WO2015146248A1 - Production method for purified palm oil and fat - Google Patents

Production method for purified palm oil and fat Download PDF

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Publication number
WO2015146248A1
WO2015146248A1 PCT/JP2015/051497 JP2015051497W WO2015146248A1 WO 2015146248 A1 WO2015146248 A1 WO 2015146248A1 JP 2015051497 W JP2015051497 W JP 2015051497W WO 2015146248 A1 WO2015146248 A1 WO 2015146248A1
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Prior art keywords
palm oil
oil
fat
palm
oils
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PCT/JP2015/051497
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French (fr)
Japanese (ja)
Inventor
浩 平井
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ニッシン グローバル リサーチ センター エスディエヌ ビーエイチディー
日清オイリオグループ株式会社
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Publication of WO2015146248A1 publication Critical patent/WO2015146248A1/en

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, 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
    • C11B3/00—Refining fats or fatty oils
    • C11B3/10—Refining fats or fatty oils by adsorption
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, 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
    • C11B3/00—Refining fats or fatty oils
    • C11B3/02—Refining fats or fatty oils by chemical reaction
    • C11B3/06—Refining fats or fatty oils by chemical reaction with bases

Definitions

  • the present invention relates to a method for producing a refined palm oil and fat.
  • Oils and fats contain trace components that are considered to be related to physiological activity.
  • trace components include 3-chloropropane-1,2-diol, glycidol, and fatty acid esters thereof.
  • the above ingredients may have nutritional problems, but if they are present in oils and fats such as vegetable oils that have been ingested from meals for many years, they may have an immediate effect on health. Is not considered, nor is the intake standard established. However, since there is a need for safer fats and oils, various methods for reducing the content of the above-described components in the fats and oils have been proposed.
  • Patent Document 1 As a method for reducing the content of 3-chloropropane-1,2-diol, glycidol, etc. in fats and oils, a method of adjusting the temperature conditions in the deodorization step (Patent Document 1), a method of contacting fats and oils with alkaline clay ( Patent Document 2), a method of bringing oil and fat into contact with water vapor in a tray-type deodorizing apparatus (Patent Document 3).
  • the present invention has been made to solve the above-described problems, and an object of the present invention is to provide a method for producing a refined palm-based fat and oil in which the content of 3-chloropropane-1,2-diol and its fatty acid ester is reduced.
  • the present inventors have found that the above-mentioned problems can be solved by the method for producing a refined palm-based fat / oil comprising a step of alkali deoxidizing crude palm oil, which is a raw oil / fat, and have completed the present invention. It was. Specifically, the present invention provides the following.
  • a method for producing a refined palm oil or fat comprising an alkali deoxidation step of alkali deoxidizing crude palm oil.
  • a method for producing a refined palm oil and fat in which the content of 3-chloropropane-1,2-diol and its fatty acid ester is reduced.
  • oil and fat is a substance containing glyceride in which glycerin and 1 to 3 fatty acids are ester-bonded. Glycerol) and monoglycerides (monoacylglycerol).
  • the fats and oils in the present invention may contain components other than glycerides derived from raw fats and oils (for example, plant sterols, lecithins, antioxidant components, pigment components, etc.), but 95% of the components constituting the fats and oils. % Or more is preferably glyceride.
  • purification palm oil fat of this invention includes the process (alkali deoxidation process) of carrying out the alkali deoxidation of the crude palm oil.
  • the “palm crude oil” in the present invention refers to unrefined fats and oils extracted from oil palm (palm palm) by a known method such as an extraction method, a compression method, or an extraction method. Since the crude palm oil contains a lot of impurities (trace metals, pigments, odor components, etc.), it is used for the purification process (usually in the order of degumming process, alkali deoxidation process, decolorization process, and deodorization process). And purified palm oil is obtained.
  • palm crude oil refers to palm fats and oils obtained by subjecting crude palm oil to at least a degumming process, and are not subjected to any refining process such as a degumming process. It is clearly different from “palm crude oil” which is an oil.
  • the "refined palm oil and fat” in the present invention refers to palm oil or fractionated oil thereof (palm olein, palm stearin, palm super olein, palm double olein, palm mid fraction, etc.).
  • Palm oil and fat in the present invention is a general term for palm oil and its fractionated oil.
  • the “palm oil” in the present invention refers to palm oil obtained by performing at least an alkali deoxidation step on the crude palm oil.
  • the crude palm oil may contain additives such as antioxidants and emulsifiers as long as the effects of the present invention are not impaired.
  • Alkaline deoxidation process Usually, in refinement
  • palm crude oil is first subjected to an alkali deoxidation step. That is, in the production method of the present invention, the alkaline deoxidation step is first performed among the purification steps.
  • 3-chloropropane-1,2-diol (hereinafter, 3-chloropropane-1,2-diol is also referred to as “3-MCPD”) and fatty acid esters thereof in oils and fats are generally increased by the following actions. It is done. That is, when fats and oils are heated in each refining step, chlorine originally contained in the fats and oils raw material (such as oil palm) acts as a so-called chlorine donor, and 3-MCPD and fatty acid esters thereof can be produced in the fats and oils.
  • 3-MCPD and fatty acid esters thereof can be produced in the fats and oils.
  • the alkali deoxidation step when the alkali deoxidation step is first performed in the purification step, the total amount of chlorine in the fats and oils (free chlorine and combined chlorine (organic chlorine and inorganic chlorine)) It has been found that the total amount) can be effectively reduced, and as a result, the content of 3-MCPD and its fatty acid ester can be reduced.
  • a refined palm system obtained by a conventional purification method by appropriately performing a purification step (degumming step, decolorization step, deodorization step, etc.) and / or a separation step.
  • a refined palm-based oil / fat having a reduced content of 3-MCPD and its fatty acid ester can be obtained while having the same flavor and appearance as the oil / fat.
  • the conditions for the alkali deoxidation step are not particularly limited, and conventionally known conditions can be applied.
  • an alkaline solution sodium hydroxide aqueous solution, sodium carbonate aqueous solution, potassium hydroxide aqueous solution, potassium carbonate aqueous solution, etc.
  • the alkali deoxidation step may be performed by stirring for 1 to 30 minutes under a temperature condition of 30 to 95 ° C. and then removing the alkali phase by centrifugation. After removing the alkaline phase, the fats and oils may be washed with water.
  • the concentration of the alkaline substance in the added alkaline solution may be 10 to 30 Baume.
  • a refined palm-based oil / fat having a reduced content of 3-MCPD and its fatty acid ester is obtained from the crude palm oil.
  • each purification step (for example, one or more of a degumming step, a decoloring step, and a deodorizing step) that is usually applied in the purification of fats and oils may be performed.
  • a refined palm-based oil and fat having excellent flavor and appearance can be obtained while the content of 3-MCPD and its fatty acid ester is reduced.
  • a degumming step may be performed after the alkali deoxidation step.
  • a refined palm-based oil and fat having a reduced content of impurities phospholipids, gums, etc.
  • the conditions for the degumming step are not particularly limited, and may be conditions used in a normal method for producing refined fats and oils.
  • an acidic substance phosphoric acid, organic acid aqueous solution, etc.
  • palm oil may be added to palm oil in an amount of 0.01 to 0.20% by mass of the oil.
