerides (XXX type triglycerides) consisting of three saturated fatty acid residues. Fractionation to remove is essential. At present, this process is often carried out by dry fractionation, but due to the characteristics of dry fractionation, if the raw material fat contains a large amount of XXX type triglyceride, it is required for the high melting point fraction to be removed. Since the X2U type triglyceride remains, it is a cause of the poor yield of the X2U type triglyceride. In order to improve the yield, solvent fractionation or complicated process control is not required, and there is nothing that is still satisfactory in terms of production efficiency. X2U from raw fats and oils rich in XXX type triglycerides There is a demand for a more efficient production method suitable for industrialization of fats and oils rich in type triglycerides.
特開昭55-71797号公報JP 55-71797 A 特開昭62-155048号公報JP 62-1555048 A WO2005/63952号公報WO2005 / 63952
 本発明の課題は、2飽和1不飽和型トリグリセリド(X2U型トリグリセリド、または、X2U)を含み、飽和脂肪酸残基のみからなるトリグリセリド(XXX型トリグリセリド、または、XXX)含量が高い油脂から、XXX型トリグリセリド含量が低く、X2U型トリグリセリドに富んだ油脂を回収するための、より効率的で工業的に適した分別方法を提供することである。 An object of the present invention is to provide a XXX type from an oil containing a saturated mono-unsaturated triglyceride (X2U type triglyceride or X2U) and containing only a saturated fatty acid residue (XXX type triglyceride or XXX). It is to provide a more efficient and industrially suitable fractionation method for recovering oils with low triglyceride content and rich in X2U type triglycerides.
 本発明者は上記課題を解決するために鋭意検討を行った結果、XXX、X2Uを特定量含有する油脂を、特定量の脂肪酸低級アルキルエステルの存在下で、加熱融解し、次いで冷却することにより、脂肪酸アルキルエステル非存在下と比較して、XXX型トリグリセリドの結晶化に対してX2U型トリグリセリドの結晶化を十分に遅延できることを見出した。すなわち、本発明は、XXX、X2Uを特定量含有する油脂を、特定量の脂肪酸低級アルキルエステルの存在下で、加熱融解し、次いで冷却によりXXXに富む結晶を晶析させ、分別により液体部(X2Uに富むオレイン部)を回収することで、上記課題を解決できるとの知見に基づいてなされたものである。 As a result of intensive studies to solve the above-mentioned problems, the present inventor heated and melted oil containing a specific amount of XXX and X2U in the presence of a specific amount of fatty acid lower alkyl ester, and then cooled. It was found that the crystallization of the X2U triglyceride can be sufficiently delayed with respect to the crystallization of the XXX triglyceride as compared with the absence of the fatty acid alkyl ester. That is, the present invention heats and melts oil containing a specific amount of XXX and X2U in the presence of a specific amount of fatty acid lower alkyl ester, then crystallizes XXX-rich crystals by cooling, and separates the liquid part ( The olein part rich in X2U) is collected based on the knowledge that the above problem can be solved.
 すなわち、本発明の態様の1つは、トリグリセリド含量が60質量%以上であって、全トリグリセリド中にXXX型トリグリセリドを10~70質量%及びX2U型トリグリセリドを10~50質量%含む油脂と、脂肪酸低級アルキルエステルとを混合し、トリグリセリド含量が10~50質量%、脂肪酸低級アルキルエステル含量が50~80%質量%である晶析原料を調製し、該晶析原料を、加熱融解し、次いで冷却して結晶を晶析させ、次いで分別することにより、X2U型トリグリセリドに富んだ液体部(オレイン部)を得る油脂の分別方法である。ただし、Xは飽和脂肪酸残基、Uは不飽和脂肪酸残基を示す。
 本発明の好ましい態様としては、前記トリグリセリド含量が60質量%以上であって、全トリグリセリド中にXXX型トリグリセリドを10~70質量%及びX2U型トリグリセリドを10~50質量%含む油脂が、パームステアリンである油脂の分別方法であり、また、エステル交換油の分別高融点画分である油脂の分別方法である。また、本発明の好ましい態様としては、前記X2U型トリグリセリドに富んだ液体部(オレイン部)の全トリグリセリド中のXXX型トリグリセリド含有量が10質量%未満である油脂の分別方法である。
That is, one aspect of the present invention is an oil and fat containing a triglyceride content of 60% by mass or more, 10 to 70% by mass of XXX triglyceride and 10 to 50% by mass of X2U triglyceride in all triglycerides, A lower alkyl ester is mixed to prepare a crystallization raw material having a triglyceride content of 10 to 50% by mass and a fatty acid lower alkyl ester content of 50 to 80% by mass. The crystallization raw material is heated and melted, and then cooled. This is a method for fractionating fats and oils to obtain a liquid part (olein part) rich in X2U type triglycerides by crystallization and then fractionation. However, X shows a saturated fatty acid residue and U shows an unsaturated fatty acid residue.
In a preferred embodiment of the present invention, the fat or oil having a triglyceride content of 60% by mass or more and containing 10 to 70% by mass of XXX type triglyceride and 10 to 50% by mass of X2U type triglyceride in total triglyceride is palm stearin. It is a method for fractionating certain fats and oils, and a method for fractionating fats and oils that are fractionated high melting point fractions of transesterified oil. Moreover, as a preferable aspect of the present invention, there is provided a method for fractionating fats and oils in which the content of XXX type triglyceride in the total triglyceride in the liquid part (olein part) rich in X2U type triglyceride is less than 10% by mass.
 本発明によれば、トリグリセリド中にX2Uと10質量%以上のXXXとを含有する油脂から、チョコレート用油脂等として口どけに悪影響を与えるXXXを排除すると同時に、有用なX2U型トリグリセリドを効率的に分画濃縮できるので、X2U型トリグリセリド製造におけるX2Uの回収率を有意に高めることができ、製造コストの低減及び品質の向上を図ることができる。 According to the present invention, from the fats and oils containing X2U and 10% by mass or more of XXX in the triglycerides, XXX which has an adverse effect on mouthfeel as fats and oils for chocolate is eliminated, and at the same time, useful X2U type triglycerides are efficiently produced. Since the fraction can be concentrated, the recovery rate of X2U in the production of X2U type triglyceride can be significantly increased, and the production cost can be reduced and the quality can be improved.
