WO2013145398A1 - Method for manufacturing glyceride composition and method for assessing necessity of second refining step for glyceride composition after first refining step - Google Patents

Method for manufacturing glyceride composition and method for assessing necessity of second refining step for glyceride composition after first refining step Download PDF

Info

Publication number
WO2013145398A1
WO2013145398A1 PCT/JP2012/076795 JP2012076795W WO2013145398A1 WO 2013145398 A1 WO2013145398 A1 WO 2013145398A1 JP 2012076795 W JP2012076795 W JP 2012076795W WO 2013145398 A1 WO2013145398 A1 WO 2013145398A1
Authority
WO
WIPO (PCT)
Prior art keywords
glyceride composition
purification step
purification
oil
glyceride
Prior art date
Application number
PCT/JP2012/076795
Other languages
French (fr)
Japanese (ja)
Inventor
一郎 日▲高▼
明子 佐々木
西山　佳孝
勇馬 小笠
浩 平井
Original Assignee
日清オイリオグループ株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 日清オイリオグループ株式会社 filed Critical 日清オイリオグループ株式会社
Publication of WO2013145398A1 publication Critical patent/WO2013145398A1/en

Links

Classifications

    • 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
    • C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter

Definitions

  • This invention relates to the manufacturing method of a glyceride composition, and the judgment method which judges the necessity of the 2nd refinement
  • Patent Document 1 a glyceride fatty acid ester or the like in a glyceride composition is obtained by deodorizing a glyceride composition containing 3-chloropropane-1,2-diol or the like under a specific temperature condition.
  • a method of reducing is disclosed.
  • Patent Document 2 discloses a re-refined palm having a specific flavor and having a good flavor by further performing a decoloring treatment and a deodorizing treatment on a refined palm soft oil subjected to at least a deodorizing treatment.
  • a method for obtaining a soft oil is disclosed.
  • the refined fats and oils are generally stored at a low temperature.
  • “returning substances” that cause deterioration of the flavor of fats and oils are generated during low-temperature storage.
  • the details of the “returning substance” are not known, the presence of this substance in the refined fat and oil causes the flavor of the fat and oil to return to the state prior to purification, resulting in a flavor deterioration called “returning odor”. It is.
  • RBD oil refined Bleached Deodorized
  • RBD oil refined Bleached Deodorized
  • returned substances may be produced in the fats and oils during the re-refining of refined oils such as RBD oil at low temperatures. For this reason, there has been a demand for a method capable of predicting the occurrence of flavor deterioration due to the return substance in the refined oil after re-refining.
  • the present invention has been made in view of the above circumstances, and provides a method for predicting the occurrence of flavor deterioration during storage at low temperatures of refined oil after re-refining.
  • the present inventors have found that there is a correlation between the peroxide value in a refined oil such as RBD oil and the generation of a return odor after the refined oil is stored at a low temperature after re-refining, thereby completing the present invention. It came to. Specifically, the present invention provides the following.
  • a determination method for determining the necessity of the second purification step for the glyceride composition after the first purification step by measuring the peroxide value of the glyceride composition after the first purification step.
  • the glyceride is an ester bond of 1 to 3 fatty acids to glycerin.
  • triacylglycerol which is the main component of fats and oils
  • diglyceride diacylglycerol
  • monoglyceride monoacylglycerol
  • the production method of the present invention includes a measurement step for measuring a peroxide value of a glyceride composition after the first purification step, and a glyceride composition after the first purification step in which the peroxide value is less than a predetermined numerical value. And a removing step for removing.
  • the flavor deterioration of fats and oils may be caused by the following mechanism. That is, when performing a 2nd refinement
  • the decolorization step the peroxide having a hydroperoxide group (—OOH) present in the glyceride composition after the first purification step is decomposed when heated in the presence of clay or the like, and 2-nonenal. Is generated.
  • the inventors of the present invention are 2-nonenal and / or derivatives thereof produced in the decolorization step in the second purification step, which is one of the substances that cause the deterioration of the flavor of fats and oils during low-temperature storage, that is, “return substances”. Identified that. It was also found that 2-nonenal and / or its derivatives once produced in the decolorization process remained in the oil even after further deodorization process.
  • the oils and fats are returned at the low temperature storage even if the second purification step is performed thereafter. Odor may be generated.
  • the glyceride composition having a low possibility of producing a return odor can be distributed as a product without re-purification, and the labor and cost relating to the second purification step can be suppressed.
  • the return odor was suppressed by appropriate quality control such as a treatment to reduce 2-nonenal during the second purification step. A glyceride composition can be obtained.
  • purification process in this invention is not specifically limited, The method normally used in the refinement
  • Chemical refining is a commonly used method for refining vegetable oils. Crude oil obtained by pressing and extracting raw material plants undergoes degumming, deoxidation, decolorization, dewaxing, and deodorization. To be refined oil.
  • RBD oil refined Bleached Deodorized
  • purification process is obtained by refine
  • RBD oil is preferable in that high quality fats and oils are easily obtained.
  • the oil and fat used as a raw material to be refined in the first refining step is not particularly limited.
  • edible fractionated oils such as palm super olein and palm mid fraction
  • these hydrogenated oils and transesterified oils edible oils produced by direct esterification reaction such as medium chain fatty acid triglycerides can be used.
  • vegetable oils with an elevated melting point of 10 ° C or higher especially palm oils (palm oil, palm kernel oil, palm olein, palm stearin, palm super olein, palm mid fraction, etc.) And its fractionated oils are preferred.
  • Peroxide value The peroxide value of the glyceride composition after the first purification step is measured based on the provisional oil analysis test method 4-2000.
  • the peroxide value of the glyceride composition after the first purification step is, for example, less than 1, preferably less than 0.7, a glyceride composition in which the formation of 2-nonenal and the return odor is suppressed can be obtained.
  • This glyceride composition can be distributed as a product as it is without being removed in the removal step described later, or a decolorization step, a deodorization step, or the like can be appropriately performed.
  • the same purification method as in the first purification step can be used, and the decolorization step and / or the deodorization step depending on the peroxide value of the glyceride composition after the first purification step.
  • the processing to be performed can be selected as appropriate. For example, if the peroxide value of the glyceride composition after the first purification step is relatively high, the decolorization step and the deodorization step are performed on the glyceride composition in the second purification step. A treatment for reducing the amount of 2-nonenal in the product can be applied.
  • the decolorization step or the deodorization step is performed in the second purification step, and 2-nonenal in the glyceride composition in any step Processing for reducing the amount can be performed.
  • a treatment for reducing the amount of 2-nonenal in the glyceride composition can be performed to obtain a glyceride composition in which the return odor is suppressed.
  • the glyceride composition is heated under a temperature condition of 100 to 270 ° C. under reduced pressure.
  • a method in which the peroxide value in the glyceride composition after heating is 1 or less can be mentioned.
  • the deodorization step may be performed under a temperature condition of 180 to 270 ° C. after the decolorization step.
  • citric acid and / or sodium citrate is added to the glyceride composition in the glyceride composition.
  • a method of adding in an amount of 5 ppm to 10 ppm is mentioned.
  • the deodorizing step may be performed under a temperature condition of 210 to 265 ° C.
  • the above method for reducing the amount of 2-nonenal in the glyceride composition may be used alone or in combination of two or more.
  • Whether the return odor of the glyceride composition obtained by the production method of the present invention is suppressed can be confirmed by the following method. 20 to 70 g of the glyceride composition is taken into a 100 ml sample bottle, sealed and stored in a cool dark place at 5 ° C. After storage (for example, after storage on the 7th day), remove the sample bottle, heat and dissolve at 50 to 80 ° C., and include a few grams in the mouth for sensory evaluation (determining whether there is a deterioration odor or return odor) Do.
  • Whether the amount of 2-nonenal produced in the glyceride composition obtained by the production method of the present invention has been reduced can be confirmed by quantifying the 2-nonenal concentration in the glyceride composition by the following method.
  • the glyceride composition is separated into a head space vial, and a volatile substance generated when heated at 50 to 100 ° C. for 30 to 100 minutes is adsorbed by an adsorbent.
  • the adsorbent is reheated at 200 to 250 ° C. for 1 to 10 minutes at the gas chromatography inlet, and the volatile substance is applied to the gas chromatography column.
  • each isolated component is detected with a detector in a column, and 2-nonenal is identified, and then quantified with a reagent manufactured by Wako Pure Chemical Industries (Wako First Grade).
  • the concentration of 2-nonenal in the glyceride composition obtained by the production method of the present invention is, for example, 1.0 to 0 ppm in the case of the glyceride composition after the first purification step that is not removed in the removal step, and preferably is 0.1. There is a possibility of 8 to 0 ppm.
  • the 2-nonenal concentration in the glyceride composition obtained by the production method of the present invention is 1.0 to 0 ppm, preferably 0.5 to 0 ppm immediately after the decolorization step as the second purification step.
  • the concentration of 2-nonenal in the glyceride composition can be, for example, 0.10 to 0 ppm after 14 days after refrigerated storage after the deodorization step. There is sex.
  • the peroxide value of the glyceride composition after the first purification step is less than a predetermined value, it is determined that the second purification step is unnecessary, and the glyceride composition can be directly distributed as a product, Or a decoloring process and a deodorizing process can also be performed suitably. Therefore, according to the determination method of the present invention, it is possible to stably supply a glyceride composition in which the return odor and the flavor deterioration of fats and oils are suppressed.
  • Each RBD palm oil is subjected to a decolorization step (corresponding to the second purification step) for 20 minutes at 105 to 110 ° C. in the presence of white clay, and then the white clay is removed by filtration to obtain a glyceride composition after decolorization.
  • a decolorization step corresponding to the second purification step
  • the white clay is removed by filtration to obtain a glyceride composition after decolorization.
  • 1 to 10 g of the obtained decolorized glyceride composition was dispensed into a headspace vial tube. Volatile substances generated when each fractionated glyceride composition was heated at 50 to 100 ° C. for 30 to 100 minutes were adsorbed with an adsorbent. The adsorbent was reheated at 200 to 250 ° C.
  • the deglyceride composition after decolorization was subjected to a deodorization step (corresponding to the second purification step) at 257 ° C. for 90 minutes under reduced pressure while blowing steam into the glyceride composition after decolorization, followed by filtration, Obtained.
  • the obtained deodorized glyceride composition was dispensed in an amount of 20 to 70 g in a 100 ml sample bottle, sealed and stored in a cool dark place at 5 ° C. On the 14th day after storage, the sample bottle was taken out, dissolved by heating at 50 to 80 ° C., and then sensory evaluation was performed with a few grams in the mouth. The five-step evaluation at that time was in accordance with the criteria shown in Table 1.
  • Example 1 and Comparative Examples 5 to 7 As in Examples 1 and 2 and Comparative Examples 1 and 2, using RBD palm oil, the peroxide value of the glyceride composition after the first purification step and the glyceride composition after the second purification step The amount of 2-nonenal produced and the presence or absence of a return odor were examined. Furthermore, the amount of 2-nonenal produced in the sample examined for the presence or absence of a return odor (that is, the glyceride composition after deodorization) was also examined. The results are shown in Table 3.
  • Examples 1 and 3 As in Examples 1 and 2 and Comparative Examples 1 and 2, using RBD palm oil, the peroxide value of the glyceride composition after the first purification step and the glyceride composition after the second purification step The amount of 2-nonenal produced and the presence or absence of a return odor were examined. However, the deodorization process of Example 3 was performed at 245 degreeC. The results are shown in Table 4.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Microbiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)