  • the palm oil that has undergone the degumming step is removed by stirring for 1 to 30 minutes under a temperature condition of 70 to 100 ° C., and then removing the gum in the fat by standing or centrifuging. Is obtained.
  • a decolorization step and a deodorization step After the alkali deoxidation step, it is preferable to perform one or more of a decolorization step and a deodorization step.
  • a refined palm-based oil and fat having a reduced content of not only 3-MCPD and its fatty acid ester but also glycidol and its fatty acid ester can be obtained.
  • the conditions for the decolorization step are not particularly limited, and may be conditions used in a normal method for producing refined fats and oils. For example, it may be carried out by adding 0.2 to 3.0% by mass of a white clay (active clay, etc.) to the palm oil and heating at 80 to 150 ° C. for 5 to 60 minutes under reduced pressure. Moreover, you may make it fill with white clay in a filter and a column, and let palm oil flow. After the decolorization step, palm oil that has undergone the decolorization step can be obtained by removing the white clay from the fats and oils by filtration or the like.
  • a white clay active clay, etc.
  • the conditions for the deodorization step are not particularly limited, and may be conditions used in a normal method for producing refined fats and oils. For example, it may be carried out by bringing palm oil into contact with water vapor at 160 to 270 ° C. for 30 to 180 minutes under reduced pressure (for example, 150 to 700 Pa).
  • the deodorization time may be continuous or discontinuous.
  • the oil after finishing the deodorizing step can be handled as palm oil that has undergone the deodorizing step.
  • the subsequent steps are not particularly limited, but the degumming step is performed first in terms of good purification efficiency. Then, it is preferable to perform a decoloring process and / or a deodorizing process. It is most preferable to carry out in the order of the degumming step, the decoloring step and the deodorizing step in that the flavor of palm oil is not impaired and the increase in acid value and / or chromaticity can be suppressed.
  • the conditions for the water washing step are not particularly limited.
  • water at 70 to 100 ° C. may be added to palm oil at 3.0 to 50 mass%.
  • the palm oil which passed through the water washing process can be obtained by performing stirring, isolation
  • a step for cooling the palm oil may be appropriately provided between the purification steps.
  • Palm oil may be subjected to a separation step.
  • fractionated fats and oils (palm olein, palm stearin, palm super olein, palm double olein, palm mid fraction, etc.) are obtained from palm oil.
  • the method for separating palm oil in the separation step is not particularly limited, and a separation method commonly used for separating refined fats and oils can be applied.
  • Specific examples of the fractionation method include a natural fractionation method, a solvent fractionation method, and a surfactant fractionation method.
  • the content of 3-MCPD and its fatty acid ester in the refined palm oil and fat is determined by the NaBr method (details in the following examples), which is a modification of the German official method (DGF Standard Methods C-III 18 (09)). As indicated, it is specified as the True MCPD value of the refined palm oil and fat.
  • NRBD palm oil is refined using two different lots of crude palm oil, and one lot (“Example 2 (NRBD-1)” in Table 2) is the same as NBD without acid palm oil. Lot was used.
  • Example 3 (NRBD-2)” in Table 2) was subjected to fractionation after the deodorization step to obtain palm olein (iodine number 56) and palm stearin. It was.
  • each purification process name described in Table 1 was arranged in chronological order from left to right.
  • “NRBD without acid palm oil” is a refined palm oil and fat obtained by processing crude palm oil in the order of “alkaline deoxidation step-1”, “decolorization step” and “deodorization step”. It is.
  • the conditions for each purification step in Table 1 are as follows.
  • the “alkali deoxidation step-1” corresponds to a step of subjecting the crude palm oil to an alkali deoxidation step.
  • Alkaline deoxidation step-1 An aqueous solution of sodium hydroxide (Baume degree: 20) was added in an excess amount of 10 mol% with respect to the acid value of the oil and fat, and the oil and fat were washed with water until neutrality. Washing step-1: The fats and oils were washed with 90 ° C. hot water (10% by mass of oil).
  • Degumming step Phosphoric acid (0.05% by mass of oil) was added to the fat under a temperature condition of 90 to 95 ° C.
  • Alkaline deoxidation step-2 An aqueous solution of sodium hydroxide (Baume degree: 20) was added in an excess amount of 10 mol% with respect to the acid value, and then the oil was washed with water until neutrality.
  • Water washing step-2 The fats and oils were washed with 90 ° C. hot water (10% by mass of oil).
  • Decolorization step Fats and oils were contacted with white clay (2% by mass of oil) for 30 minutes under a temperature condition of 90 to 95 ° C.
  • Deodorization step Fats and oils were heated for 1 hour under a temperature condition of 230 to 235 ° C.
  • Test 2 Analysis of oil and fat
  • the MCPD-FS value refers to a value determined by quantifying the total amount of glycidol and 3-MCPD and their fatty acid esters as the amount of 3-MCPD educt. The obtained results are shown in the “FS (ppm)” section of Tables 2 and 3.
  • the True MCPD value refers to a value determined by quantifying the total amount of 3-MCPD and its fatty acid ester as the amount of 3-MCPD educt. The obtained results are shown in the “MCPD (ppm)” section of Tables 2 and 3.
  • the GC-MS analysis conditions in the NaBr method are as follows. Analyzer: Shimadzu Corporation, Model name: QP-2010 Column: Product name: HP-5MS, manufactured by Agilent Technology (length 30 m, diameter 0.25 mm) Column temperature: 60 ° C. (1 minute) to 120 ° C. (temperature increase rate 10 ° C./min) to 190 ° C. (temperature increase rate 6 ° C./min) to 280 ° C. (temperature increase rate 20 ° C./min) Detector: MS (EI, SIM mode) Splitless: 1 ⁇ L injection Carrier gas: He

Abstract

The objective of the present invention is to provide a production method for purified palm oil and fat wherein the contents in 3-chloropropane-1, 2-diol, and fatty acid esters thereof have been reduced. The present invention provides a production method for purified palm oil and fat, comprising an alkaline deacidification step whereby a crude palm oil is alkaline-deacidified. One or more among a degumming step, a decolorization step, and a deodorization step may be included after the alkaline deacidification step. The decolorization step may be included after the degumming step and the deodorization step may be included after the decolorization step.

Description

精製パーム系油脂の製造方法Method for producing refined palm oil
　本発明は、精製パーム系油脂の製造方法に関する。 The present invention relates to a method for producing a refined palm oil and fat.
　油脂中には生理活性に関係すると考えられる微量成分が存在する。このような微量成分としては、例えば、３－クロロプロパン－１，２－ジオール、グリシドール、及びこれらの脂肪酸エステル等が挙げられる。上記成分については、栄養学上の問題がある可能性が指摘されているが、長年にわたって食事等から摂取されてきた植物油等の油脂中に存在するレベルであれば、健康に直ちに影響を及ぼすとは考えられず、摂取基準等も定められていない。しかし、より安全性の高い油脂に対するニーズがあるため、油脂中の上記成分の含有量を低減する方法が各種提案されている。 Oils and fats contain trace components that are considered to be related to physiological activity. Examples of such trace components include 3-chloropropane-1,2-diol, glycidol, and fatty acid esters thereof. It has been pointed out that the above ingredients may have nutritional problems, but if they are present in oils and fats such as vegetable oils that have been ingested from meals for many years, they may have an immediate effect on health. Is not considered, nor is the intake standard established. However, since there is a need for safer fats and oils, various methods for reducing the content of the above-described components in the fats and oils have been proposed.