 以下、本発明を詳細に説明する。
 本発明の分別方法に用いる油脂は、トリグリセリド含量が60質量%以上であって、全トリグリセリド中にXXX型トリグリセリドを10~70質量%及びX2U型トリグリセリドを10~50質量%含む油脂である。ここで、Xはトリグリセリドの飽和脂肪酸残基を表し、Uは不飽和脂肪酸残基を表す。XXX型トリグリセリド(XXX)は、3つの飽和脂肪酸残基からなるトリグリセリドを表し、X2U型トリグリセリド(X2U)は、2つの飽和脂肪酸残基と1つの不飽和脂肪酸残基を有するトリグリセリドを表す。製菓製パン用途に有用であることから、飽和脂肪酸残基Xは、炭素数16~22の飽和脂肪酸残基であることが好ましく、特にステアロイル基(S)、パルミトイル基(P)、ベヘノイル基(B)であることが好ましい。また同様の理由で、不飽和脂肪酸残基Uは、オレイル基(O)、リノロイル基(L)、リノレイル基(Ln)であるのが好ましい。さらに、X2U型トリグリセリドを構成する飽和脂肪酸残基としては、同一の飽和脂肪酸残基を有するものが好ましい。
 なお、本発明の分別方法に用いる油脂は、グリセリド(モノグリセリド、ジグリセリド及びトリグリセリドの混合物)を指す。
Hereinafter, the present invention will be described in detail.
The fats and oils used in the fractionation method of the present invention are fats and oils having a triglyceride content of 60% by mass or more and containing 10 to 70% by mass of XXX type triglycerides and 10 to 50% by mass of X2U type triglycerides in the total triglycerides. Here, X represents a saturated fatty acid residue of triglyceride, and U represents an unsaturated fatty acid residue. The XXX type triglyceride (XXX) represents a triglyceride composed of three saturated fatty acid residues, and the X2U type triglyceride (X2U) represents a triglyceride having two saturated fatty acid residues and one unsaturated fatty acid residue. The saturated fatty acid residue X is preferably a saturated fatty acid residue having 16 to 22 carbon atoms because it is useful for confectionery and bakery purposes. In particular, a stearoyl group (S), a palmitoyl group (P), a behenoyl group ( B) is preferred. For the same reason, the unsaturated fatty acid residue U is preferably an oleyl group (O), a linoloyl group (L), or a linoleyl group (Ln). Furthermore, as a saturated fatty acid residue which comprises X2U type | mold triglyceride, what has the same saturated fatty acid residue is preferable.
In addition, the fats and oils used for the fractionation method of the present invention refer to glycerides (a mixture of monoglyceride, diglyceride and triglyceride).
 本発明の分別方法に用いる油脂は、トリグリセリド含量が70質量%以上であることが好ましく、全トリグリセリド中にXXX型トリグリセリドを20~50質量%及びX2U型トリグリセリドを20~50質量%含有することが好ましい。また、全トリグリセリド中のXXX型トリグリセリドとX2U型トリグリセリドの合計含量は、60質量%以上であることが好ましく、65質量%以上であることがより好ましく、70~90質量%であることが更に好ましい。本発明の分別方法に用いる油脂のトリグリセリド含量、全トリグリセリド中のXXX型トリグリセリド含量及びX2U型トリグリセリド含量が上記範囲にあると、XXX型トリグリセリドとX2U型トリグリセリドとを効率的に分別できるので好ましい。 The oil and fat used in the fractionation method of the present invention preferably has a triglyceride content of 70% by mass or more, and the total triglyceride contains 20 to 50% by mass of XXX type triglyceride and 20 to 50% by mass of X2U type triglyceride. preferable. The total content of XXX type triglyceride and X2U type triglyceride in the total triglyceride is preferably 60% by mass or more, more preferably 65% by mass or more, and further preferably 70 to 90% by mass. . It is preferable that the triglyceride content of fats and oils used in the fractionation method of the present invention, the XXX type triglyceride content and the X2U type triglyceride content in the total triglyceride are in the above ranges, because XXX type triglyceride and X2U type triglyceride can be efficiently separated.
 本発明の分別方法に用いる油脂の好ましい態様としては、トリグリセリド含量が90質量%以上であって、全トリグリセリド中のXXX含量が20~70質量%、X2U含量が20~50質量%である、例えば、パームステアリン、シア脂ステアリン分別高融点画分、サル脂ステアリン分別高融点画分などが挙げられる。本発明により、前記天然油脂の高融点画分(ステアリン部)を更に分別することで、製菓用油脂として有用なX2U型トリグリセリドの回収率を高めることができる。 As a preferred embodiment of the fats and oils used in the fractionation method of the present invention, the triglyceride content is 90% by mass or more, the XXX content in the total triglycerides is 20 to 70% by mass, and the X2U content is 20 to 50% by mass. , Palm stearin, shea fat stearin fractionation high melting point fraction, sal fat stearin fractionation high melting point fraction, and the like. According to the present invention, by further fractionating the high melting point fraction (stearin part) of the natural fats and oils, it is possible to increase the recovery rate of X2U type triglycerides useful as confectionery fats and oils.