Abstract

To provide a method for predicting the occurrence of flavor degradation when a refined oil that has been re-refined is stored at a low temperature. This method for manufacturing a glyceride composition is characterized by including the following: a measurement step in which the peroxide value of a glyceride composition after a first refining step is measured; and a removal step in which post-first-refining-step glyceride composition with a peroxide value greater than or equal to a prescribed value is removed. The 2-nonenal concentration of the glyceride composition after the removal step may be from 1.0 to 0 ppm.

Description

グリセリド組成物の製造方法、及び第１の精製工程後のグリセリド組成物に対する第２の精製工程の必要性を判断する判断方法Method for producing glyceride composition and determination method for judging necessity of second purification step for glyceride composition after first purification step
　本発明は、グリセリド組成物の製造方法、及び第１の精製工程後のグリセリド組成物（ＲＢＤ油等）に対する第２の精製工程の必要性を判断する判断方法に関する。 This invention relates to the manufacturing method of a glyceride composition, and the judgment method which judges the necessity of the 2nd refinement | purification process with respect to the glyceride composition (RBD oil etc.) after a 1st refinement | purification process.
　近年、油脂の風味や安定性を向上させるための試みが種々、なされている。油脂の風味や安定性等の品質の低下には、様々な要素が関係しており、それぞれの要素に応じた油脂の品質の改善方法等が報告されている。また、油脂中に存在する、生理活性に関係すると考えられる微量成分を調整する方法についても多数報告されている。 In recent years, various attempts have been made to improve the flavor and stability of fats and oils. Various factors are related to the deterioration of quality such as the flavor and stability of fats and oils, and methods for improving the quality of fats and oils according to each factor have been reported. In addition, many methods for adjusting trace components present in fats and oils that are considered to be related to physiological activity have been reported.
　例えば、特許文献１には、３－クロロプロパン－１，２－ジオール等を含有するグリセリド組成物を、特定の温度条件にて脱臭処理等することにより、グリセリド組成物中のグリシドールの脂肪酸エステル等を低減する方法が開示されている。また、特許文献２には、少なくとも脱臭処理が施された精製パーム軟質油に、さらに、脱色処理と脱臭処理とを施すことで、特定の色度を有する、良好な風味を備えた再精製パーム軟質油を得る方法が開示されている。また、特許文献３には、規則充填材を具備した薄膜式カラムを用いた精製処理とトレイ式装置を用いた精製処理とを組み合わせて、全構成脂肪酸中のトランス脂肪酸含量が１質量％以下の油脂を精製する方法が開示されている。 For example, in Patent Document 1, a glyceride fatty acid ester or the like in a glyceride composition is obtained by deodorizing a glyceride composition containing 3-chloropropane-1,2-diol or the like under a specific temperature condition. A method of reducing is disclosed. Patent Document 2 discloses a re-refined palm having a specific flavor and having a good flavor by further performing a decoloring treatment and a deodorizing treatment on a refined palm soft oil subjected to at least a deodorizing treatment. A method for obtaining a soft oil is disclosed. Moreover, in patent document 3, the refinement | purification process using the thin film type column which comprised the regular packing material, and the refinement | purification process using a tray type apparatus are combined, and trans-fatty acid content in all the constituent fatty acids is 1 mass% or less. A method for purifying fats and oils is disclosed.
　また、油脂の酸化による劣化に伴う、油脂の風味上好ましくない化合物の生成を抑制するために、一般的に、精製された油脂は低温下で保存される。しかし、特にパーム系油脂に関しては、低温保存時において、油脂の風味の劣化を引き起こす「戻り物質」が生成することが知られている。「戻り物質」に関して、詳細は知られていないものの、この物質が、精製された油脂中に存在することにより、油脂の風味が精製前の状態に戻り、「戻り臭」と呼ばれる風味劣化が引き起こされる。 In addition, in order to suppress the formation of compounds that are unfavorable in the flavor of fats and oils due to deterioration due to oxidation of the fats and oils, the refined fats and oils are generally stored at a low temperature. However, it is known that especially for palm-based fats and oils, “returning substances” that cause deterioration of the flavor of fats and oils are generated during low-temperature storage. Although the details of the “returning substance” are not known, the presence of this substance in the refined fat and oil causes the flavor of the fat and oil to return to the state prior to purification, resulting in a flavor deterioration called “returning odor”. It is.
　例えば、海外で圧搾された原油は、フィジカル精製工程と呼ばれる精製工程を施され、いわゆるＲＢＤ油（Ｒｅｆｉｎｅｄ　Ｂｌｅａｃｈｅｄ　Ｄｅｏｄｏｒｉｚｅｄ）等の精製油として我が国へ輸入される。輸入されたＲＢＤ油の大半は、我が国において再精製されるものの、ＲＢＤ油等の精製油を再精製後に低温下で保存している間、油脂中に「戻り物質」が生じることがある。そのため、再精製後の精製油について、戻り物質による風味劣化の発生を予測できる方法が望まれていた。 For example, crude oil squeezed overseas is subjected to a refining process called a physical refining process and imported into Japan as a refined oil such as so-called RBD oil (Refined Bleached Deodorized). Although most of the imported RBD oil is re-refined in Japan, “returned substances” may be produced in the fats and oils during the re-refining of refined oils such as RBD oil at low temperatures. For this reason, there has been a demand for a method capable of predicting the occurrence of flavor deterioration due to the return substance in the refined oil after re-refining.
特開２０１１－０７４３５８号公報JP 2011-074358 A 特開２０１１－０３０４８２号公報JP 2011-030482 A 特許４５１６８９７号公報Japanese Patent No. 4516897
　本発明は、以上のような事情に鑑みてなされたものであり、再精製後の精製油の、低温下での保存時における風味劣化の発生を予測する方法を提供する。 The present invention has been made in view of the above circumstances, and provides a method for predicting the occurrence of flavor deterioration during storage at low temperatures of refined oil after re-refining.
　本発明者らは、ＲＢＤ油等の精製油中の過酸化物価と、当該精製油を再精製後に低温下で保存した後の戻り臭の発生に相関があることを見出し、本発明を完成するに至った。具体的には、本発明は以下のようなものを提供する。 The present inventors have found that there is a correlation between the peroxide value in a refined oil such as RBD oil and the generation of a return odor after the refined oil is stored at a low temperature after re-refining, thereby completing the present invention. It came to. Specifically, the present invention provides the following.
　（１）　第１の精製工程後のグリセリド組成物の過酸化物価を測定する測定工程と、
　上記過酸化物価が所定の数値以上である第１の精製工程後のグリセリド組成物を除去する除去工程と、
を含むグリセリド組成物の製造方法。 (1) a measurement step for measuring the peroxide value of the glyceride composition after the first purification step;
A removal step of removing the glyceride composition after the first purification step, wherein the peroxide value is a predetermined numerical value or more;
The manufacturing method of the glyceride composition containing this.
　（２）　上記除去工程後のグリセリド組成物中の２－ノネナール濃度は、１．０～０ｐｐｍである（１）に記載のグリセリド組成物の製造方法。 (2) The method for producing a glyceride composition according to (1), wherein the 2-nonenal concentration in the glyceride composition after the removing step is 1.0 to 0 ppm.
　（３）　上記除去工程で除去された第１の精製工程後のグリセリド組成物に対して、第２の精製工程を行う工程を含む（１）又は（２）に記載のグリセリド組成物の製造方法。 (3) The manufacturing method of the glyceride composition as described in (1) or (2) including the process of performing a 2nd refinement | purification process with respect to the glyceride composition after the 1st refinement | purification process removed at the said removal process. .