　油脂中の３－クロロプロパン－１，２－ジオール、グリシドール等の含有量を低減する方法としては、脱臭工程の温度条件を調整する方法（特許文献１）、油脂とアルカリ白土とを接触させる方法（特許文献２）、トレイ式脱臭装置において油脂と水蒸気とを接触させる方法（特許文献３）が挙げられる。 As a method for reducing the content of 3-chloropropane-1,2-diol, glycidol, etc. in fats and oils, a method of adjusting the temperature conditions in the deodorization step (Patent Document 1), a method of contacting fats and oils with alkaline clay ( Patent Document 2), a method of bringing oil and fat into contact with water vapor in a tray-type deodorizing apparatus (Patent Document 3).
特開２０１１－０７４３５８号公報JP 2011-074358 A 日本特許第５２１６９４２号明細書Japanese Patent No. 5216942 特開２０１３－１１２７６１号公報JP 2013-112761 A
　しかし、従来の技術を使用しても、３－クロロプロパン－１，２－ジオール及びその脂肪酸エステルの含有量を十分に低減できない可能性があった。油脂のなかでも、消費量の多いパーム系油脂においては、３－クロロプロパン－１，２－ジオール及びその脂肪酸エステルの含有量を低減することが特に要求され得る。 However, there was a possibility that the content of 3-chloropropane-1,2-diol and its fatty acid ester could not be reduced sufficiently even by using conventional techniques. Among the fats and oils, palm oils and fats that consume a large amount can be particularly required to reduce the content of 3-chloropropane-1,2-diol and fatty acid esters thereof.
　本発明は、上記課題を解決するためになされたものであり、３－クロロプロパン－１，２－ジオール及びその脂肪酸エステルの含有量が低減された精製パーム系油脂の製造方法を提供することを目的とする。 The present invention has been made to solve the above-described problems, and an object of the present invention is to provide a method for producing a refined palm-based fat and oil in which the content of 3-chloropropane-1,2-diol and its fatty acid ester is reduced. And
　本発明者らは、原料油脂であるパーム粗油に対してアルカリ脱酸する工程を含む精製パーム系油脂の製造方法によれば、上記課題を解決できる点を見出し、本発明を完成するに至った。具体的には、本発明は下記のものを提供する。 The present inventors have found that the above-mentioned problems can be solved by the method for producing a refined palm-based fat / oil comprising a step of alkali deoxidizing crude palm oil, which is a raw oil / fat, and have completed the present invention. It was. Specifically, the present invention provides the following.
　（１）　パーム粗油をアルカリ脱酸するアルカリ脱酸工程を含む、精製パーム系油脂の製造方法。 (1) A method for producing a refined palm oil or fat, comprising an alkali deoxidation step of alkali deoxidizing crude palm oil.
　（２）　前記アルカリ脱酸工程の後に、脱ガム工程、脱色工程及び脱臭工程のうちの１以上を含む、（１）に記載の精製パーム系油脂の製造方法。 (2) The method for producing a refined palm-based oil or fat according to (1), which comprises one or more of a degumming step, a decoloring step, and a deodorizing step after the alkali deoxidation step.
　（３）　前記脱ガム工程の後に前記脱色工程を含み、前記脱色工程の後に前記脱臭工程を含む、（２）に記載の精製パーム系油脂の製造方法。 (3) The method for producing a refined palm oil fat according to (2), which includes the decoloring step after the degumming step and includes the deodorizing step after the decoloring step.
　（４）　前記脱臭工程の後に分別工程を含む、（３）に記載の精製パーム系油脂の製造方法。 (4) The method for producing a refined palm oil or fat according to (3), which includes a separation step after the deodorization step.
　本発明によれば、３－クロロプロパン－１，２－ジオール及びその脂肪酸エステルの含有量が低減された精製パーム系油脂の製造方法が提供される。 According to the present invention, there is provided a method for producing a refined palm oil and fat in which the content of 3-chloropropane-1,2-diol and its fatty acid ester is reduced.
　以下、本発明の実施形態について説明するが、本発明は以下の実施形態に限定されるものではない。なお、本発明における「油脂」とは、グリセリンと、１～３個の脂肪酸とがエステル結合したグリセリドを含む物質であり、油脂の主要成分であるトリグリセリド（トリアシルグリセロール）のほか、ジグリセリド（ジアシルグリセロール）及びモノグリセリド（モノアシルグリセロール）を含み得る。また、本発明における油脂には、原料油脂由来のグリセリド以外の成分（例えば、植物ステロール、レシチン、抗酸化成分、色素成分等）が含まれてもよいが、油脂を構成する成分のうち９５質量％以上はグリセリドであることが好ましい。 Hereinafter, embodiments of the present invention will be described, but the present invention is not limited to the following embodiments. In the present invention, “oil and fat” is a substance containing glyceride in which glycerin and 1 to 3 fatty acids are ester-bonded. Glycerol) and monoglycerides (monoacylglycerol). In addition, the fats and oils in the present invention may contain components other than glycerides derived from raw fats and oils (for example, plant sterols, lecithins, antioxidant components, pigment components, etc.), but 95% of the components constituting the fats and oils. % Or more is preferably glyceride.
［本発明の精製パーム系油脂の製造方法］
　本発明の精製パーム系油脂の製造方法（以下、「本発明の製造方法」という。）は、パーム粗油をアルカリ脱酸する工程（アルカリ脱酸工程）を含む。 [Method for producing refined palm oil / fat of the present invention]
The manufacturing method (henceforth "the manufacturing method of this invention") of the refinement | purification palm oil fat of this invention includes the process (alkali deoxidation process) of carrying out the alkali deoxidation of the crude palm oil.
（パーム粗油）
　本発明における「パーム粗油」とは、アブラヤシ（パーム椰子）から、抽出法、圧搾法、又は圧抽法等の公知の方法によって採油された未精製の油脂を指す。パーム粗油は、不純物（微量金属、色素、におい成分等）を多く含んでいるため、精製工程（通常は、脱ガム工程、アルカリ脱酸工程、脱色工程、及び脱臭工程の順）に供されて精製され、精製パーム系油脂が得られる。なお、一般的に、「パーム原油」と呼ばれる油脂は、パーム粗油を少なくとも脱ガム工程に供することで得られるパーム油脂を指し、脱ガム工程等の精製工程に一切供されていない未精製の油脂である「パーム粗油」とは明確に異なる。なお、本発明における「精製パーム系油脂」とは、パーム油、又は、その分別油（パームオレイン、パームステアリン、パームスーパーオレイン、パームダブルオレイン、パームミッドフラクション等）を指す。本発明における「パーム油脂」とは、パーム油、及び、その分別油の総称である。本発明における「パーム油」とは、パーム粗油に対して少なくともアルカリ脱酸工程を行って得られたパーム油を指す。 (Palm crude oil)
The “palm crude oil” in the present invention refers to unrefined fats and oils extracted from oil palm (palm palm) by a known method such as an extraction method, a compression method, or an extraction method. Since the crude palm oil contains a lot of impurities (trace metals, pigments, odor components, etc.), it is used for the purification process (usually in the order of degumming process, alkali deoxidation process, decolorization process, and deodorization process). And purified palm oil is obtained. In general, fats and oils referred to as “palm crude oil” refers to palm fats and oils obtained by subjecting crude palm oil to at least a degumming process, and are not subjected to any refining process such as a degumming process. It is clearly different from “palm crude oil” which is an oil. In addition, the "refined palm oil and fat" in the present invention refers to palm oil or fractionated oil thereof (palm olein, palm stearin, palm super olein, palm double olein, palm mid fraction, etc.). “Palm oil and fat” in the present invention is a general term for palm oil and its fractionated oil. The “palm oil” in the present invention refers to palm oil obtained by performing at least an alkali deoxidation step on the crude palm oil.