 本発明の分別方法に用いる油脂のまた別の好ましい態様としては、例えば、2位にオレオイル基を50質量%以上有するトリグリセリドを脂肪酸低級アルキルエステル (脂肪酸自体を用いる場合も含む) とエステル交換反応を行い、次いで蒸留して得られた蒸留残渣の乾式分別によって得られる高融点画分を使用してもよい。より具体的には、トリオレオイルグリセリン、シア脂低融点部分 (例えばヨウ素価70~80)、ハイオレイックヒマワリ油、ハイオレイックローリノレン菜種油、ハイオレイック紅花油、パーム油、パーム分画油などの原料油脂に、飽和脂肪酸低級アルキルエステルを加え、1,3選択性リパーゼ、例えばリゾプス系リパーゼ、アスペルギルス系リパーゼ、ムコール系リパーゼ、パンクレアチックリパーゼ、米ヌカリパーゼなどを作用させて、エステル交換反応を行う。次いで蒸留により、未反応の飽和脂肪酸低級アルキルエステルや副生するオレイン酸などの脂肪酸及びその低級アルキルエステルを除いた残渣を得て、該残渣を乾式分別してXOX型トリグリセリドに富む低融点画分を取り除いた高融点画分(固体部、ステアリン部)を好適に使用できる。 Another preferred embodiment of the fat used in the fractionation method of the present invention is, for example, a triglyceride having an oleoyl group of 50% by mass or more at the 2-position with a fatty acid lower alkyl ester cocoon (including the case where the fatty acid itself is used) and a transesterification reaction. Then, a high melting point fraction obtained by dry fractionation of a distillation residue obtained by distillation and then distillation may be used. More specifically, such as trioleoyl glycerin, shea butter low melting point rice cake (for example, iodine value 70-80), high oleic sunflower oil, high oleic lorinolen rapeseed oil, high oleic safflower oil, palm oil, palm fraction oil, etc. Saturated fatty acid lower alkyl ester is added to raw oil and fat, and 1,3-selective lipase such as lysops lipase, Aspergillus lipase, mucor lipase, pancreatic lipase, rice nuclei lipase, etc. is allowed to act on the transesterification reaction. . Next, a residue obtained by removing unreacted saturated fatty acid lower alkyl ester and by-product fatty acid such as oleic acid and its lower alkyl ester by distillation is obtained, and the residue is subjected to dry fractionation to obtain a low melting point fraction rich in XOX type triglyceride. The removed high melting point fraction (solid portion, stearin portion) can be suitably used.
 前記高融点画分は、X2U型トリグリセリド(XOX)を製造する際に産生する副生物あり、油脂(グリセリド)中のトリグリセリド含量が60質量%以上であって、全トリグリセリド中のXXX含量が10~70質量%、X2U含量が10~50質量%である。前記高融点画分から、本発明の分別方法によりX2U型トリグリセリドを回収することで、X2U型トリグリセリドの生産効率を高めることができる。 The high melting point fraction is a by-product produced when X2U type triglyceride (XOX) is produced, the triglyceride content in fats and oils (glycerides) is 60% by mass or more, and the XXX content in all triglycerides is 10 to 10%. 70% by mass and X2U content is 10-50% by mass. By recovering the X2U triglyceride from the high melting point fraction by the fractionation method of the present invention, the production efficiency of the X2U triglyceride can be increased.
 前記高融点画分について更に詳細に説明する。前記高融点画分を産生する工程で使用される上記1,3選択性リパーゼとしては、リゾプス属のリゾプス デレマー(Rhizopus delemar)及びリゾプス オリザエ(Rhizopus oryzae)が好ましい。これらのリパーゼとしては、ロビン社の商品:ピカンターゼR8000や、天野エンザイム社の商品:リパーゼF-AP15等が挙げられるが、最も適したリパーゼとしては Rhizopus oryzae由来、天野エンザイム社の商品:リパーゼDF(Amano)15-K(リパーゼDともいう)が挙げられる。このものは粉末リパーゼである。なお、このリパーゼDF(Amano)15-Kについては、従来はRhizopus delemar由来の表記であった。ここで、使用するリパーゼとしては、リパーゼの培地成分等を含有したリパーゼ含有水溶液を乾燥して得られたものでもよい。粉末リパーゼとしては、球状で、水分含量が10質量%以下であるものを用いるのが好ましい。特に、リパーゼ粉末の90質量%以上が粒径1~100μmであるのが好ましい。又、粉末リパーゼはpHが6~7.5に調整されてなるリパーゼ含有水溶液を噴霧乾燥して製造されるものが好ましい。上記リパーゼを、大豆粉末を用いて造粒し、粉末化した造粒粉末リパーゼ(粉末リパーゼともいう)を用いるのも好ましい。また、市販の固定化リパーゼも好適に使用できる。例えば、ノボザイムズ社製の商品名Lipozyme RM IM、Lipozyme TL IM等が挙げられる。 The high melting point fraction will be described in more detail. As the 1,3-selective lipase used in the step of producing the high melting point fraction, Rhizopus delemar and Rhizopus oryzae belonging to the genus Rhizopus are preferable. Examples of these lipases include Robin's product: Picantase R8000 and Amano Enzyme's product: Lipase F-AP15. The most suitable lipase is derived from Rhizopus oryzae, Amano Enzyme's product: Lipase DF ( Amano) 15-K (also referred to as lipase D). This is a powder lipase. The lipase DF (Amano) 15-K has conventionally been derived from Rhizopus delemar. Here, the lipase used may be obtained by drying a lipase-containing aqueous solution containing a lipase medium component or the like. The powder lipase is preferably spherical and has a water content of 10% by mass or less. In particular, 90% by mass or more of the lipase powder preferably has a particle size of 1 to 100 μm. The powder lipase is preferably produced by spray-drying a lipase-containing aqueous solution whose pH is adjusted to 6 to 7.5. It is also preferable to use granulated powder lipase (also referred to as powder lipase) obtained by granulating the lipase with soybean powder and then pulverizing it. Commercially available immobilized lipase can also be used suitably. For example, trade names such as Lipozyme®RM®IM, Lipozyme®TL®IM manufactured by Novozymes, and the like can be mentioned.