　（４）　上記第２の精製工程後のグリセリド組成物中の２－ノネナール濃度は、１．０～０ｐｐｍである（３）に記載のグリセリド組成物の製造方法。 (4) The method for producing a glyceride composition according to (3), wherein the 2-nonenal concentration in the glyceride composition after the second purification step is 1.0 to 0 ppm.
　（５）　上記第１の精製工程後のグリセリド組成物は、上昇融点１０℃以上の植物油である（１）から（４）のいずれかに記載のグリセリド組成物の製造方法。 (5) The method for producing a glyceride composition according to any one of (1) to (4), wherein the glyceride composition after the first purification step is a vegetable oil having a rising melting point of 10 ° C. or higher.
　（６）　上記第１の精製工程後のグリセリド組成物は、ＲＢＤ油である（１）から（５）のいずれかに記載のグリセリド組成物の製造方法。 (6) The method for producing a glyceride composition according to any one of (1) to (5), wherein the glyceride composition after the first purification step is RBD oil.
　（７）　第１の精製工程後のグリセリド組成物の過酸化物価を測定することで、第１の精製工程後のグリセリド組成物に対する第２の精製工程の必要性を判断する判断方法。 (7) A determination method for determining the necessity of the second purification step for the glyceride composition after the first purification step by measuring the peroxide value of the glyceride composition after the first purification step.
　本発明によれば、再精製後の精製油の、低温下での保存時における風味劣化の発生を予測する方法が提供される。 According to the present invention, there is provided a method for predicting the occurrence of flavor deterioration during storage at low temperature of refined oil after re-refining.
　以下、本発明の実施形態について具体的に説明する。なお、本発明では、グリセリドは、グリセリンに脂肪酸が１～３個エステル結合したものであり、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）、モノグリセリド（モノアシルグリセロール）も含むものとする。 Hereinafter, embodiments of the present invention will be specifically described. In the present invention, the glyceride is an ester bond of 1 to 3 fatty acids to glycerin. In addition to triglyceride (triacylglycerol), which is the main component of fats and oils, diglyceride (diacylglycerol), monoglyceride (monoacylglycerol) ).
　本発明の製造方法は、第１の精製工程後のグリセリド組成物の過酸化物価を測定する測定工程と、上記過酸化物価が所定の数値未満である第１の精製工程後のグリセリド組成物を除去する除去工程と、を含むことを特徴とする。 The production method of the present invention includes a measurement step for measuring a peroxide value of a glyceride composition after the first purification step, and a glyceride composition after the first purification step in which the peroxide value is less than a predetermined numerical value. And a removing step for removing.
　本発明者による検討の結果、油脂の風味劣化は、下記の機構が一因となって生じる可能性があることが見出された。すなわち、ＲＢＤ油等の、第１の精製工程が行われたグリセリド組成物（すなわち、第１の精製工程後のグリセリド組成物）について、さらに第２の精製工程を行う場合、第２の精製工程における脱色工程において、第１の精製工程後のグリセリド組成物中に存在する、ヒドロペルオキシド基（－ＯＯＨ）を有する過酸化物が、白土等の存在下で加熱されると分解し、２－ノネナールを生成する。本発明者らは、第２の精製工程における脱色工程において生成された２－ノネナール及び／又はその誘導体等が、低温保存時の油脂の風味劣化をもたらす物質、すなわち「戻り物質」のひとつであることを特定した。また、脱色工程で一旦生成した２－ノネナール及び／又はその誘導体等は、その後、さらに脱臭工程等を行っても油脂中に残留していることも分かった。 As a result of examination by the present inventors, it was found that the flavor deterioration of fats and oils may be caused by the following mechanism. That is, when performing a 2nd refinement | purification process further about the glyceride composition (namely, glyceride composition after a 1st refinement | purification process) in which the 1st refinement | purification processes were performed, such as RBD oil, the 2nd refinement | purification process In the decolorization step, the peroxide having a hydroperoxide group (—OOH) present in the glyceride composition after the first purification step is decomposed when heated in the presence of clay or the like, and 2-nonenal. Is generated. The inventors of the present invention are 2-nonenal and / or derivatives thereof produced in the decolorization step in the second purification step, which is one of the substances that cause the deterioration of the flavor of fats and oils during low-temperature storage, that is, “return substances”. Identified that. It was also found that 2-nonenal and / or its derivatives once produced in the decolorization process remained in the oil even after further deodorization process.
　つまり、油脂の精製を行っても、第１の精製工程後のグリセリド組成物中に過酸化物が含まれていると、その後第２の精製工程を行っても、油脂の低温保存時に、戻り臭が発生する可能性がある。 In other words, even if the fats and oils are purified, if the peroxide is contained in the glyceride composition after the first purification step, the oils and fats are returned at the low temperature storage even if the second purification step is performed thereafter. Odor may be generated.
　そこで、本発明者が鋭意検討した結果、第１の精製工程後のグリセリド組成物の過酸化物価と、第２の精製工程後のグリセリド組成物中の２－ノネナール量との間には相関関係があり、第１の精製工程後のグリセリド組成物の過酸化物価が低い（又は高い）場合は、低温保存時の、第２の精製工程後のグリセリド組成物中の２－ノネナール量も低い（又は高い）ことが見出された。 Therefore, as a result of intensive studies by the present inventors, there is a correlation between the peroxide value of the glyceride composition after the first purification step and the amount of 2-nonenal in the glyceride composition after the second purification step. When the peroxide value of the glyceride composition after the first purification step is low (or high), the amount of 2-nonenal in the glyceride composition after the second purification step during low-temperature storage is also low ( (Or high).
　そのため、第１の精製工程後のグリセリド組成物の過酸化物価を測定することによって、当該グリセリド組成物を第２の精製工程によって再精製後、低温保存時に戻り臭を生じる可能性を予測することができる。その結果、戻り臭を生じる可能性が低いグリセリド組成物については、再精製をすることなく製品としてそのまま流通させることができ、第２の精製工程に関する労力やコストを抑制できる。また、戻り臭を生じる可能性が高いグリセリド組成物に対しては、第２の精製工程時に２－ノネナールを低減させる処理を行う等の適切な品質管理をすることによって、戻り臭が抑制されたグリセリド組成物を得ることができる。 Therefore, by measuring the peroxide value of the glyceride composition after the first purification step, predict the possibility of producing a return odor during low-temperature storage after the glyceride composition is re-purified by the second purification step. Can do. As a result, the glyceride composition having a low possibility of producing a return odor can be distributed as a product without re-purification, and the labor and cost relating to the second purification step can be suppressed. In addition, for glyceride compositions that have a high possibility of producing a return odor, the return odor was suppressed by appropriate quality control such as a treatment to reduce 2-nonenal during the second purification step. A glyceride composition can be obtained.
　［測定工程］
　本発明の製造方法においては、第１の精製工程後のグリセリド組成物の過酸化物価を測定する。 [Measurement process]
In the production method of the present invention, the peroxide value of the glyceride composition after the first purification step is measured.
　（第１の精製工程）
　本発明における第１の精製工程において使用される精製方法は、特に限定されず、油脂の精製において通常使用される方法であってもよい。例えば、植物油の精製方法には、ケミカル精製（ケミカルリファイニング）と、フィジカル精製（フィジカルリファイニング）とがあるが、第１の精製工程においては、いずれの精製方法を用いてもよい。 (First purification step)
The refinement | purification method used in the 1st refinement | purification process in this invention is not specifically limited, The method normally used in the refinement | purification of fats and oils may be sufficient. For example, there are chemical purification (chemical refining) and physical refining (physical refining) as a method for purifying vegetable oil, and any purification method may be used in the first purification step.