　パーム粗油には、本発明の効果を阻害しない範囲で、抗酸化物質、乳化剤等の添加剤等が含まれていてもよい。 The crude palm oil may contain additives such as antioxidants and emulsifiers as long as the effects of the present invention are not impaired.
（アルカリ脱酸工程）
　通常、パーム粗油の精製においては、最初に、パーム粗油を脱ガム工程に供し、次いで、アルカリ脱酸工程等の工程に供する。他方、本発明の製造方法においては、最初に、パーム粗油をアルカリ脱酸工程に供する。つまり、本発明の製造方法においては、精製工程のうち、アルカリ脱酸工程が最初に行われる。 (Alkaline deoxidation process)
Usually, in refinement | purification of a crude palm oil, a crude palm oil is first used for a degumming process, Then, it uses for processes, such as an alkali deoxidation process. On the other hand, in the production method of the present invention, palm crude oil is first subjected to an alkali deoxidation step. That is, in the production method of the present invention, the alkaline deoxidation step is first performed among the purification steps.
　油脂中の３－クロロプロパン－１，２－ジオール（以下、３－クロロプロパン－１，２－ジオールを「３－ＭＣＰＤ」ともいう。）及びその脂肪酸エステルは、一般的に下記の作用によって増加すると考えられる。すなわち、各精製工程において油脂が加熱されると、油脂の原料（アブラヤシ等）にもともと含まれる塩素が、いわゆる塩素ドナーとして作用し、３－ＭＣＰＤ及びその脂肪酸エステルが油脂中に生成され得る。 It is considered that 3-chloropropane-1,2-diol (hereinafter, 3-chloropropane-1,2-diol is also referred to as “3-MCPD”) and fatty acid esters thereof in oils and fats are generally increased by the following actions. It is done. That is, when fats and oils are heated in each refining step, chlorine originally contained in the fats and oils raw material (such as oil palm) acts as a so-called chlorine donor, and 3-MCPD and fatty acid esters thereof can be produced in the fats and oils.
　従来は、パーム粗油を脱ガム工程に供した後に、アルカリ脱酸工程を経たパーム油（ＮＢＤパーム油等）においては、パーム油中の塩素の含有量が十分に低減されていると考えられていた。脱ガム工程においては、油脂を酸処理することによって不純物（リン脂質、ガム質等）を除去するが、脱ガム工程の後にアルカリ脱酸工程を行うことで、脱ガム工程の後に残存する酸を除去しつつ、さらには、アルカリと反応しやすい塩素をも除去できると期待されていたからである。また、油脂中の塩素の含有量を補強的に低減させる方法として、パーム粗油を水洗することによって油脂中の塩素の含有量を低減した後に脱ガム工程等の精製工程に供する方法が提案されていた。 Conventionally, in the palm oil (NBD palm oil etc.) which passed the alkali deoxidation process after using a crude palm oil for the degumming process, it is thought that content of chlorine in palm oil is fully reduced. It was. In the degumming process, impurities (phospholipids, gums, etc.) are removed by acid treatment of fats and oils, but by performing an alkaline deoxidation process after the degumming process, the acid remaining after the degumming process is removed. This is because it was expected that chlorine that easily reacts with alkali could be removed while removing. In addition, as a method for reinforcingly reducing the chlorine content in fats and oils, a method for reducing the chlorine content in fats and oils by washing the crude palm oil with water and then subjecting it to a purification step such as a degumming step has been proposed. It was.
　しかし、本発明者による検討の結果、脱ガム工程の後に、アルカリ脱酸工程を行っても、油脂中の塩素の含有量を十分に低減できないことが見出された。また、パーム粗油を水洗しても、油脂中の遊離塩素量を低減できるが、結合塩素（有機塩素及び無機塩素）の含有量は低減できないことが見出された。３－ＭＣＰＤ及びその脂肪酸エステルは、主に、油脂中の有機塩素が塩素ドナーとして作用することで生成されると考えられるため、油脂中の３－ＭＣＰＤ及びその脂肪酸エステルの含有量を低減させるためには、遊離塩素だけではなく、結合塩素の含有量をも低減させる必要がある。 However, as a result of examination by the present inventors, it has been found that the chlorine content in fats and oils cannot be sufficiently reduced even if an alkali deoxidation step is performed after the degumming step. Further, it was found that even if the crude palm oil was washed with water, the amount of free chlorine in the oil and fat could be reduced, but the content of combined chlorine (organic chlorine and inorganic chlorine) could not be reduced. Since 3-MCPD and its fatty acid ester are thought to be generated mainly by the action of organic chlorine in fats and oils as a chlorine donor, in order to reduce the content of 3-MCPD and its fatty acid esters in fats and oils It is necessary to reduce not only free chlorine but also bound chlorine content.
　そこで、本発明者が鋭意検討した結果、意外にも、精製工程のうち、アルカリ脱酸工程を最初に行うと、油脂中の総塩素量（遊離塩素と結合塩素（有機塩素及び無機塩素）の合計量）を効果的に低減でき、その結果、３－ＭＣＰＤ及びその脂肪酸エステルの含有量を低減できることが見出された。パーム粗油をアルカリ脱酸工程に供した後に、適宜、精製工程（脱ガム工程、脱色工程、脱臭工程等）及び／又は分別工程を行うことで、従来の精製方法によって得られた精製パーム系油脂と同等の風味や外観等を備えながら、３－ＭＣＰＤ及びその脂肪酸エステルの含有量が低減された精製パーム系油脂を得ることができる。 Therefore, as a result of intensive studies by the inventor, surprisingly, when the alkali deoxidation step is first performed in the purification step, the total amount of chlorine in the fats and oils (free chlorine and combined chlorine (organic chlorine and inorganic chlorine)) It has been found that the total amount) can be effectively reduced, and as a result, the content of 3-MCPD and its fatty acid ester can be reduced. After subjecting the crude palm oil to the alkali deoxidation step, a refined palm system obtained by a conventional purification method by appropriately performing a purification step (degumming step, decolorization step, deodorization step, etc.) and / or a separation step. A refined palm-based oil / fat having a reduced content of 3-MCPD and its fatty acid ester can be obtained while having the same flavor and appearance as the oil / fat.