 上記エステル交換反応においては、油脂(2位にオレオイル基を50質量%以上有するトリグリセリド)と脂肪酸低級アルキルエステルとを、質量比20:80~50:50、好ましくは25:75~45:55の割合で混合した反応原料に、上記1,3選択性リパーゼを添加して、常法でエステル交換反応を行うことができる。この場合、反応原料100質量部当り、リパーゼを0.01~10質量部(好ましくは0.01~2質量部、より好ましくは0.1~1.5質量部)添加し、35~100℃の温度(好ましくは35~80℃、より好ましくは40~60℃)で、0.1~50時間(好ましくは0.5~30時間、より好ましくは1~20時間)エステル交換反応を行うのが好ましい。反応はバッチ式で行うのが好ましい。反応温度は反応基質である油脂が溶解する温度で酵素活性を有する温度であれば何度でもかまわない。最適な反応時間は、酵素添加量、反応温度などにより変化するので、適宜調整すれば良い。エステル交換反応後、蒸留して、未反応原料や副生する脂肪酸や、脂肪酸低級アルキルエステルを50質量%以下になるまで除き、18~38℃、好ましくは22~34℃で乾式分別を行うことで本発明の分別方法に用いる油脂を含む高融点画分が得られる。 In the transesterification reaction, a fat / oil (triglyceride having an oleoyl group at 50% by mass or more at the 2-position) and a fatty acid lower alkyl ester are in a mass ratio of 20:80 to 50:50, preferably 25:75 to 45:55. The 1,3-selective lipase can be added to the reaction raw material mixed at a ratio of 1, and the transesterification reaction can be carried out by a conventional method. In this case, 0.01 to 10 parts by mass (preferably 0.01 to 2 parts by mass, more preferably 0.1 to 1.5 parts by mass) of lipase is added per 100 parts by mass of the reaction raw material, and 35 to 100 ° C. The transesterification reaction is carried out at a temperature (preferably 35 to 80 ° C., more preferably 40 to 60 ° C.) for 0.1 to 50 hours (preferably 0.5 to 30 hours, more preferably 1 to 20 hours). Is preferred. The reaction is preferably carried out batchwise. The reaction temperature may be any number of times as long as it is a temperature at which fats and oils as reaction substrates dissolve and has enzyme activity. The optimal reaction time varies depending on the amount of enzyme added, reaction temperature, etc., and may be adjusted as appropriate. After the transesterification reaction, distillation is carried out to remove unreacted raw materials, by-product fatty acids and fatty acid lower alkyl esters to 50% by mass or less, and dry fractionation at 18 to 38 ° C., preferably 22 to 34 ° C. Thus, a high melting point fraction containing oils and fats used in the fractionation method of the present invention is obtained.
 本発明の分別方法に用いる脂肪酸低級アルキルエステルとしては、炭素数16~22の脂肪酸の低級アルコールエステルが好ましく、飽和脂肪酸低級アルキルエステル、不飽和脂肪酸低級アルキルエステル、またはそれらの混合物であってもよい。特に、炭素数1~6のアルコールとのエステルが好ましく、メタノール、エタノール、イソプロピルアルコールとのエステルが好ましい。中でも、食用油脂の加工という点からエタノールとのエステルが好ましい。 The fatty acid lower alkyl ester used in the fractionation method of the present invention is preferably a lower alcohol ester of a fatty acid having 16 to 22 carbon atoms, and may be a saturated fatty acid lower alkyl ester, an unsaturated fatty acid lower alkyl ester, or a mixture thereof. . In particular, an ester with an alcohol having 1 to 6 carbon atoms is preferable, and an ester with methanol, ethanol or isopropyl alcohol is preferable. Among these, an ester with ethanol is preferable from the viewpoint of processing of edible fats and oils.
 本発明の分別方法に用いる晶析原料は、前記トリグリセリド含量が60質量%以上であって、全トリグリセリド中にXXX型トリグリセリドを10~70質量%及びX2U型トリグリセリドを10~50質量%含む油脂と、脂肪酸低級アルキルエステルとを混合することにより得られる、トリグリセリド含量が10~50質量%、脂肪酸低級アルキルエステル含量が50~80%質量%である混合物である。本発明の分別方法に用いる晶析原料は、トリグリセリド含量が15~50質量%、脂肪酸低級アルキルエステル含量が50~75質量%であることがより好ましく、トリグリセリド含量が20~45質量%、脂肪酸低級アルキルエステル含量が55~70質量%であることが更に好ましい。また、本発明の分別方法に用いる晶析原料中のトリグリセリドと脂肪酸低級アルキルエステルの合計含量は、80質量%以上であることが好ましい。本発明の分別方法に用いる晶析原料中のトリグリセリド含量と脂肪酸低級アルキルエステル含量が上記範囲にある場合、XXX型トリグリセリドとX2U型トリグリセリドとを効率的に分別できるので好ましい。 The crystallization raw material used in the fractionation method of the present invention has an oil and fat having a triglyceride content of 60% by mass or more, 10 to 70% by mass of XXX type triglyceride and 10 to 50% by mass of X2U type triglyceride in all triglycerides, , A mixture having a triglyceride content of 10 to 50% by mass and a fatty acid lower alkyl ester content of 50 to 80% by mass obtained by mixing with a fatty acid lower alkyl ester. The crystallization raw material used in the fractionation method of the present invention preferably has a triglyceride content of 15 to 50% by mass and a fatty acid lower alkyl ester content of 50 to 75% by mass, a triglyceride content of 20 to 45% by mass, More preferably, the alkyl ester content is 55 to 70% by mass. Moreover, it is preferable that the total content of the triglyceride and the fatty acid lower alkyl ester in the crystallization raw material used in the fractionation method of the present invention is 80% by mass or more. When the triglyceride content and the fatty acid lower alkyl ester content in the crystallization raw material used in the fractionation method of the present invention are in the above ranges, it is preferable because the XXX triglyceride and the X2U triglyceride can be efficiently separated.
 本発明の分別方法に用いる晶析原料を調製するには、前記トリグリセリド含量が60質量%以上であって、全トリグリセリド中にXXX型トリグリセリドを10~70質量%及びX2U型トリグリセリドを10~50質量%含む油脂と、脂肪酸低級アルキルエステルとを、質量比で20:80~50:50の割合で混合することが好ましく、質量比25:75~50:50の割合で混合することがより好ましく、質量比30:70~45:55の割合で混合することが更に好ましい。 In order to prepare a crystallization raw material used in the fractionation method of the present invention, the triglyceride content is 60% by mass or more, and 10 to 70% by mass of XXX type triglyceride and 10 to 50% by mass of X2U type triglyceride in all triglycerides. % Fat and fatty acid lower alkyl ester are preferably mixed at a mass ratio of 20:80 to 50:50, more preferably mixed at a mass ratio of 25:75 to 50:50, It is more preferable to mix at a mass ratio of 30:70 to 45:55.
 本発明の分別方法に用いる晶析原料の好ましい態様としては、例えば、油脂中のトリグリセリド含が90質量%以上であり、全トリグリセリド中のXXX含量が20~70質量%、X2U含量が20~50質量%であるパームステアリンと、脂肪酸低級アルキルエステルとを、例えば、質量比で30:70~45:55の割合で混合した混合物が挙げられる。 As a preferred embodiment of the crystallization raw material used in the fractionation method of the present invention, for example, the triglyceride content in the oil and fat is 90% by mass or more, the XXX content in the total triglyceride is 20 to 70% by mass, and the X2U content is 20 to 50%. Examples thereof include a mixture in which palm stearin which is mass% and a fatty acid lower alkyl ester are mixed at a mass ratio of 30:70 to 45:55.