　ケミカル精製は、植物油の精製方法として、通常行われている方法であり、原料となる植物を圧搾・抽出した原油が、脱ガム処理、脱酸処理、脱色処理、脱ろう処理、脱臭処理を経ることで精製され、精製油となる。 Chemical refining is a commonly used method for refining vegetable oils. Crude oil obtained by pressing and extracting raw material plants undergoes degumming, deoxidation, decolorization, dewaxing, and deodorization. To be refined oil.
　フィジカル精製は、パーム油やヤシ油等にてよく行われている方法であり、原料となるパームやヤシ等を圧搾した原油が、脱ガム処理、脱色処理、脱酸処理、脱臭処理を経ることで精製され、精製油となる。フィジカル精製によって得られるグリセリド組成物は、ＲＢＤ油（Ｒｅｆｉｎｅｄ　Ｂｌｅａｃｈｅｄ　Ｄｅｏｄｏｒｉｚｅｄ）と呼ばれる。 Physical refining is a common practice with palm oil, palm oil, etc., and crude oil that has been squeezed from palm or palm as raw material undergoes degumming, decolorization, deoxidation, and deodorization. To be refined oil. The glyceride composition obtained by physical refining is called RBD oil (Refined Bleached Deodorized).
　原料となる油脂を、第１の精製工程において、上記の精製方法等を使用して精製することで、第１の精製工程後のグリセリド組成物が得られる。本発明における第１の精製工程後のグリセリド組成物としては、品質の高い油脂が得られやすいという点でＲＢＤ油が好ましい。 The glyceride composition after the 1st refinement | purification process is obtained by refine | purifying the fats and oils used as a raw material in said 1st refinement | purification process using said refinement | purification method. As the glyceride composition after the first purification step in the present invention, RBD oil is preferable in that high quality fats and oils are easily obtained.
　第１の精製工程において精製される、原料となる油脂としては、特に限定されないが、例えば、菜種油、大豆油、米油、サフラワー油、ぶどう油、ひまわり油、小麦はい芽油、とうもろこし油、綿実油、ごま油、落花生油、フラックス油、エゴマ油、オリーブ油、パーム油、パーム核油、ヤシ油等の植物油、これら２種以上を混合した調合植物油、又は、これらを分別したパームオレイン、パームステアリン、パームスーパーオレイン、パームミッドフラクション等の食用分別油、これらの水素添加油、エステル交換油等のほか、中鎖脂肪酸トリグリセリドのような直接エステル化反応により製造された食用油を用いることができる。低温時の風味の劣化が顕著であるという理由から、上昇融点が１０℃以上の植物油、特にパーム系油脂（パーム油、パーム核油、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、パームミッドフラクション等）及びその分別油が好ましい。 The oil and fat used as a raw material to be refined in the first refining step is not particularly limited. For example, rapeseed oil, soybean oil, rice oil, safflower oil, grape oil, sunflower oil, wheat germ oil, corn oil, Cotton oil, sesame oil, peanut oil, flux oil, sesame oil, olive oil, palm oil, palm kernel oil, coconut oil and other vegetable oils, mixed vegetable oils that are a mixture of two or more of these, or palm olein, palm stearin separated from these In addition to edible fractionated oils such as palm super olein and palm mid fraction, these hydrogenated oils and transesterified oils, edible oils produced by direct esterification reaction such as medium chain fatty acid triglycerides can be used. Because of the remarkable deterioration of flavor at low temperatures, vegetable oils with an elevated melting point of 10 ° C or higher, especially palm oils (palm oil, palm kernel oil, palm olein, palm stearin, palm super olein, palm mid fraction, etc.) And its fractionated oils are preferred.
　（過酸化物価）
　第１の精製工程後のグリセリド組成物の過酸化物価は、基準油脂分析試験法　暫４－２０００に基づき測定する。 (Peroxide value)
The peroxide value of the glyceride composition after the first purification step is measured based on the provisional oil analysis test method 4-2000.
　第１の精製工程後のグリセリド組成物の過酸化物価が、例えば、１未満、好ましくは０．７未満であれば、２－ノネナールの生成及び戻り臭が抑制されたグリセリド組成物が得られる。このグリセリド組成物は後述する除去工程で除去されることなく、そのまま製品として流通させることもできるし、脱色工程や脱臭工程等を適宜行うこともできる。 If the peroxide value of the glyceride composition after the first purification step is, for example, less than 1, preferably less than 0.7, a glyceride composition in which the formation of 2-nonenal and the return odor is suppressed can be obtained. This glyceride composition can be distributed as a product as it is without being removed in the removal step described later, or a decolorization step, a deodorization step, or the like can be appropriately performed.
　［除去工程］
　第１の精製工程後のグリセリド組成物の過酸化物価が１以上、好ましくは０．７以上である第１の精製工程後のグリセリド組成物は、製品として流通するグリセリド組成物のロットから除去され、適宜、後述する第２の精製工程に供される。 [Removal process]
The glyceride composition after the first purification step in which the peroxide value of the glyceride composition after the first purification step is 1 or more, preferably 0.7 or more, is removed from the lot of the glyceride composition distributed as a product. As appropriate, it is subjected to a second purification step described later.
　（第２の精製工程）
　本発明における第２の精製工程においては、第１の精製工程と同様の精製方法を使用でき、第１の精製工程後のグリセリド組成物の過酸化物価に応じて、脱色工程及び／又は脱臭工程等で行うべき処理を適宜選択することができる。例えば、第１の精製工程後のグリセリド組成物の過酸化物価が比較的高ければ、当該グリセリド組成物に対して、第２の精製工程において脱色工程及び脱臭工程を行い、両工程において、グリセリド組成物中の２－ノネナール量を減少させるための処理を施すことができる。第１の精製工程後のグリセリド組成物の過酸化物価が比較的低ければ、第２の精製工程において脱色工程又は脱臭工程のいずれかを行い、いずれかの工程においてグリセリド組成物中の２－ノネナール量を減少させるための処理を施すことができる。第２の精製工程において、グリセリド組成物中の２－ノネナール量を減少させるための処理を施すことで、戻り臭が抑制されたグリセリド組成物を得ることができる。 (Second purification step)
In the second purification step of the present invention, the same purification method as in the first purification step can be used, and the decolorization step and / or the deodorization step depending on the peroxide value of the glyceride composition after the first purification step. The processing to be performed can be selected as appropriate. For example, if the peroxide value of the glyceride composition after the first purification step is relatively high, the decolorization step and the deodorization step are performed on the glyceride composition in the second purification step. A treatment for reducing the amount of 2-nonenal in the product can be applied. If the peroxide value of the glyceride composition after the first purification step is relatively low, either the decolorization step or the deodorization step is performed in the second purification step, and 2-nonenal in the glyceride composition in any step Processing for reducing the amount can be performed. In the second purification step, a treatment for reducing the amount of 2-nonenal in the glyceride composition can be performed to obtain a glyceride composition in which the return odor is suppressed.
　脱色工程における、グリセリド組成物中の２－ノネナール量を減少させるための方法としては、例えば、脱色工程の前に、グリセリド組成物を、減圧下、１００～２７０℃の温度条件下にて加熱し、加熱後におけるグリセリド組成物中の過酸化物価を１以下とする方法が挙げられる。当該方法においては、脱色工程の後に、１８０～２７０℃の温度条件下で脱臭工程を行ってもよい。 As a method for reducing the amount of 2-nonenal in the glyceride composition in the decolorization step, for example, before the decolorization step, the glyceride composition is heated under a temperature condition of 100 to 270 ° C. under reduced pressure. A method in which the peroxide value in the glyceride composition after heating is 1 or less can be mentioned. In this method, the deodorization step may be performed under a temperature condition of 180 to 270 ° C. after the decolorization step.