　アルカリ脱酸工程の条件としては、特に限定されず、従来公知の条件を適用できる。例えば、アルカリ溶液（水酸化ナトリウム水溶液、炭酸ナトリウム水溶液、水酸化カリウム水溶液、炭酸カリウム水溶液等）をパーム粗油に、油脂の酸価に対して５０～１５０モル％加えてもよく、好ましくは１００～１５０モル％加えてもよい。アルカリ脱酸工程は、３０～９５℃の温度条件下で、１分間～３０分間撹拌し、その後、遠心分離でアルカリ相を除去することによって行ってもよい。アルカリ相を除去した後、油脂を水洗してもよい。なお、添加するアルカリ溶液中のアルカリ性物質の濃度は、ボーメ度１０～３０であってもよい。 The conditions for the alkali deoxidation step are not particularly limited, and conventionally known conditions can be applied. For example, an alkaline solution (sodium hydroxide aqueous solution, sodium carbonate aqueous solution, potassium hydroxide aqueous solution, potassium carbonate aqueous solution, etc.) may be added to the crude palm oil in an amount of 50 to 150 mol%, preferably 100 Up to 150 mol% may be added. The alkali deoxidation step may be performed by stirring for 1 to 30 minutes under a temperature condition of 30 to 95 ° C. and then removing the alkali phase by centrifugation. After removing the alkaline phase, the fats and oils may be washed with water. The concentration of the alkaline substance in the added alkaline solution may be 10 to 30 Baume.
　本発明におけるアルカリ脱酸工程を行うことで、パーム粗油から、３－ＭＣＰＤ及びその脂肪酸エステルの含有量が低減された精製パーム系油脂が得られる。 By performing the alkaline deoxidation step in the present invention, a refined palm-based oil / fat having a reduced content of 3-MCPD and its fatty acid ester is obtained from the crude palm oil.
（脱ガム工程、脱色工程及び脱臭工程）
　アルカリ脱酸工程の後には、油脂の精製において通常適用される各精製工程（例えば、脱ガム工程、脱色工程及び脱臭工程のうちの１以上）を行ってもよい。かかる精製工程を経ることで、３－ＭＣＰＤ及びその脂肪酸エステルの含有量が低減されていながら、風味や外観等に優れる精製パーム系油脂を得ることができる。 (Degumming process, decoloring process and deodorizing process)
After the alkali deoxidation step, each purification step (for example, one or more of a degumming step, a decoloring step, and a deodorizing step) that is usually applied in the purification of fats and oils may be performed. By undergoing such a purification step, a refined palm-based oil and fat having excellent flavor and appearance can be obtained while the content of 3-MCPD and its fatty acid ester is reduced.
　例えば、アルカリ脱酸工程の後には、脱ガム工程を行ってもよい。脱ガム工程を行うことにより、不純物（リン脂質、ガム質等）の含有量が低減された精製パーム系油脂が得られる。 For example, a degumming step may be performed after the alkali deoxidation step. By performing the degumming step, a refined palm-based oil and fat having a reduced content of impurities (phospholipids, gums, etc.) is obtained.
　脱ガム工程の条件は特に限定されず、通常の精製油脂の製造方法で使用される条件であってもよい。例えば、酸性物質（リン酸、有機酸水溶液等）を、パーム油に、対油０．０１～０．２０質量％加えてもよい。かかる工程は、７０～１００℃の温度条件下で、１分間～３０分間撹拌し、その後、静置又は遠心分離することによって油脂中のガム質を除去することにより、脱ガム工程を経たパーム油が得られる。 The conditions for the degumming step are not particularly limited, and may be conditions used in a normal method for producing refined fats and oils. For example, an acidic substance (phosphoric acid, organic acid aqueous solution, etc.) may be added to palm oil in an amount of 0.01 to 0.20% by mass of the oil. In this process, the palm oil that has undergone the degumming step is removed by stirring for 1 to 30 minutes under a temperature condition of 70 to 100 ° C., and then removing the gum in the fat by standing or centrifuging. Is obtained.
　アルカリ脱酸工程の後には、脱色工程及び脱臭工程のうちの１以上を行うことが好ましい。脱色工程及び脱臭工程のうちの１以上を行うことで、３－ＭＣＰＤ及びその脂肪酸エステルだけではなく、グリシドール及びその脂肪酸エステルの含有量が低減された精製パーム系油脂が得られる。 After the alkali deoxidation step, it is preferable to perform one or more of a decolorization step and a deodorization step. By performing one or more of the decolorization step and the deodorization step, a refined palm-based oil and fat having a reduced content of not only 3-MCPD and its fatty acid ester but also glycidol and its fatty acid ester can be obtained.
　脱色工程の条件は特に限定されず、通常の精製油脂の製造方法で使用される条件であってもよい。例えば、パーム油に白土（活性白土等）を対油０．２～３．０質量％加えて、減圧下、８０～１５０℃で５～６０分間、加熱させることで行ってもよい。また、ろ過器やカラムの中に白土を充填し、パーム油を通液させてもよい。脱色工程の後、ろ過等により白土を油脂から除去することで、脱色工程を経たパーム油を得ることができる。 The conditions for the decolorization step are not particularly limited, and may be conditions used in a normal method for producing refined fats and oils. For example, it may be carried out by adding 0.2 to 3.0% by mass of a white clay (active clay, etc.) to the palm oil and heating at 80 to 150 ° C. for 5 to 60 minutes under reduced pressure. Moreover, you may make it fill with white clay in a filter and a column, and let palm oil flow. After the decolorization step, palm oil that has undergone the decolorization step can be obtained by removing the white clay from the fats and oils by filtration or the like.
　脱臭工程の条件は特に限定されず、通常の精製油脂の製造方法で使用される条件であってもよい。例えば、減圧下（例えば、１５０～７００Ｐａ）、１６０～２７０℃で３０～１８０分間、パーム油と水蒸気とを接触させることで行ってもよい。脱臭時間は、連続していてもよく、不連続であってもよい。脱臭工程を終えた後の油は、そのまま脱臭工程を経たパーム油として扱うことができる。 The conditions for the deodorization step are not particularly limited, and may be conditions used in a normal method for producing refined fats and oils. For example, it may be carried out by bringing palm oil into contact with water vapor at 160 to 270 ° C. for 30 to 180 minutes under reduced pressure (for example, 150 to 700 Pa). The deodorization time may be continuous or discontinuous. The oil after finishing the deodorizing step can be handled as palm oil that has undergone the deodorizing step.
　アルカリ脱酸工程の後に、脱ガム工程、脱色工程及び脱臭工程のうちの２以上を行う場合、その先後は特に限定されないが、精製効率が良好であるという点で、脱ガム工程を最初に行い、次いで脱色工程及び／又は脱臭工程を行うことが好ましい。パーム油の風味を損なわず、かつ酸価及び／又は色度の上昇を抑えられるという点で、脱ガム工程、脱色工程及び脱臭工程の順で行うことが最も好ましい。 When performing two or more of the degumming step, the decoloring step and the deodorizing step after the alkali deoxidation step, the subsequent steps are not particularly limited, but the degumming step is performed first in terms of good purification efficiency. Then, it is preferable to perform a decoloring process and / or a deodorizing process. It is most preferable to carry out in the order of the degumming step, the decoloring step and the deodorizing step in that the flavor of palm oil is not impaired and the increase in acid value and / or chromaticity can be suppressed.