 本発明の分別方法に用いる晶析原料のまた別の好ましい態様としては、例えば、油脂(グリセリド)中のトリグリセリド含量が60質量%以上であって、全トリグリセリド中のXXX含量が10~70質量%、X2U含量が10~50質量%である前記高融点画分と、脂肪酸低級アルキルエステルとを、例えば、質量比で30:70~45:55の割合で混合した混合物が挙げられる。 As another preferred embodiment of the crystallization raw material used in the fractionation method of the present invention, for example, the triglyceride content in fats and oils (glycerides) is 60% by mass or more, and the XXX content in all triglycerides is 10 to 70% by mass. And a mixture of the high melting point fraction having an X2U content of 10 to 50% by mass and the fatty acid lower alkyl ester in a mass ratio of 30:70 to 45:55, for example.
 本発明の分別方法は、晶析原料に脂肪酸低級アルキルエステルを50~80質量%含有する以外は、通常の油脂の乾式分別と同様に行うことができる。乾式分別は、一般的には加熱融解させた晶析原料を槽内で攪拌しながら冷却し、結晶を析出させた後、圧搾及び/又はろ過によって高融点画分(固体部)と低融点画分(液体部)を得ることにより行うことができる。加熱融解は、晶析原料と脂肪酸低級アルキルエステルの両者が相互に溶解して液状にできる温度であればよく、晶析原料に含まれるトリグリセリド及び脂肪酸低級アルキルエステルの含量及び組成によっても異なるが、例えば、60~100℃、好ましくは、70~90℃である。分別温度は、晶析原料に含まれるトリグリセリド及び脂肪酸低級アルキルエステルの含量及び組成によっても異なるが10~40℃、より好ましくは、15~35℃で行うことができる。 The fractionation method of the present invention can be carried out in the same manner as usual dry fractionation of fats and oils, except that the crystallization raw material contains 50 to 80% by mass of a fatty acid lower alkyl ester. In the dry fractionation, the crystallization raw material heated and melted is generally cooled while stirring in a tank to precipitate crystals, and then a high melting point fraction (solid part) and a low melting point fraction are obtained by pressing and / or filtration. This can be done by obtaining a minute (liquid part). The heat melting may be a temperature at which both the crystallization raw material and the fatty acid lower alkyl ester can be dissolved to form a liquid and varies depending on the content and composition of the triglyceride and the fatty acid lower alkyl ester contained in the crystallization raw material, For example, the temperature is 60 to 100 ° C., preferably 70 to 90 ° C. The fractionation temperature varies depending on the content and composition of the triglyceride and fatty acid lower alkyl ester contained in the crystallization raw material, but can be carried out at 10 to 40 ° C., more preferably 15 to 35 ° C.
 以上の工程を経ることにより、トリグリセリド含量が60質量%以上であって、全トリグリセリド中にXXX型トリグリセリドを10~70質量%及びX2U型トリグリセリドを10~50質量%含む油脂と、脂肪酸低級アルキルエステルとを混合し、トリグリセリド含量が10~50質量%、脂肪酸低級アルキルエステル含量が50~80%質量%である晶析原料から、X2U型トリグリセリドに富んだ液体部(オレイン部)を得ることができる。 Through the above steps, an oil and fat having a triglyceride content of 60% by mass or more, 10 to 70% by mass of XXX type triglyceride and 10 to 50% by mass of X2U type triglyceride in all triglycerides, and fatty acid lower alkyl ester And a liquid part (olein part) rich in X2U triglyceride can be obtained from a crystallization raw material having a triglyceride content of 10 to 50% by mass and a fatty acid lower alkyl ester content of 50 to 80% by mass. .
 本発明の分別方法により得られるX2U型トリグリセリドに富んだ液体部(オレイン部)は、全トリグリセリド中のXXX含量が10質量%未満であることが好ましく、5質量%以下であることがより好ましい。また、全トリグリセリド中のX2U含量が50質量%を超えることが好ましく、60質量%以上であることが更に好ましい。本発明の分別方法により得られるX2U型トリグリセリドに富んだ液体部(オレイン部)は、例えば単体もしくはその他油脂と混合して、製菓製パン用途に使用できる。また、更に分別工程を経ることにより、全トリグリセリド中のX2U含量が70質量%以上である高純度X2U型油脂を製造する原料油脂として使用できる。 The liquid part (olein part) rich in X2U type triglyceride obtained by the fractionation method of the present invention preferably has a XXX content in all triglycerides of less than 10% by mass, more preferably 5% by mass or less. Moreover, it is preferable that the X2U content in all the triglycerides exceeds 50 mass%, and it is still more preferable that it is 60 mass% or more. The liquid part (olein part) rich in X2U type triglyceride obtained by the fractionation method of the present invention can be used, for example, alone or mixed with other fats and oils for confectionery bread applications. Moreover, it can use as raw material fats and oils which manufacture the high purity X2U type | mold fat and oil whose X2U content in all the triglycerides is 70 mass% or more by passing through a fractionation process.
 本発明の油脂の分別方法は、また、エステル交換と組み合わせて、X2U型トリグリセリドを製造する工程に組み込んで利用することが好ましい。すなわち、油脂のみ、もしくは、油脂と脂肪酸及び/または脂肪酸低級アルキルエステルとの混合物をエステル交換することにより、X2U型トリグリセリドを含むエステル交換油を得、該エステル交換油を分別することで、低融点もしくは中融点画分にX2U型トリグリセリドに富む油脂を得、残余の高融点画分を本発明の分別方法に供することにより、XXX含量が低くX2U型トリグリセリドに富んだ低融点画分(液体部)を回収し、該低融点画分を例えば分別前のX2U型トリグリセリドを含むエステル交換油に戻すことにより、X2U型トリグリセリドの回収率を高める製造工程とすることができる。 The method for fractionating fats and oils of the present invention is also preferably used by being incorporated into a process for producing X2U type triglycerides in combination with transesterification. That is, by transesterifying only a fat or oil, or a mixture of fat and fatty acid and / or fatty acid lower alkyl ester, a transesterified oil containing X2U type triglyceride is obtained, and the transesterified oil is fractionated to obtain a low melting point. Alternatively, an oil and fat rich in X2U type triglyceride is obtained in the middle melting point fraction, and the remaining high melting point fraction is subjected to the fractionation method of the present invention, so that the low melting point fraction low in XXX content and rich in X2U type triglyceride (liquid part) Is recovered, and the low-melting-point fraction is returned to, for example, transesterified oil containing X2U triglyceride before fractionation, whereby a production process for increasing the recovery rate of X2U triglyceride can be achieved.
