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WO2013018430A1 - Procédé pour la production d'une composition de glycérides - Google Patents

Procédé pour la production d'une composition de glycérides Download PDF

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Publication number
WO2013018430A1
WO2013018430A1 PCT/JP2012/064131 JP2012064131W WO2013018430A1 WO 2013018430 A1 WO2013018430 A1 WO 2013018430A1 JP 2012064131 W JP2012064131 W JP 2012064131W WO 2013018430 A1 WO2013018430 A1 WO 2013018430A1
Authority
WO
WIPO (PCT)
Prior art keywords
glyceride composition
ppm
citric acid
oils
oil
Prior art date
Application number
PCT/JP2012/064131
Other languages
English (en)
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 WO2013018430A1 publication Critical patent/WO2013018430A1/fr

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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
    • C11B5/00—Preserving by using additives, e.g. anti-oxidants
    • C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B20/00—Preservation of edible oils or fats
    • A23B20/30—Preservation of other edible oils or fats, e.g. shortenings or cooking oils
    • 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
    • C11B3/12—Refining fats or fatty oils by distillation
    • C11B3/14—Refining fats or fatty oils by distillation with the use of indifferent gases or vapours, e.g. steam

Definitions

  • the present invention relates to a method for producing a glyceride composition and a glyceride composition produced through the production method.
  • 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. Further, Patent Document 2 discloses a re-refined palm soft oil having a good flavor having a specific chromaticity by further performing a decoloring process and a deodorizing process on a refined palm soft oil subjected to at least a deodorizing process. Is disclosed.
  • the purified fats and oils are generally stored at a low temperature.
  • a “returning substance” that causes deterioration of the flavor of fats and oils is generated during low-temperature storage.
  • the details of the “returning substance” are not known, the presence of this substance in the refined fats and oils causes the flavor of the fats and oils to return to the state prior to purification, causing a flavor deterioration called “returning odor”. .
  • RBD oil refined Bleached Deodorized
  • returned substances may be produced in fats and oils during storage of RBD oils at low temperatures.
  • the present invention has been made in view of the circumstances as described above, and provides a method for suppressing the deterioration of the flavor of fats and oils during storage at low temperatures.
  • the present inventors can suppress the production of “returning substances” generated during storage at low temperatures by adding a predetermined amount of citric acid, ascorbic acid, or citric acid monoglyceride to the glyceride composition.
  • the present invention has been completed. Specifically, the present invention provides the following.
  • the manufacturing method of a glyceride composition including the process of adding either of the following to a glyceride composition in a deodorizing process.
  • Citric acid in an amount of 0.5 ppm to 10 ppm in the glyceride composition
  • Ascorbic acid in an amount of 5 ppm to 100 ppm in the glyceride composition
  • Citric acid monoglyceride in an amount of 250 ppm or less
  • 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 method for producing a glyceride composition of the present invention is characterized by including a step of adding a predetermined amount of citric acid, ascorbic acid, or citric acid monoglyceride to the glyceride composition in the deodorization step.
  • the present inventors have found that when a conventional amount of a compound having a chelating effect (for example, 20 to 1000 ppm of citric acid) is added to the fat and oil in the deodorizing step, the amount of 2-nonenal produced in the fat and oil is increased. I found that it would increase.
  • a conventional amount of a compound having a chelating effect for example, 20 to 1000 ppm of citric acid
  • the glyceride composition has a chelate effect in an amount smaller than the conventional amount, (I) citric acid in an amount of 0.5 ppm to 10 ppm in the glyceride composition (ii) ascorbic acid in an amount of 5 ppm to 100 ppm in the glyceride composition, or (iii) 5 ppm to 250 ppm in the glyceride composition
  • citric acid in an amount of 0.5 ppm to 10 ppm in the glyceride composition
  • ascorbic acid in an amount of 5 ppm to 100 ppm in the glyceride composition
  • 5 ppm to 250 ppm in the glyceride composition By adding any one of the above-mentioned amounts of citric acid monoglyceride, the formation of 2-nonenal in fats and oils during storage at low temperature is suppressed while suppressing the formation of unfavorable compounds due to the automatic oxidation of fats and oils and the flavor of fats and oils