　アルカリ脱酸工程の後に、脱ガム工程、脱色工程及び脱臭工程のうちの１以上を行う場合、脱ガム工程、脱色工程及び脱臭工程の各工程の前後においては、パーム油を水洗してもよい。油脂の水洗工程を行うことにより、パーム油中の塩素含量をより低減できるので、３－ＭＣＰＤ及びその脂肪酸エステルの含有量をより低減できる。 When performing one or more of a degumming process, a decoloring process, and a deodorizing process after an alkali deoxidation process, before and after each process of a degumming process, a decoloring process, and a deodorizing process, you may wash palm oil with water. . By performing the oil / fat washing step, the chlorine content in palm oil can be further reduced, so the content of 3-MCPD and its fatty acid ester can be further reduced.
　水洗工程の条件は、特に限定されず、例えば、パーム油に、７０～１００℃の水を対油３．０～５０質量％加えてもよい。パーム油に水を加えた後、適宜撹拌、分離、乾燥等を行うことによって水洗工程を経たパーム油を得ることができる。 The conditions for the water washing step are not particularly limited. For example, water at 70 to 100 ° C. may be added to palm oil at 3.0 to 50 mass%. After adding water to palm oil, the palm oil which passed through the water washing process can be obtained by performing stirring, isolation | separation, drying, etc. suitably.
　アルカリ脱酸工程の後、各精製工程間においては、適宜パーム油を冷却する工程を設けてもよい。 After the alkali deoxidation step, a step for cooling the palm oil may be appropriately provided between the purification steps.
（分別工程）
　上記の工程（つまり、アルカリ脱酸、並びに、脱ガム工程、脱色工程及び脱臭工程のうちの１以上）を行った後には、パーム油を分別工程に供してもよい。分別工程を行うことにより、パーム油から分別油脂（パームオレイン、パームステアリン、パームスーパーオレイン、パームダブルオレイン、パームミッドフラクション等）が得られる。 (Separation process)
After performing the above steps (that is, one or more of alkali deoxidation, degumming step, decoloring step, and deodorizing step), palm oil may be subjected to a separation step. By performing the fractionation step, fractionated fats and oils (palm olein, palm stearin, palm super olein, palm double olein, palm mid fraction, etc.) are obtained from palm oil.
　分別工程におけるパーム油の分別方法は特に限定されず、精製油脂を分別するために通常使用される分別方法を適用できる。具体的な分別方法としては、自然分別法、溶剤分別法、界面活性剤分別法等が挙げられる。 The method for separating palm oil in the separation step is not particularly limited, and a separation method commonly used for separating refined fats and oils can be applied. Specific examples of the fractionation method include a natural fractionation method, a solvent fractionation method, and a surfactant fractionation method.
［精製パーム系油脂中の３－ＭＣＰＤ及びその脂肪酸エステルの含有量の特定］
　本発明の製造方法によれば、３－ＭＣＰＤ及びその脂肪酸エステルの含有量が低減された精製パーム系油脂を得ることができる。精製パーム系油脂中の３－ＭＣＰＤ及びその脂肪酸エステルの含有量は下記の方法で特定する。 [Specification of content of 3-MCPD and fatty acid ester in refined palm oil and fat]
According to the production method of the present invention, it is possible to obtain a refined palm-based oil and fat in which the content of 3-MCPD and its fatty acid ester is reduced. The content of 3-MCPD and its fatty acid ester in the refined palm oil and fat is specified by the following method.
　すなわち、精製パーム系油脂中の３－ＭＣＰＤ及びその脂肪酸エステルの含有量は、ドイツ公定法（ＤＧＦ　Ｓｔａｎｄａｒｄ　Ｍｅｔｈｏｄｓ　Ｃ－ＩＩＩ　１８（０９））の変法であるＮａＢｒ法（詳細は、下記実施例に示されるとおりである。）に従って、精製パーム系油脂のＴｒｕｅ　ＭＣＰＤ値として特定される。 That is, the content of 3-MCPD and its fatty acid ester in the refined palm oil and fat is determined by the NaBr method (details in the following examples), which is a modification of the German official method (DGF Standard Methods C-III 18 (09)). As indicated, it is specified as the True MCPD value of the refined palm oil and fat.
　以下、実施例を示し、本発明を具体的に説明するが、本発明はこれらの実施例に限定されるものではない。 Hereinafter, the present invention will be specifically described with reference to examples. However, the present invention is not limited to these examples.
［試験１：パーム粗油の精製］
　パーム粗油（ＩＳＦ社製）を１７００ｇ使用して、表１記載の精製工程で精製し、各精製油脂（「ＮＲＢＤ　ｗｉｔｈｏｕｔ　ａｃｉｄ　パーム油」、「ＮＲＢＤパーム油」、「ＲＢＤパーム油」、「ＮＢＤパーム油」、「ＲｗＢＤパーム油」、及び「ｗＲＢＤパーム油」）を製造した。以下、得られた各精製油脂は、単に、「ＮＢＤ　ｗｉｔｈｏｕｔ　ａｃｉｄ」、「ＮＲＢＤ」等ともいう。ＮＢＤ　ｗｉｔｈｏｕｔ　ａｃｉｄ　パーム油、及びＮＲＢＤパーム油が、本発明の製造方法によって得られる精製パーム系油脂に相当する。 [Test 1: Purification of crude palm oil]
1700 g of crude palm oil (manufactured by ISF Co., Ltd.) was used in the purification process shown in Table 1 to refine each refined fat (“NRBD without acid palm oil”, “NRBD palm oil”, “RBD palm oil”, “NBD”). Palm oil "," RwBD palm oil ", and" wRBD palm oil "). Hereinafter, the obtained refined fats and oils are also simply referred to as “NBD without acid”, “NRBD”, and the like. NBD without acid palm oil and NRBD palm oil correspond to the refined palm oil and fat obtained by the production method of the present invention.
　なお、ＮＲＢＤ　ｗｉｔｈｏｕｔ　ａｃｉｄ　パーム油、ＲＢＤパーム油、ＮＢＤパーム油、ＲｗＢＤパーム油は、同一ロットのパーム粗油を使用し、ｗＲＢＤパーム油は、該ロットとは別ロットのパーム粗油を使用した。ＮＲＢＤパーム油については、異なる２つのロットのパーム粗油を使用して精製を行い、一方のロット（表２中の「実施例２（ＮＲＢＤ－１）」）は、ＮＢＤ　ｗｉｔｈｏｕｔ　ａｃｉｄ　パーム油と同じロットを使用した。得られた２つのＮＲＢＤパーム油のうち一方（表２中の「実施例３（ＮＲＢＤ－２）」）については、脱臭工程後に分別を行い、パームオレイン（ヨウ素価５６）、及びパームステアリンを得た。 The NRBD without acid palm oil, RBD palm oil, NBD palm oil, and RwBD palm oil used the same lot of palm crude oil, and wRBD palm oil used a different lot of palm crude oil. NRBD palm oil is refined using two different lots of crude palm oil, and one lot (“Example 2 (NRBD-1)” in Table 2) is the same as NBD without acid palm oil. Lot was used. One of the two obtained NRBD palm oils (“Example 3 (NRBD-2)” in Table 2) was subjected to fractionation after the deodorization step to obtain palm olein (iodine number 56) and palm stearin. It was.