 本発明の油脂の分別方法とエステル交換とを組み合わせたX2U型トリグリセリド製造の好ましい態様としては、前述のように、2位にオレオイル基を50質量%以上有するトリグリセリドを飽和脂肪酸低級アルキルエステル (脂肪酸自体を用いる場合も含む) とエステル交換反応を行い、次いで蒸留して得られた蒸留残渣の乾式分別によって得られる、油脂(グリセリド)中のトリグリセリド含量が60質量%以上であって、全トリグリセリド中のXXX含量が10~70質量%、X2U含量が10~50質量%である前記高融点画分と、脂肪酸低級アルキルエステルとを混合して、トリグリセリド含量が10~50質量%、脂肪酸低級アルキルエステル含量が50~80%質量%である晶析原料を調製し、該晶析原料を、加熱融解し、次いで冷却して結晶を晶析させ、次いで分別することにより、全トリグリセリド中のXXX含量が10質量%未満であり、X2U含量が50質量%を超える、X2U型トリグリセリドに富んだ液体部(オレイン部)を回収し、該液体部を分別前のエステル交換油に戻すことでX2U型トリグリセリドの回収率を高める製造工程が挙げられる。 As a preferred embodiment of the production of X2U type triglyceride combining the method for fractionating fats and oils of the present invention and transesterification, a triglyceride having an oleoyl group at 50% by mass or more at the 2-position is saturated fatty acid lower alkyl ester (fatty acid (Including the case of using itself) After transesterification with soot, the triglyceride content in fats and oils (glycerides) obtained by dry fractionation of the distillation residue obtained by distillation is 60% by mass or more, and in all triglycerides The high melting point fraction having a XXX content of 10 to 70% by mass and an X2U content of 10 to 50% by mass and a fatty acid lower alkyl ester are mixed to obtain a triglyceride content of 10 to 50% by mass and a fatty acid lower alkyl ester. Preparing a crystallization raw material having a content of 50 to 80% by mass, melting the crystallization raw material by heating, The mixture is cooled to crystallize the crystals, and then fractionated to obtain a liquid part (olein part) rich in X2U type triglyceride having an XXX content of less than 10% by mass and an X2U content of more than 50% by mass. ) And returning the liquid part to the transesterified oil before fractionation, thereby increasing the recovery rate of the X2U triglyceride.
 以下、本発明を実施例によってさらに詳細に説明するが、本発明は以下の実施例の内容に限定して解釈されるものではない。 Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is not construed as being limited to the contents of the following examples.
 〔実施例1〕
 パームステアリン(ヨウ素価30)120.0gに、パルミチン酸エチルエステル(商品名:エチルパルミテート、(株)井上香料製造所製)180.5gを混合し、脂肪酸エチルエステル含量が60.1質量%である晶析原料1を300.5g得た。得られた晶析原料1 (300.5g) を80℃にて完全溶解後、撹拌を行いながら15℃にて3時間冷却し、圧搾ろ過(圧搾圧力7kgf/cm2、日清オイリオ自作加圧ろ過機使用)にて固液分離を行い、固体部1(86.6g)及び液体部1(193.1g)を得た。圧搾ろ過前の晶析原料1は、流動性が非常に高く、スムーズに圧搾機に導入され、圧搾ろ過することができた。表1に各工程油の分析値を示した。尚、脂肪酸エチルエステル含量およびトリグリセリド(TAG)含量・組成の分析はGLC法を用いて行った。
[Example 1]
Palm stearic acid (iodine value 30) 120.0 g was mixed with palmitic acid ethyl ester (trade name: ethyl palmitate, manufactured by Inoue Fragrance Co., Ltd.) 180.5 g, and the fatty acid ethyl ester content was 60.1% by mass. 300.5 g of crystallization raw material 1 was obtained. The obtained crystallization raw material 1 (300.5 g) was completely dissolved at 80 ° C. and then cooled at 15 ° C. for 3 hours with stirring, followed by squeeze filtration (squeezing pressure 7 kgf / cm 2 , Nisshin Oilio's own pressurization) Solid-liquid separation was performed using a filter) to obtain a solid part 1 (86.6 g) and a liquid part 1 (193.1 g). The crystallization raw material 1 before the press filtration had very high fluidity, and was smoothly introduced into the press and could be subjected to the press filtration. Table 1 shows the analysis value of each process oil. The fatty acid ethyl ester content and triglyceride (TAG) content and composition were analyzed using the GLC method.
Figure JPOXMLDOC01-appb-T000001
 本発明の分別方法によって得られる液体部1は、晶析原料1と比較して、全トリグリセリド中のXXX含量が有意に低く(1.8質量%)、X2Uが有意に濃縮(63.3質量%)されていることが分る。
Figure JPOXMLDOC01-appb-T000001
Compared with the crystallization raw material 1, the liquid part 1 obtained by the fractionation method of the present invention has a significantly lower XXX content in all triglycerides (1.8% by mass) and a significant concentration of X2U (63.3% by mass). %).
 〔実施例2〕
(粉末リパーゼ組成物Aの調製)
 天野エンザイム社の商品:リパーゼDF(Amano)15-K(リパーゼDともいう)の酵素溶液(150000U/ml)に、予めオートクレーブ滅菌(121℃、15分)を行い、室温程度に冷やした脱臭全脂大豆粉末(脂肪含有量が23質量%、商品名:アルファプラスHS-600、日清コスモフーズ(株)社製)10%水溶液を攪拌しながら3倍量加え、0.5N NaOH溶液でpH7.8に調整後、噴霧乾燥(東京理科器械(株)社、SD-1000型)を行い、粉末リパーゼ組成物Aを得た。
[Example 2]
(Preparation of powder lipase composition A)
Amano Enzyme Co., Ltd .: Enzyme solution (150,000 U / ml) of lipase DF (Amano) 15-K (also referred to as lipase D) was autoclaved (121 ° C., 15 minutes) in advance and cooled to room temperature. Fat soy powder (fat content is 23% by mass, trade name: Alpha Plus HS-600, manufactured by Nisshin Cosmo Foods Co., Ltd.) 10% aqueous solution is added in 3 times amount with stirring, pH 7 with 0.5N NaOH solution After adjustment to 0.8, spray drying (Tokyo Science Instrument Co., Ltd., SD-1000 type) was performed to obtain a powder lipase composition A.