  • citric acid, ascorbic acid, or citric acid monoglyceride in the present invention can be used in combination with other compounds having a chelating effect.
  • examples of other compounds having a chelating effect include phosphoric acid and C2-8 carboxylic acid.
  • deodorization process In the method for producing a glyceride composition of the present invention, deodorization may be carried out under the temperature conditions of 210 to 265 ° C., preferably 215 to 260 ° C., more preferably used in the usual method for producing fats and oils. 215-245 ° C. Even if the glyceride composition is deodorized under a temperature condition lower than the temperature condition used in the usual method for producing fats and oils, by adding citric acid, ascorbic acid or citric acid monoglyceride, Formation can be preferably suppressed.
  • the deodorizing time is preferably 10 to 150 minutes, more preferably 30 to 100 minutes.
  • the apparatus used in the deodorization step is not particularly limited, and may be a tray type apparatus used in the production of ordinary deodorized oil.
  • Addition of citric acid, ascorbic acid, or citric acid monoglyceride to the glyceride composition in the deodorization step can be performed at any stage in the deodorization step. Since citric acid, ascorbic acid, or citric acid monoglyceride is decomposed and removed under the heating conditions of the deodorization process, in order to fully exert the chelating effect of citric acid, ascorbic acid, or citric acid monoglyceride, the end of the deodorization process It is preferable to add to. “The end of the deodorization process” will be described by taking a tray-type device as an example.
  • the tray type apparatus includes a deodorizing tower having several trays.
  • Deodorization of the glyceride composition is performed by heating the glyceride composition by exposure to water vapor or the like while lowering the glyceride composition from the upper tray to the lower tray of the deodorization tower.
  • the stage where the oil temperature of the glyceride composition descending to the lower tray in the deodorization tower reaches 110 to 180 ° C. can be called “the end of the deodorization process”.
  • citric acid, ascorbic acid, or citric acid It is preferable to add an aqueous solution of monoglyceride.
  • 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 glyceride composition is not particularly limited, but a refined oil or an unrefined oil may be used. According to the present invention, it is possible to preferably suppress the production of “return substances” in oils and fats stored at low temperatures regardless of refined oils and non-refined oils.
  • Examples of the refined oil include rapeseed oil, soybean oil, rice oil, safflower oil, grape oil, sunflower oil, wheat germ oil, corn oil, cottonseed oil, sesame oil, peanut oil, flux oil, Edible oils such as sesame oil, olive oil, palm oil, palm kernel oil, coconut oil, mixed vegetable oils mixed with two or more of these, or palm olein, palm stearin, palm super olein, palm mid fraction, etc.
  • edible oils produced by a direct esterification reaction such as medium-chain fatty acid triglycerides can be used.
  • Palm-based oils and fats (palm oil, palm kernel oil, palm olein, palm stearin, palm super olein, palm mid-fraction, etc.) and fractionated oils thereof are preferred because of the remarkable deterioration in flavor at low temperatures.
  • save by a "returning substance” can be preferably suppressed also in the blend fats and oils which mix
  • Plant oil purification methods include chemical refining (chemical refining) and physical refining (physical refining), and any refining method may be used.
  • the former chemical refining is a method usually used for refining vegetable oils. Crude oil obtained by squeezing and extracting the plant as raw material is degummed, deoxidized, decolorized, and dewaxed. After being deodorized, it is refined and becomes refined oil.
  • the latter physical refining is a method that is often performed with palm oil, palm oil or the like, and crude oil obtained by pressing palm or palm as a raw material is degummed, decolorized, or deoxidized. After being deodorized, it is refined and becomes refined oil.
  • the glyceride composition of the present invention is obtained by the above-described method for producing the glyceride composition of the present invention. According to the glyceride composition of the present invention, the amount of “returning substance” in the glyceride composition, ie, 2-nonenal, is suppressed, and the flavor deterioration of fats and oils is suppressed.
  • Comparative Example 2 Except performing a deodorizing process at 245 degreeC, it processed by the method equivalent to the comparative example 1, and the glyceride composition of the comparative example 2 was obtained.
  • Comparative Example 4 A glyceride composition of Comparative Example 4 was obtained by performing the same treatment as Comparative Example 1 except that the deodorization treatment was performed at 200 ° C. and citric acid was added to 30 ppm in the glyceride composition.