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000001
　なお、表１中に記載された各精製工程名は、左から右へ時系列順に並べた。例えば、「ＮＲＢＤ　ｗｉｔｈｏｕｔ　ａｃｉｄ　パーム油」は、パーム粗油に対して、「アルカリ脱酸工程－１」、「脱色工程」及び「脱臭工程」の順で処理を行って得られた精製パーム系油脂である。 In addition, each purification process name described in Table 1 was arranged in chronological order from left to right. For example, “NRBD without acid palm oil” is a refined palm oil and fat obtained by processing crude palm oil in the order of “alkaline deoxidation step-1”, “decolorization step” and “deodorization step”. It is.
　表１中の各精製工程の条件は下記のとおりである。なお、「アルカリ脱酸工程－１」が、パーム粗油をアルカリ脱酸工程する工程に相当する。
　アルカリ脱酸工程－１：水酸化ナトリウム水溶液（ボーメ度：２０）を油脂の酸価に対して１０モル％過剰量添加した後、中性になるまで油脂を水洗した。
　水洗工程－１：９０℃の湯（対油１０質量％）で油脂を水洗した。
　脱ガム工程：９０～９５℃の温度条件下で、リン酸（対油０．０５質量％）を油脂に添加した。
　アルカリ脱酸工程－２：水酸化ナトリウム水溶液（ボーメ度：２０）を酸価に対して１０モル％過剰量添加した後、中性になるまで油脂を水洗した。
　水洗工程－２：９０℃の湯（対油１０質量％）で油脂を水洗した。
　脱色工程：９０～９５℃の温度条件下で、油脂を、白土（対油２質量％）と３０分間接触させた。
　脱臭工程：２３０～２３５℃の温度条件下で、油脂を１時間加熱した。 The conditions for each purification step in Table 1 are as follows. The “alkali deoxidation step-1” corresponds to a step of subjecting the crude palm oil to an alkali deoxidation step.
Alkaline deoxidation step-1: An aqueous solution of sodium hydroxide (Baume degree: 20) was added in an excess amount of 10 mol% with respect to the acid value of the oil and fat, and the oil and fat were washed with water until neutrality.
Washing step-1: The fats and oils were washed with 90 ° C. hot water (10% by mass of oil).
Degumming step: Phosphoric acid (0.05% by mass of oil) was added to the fat under a temperature condition of 90 to 95 ° C.
Alkaline deoxidation step-2: An aqueous solution of sodium hydroxide (Baume degree: 20) was added in an excess amount of 10 mol% with respect to the acid value, and then the oil was washed with water until neutrality.
Water washing step-2: The fats and oils were washed with 90 ° C. hot water (10% by mass of oil).
Decolorization step: Fats and oils were contacted with white clay (2% by mass of oil) for 30 minutes under a temperature condition of 90 to 95 ° C.
Deodorization step: Fats and oils were heated for 1 hour under a temperature condition of 230 to 235 ° C.
［試験２：油脂の分析］
　上記試験１において、各精製工程後の油脂中のＭＣＰＤ－ＦＳ値、Ｔｒｕｅ　ＭＣＰＤ値、及びＣｌ量を下記の方法で算出した。 [Test 2: Analysis of oil and fat]
In Test 1 above, the MCPD-FS value, True MCPD value, and Cl content in the fat after each purification step were calculated by the following methods.
（ＭＣＰＤ－ＦＳ値の定量）
　ドイツ公定法　ＤＧＦ　Ｓｔａｎｄａｒｄ　Ｍｅｔｈｏｄｓ　Ｃ－ＩＩＩ　１８（０９）に準じて、油脂のＭＣＰＤ－ＦＳ値を定量した。ＭＣＰＤ－ＦＳ値とは、グリシドール及び３－ＭＣＰＤ、並びにそれらの脂肪酸エステルの総量を３－ＭＣＰＤ遊離体量として定量した値を指す。得られた結果を、表２及び３の「ＦＳ（ｐｐｍ）」の項に示す。 (Quantification of MCPD-FS value)
According to the German official method DGF Standard Methods C-III 18 (09), the MCPD-FS value of fats and oils was quantified. The MCPD-FS value refers to a value determined by quantifying the total amount of glycidol and 3-MCPD and their fatty acid esters as the amount of 3-MCPD educt. The obtained results are shown in the “FS (ppm)” section of Tables 2 and 3.
（Ｔｒｕｅ　ＭＣＰＤ値の定量）
　ドイツ公定法（ＤＧＦ　Ｓｔａｎｄａｒｄ　Ｍｅｔｈｏｄｓ　Ｃ－ＩＩＩ　１８（０９））の変法である、下記ＮａＢｒ法に従って、油脂のＴｒｕｅ　ＭＣＰＤ値を定量した。Ｔｒｕｅ　ＭＣＰＤ値とは、３－ＭＣＰＤ及びその脂肪酸エステルの総量を３－ＭＣＰＤ遊離体量として定量した値を指す。得られた結果を、表２及び３の「ＭＣＰＤ（ｐｐｍ）」の項に示す。 (Quantification of True MCPD value)
According to the following NaBr method, which is a modification of the German official method (DGF Standard Methods C-III 18 (09)), the True MCPD value of fats and oils was quantified. The True MCPD value refers to a value determined by quantifying the total amount of 3-MCPD and its fatty acid ester as the amount of 3-MCPD educt. The obtained results are shown in the “MCPD (ppm)” section of Tables 2 and 3.
〔ＮａＢｒ法〕
　油脂１００ｍｇに、５０μＬの内部標準物質（３－ＭＣＰＤ－ｄ５　２０μｇ／ｍＬ溶液）を加えた後、１ｍＬのナトリウムメトキシド溶液（０．５ｍｏｌ／Ｌ　メタノール）を加え、室温にて反応させ、エステルのけん化分解を行った。次いで、得られた反応物に酢酸を微量に含んだ３ｍＬの臭化ナトリウム水溶液（５０％）と３ｍＬのヘキサンとを加えて混合した後、ヘキサンを除去した。なお、この際に３－ＭＣＰＤ及び３－ＭＣＰＤ脂肪酸エステルが、全て３－ＭＣＰＤ遊離体に変換される。その後、５００μＬのフェニルホウ酸水溶液（１２．５％）により誘導体化し、２ｍＬのヘキサンにて抽出し、ガスクロマトグラフ質量分析（ＧＣ－ＭＳ）装置を使用して測定を行った。当該測定によって得られたクロマトグラムを用い、内部標準である３－ＭＣＰＤ－ｄ５と、３－ＭＣＰＤのイオン強度を比較することで、油脂中の３－ＭＣＰＤ及び３－ＭＣＰＤ脂肪酸エステルの総量を３－ＭＣＰＤ遊離体換算量として算出した。 [NaBr method]
After adding 50 μL of internal standard substance (3-MCPD-d5 20 μg / mL solution) to 100 mg of oil and fat, add 1 mL of sodium methoxide solution (0.5 mol / L methanol) and react at room temperature. Saponification decomposition was performed. Next, 3 mL of an aqueous solution of sodium bromide (50%) containing a small amount of acetic acid and 3 mL of hexane were added to and mixed with the obtained reaction product, and then hexane was removed. At this time, all of 3-MCPD and 3-MCPD fatty acid ester are converted into 3-MCPD free form. Thereafter, it was derivatized with 500 μL of an aqueous phenylboric acid solution (12.5%), extracted with 2 mL of hexane, and measured using a gas chromatograph mass spectrometer (GC-MS). Using the chromatogram obtained by the measurement, the total amount of 3-MCPD and 3-MCPD fatty acid ester in the fats and oils was compared by comparing the ionic strength of 3-MCPD-d5 which is an internal standard and 3-MCPD. Calculated as MCPD free body equivalent.