 ハイオレイックヒマワリ油(商品名:オレインリッチ、昭和産業(株)製)6400gに、ステアリン酸エチル(商品名:エチルステアレート、(株)井上香料製造所製)9600gを混合し、粉末リパーゼ組成物Aを0.3質量%添加し、50℃で16時間攪拌反応させた。ろ過処理により酵素粉末を除去し、反応物2を15900g得た。得られた反応物2(15808g)を薄膜蒸留にかけ、蒸留温度140℃にて反応物から脂肪酸エチルを除去し、トリグリセリド含量が80.2質量%、脂肪酸エチル含量が18.2質量%である蒸留残渣2-1(8052g)及び蒸留留分2(7828g)を得た。得られた蒸留残渣2-1(8000g)を50℃にて完全溶解後、撹拌を行いながら27℃で3時間冷却し、圧搾ろ過(圧搾圧力7kgf/cm2、日清オイリオ自作加圧ろ過機使用)にて固液分離を行い、固体部2-1(532.4g)及び液体部2-1(7068g)を得た。得られた固体部2-1(120.3g)に、蒸留留分2(179.8g)を添加し、全油脂組成物中の脂肪酸エチルエステル含量が66.6%の晶析原料2を300.1g得た。得られた晶析原料2(300.1g)を80℃にて完全溶解後、撹拌を行いながら30℃にて3時間冷却し、圧搾ろ過(圧搾圧力7kgf/cm2、日清オイリオ自作加圧ろ過機使用)にて固液分離を行い、固体部2-2(66.1g)及び液体部2-2(211.6g)を得た。圧搾ろ過前の晶析原料2は、流動性が非常に高く、スムーズに圧搾機に導入され、圧搾ろ過することができた。表2に各工程油の分析値を示した。尚、脂肪酸エチルエステル含量およびトリグリセリド(TAG)含量・組成の分析はGLC法を用いて行った。 6600 g of high oleic sunflower oil (trade name: olein rich, manufactured by Showa Sangyo Co., Ltd.) is mixed with 9600 g of ethyl stearate (trade name: ethyl stearate, manufactured by Inoue Fragrance Co., Ltd.), and a powder lipase composition The product A was added in an amount of 0.3% by mass, and the reaction was stirred at 50 ° C. for 16 hours. The enzyme powder was removed by filtration to obtain 15900 g of reaction product 2. The obtained reaction product 2 (15808 g) was subjected to thin film distillation, and fatty acid ethyl was removed from the reaction product at a distillation temperature of 140 ° C., and the triglyceride content was 80.2% by mass and the fatty acid ethyl content was 18.2% by mass. Residue 2-1 (8052 g) and distillation fraction 2 (7828 g) were obtained. The obtained distillation residue 2-1 (8000 g) was completely dissolved at 50 ° C., then cooled at 27 ° C. for 3 hours with stirring, and subjected to pressure filtration (pressing pressure 7 kgf / cm 2 , Nisshin Oilio self-made pressure filter) Used) to obtain a solid part 2-1 (532.4 g) and a liquid part 2-1 (7068 g). Distilled fraction 2 (179.8 g) was added to the obtained solid part 2-1 (120.3 g), and 300% of crystallization raw material 2 having a fatty acid ethyl ester content of 66.6% in the total oil and fat composition was added. 0.1 g was obtained. The obtained crystallization raw material 2 (300.1 g) was completely dissolved at 80 ° C., then cooled for 3 hours at 30 ° C. with stirring, and pressed and filtered (squeezing pressure 7 kgf / cm 2 , Nisshin Oilio's own pressurization) Solid-liquid separation was performed using a filter) to obtain a solid part 2-2 (66.1 g) and a liquid part 2-2 (211.6 g). The crystallization raw material 2 before the press filtration had very high fluidity, and was smoothly introduced into the press and could be press filtered. Table 2 shows the analysis value of each process oil. The fatty acid ethyl ester content and triglyceride (TAG) content and composition were analyzed using the GLC method.
Figure JPOXMLDOC01-appb-T000002
 本発明の分別方法によって得られる液体部2-2は、晶析原料2と比較して、全トリグリセリド中のXXX含量が有意に低く(2.9質量%)、X2Uが有意に濃縮(63.0質量%)されていることが分る。
Figure JPOXMLDOC01-appb-T000002
The liquid part 2-2 obtained by the fractionation method of the present invention has a significantly lower XXX content (2.9% by mass) in the total triglycerides than the crystallization raw material 2 and a significant concentration of X2U (63. 0 mass%).
 〔比較例1〕
 実施例2の方法で得た固体部2-1(250g)を、蒸留温度200℃にて水蒸気蒸留を行い、脂肪酸エチルエステルを除去し、脂肪酸エチルエステル含量が痕跡%である蒸留残渣2-2(168.4g)を得た。得られた蒸留残渣(150g)を80℃にて完全溶解後、撹拌を行いながら45℃で3時間冷却し、圧搾ろ過(圧搾圧力7kgf/cm2、日清オイリオ自作加圧ろ過機使用)にて固液分離を行い、固体部2-3(66.9g)及び液体部2-3(64.7g)を得た。圧搾ろ過前の蒸留残渣2-2は、ろ過機へ送液する際の流動性が悪く、また微細な結晶がろ液(液体部)に漏れており、固液分離が不十分であった。表3に各工程油の分析値を示した。尚、脂肪酸エチルエステル含量およびトリグリセリド(TAG)含量・組成の分析はGLC法を用いて行った。
[Comparative Example 1]
The solid part 2-1 (250 g) obtained by the method of Example 2 was subjected to steam distillation at a distillation temperature of 200 ° C. to remove the fatty acid ethyl ester, and the distillation residue 2-2 having a fatty acid ethyl ester content of trace%. (168.4 g) was obtained. The obtained distillation residue (150 g) was completely dissolved at 80 ° C., then cooled at 45 ° C. for 3 hours while stirring, and subjected to pressure filtration (pressing pressure 7 kgf / cm 2 , using a Nisshin Oilio self-made pressure filter). Solid-liquid separation was performed to obtain a solid part 2-3 (66.9 g) and a liquid part 2-3 (64.7 g). The distillation residue 2-2 before the press filtration had poor fluidity when being sent to the filter, and fine crystals leaked into the filtrate (liquid part), resulting in insufficient solid-liquid separation. Table 3 shows the analysis value of each process oil. The fatty acid ethyl ester content and triglyceride (TAG) content and composition were analyzed using the GLC method.