　また、脱色工程における、グリセリド組成物中の２－ノネナール量を減少させるための方法としては、減圧条件下で、上記グリセリド組成物の全質量に対して０．３質量％以上の水蒸気の吹き込みを行いながらグリセリド組成物を脱色する方法が挙げられる。 In addition, as a method for reducing the amount of 2-nonenal in the glyceride composition in the decolorization step, 0.3% by mass or more of water vapor is blown into the total mass of the glyceride composition under reduced pressure. The method of decoloring a glyceride composition while performing is mentioned.
　脱臭工程における、グリセリド組成物中の２－ノネナール量を減少させるための方法としては、例えば、脱臭工程において、グリセリド組成物に、クエン酸及び／又はクエン酸ナトリウムを、上記グリセリド組成物中０．５ｐｐｍ以上１０ｐｐｍ以下となる量で添加する方法が挙げられる。当該脱臭工程は、２１０～２６５℃の温度条件下で行ってもよい。 As a method for reducing the amount of 2-nonenal in the glyceride composition in the deodorization step, for example, in the deodorization step, citric acid and / or sodium citrate is added to the glyceride composition in the glyceride composition. A method of adding in an amount of 5 ppm to 10 ppm is mentioned. The deodorizing step may be performed under a temperature condition of 210 to 265 ° C.
　上記のグリセリド組成物中の２－ノネナール量を減少させるための方法は、単独で使用してもよく、複数を組み合わせて使用してもよい。 The above method for reducing the amount of 2-nonenal in the glyceride composition may be used alone or in combination of two or more.
　［本発明の製造方法により得られるグリセリド組成物］
　本発明の製造方法により得られるグリセリド組成物は、グリセリド組成物中の「戻り物質」すなわち２－ノネナールの生成量が低減されており、戻り臭や油脂の風味劣化が抑制されている。 [Glyceride composition obtained by the production method of the present invention]
In the glyceride composition obtained by the production method of the present invention, the amount of “returning substance”, that is, 2-nonenal, in the glyceride composition is reduced, and the return odor and the deterioration of the flavor of fats and oils are suppressed.
　本発明の製造方法により得られたグリセリド組成物の戻り臭が抑制されているかどうかは、下記の方法で確認できる。グリセリド組成物を、１００ｍｌサンプル瓶に２０～７０ｇ分取し、密栓後５℃にて冷暗所に保存する。保存後（例えば７日目の保存後）においてサンプル瓶を取り出し、５０～８０℃にて加温溶解した後に、数ｇを口に含んで官能評価（劣化臭や戻り臭の有無の判断）を行う。 Whether the return odor of the glyceride composition obtained by the production method of the present invention is suppressed can be confirmed by the following method. 20 to 70 g of the glyceride composition is taken into a 100 ml sample bottle, sealed and stored in a cool dark place at 5 ° C. After storage (for example, after storage on the 7th day), remove the sample bottle, heat and dissolve at 50 to 80 ° C., and include a few grams in the mouth for sensory evaluation (determining whether there is a deterioration odor or return odor) Do.
　本発明の製造方法により得られたグリセリド組成物中の２－ノネナールの生成量が低減されているかどうかは、下記の方法でグリセリド組成物中の２－ノネナール濃度を定量することで確認できる。グリセリド組成物をヘッドスペース用バイアル管に分取し、５０～１００℃にて３０～１００分加温した際に発生する揮発性物質を吸着剤にて吸着させる。この吸着剤をガスクロマトグラフィーの注入口にて２００～２５０℃で１～１０分間再加熱し、揮発性物質をガスクロマトグラフィーのカラムに供する。次いで、カラムにて、単離した各成分を検出器にて検知し、２－ノネナールを同定した後、和光純薬工業製試薬（和光一級）によって定量する。 Whether the amount of 2-nonenal produced in the glyceride composition obtained by the production method of the present invention has been reduced can be confirmed by quantifying the 2-nonenal concentration in the glyceride composition by the following method. The glyceride composition is separated into a head space vial, and a volatile substance generated when heated at 50 to 100 ° C. for 30 to 100 minutes is adsorbed by an adsorbent. The adsorbent is reheated at 200 to 250 ° C. for 1 to 10 minutes at the gas chromatography inlet, and the volatile substance is applied to the gas chromatography column. Next, each isolated component is detected with a detector in a column, and 2-nonenal is identified, and then quantified with a reagent manufactured by Wako Pure Chemical Industries (Wako First Grade).
　本発明の製造方法により得られるグリセリド組成物中の２－ノネナール濃度は、例えば、除去工程において除去されない第１の精製工程後のグリセリド組成物の場合、１．０～０ｐｐｍとなり、好ましくは０．８～０ｐｐｍとなる可能性がある。 The concentration of 2-nonenal in the glyceride composition obtained by the production method of the present invention is, for example, 1.0 to 0 ppm in the case of the glyceride composition after the first purification step that is not removed in the removal step, and preferably is 0.1. There is a possibility of 8 to 0 ppm.
　また、本発明の製造方法により得られるグリセリド組成物中の２－ノネナール濃度は、第２の精製工程として脱色工程を行った直後では１．０～０ｐｐｍとなり、好ましくは０．５～０ｐｐｍとなる可能性がある。また、第２の精製工程として脱色工程後に脱臭工程を行った場合、脱臭工程後冷蔵保存して１４日後に、グリセリド組成物中の２－ノネナール濃度は、例えば、０．１０～０ｐｐｍとなる可能性がある。 Also, the 2-nonenal concentration in the glyceride composition obtained by the production method of the present invention is 1.0 to 0 ppm, preferably 0.5 to 0 ppm immediately after the decolorization step as the second purification step. there is a possibility. Further, when the deodorization step is performed after the decolorization step as the second purification step, the concentration of 2-nonenal in the glyceride composition can be, for example, 0.10 to 0 ppm after 14 days after refrigerated storage after the deodorization step. There is sex.
　［第１の精製工程後のグリセリド組成物に対する第２の精製工程の必要性を判断する判断方法］
　本発明の判断方法によれば、上述の通り、第１の精製工程後のグリセリド組成物の過酸化物価を測定することで、第１の精製工程後のグリセリド組成物に対する第２の精製工程の必要性を判断することができる。第１の精製工程後のグリセリド組成物の過酸化物価が所定の数値以上である場合、第２の精製工程が必要であると判断し、当該グリセリド組成物に対して上述の通り第２の精製工程を行い、戻り臭の抑制されたグリセリド組成物を得ることができる。第１の精製工程後のグリセリド組成物の過酸化物価が所定の数値未満である場合、第２の精製工程が不要であると判断し、当該グリセリド組成物はそのまま製品として流通させることができ、又は適宜脱色工程や脱臭工程を行うこともできる。従って、本発明の判断方法によれば、戻り臭や油脂の風味劣化が抑制されたグリセリド組成物を安定的に供給できる。 [Judgment method for judging necessity of second purification step for glyceride composition after first purification step]
According to the determination method of the present invention, as described above, by measuring the peroxide value of the glyceride composition after the first purification step, the second purification step for the glyceride composition after the first purification step is performed. Necessity can be judged. When the peroxide value of the glyceride composition after the first purification step is greater than or equal to a predetermined numerical value, it is determined that the second purification step is necessary, and the second purification is performed on the glyceride composition as described above. A glyceride composition in which a return odor is suppressed can be obtained by performing the process. When the peroxide value of the glyceride composition after the first purification step is less than a predetermined value, it is determined that the second purification step is unnecessary, and the glyceride composition can be directly distributed as a product, Or a decoloring process and a deodorizing process can also be performed suitably. Therefore, according to the determination method of the present invention, it is possible to stably supply a glyceride composition in which the return odor and the flavor deterioration of fats and oils are suppressed.
　以下、本発明の実施例に基づいてさらに詳細に説明するが、本発明はこれらの記載に何ら限定されるものではない。 Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not limited to these descriptions.
　［実施例１及び２ならびに比較例１及び２］
　下記のように、第１の精製工程後のグリセリド組成物の過酸化物価と、第２の精製工程後のグリセリド組成物中の２－ノネナール生成量及び戻り臭の有無を検討した。 [Examples 1 and 2 and Comparative Examples 1 and 2]