  • Comparative Example 5 The glyceride composition of Comparative Example 5 was obtained in the same manner as in Comparative Example 1 except that ascorbic acid was added to 1 ppm in the glyceride composition instead of citric acid.
  • Comparative Example 6 The glyceride composition of Comparative Example 6 was obtained in the same manner as in Comparative Example 1 except that ascorbic acid was added to 3 ppm in the glyceride composition instead of citric acid.
  • Comparative Example 7 A glyceride composition of Comparative Example 7 was obtained in the same manner as in Comparative Example 1 except that citric acid monoglyceride was added to 300 ppm in the glyceride composition instead of citric acid.
  • citric acid MG indicates citric acid monoglyceride.
  • Example 1 Except for adding citric acid to 3 ppm in the glyceride composition, the treatment was carried out by the same method as in Comparative Example 1, and the glyceride composition of Example 1 was obtained.
  • Example 2 Except having added citric acid so that it might become 10 ppm in a glyceride composition, it processed by the method equivalent to the comparative example 1, and the glyceride composition of Example 2 was obtained.
  • Example 3 The glyceride composition of Example 3 was obtained by carrying out the treatment in the same manner as in Comparative Example 1 except that the deodorization treatment was performed at 245 ° C. and citric acid was added to 3 ppm in the glyceride composition.
  • Example 4 The glyceride composition of Example 4 was obtained by carrying out the deodorization treatment at 245 ° C. and carrying out the same treatment as in Comparative Example 1 except that citric acid was added to 10 ppm in the glyceride composition.
  • Example 5 The glyceride composition of Example 5 was obtained by performing the same treatment as in Comparative Example 1 except that citric acid was added to 1 ppm in the glyceride composition.
  • Example 6 A glyceride composition of Example 6 was obtained in the same manner as in Comparative Example 1, except that ascorbic acid was added to 10 ppm in the glyceride composition instead of citric acid.
  • Example 7 The glyceride composition of Example 7 was obtained by performing the same treatment as in Comparative Example 1 except that ascorbic acid was added instead of citric acid.
  • Example 8 A glyceride composition of Example 8 was obtained by performing the same treatment as in Comparative Example 1 except that ascorbic acid was added to 100 ppm in the glyceride composition instead of citric acid.
  • Example 9 A glyceride composition of Example 9 was obtained in the same manner as in Comparative Example 1, except that citric acid monoglyceride was added to 10 ppm in the glyceride composition instead of citric acid.
  • citric acid MG indicates citric acid monoglyceride.
  • Example 10 A glyceride composition of Example 10 was obtained in the same manner as in Comparative Example 1 except that citric acid monoglyceride was added to 100 ppm in the glyceride composition instead of citric acid.
  • Example 11 A glyceride composition of Example 11 was obtained in the same manner as in Comparative Example 1, except that citric acid monoglyceride was added to 200 ppm in the glyceride composition instead of citric acid.
  • Each 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 of storage, the sample bottle was taken out and dissolved by heating at 50 to 80 ° C., and then sensory evaluation was performed with a few grams in the mouth. In this case, the five-step evaluation was in accordance with the criteria described in Table 1.
  • 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 “Presence / absence of low temperature return odor” in Tables 2-4.
  • Each 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 third day of storage take out the sample bottle, separate 1-10 g of each glyceride composition into a headspace vial tube, and adsorb volatile substances generated when heated at 50-100 ° C for 30-100 minutes Adsorbed with an agent.
  • 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.
  • each component isolated by the column was detected by a detector to identify 2-nonenal, and then quantified with a reagent manufactured by Wako Pure Chemical Industries (Wako First Grade). The results are shown in “2-nonenal production” in Tables 2-4.
  • the trans fatty acid conversion rate in the glyceride composition was determined as follows. First, the trans fatty acid content in all the constituent fatty acids in the glyceride compositions of each Example and each Comparative Example was measured based on AOCS (American Official Chemistry's Society) Official Method Ce 1f-96. Subsequently, the trans fatty acid conversion rate was calculated
  • Trans fatty acid conversion ratio of unsaturated fatty acid ((trans isomer mass of unsaturated fatty acid constituting the refined fat / oil ⁇ trans isomer mass of unsaturated fatty acid constituting the fat / oil before purification)) / (Mass of total fatty acids constituting the oil before refining)) ⁇ 100