Figure JPOXMLDOC01-appb-T000003
 晶析原料に脂肪酸低級アルキルエステルを用いることのない比較例1の液体部2-3では、全トリグリセリド中のXXXの除去が十分でなく(17.7質量%)、X2Uの濃縮(49.1質量%)も十分ではないことが分る。
Figure JPOXMLDOC01-appb-T000003
In the liquid part 2-3 of Comparative Example 1 in which no fatty acid lower alkyl ester was used as a crystallization raw material, XXX in the total triglyceride was not sufficiently removed (17.7% by mass), and X2U was concentrated (49.1). Mass%) is also not sufficient.
 〔参考例1〕
 比較例1と同様の方法で得た蒸留残渣2-2(100g)を、80℃にて完全溶解しアセトン300gを添加した後に、撹拌を行いながら35℃で3時間冷却し、水流アスピレーターを用いて減圧ろ過(ヤマト科学株式会社 ハンディアスピレーターWP51)にて固液分離を行った。減圧ろ過の際、固体部を新たに150gのアセトンで洗浄し、結晶表面に残存している液体部を洗浄する操作を行った。得られた固体部と液体部から加熱減圧処理によってアセトンを完全に除去し、固体部2-4 (47.2g) 及び液体部2-4 (52.5g) を得た。表4に各工程油の分析値を示した。尚、脂肪酸エチルエステル含量およびトリグリセリド(TAG)含量・組成の分析はGLC法を用いて行った。
[Reference Example 1]
Distillation residue 2-2 (100 g) obtained in the same manner as in Comparative Example 1 was completely dissolved at 80 ° C. and 300 g of acetone was added, followed by cooling at 35 ° C. for 3 hours with stirring, using a water flow aspirator. Then, solid-liquid separation was performed by vacuum filtration (Yamato Scientific Co., Ltd. Handia Spirator WP51). During the filtration under reduced pressure, the solid part was newly washed with 150 g of acetone, and the liquid part remaining on the crystal surface was washed. Acetone was completely removed from the obtained solid part and liquid part by heating under reduced pressure to obtain solid part 2-4 (47.2 g) and liquid part 2-4 (52.5 g). Table 4 shows the analysis value of each process oil. The fatty acid ethyl ester content and triglyceride (TAG) content and composition were analyzed using the GLC method.
Figure JPOXMLDOC01-appb-T000004
 実施例1、2と比較すると、本発明の分別方法は、溶剤分別と同等以上の分別精度が得られることが分る。
Figure JPOXMLDOC01-appb-T000004
Compared with Examples 1 and 2, it can be seen that the fractionation method of the present invention can obtain a fractionation accuracy equal to or higher than that of solvent fractionation.

Claims (4)

  1.  トリグリセリド含量が60質量%以上であって、全トリグリセリド中にXXX型トリグリセリド(式中、Xは飽和脂肪酸残基を示す)を10~70質量%及びX2U型トリグリセリド(式中、Xは飽和脂肪酸残基、Uは不飽和脂肪酸残基を示す)を10~50質量%含む油脂と、脂肪酸低級アルキルエステルとを混合し、トリグリセリド含量が10~50質量%、脂肪酸低級アルキルエステル含量が50~80%質量%である晶析原料を調製し、該晶析原料を、加熱融解し、次いで冷却して結晶を晶析させ、次いで分別することにより、X2U型トリグリセリドに富んだ液体部(オレイン部)を得ることを特徴とする油脂の分別方法。 The triglyceride content is 60% by mass or more, and 10 to 70% by mass of XXX type triglyceride (wherein X represents a saturated fatty acid residue) and X2U type triglyceride (where X is a saturated fatty acid residue) in all triglycerides. Group, U represents an unsaturated fatty acid residue) and a fatty acid lower alkyl ester is mixed, and the triglyceride content is 10 to 50% by mass, and the fatty acid lower alkyl ester content is 50 to 80%. The liquid part (olein part) rich in X2U type triglyceride is prepared by preparing a crystallization raw material of mass%, heating and melting the crystallization raw material, then cooling to crystallize the crystal, and then fractionating. A method for separating fats and oils, characterized in that it is obtained.
  2.  前記トリグリセリド含量が60質量%以上であって、全トリグリセリド中にXXX型トリグリセリドを10~70質量%及びX2U型トリグリセリドを10~50質量%含む油脂が、パームステアリンであることを特徴とする請求項1記載の油脂の分別方法。 The fat or oil having a triglyceride content of 60% by mass or more and containing 10 to 70% by mass of XXX type triglyceride and 10 to 50% by mass of X2U type triglyceride in all triglycerides is palm stearin. The method for fractionating fats and oils according to 1.
  3.  前記トリグリセリド含量が60質量%以上であって、全トリグリセリド中にXXX型トリグリセリドを10~70質量%及びX2U型トリグリセリドを10~50質量%含む油脂が、エステル交換油の分別高融点画分であることを特徴とする請求項1記載の油脂の分別方法。 The oil having a triglyceride content of 60% by mass or more and containing 10 to 70% by mass of XXX type triglyceride and 10 to 50% by mass of X2U type triglyceride in the total triglyceride is a fractionated high melting point fraction of transesterified oil. The method for separating fats and oils according to claim 1.
  4.  前記X2U型トリグリセリドに富んだ液体部(オレイン部)の全トリグリセリド中のXXX型トリグリセリド含有量が10質量%未満であることを特徴とする、請求項1~3の何れか1項に記載の油脂の分別方法。 The fat or oil according to any one of claims 1 to 3, wherein the content of XXX triglyceride in the total triglyceride in the liquid part (olein part) rich in X2U triglyceride is less than 10% by mass. Sorting method.
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