As described below, the peroxide value of the glyceride composition after the first purification step, the amount of 2-nonenal produced in the glyceride composition after the second purification step, and the presence or absence of a return odor were examined.
　（過酸化物価）
　異なる４つのロットのＲＢＤパーム油（原産国マレーシア又は／及びインドネシア製；第１の精製工程後のグリセリド組成物に相当）について、基準油脂分析試験法　暫４－２０００に基づき過酸化物価（ＰＯＶ）を測定した。その結果を表２に示す。 (Peroxide value)
For four different lots of RBD palm oil (made in Malaysia or / and Indonesia; corresponding to the glyceride composition after the first refining process), the peroxide value (POV) based on provisional oil analysis test method 4-2000 Was measured. The results are shown in Table 2.
　（２－ノネナール生成量）
　各ＲＢＤパーム油に対して、白土の存在下で、１０５～１１０℃で２０分間脱色工程（第２の精製工程に相当）を行った後、ろ過により白土を除去して、脱色後のグリセリド組成物を得た。得られた脱色後のグリセリド組成物１～１０ｇをヘッドスペース用バイアル管に分取した。分取した各グリセリド組成物を、５０～１００℃にて３０～１００分加温した際に発生する揮発性物質を吸着剤にて吸着させた。この吸着剤をガスクロマトグラフィーの注入口にて２００～２５０℃で１～１０分間再加熱し、揮発性物質をガスクロのカラムに供した。次いで、カラムにて単離した各成分を検出器にて検知し、２－ノネナールを同定した後、和光純薬工業製試薬（和光一級）によって定量した。その結果を表２に示す。 (2-nonenal production)
Each RBD palm oil is subjected to a decolorization step (corresponding to the second purification step) for 20 minutes at 105 to 110 ° C. in the presence of white clay, and then the white clay is removed by filtration to obtain a glyceride composition after decolorization. I got a thing. 1 to 10 g of the obtained decolorized glyceride composition was dispensed into a headspace vial tube. Volatile substances generated when each fractionated glyceride composition was heated at 50 to 100 ° C. for 30 to 100 minutes were adsorbed with an adsorbent. The adsorbent was reheated at 200 to 250 ° C. for 1 to 10 minutes at the gas chromatography inlet, and the volatile substance was applied to a gas chromatography column. Next, each component isolated by the column was detected by a detector, 2-nonenal was identified, and then quantified with a reagent manufactured by Wako Pure Chemical Industries (Wako First Grade). The results are shown in Table 2.
　（戻り臭の有無）
　上述の脱色後のグリセリド組成物に水蒸気を吹き込みながら、減圧下、２５７℃で９０分間脱臭工程（第２の精製工程に相当）を行った後に、ろ過を実施し、脱臭後のグリセリド組成物を得た。得られた脱臭後のグリセリド組成物を、１００ｍｌサンプル瓶に２０～７０ｇ分取し、密栓後５℃にて冷暗所に保存した。保存後１４日目においてサンプル瓶を取り出し、５０～８０℃にて加温溶解した後に、数ｇを口に含んで官能評価を行った。その際の５段階評価は、表１記載の基準に従った。 (With or without return odor)
The deglyceride composition after decolorization was subjected to a deodorization step (corresponding to the second purification step) at 257 ° C. for 90 minutes under reduced pressure while blowing steam into the glyceride composition after decolorization, followed by filtration, Obtained. The obtained deodorized glyceride composition was dispensed in an amount of 20 to 70 g in a 100 ml sample bottle, sealed and stored in a cool dark place at 5 ° C. On the 14th day after storage, the sample bottle was taken out, dissolved by heating at 50 to 80 ° C., and then sensory evaluation was performed with a few grams in the mouth. The five-step evaluation at that time was in accordance with the criteria shown in Table 1.
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000001
　各グリセリド組成物についての官能評価の結果が「３以上」であるものを、低温戻り臭「無し」とし、官能評価の結果が「３未満」であるものを、低温戻り臭「有り」とした。その結果を表２に示す。 For each glyceride composition, the sensory evaluation result of “3 or more” was regarded as “low” low temperature return odor, and the sensory evaluation result of “less than 3” was defined as low temperature return odor “present”. . The results are shown in Table 2.
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000002
　表２の結果より、第１の精製工程後のグリセリド組成物の過酸化物価が低ければ、第２の精製工程（脱色工程）後のグリセリド組成物の２－ノネナールの生成量も低いことが確認された。また、第１の精製工程後のグリセリド組成物の過酸化物価が低ければ、第２の精製工程（脱色工程及び脱臭工程）後のグリセリド組成物の戻り臭は抑制されていることが確認された。 From the results in Table 2, it is confirmed that if the peroxide value of the glyceride composition after the first purification step is low, the amount of 2-nonenal produced in the glyceride composition after the second purification step (decolorization step) is also low. It was done. Moreover, if the peroxide value of the glyceride composition after the first purification step was low, it was confirmed that the return odor of the glyceride composition after the second purification step (decolorization step and deodorization step) was suppressed. .
　［実施例１及び比較例５～７］
　実施例１及び２ならびに比較例１及び２と同様に、ＲＢＤパーム油を使用して、第１の精製工程後のグリセリド組成物の過酸化物価と、第２の精製工程後のグリセリド組成物中の２－ノネナール生成量及び戻り臭の有無を検討した。さらに、戻り臭の有無について検討した試料（すなわち、脱臭後のグリセリド組成物）中の２－ノネナール生成量についても検討した。その結果を表３に示す。 [Example 1 and Comparative Examples 5 to 7]
As in Examples 1 and 2 and Comparative Examples 1 and 2, using RBD palm oil, the peroxide value of the glyceride composition after the first purification step and the glyceride composition after the second purification step The amount of 2-nonenal produced and the presence or absence of a return odor were examined. Furthermore, the amount of 2-nonenal produced in the sample examined for the presence or absence of a return odor (that is, the glyceride composition after deodorization) was also examined. The results are shown in Table 3.
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-T000003
　表３の結果より、第１の精製工程後のグリセリド組成物の過酸化物価が低ければ、精製工程（脱色工程及び脱臭工程）後のグリセリド組成物の２－ノネナールの生成量も低いことが確認された。また、第１の精製工程後のグリセリド組成物の過酸化物価が低ければ、精製工程（脱色工程及び脱臭工程）後のグリセリド組成物の戻り臭は抑制されていることが確認された。 From the results in Table 3, it is confirmed that if the peroxide value of the glyceride composition after the first purification step is low, the amount of 2-nonenal produced in the glyceride composition after the purification step (decolorization step and deodorization step) is also low. It was done. Moreover, if the peroxide value of the glyceride composition after a 1st refinement | purification process is low, it was confirmed that the return odor of the glyceride composition after a refinement | purification process (a decoloring process and a deodorizing process) is suppressed.
　［実施例１及び３］
　実施例１及び２ならびに比較例１及び２と同様に、ＲＢＤパーム油を使用して、第１の精製工程後のグリセリド組成物の過酸化物価と、第２の精製工程後のグリセリド組成物中の２－ノネナール生成量及び戻り臭の有無を検討した。ただし、実施例３の脱臭工程は２４５℃で行った。その結果を表４に示す。 [Examples 1 and 3]
As in Examples 1 and 2 and Comparative Examples 1 and 2, using RBD palm oil, the peroxide value of the glyceride composition after the first purification step and the glyceride composition after the second purification step The amount of 2-nonenal produced and the presence or absence of a return odor were examined. However, the deodorization process of Example 3 was performed at 245 degreeC. The results are shown in Table 4.
Figure JPOXMLDOC01-appb-T000004
Figure JPOXMLDOC01-appb-T000004
　表４の結果より、同値の過酸化物価を有する第１の精製工程後のグリセリド組成物について、第２の精製工程（脱臭工程）時の温度条件が異なっていても、得られるグリセリド組成物の戻り臭は抑制されていることが確認された。 From the results of Table 4, the glyceride composition after the first purification step having the same peroxide value is obtained even if the temperature conditions during the second purification step (deodorization step) are different. It was confirmed that the return odor was suppressed.