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Microbiology (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Zoology (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Fats And Perfumes (AREA)
  • Edible Oils And Fats (AREA)

Abstract

L'invention porte sur un procédé pour la suppression de la dégradation du goût d'une huile ou matière grasse pendant le stockage à de basses températures. Le procédé pour la production d'une composition de glycérides de la présente invention est caractérisé en ce qu'il comprend une étape dans laquelle l'un des composants (i)-(iii) décrits ci-dessous est ajouté à une composition de glycérides dans un processus de désodorisation : (i) de l'acide citrique à raison de 0,5 ppm à 10 ppm (inclus) par rapport à la composition de glycérides ; (ii) de l'acide ascorbique à raison de 5 ppm à 100 ppm (inclus) par rapport à la composition de glycérides ; (iii) du citrate de monoglycéride à raison de 5 ppm à 250 ppm (inclus) par rapport à la composition de glycérides.
PCT/JP2012/064131 2011-07-29 2012-05-31 Procédé pour la production d'une composition de glycérides WO2013018430A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2011166895 2011-07-29
JP2011-166895 2011-07-29
JP2012081849A JP6021382B2 (ja) 2011-07-29 2012-03-30 グリセリド組成物の製造方法
JP2012-081849 2012-03-30

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WO2013018430A1 true WO2013018430A1 (fr) 2013-02-07

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MY (1) MY165750A (fr)
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025004509A1 (fr) * 2023-06-29 2025-01-02 株式会社Ｊ－オイルミルズ Procédé de production d'une composition d'huile/matière grasse pour friture et procédé de prévention d'augmentation d'indice d'acidité dans une composition d'huile/matière grasse pour friture

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6704683B2 (ja) * 2014-06-24 2020-06-03 花王株式会社 油相及び水相を含有する液体調味料の製造方法
JP7239908B2 (ja) * 2021-03-29 2023-03-15 不二製油株式会社 物理精製パーム油（ｒｂｄｐо）の製造方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08283773A (ja) * 1995-04-20 1996-10-29 Sho Yonezawa 化学合成添加物無添加サラダ油製造方法
WO2001096506A1 (fr) * 2000-06-12 2001-12-20 Fuji Oil Company, Limited Procede servant a produire de la graisse
JP2007056181A (ja) * 2005-08-26 2007-03-08 Toyo Olive Co Ltd 機能性オリーブ油、その製造方法およびその用途
WO2010050449A1 (fr) * 2008-10-28 2010-05-06 日清オイリオグループ株式会社 Huile de palme, distillats désodorisés et procédés de fabrication correspondants

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001096506A (ja) * 1999-09-30 2001-04-10 Shoichi Tanaka 平面切削加工装置
JP5700503B2 (ja) * 2009-09-07 2015-04-15 日清オイリオグループ株式会社 グリセリド組成物及び該グリセリド組成物の製造方法
MY158557A (en) * 2009-09-30 2016-10-14 Fuji Oil Holdings Inc Method for reducing chloropropanols and formative substance thereof, glycidol fatty acid esters, in glyceride oils

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08283773A (ja) * 1995-04-20 1996-10-29 Sho Yonezawa 化学合成添加物無添加サラダ油製造方法
WO2001096506A1 (fr) * 2000-06-12 2001-12-20 Fuji Oil Company, Limited Procede servant a produire de la graisse
JP2007056181A (ja) * 2005-08-26 2007-03-08 Toyo Olive Co Ltd 機能性オリーブ油、その製造方法およびその用途
WO2010050449A1 (fr) * 2008-10-28 2010-05-06 日清オイリオグループ株式会社 Huile de palme, distillats désodorisés et procédés de fabrication correspondants

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025004509A1 (fr) * 2023-06-29 2025-01-02 株式会社Ｊ－オイルミルズ Procédé de production d'une composition d'huile/matière grasse pour friture et procédé de prévention d'augmentation d'indice d'acidité dans une composition d'huile/matière grasse pour friture

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Publication number Publication date
JP6021382B2 (ja) 2016-11-09
MY165750A (en) 2018-04-23
JP2013049829A (ja) 2013-03-14

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