　ＮａＢｒ法におけるＧＣ－ＭＳ分析条件は下記のとおりである。
　分析装置：島津製作所株式会社製、機種名：ＱＰ－２０１０
　カラム：製品名：ＨＰ－５ＭＳ、Ａｇｉｌｅｎｔ　Ｔｅｃｈｎｏｌｏｇｙ社製（長さ３０ｍ、径０．２５ｍｍ）
　カラム温度：６０℃（１分）～１２０℃（昇温速度１０℃／分）～１９０℃（昇温速度６℃／分）～２８０℃（昇温速度２０℃／分）
　検出器：ＭＳ（ＥＩ，ＳＩＭモード）
　スプリットレス：１μＬ注入
　キャリアガス：Ｈｅ The GC-MS analysis conditions in the NaBr method are as follows.
Analyzer: Shimadzu Corporation, Model name: QP-2010
Column: Product name: HP-5MS, manufactured by Agilent Technology (length 30 m, diameter 0.25 mm)
Column temperature: 60 ° C. (1 minute) to 120 ° C. (temperature increase rate 10 ° C./min) to 190 ° C. (temperature increase rate 6 ° C./min) to 280 ° C. (temperature increase rate 20 ° C./min)
Detector: MS (EI, SIM mode)
Splitless: 1 μL injection Carrier gas: He
（Ｃｌ量の定量）
　油脂中のＣｌ量（総塩素含量）を、塩素分析装置（ＮＳＸ－２１００Ｈ、株式会社三菱化学アナリテック製）によって測定した。この方法では、油脂中に含まれる総塩素量（遊離塩素と結合塩素（有機塩素及び無機塩素）の合計量）が算出される。得られた結果を、表２及び３の「Ｃｌ（ｐｐｍ）」の項に示す。 (Quantification of Cl content)
The amount of Cl (total chlorine content) in the fats and oils was measured by a chlorine analyzer (NSX-2100H, manufactured by Mitsubishi Chemical Analytech Co., Ltd.). In this method, the total amount of chlorine contained in the oil and fat (the total amount of free chlorine and combined chlorine (organic chlorine and inorganic chlorine)) is calculated. The obtained results are shown in the “Cl (ppm)” section of Tables 2 and 3.
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-T000003
　表２に示されるとおり、パーム粗油をアルカリ脱酸する工程（アルカリ脱酸工程－１）を含む本発明の製造方法によれば、３－ＭＣＰＤ及びその脂肪酸エステルの含有量が低減された精製パーム系油脂が得られる（各実施例の「ＭＣＰＤ（ｐｐｍ）」の項を参照。）。通常、脱臭工程を経ると、Ｔｒｕｅ　ＭＣＰＤ値が増加することが知られるが、本発明によれば、脱臭工程後であっても、Ｔｒｕｅ　ＭＣＰＤ値の増加が抑制されている（各実施例の「脱臭工程の後」の項を参照。）。３－ＭＣＰＤ及びその脂肪酸エステルの総量の低減効果は、脱臭工程後に分別工程を行っても損なわれなかった（実施例３の「分別後」の項を参照。）。 As shown in Table 2, according to the production method of the present invention including the step of alkaline deoxidation of crude palm oil (alkali deoxidation step-1), the purification with reduced content of 3-MCPD and its fatty acid ester Palm-based fats and oils are obtained (see “MCPD (ppm)” in each example). Normally, it is known that the True MCPD value increases after the deodorization step. However, according to the present invention, even after the deodorization step, the increase in the True MCPD value is suppressed (see “ (See the section “After deodorization process”). The effect of reducing the total amount of 3-MCPD and its fatty acid ester was not impaired even when the fractionation step was performed after the deodorization step (see “after fractionation” in Example 3).
　他方、表３に示されるとおり、パーム粗油をアルカリ脱酸する工程を含まない製造方法においては、精製油脂中の３－ＭＣＰＤ及びその脂肪酸エステルの総量が高かった（各比較例の「ＭＣＰＤ（ｐｐｍ）」の項を参照。）。 On the other hand, as shown in Table 3, the total amount of 3-MCPD and its fatty acid ester in the refined fats and oils was high in the production method not including the step of alkaline deoxidation of the crude palm oil (“MCPD ( ppm) ").
　表３中の比較例２に示されるとおり、パーム粗油を脱ガム工程に供した後にアルカリ脱酸工程（アルカリ脱酸工程－２）を行っても、油脂中の３－ＭＣＰＤ及びその脂肪酸エステルの含有量が低減しなかった。 As shown in Comparative Example 2 in Table 3, 3-MCPD and its fatty acid ester in fats and oils even when an alkali deoxidation step (alkali deoxidation step-2) was performed after the crude palm oil was subjected to the degumming step The content of was not reduced.
　表３中の比較例３及び４に示されるとおり、アルカリ脱酸工程の代わりに水洗工程を行っても、油脂中の３－ＭＣＰＤ及びその脂肪酸エステルの含有量が十分に低減しなかった。 As shown in Comparative Examples 3 and 4 in Table 3, the content of 3-MCPD and its fatty acid ester in fats and oils was not sufficiently reduced even when the water washing step was performed instead of the alkali deoxidation step.

Claims (4)

  1. 　パーム粗油をアルカリ脱酸するアルカリ脱酸工程を含む、精製パーム系油脂の製造方法。 A method for producing a refined palm oil or fat comprising an alkali deoxidation step of alkali deoxidizing crude palm oil.
  2. 　前記アルカリ脱酸工程の後に、脱ガム工程、脱色工程及び脱臭工程のうちの１以上を含む、請求項１に記載の精製パーム系油脂の製造方法。 The manufacturing method of the refine | purified palm oil fat of Claim 1 including one or more of a degumming process, a decoloring process, and a deodorizing process after the said alkali deoxidation process.
  3. 　前記脱ガム工程の後に前記脱色工程を含み、前記脱色工程の後に前記脱臭工程を含む、請求項２に記載の精製パーム系油脂の製造方法。 The manufacturing method of the refine | purified palm oil fat of Claim 2 including the said decoloring process after the said degumming process and including the said deodorizing process after the said decoloring process.
  4. 　前記脱臭工程の後に分別工程を含む、請求項３に記載の精製パーム系油脂の製造方法。 The manufacturing method of the refine | purified palm oil fat of Claim 3 including a fractionation process after the said deodorizing process.
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CN114144506A (en) * 2019-07-17 2022-03-04 日清奥利友集团株式会社 Method for producing refined fat

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WO2018043701A1 (en) * 2016-09-02 2018-03-08 太陽油脂株式会社 Fat composition for use in infant formula
JPWO2018043701A1 (en) * 2016-09-02 2019-06-24 太陽油脂株式会社 Fat composition for use in infant formula
CN114144506A (en) * 2019-07-17 2022-03-04 日清奥利友集团株式会社 Method for producing refined fat

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