Claims (7)

  1. 　第１の精製工程後のグリセリド組成物の過酸化物価を測定する測定工程と、
    　前記過酸化物価が所定の数値以上である第１の精製工程後のグリセリド組成物を除去する除去工程と、
    を含むグリセリド組成物の製造方法。     A measurement step for measuring the peroxide value of the glyceride composition after the first purification step;
    A removal step of removing the glyceride composition after the first purification step, wherein the peroxide value is a predetermined numerical value or more;
    The manufacturing method of the glyceride composition containing this.
  2. 　前記除去工程後のグリセリド組成物中の２－ノネナール濃度は、１．０～０ｐｐｍである請求項１に記載のグリセリド組成物の製造方法。 The method for producing a glyceride composition according to claim 1, wherein the 2-nonenal concentration in the glyceride composition after the removing step is 1.0 to 0 ppm.
  3. 　前記除去工程で除去された第１の精製工程後のグリセリド組成物に対して、第２の精製工程を行う工程を含む請求項１又は２に記載のグリセリド組成物の製造方法。 The manufacturing method of the glyceride composition of Claim 1 or 2 including the process of performing a 2nd refinement | purification process with respect to the glyceride composition after the 1st refinement | purification process removed by the said removal process.
  4. 　前記第２の精製工程後のグリセリド組成物中の２－ノネナール濃度は、１．０～０ｐｐｍである請求項３に記載のグリセリド組成物の製造方法。 The method for producing a glyceride composition according to claim 3, wherein the 2-nonenal concentration in the glyceride composition after the second purification step is 1.0 to 0 ppm.
  5. 　前記第１の精製工程後のグリセリド組成物は、上昇融点１０℃以上の植物油である請求項１から４のいずれか１項に記載のグリセリド組成物の製造方法。 The method for producing a glyceride composition according to any one of claims 1 to 4, wherein the glyceride composition after the first purification step is a vegetable oil having a rising melting point of 10 ° C or higher.
  6. 　前記第１の精製工程後のグリセリド組成物は、ＲＢＤ油である請求項１から５のいずれか１項に記載のグリセリド組成物の製造方法。 The method for producing a glyceride composition according to any one of claims 1 to 5, wherein the glyceride composition after the first purification step is RBD oil.
  7. 　第１の精製工程後のグリセリド組成物の過酸化物価を測定することで、第１の精製工程後のグリセリド組成物に対する第２の精製工程の必要性を判断する判断方法。 A determination method for determining the necessity of the second purification step for the glyceride composition after the first purification step by measuring the peroxide value of the glyceride composition after the first purification step.
PCT/JP2012/076795 2012-03-29 2012-10-17 Method for manufacturing glyceride composition and method for assessing necessity of second refining step for glyceride composition after first refining step WO2013145398A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2012076515A JP5917976B2 (en) 2012-03-29 2012-03-29 Method for producing glyceride composition and determination method for judging necessity of second purification step for glyceride composition after first purification step
JP2012-076515 2012-03-29

Publications (1)

Publication Number Publication Date
WO2013145398A1 true WO2013145398A1 (en) 2013-10-03

Family

ID=49258738

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2012/076795 WO2013145398A1 (en) 2012-03-29 2012-10-17 Method for manufacturing glyceride composition and method for assessing necessity of second refining step for glyceride composition after first refining step

Country Status (3)

Country Link
JP (1) JP5917976B2 (en)
MY (1) MY161111A (en)
WO (1) WO2013145398A1 (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07188692A (en) * 1993-12-27 1995-07-25 Ikeda Shiyokuken Kk Removal of peroxide from composition containing highly unsaturated fatty acid
JP2006045274A (en) * 2004-08-02 2006-02-16 Kaneka Corp Method for refining fat and oil
JP2011030482A (en) * 2009-07-31 2011-02-17 Nisshin Oillio Group Ltd Re-refined palm soft oil, and edible oil and fat composition and food and drink containing the re-refined palm soft oil

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07188692A (en) * 1993-12-27 1995-07-25 Ikeda Shiyokuken Kk Removal of peroxide from composition containing highly unsaturated fatty acid
JP2006045274A (en) * 2004-08-02 2006-02-16 Kaneka Corp Method for refining fat and oil
JP2011030482A (en) * 2009-07-31 2011-02-17 Nisshin Oillio Group Ltd Re-refined palm soft oil, and edible oil and fat composition and food and drink containing the re-refined palm soft oil

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"Flavour deterioration of soya-bean oil: Identification of intense odour compounds formed during flavour reversion.", FETT WISS TECHNOL, vol. 90, no. 9, 1988, pages 332 - 336 *

Also Published As

Publication number Publication date
JP2013203963A (en) 2013-10-07
MY161111A (en) 2017-04-14
JP5917976B2 (en) 2016-05-18

Similar Documents

Publication Publication Date Title
US9765281B2 (en) Removal of unwanted propanol components
JP4516897B2 (en) Edible oil and fat manufacturing method and edible oil and fat
US11814601B2 (en) Method for reducing content of saturated hydrocarbon, and refined palm-based oils and/or fats
JP5955119B2 (en) Method for producing edible fats and oils
EP2738243B1 (en) Purified glyceride composition and method for producing purified glyceride composition
JP5399544B1 (en) Method for producing refined fats and oils
JP6581715B2 (en) Method for producing refined palm oil and fat, and method for reducing glycidol, 3-chloropropane-1,2-diol, fatty acid ester and / or diglyceride in refined palm oil and fat
TWI556744B (en) Manufacture of grease
WO2015146248A1 (en) Production method for purified palm oil and fat
JP5873690B2 (en) Method for producing edible oil and fat and method for producing processed oil and fat product
JP5924755B2 (en) Method for producing glyceride composition
JP6253729B2 (en) Oil and fat manufacturing method
JP6021382B2 (en) Method for producing glyceride composition
JP5917976B2 (en) Method for producing glyceride composition and determination method for judging necessity of second purification step for glyceride composition after first purification step
JP5917975B2 (en) Method for producing glyceride composition
JP6857017B2 (en) Oil composition
JP7463129B2 (en) Quantitative method for wax esters in fats and oils
RU2786668C9 (en) Food oil refining
RU2786668C2 (en) Food oil refining
JP2016169391A (en) Palm-based oil and fat

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12872771

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 12872771

Country of ref document: EP

Kind code of ref document: A1