WO2011055732A1 - Procédé de réduction de chloropropanols et de substances formant du chloropropanol dans une huile ou matière grasse glycéridique - Google Patents

Procédé de réduction de chloropropanols et de substances formant du chloropropanol dans une huile ou matière grasse glycéridique Download PDF

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Publication number
WO2011055732A1
WO2011055732A1 PCT/JP2010/069548 JP2010069548W WO2011055732A1 WO 2011055732 A1 WO2011055732 A1 WO 2011055732A1 JP 2010069548 W JP2010069548 W JP 2010069548W WO 2011055732 A1 WO2011055732 A1 WO 2011055732A1
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Prior art keywords
fat
glyceride
oil
sfc
chloropropanols
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Application number
PCT/JP2010/069548
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English (en)
Japanese (ja)
Inventor
雅充 栗山
陽子 黒澤
仁美 尾森
暁 森田
朋美 井上
太 横溝
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不二製油株式会社
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Priority to JP2011539373A priority Critical patent/JPWO2011055732A1/ja
Publication of WO2011055732A1 publication Critical patent/WO2011055732A1/fr

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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
    • C11B3/02—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 reducing chloropropanols and substances forming the same in glyceride oils and fats.
  • Chloropropanol is a general term for substances in which chlorine is bonded to propanol, but 3-chloropropanediol, which is one of these substances, has conventionally been produced in small quantities as a by-product when mainly producing amino acid solutions such as soy sauce. In addition, it is said that it is formed by the presence of lipids and salt in the process of cooking food.
  • Non-Patent Document 1 Korean Patent Document 1
  • Non-Patent Document 2 glycidol fatty acid esters are present as forming substances in the process of producing chloropropanols in glyceride oils.
  • An object of the present invention is to provide a method for reducing chloropropanols such as 3-chloropropanediol and 3-chloropropanediol fatty acid ester and glycidol fatty acid ester which is a forming substance thereof.
  • the present inventors can reduce chloropropanols and their forming substances in glyceride oils and fats by purifying glyceride oils and fats that have undergone decolorization and deodorization processes after contacting with an alkaline aqueous solution. As a result, the present invention has been completed.
  • the present inventors contacted a glyceride oil / fat that has undergone decoloring and deodorizing processes with a solid alkaline substance having a weight ratio of 150 to 750 ppm, and SFC (20 ° C. and / or 35 ° C.) of the obtained oil / fat.
  • SFC 20 ° C. and / or 35 ° C.
  • the first of the present invention is a method for reducing chloropropanols and their forming substances in glyceride fats and oils, wherein the glyceride fats and oils that have undergone decoloring and deodorizing steps are purified after contacting with an alkaline aqueous solution.
  • the second is the method described in the first, wherein the glyceride oil is purified at 230 ° C. or lower after contact with the alkaline aqueous solution.
  • the third method is either the first method or the second method in which the glyceride fat is washed with water after the contact with the alkaline aqueous solution and before purification.
  • a solid alkaline substance with a weight ratio of 150 to 750 ppm is brought into contact with the glyceride fats and oils that have undergone the decoloring and deodorizing steps, and the SFC (20 ° C and / or 35 ° C) of the resulting fats and oils is brought into contact with the solid alkaline substances
  • SFC Solid Fat Content / solid fat index
  • the fifth is the method according to the fourth, wherein the solid alkaline substance is in the form of a powder containing 60% by weight or more of particles having a particle diameter of 1.2 mm or less.
  • 3-chloropropanediol and 3-chloropropanediol fatty acid ester which are chloropropanols in glyceride fats and oils, and glycidol fatty acid ester which is a forming substance thereof can be reduced.
  • oils and fats used in the present invention include soybean oil, rapeseed oil, corn oil, cottonseed oil, peanut oil, sunflower oil, rice bran oil, safflower oil, safflower oil, olive oil, sesame oil, palm oil, palm oil, palm kernel oil and other plants.
  • Oils and fats such as beef tallow and pork tallow, and processed oils and fats that have been subjected to separation, hydrogenation, transesterification, etc., or a combination of these. Among them, among these, it can be preferably applied to palm oils.
  • alkali metal or alkaline earth metal hydroxides and carbonates can be used, and specifically, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate. Sodium hydrogen carbonate or the like can be used.
  • alkaline agents may be those generally used for foods and pharmaceuticals, and may be used alone or in combination of two or more. Among these, sodium hydroxide is preferably used.
  • a glyceride fat is purified after contacting with a sodium hydroxide aqueous solution
  • a prescribed amount of the sodium hydroxide aqueous solution is added to the glyceride fat heated to 70 ° C., and the oil layer is dehydrated after stirring and centrifuging.
  • chloropropanols and their forming substances in glyceride fats and oils can be reduced.
  • the method of the present invention preferably further performs decolorization and deodorization purification after contact with the aqueous alkali solution.
  • the purification step at this time is carried out at 230 ° C. or lower, the chloropropanols in the glyceride oil and fat and its The effect of reducing the forming substance is obtained, which is preferable.
  • the method of the present invention can further reduce chloropropanols and substances forming the same in glyceride fats and oils by washing with an aqueous alkali solution and before purification.
  • alkoxide compounds alkali metal or alkaline earth metal hydroxides, and carbonates
  • sodium methoxide, sodium hydroxide, hydroxide Potassium, calcium hydroxide, sodium carbonate, sodium hydrogen carbonate and the like can be used.
  • These solid alkaline substances may be those generally used for foods and pharmaceuticals, and may be used alone or in combination of two or more.
  • sodium methoxide is preferably used.
  • a solid alkali substance having a weight ratio of 150 to 750 ppm is brought into contact with the glyceride fat that has undergone the decoloring and deodorizing steps.
  • SFC (20 ° C. and / or 35 ° C.) is in the range of 0.9 to 1.1 with respect to SFC (20 ° C. and / or 35 ° C.) of fats and oils when obtained without contact with solid alkaline substance It is difficult and unpreferable.
  • SFC (20 degreeC and / or 35 degreeC) of the obtained fats and oils is made without contacting a solid alkali substance.
  • the SFC (20 ° C. and / or 35 ° C.) of the fat when obtained is characterized by being in the range of 0.9 to 1.1, and by making it within this range, the physical properties of the fat and oil are greatly increased.
  • chloropropanols such as 3-chloropropanediol and 3-chloropropanediol fatty acid ester, and glycidol fatty acid ester as a forming substance thereof in the glyceride oil can be reduced.
  • the above range is not substantially exceeded.
  • it can be controlled within the above range by a method such as shortening the contact time.
  • purification such as decolorization and deodorization is preferably performed, and either decolorization or deodorization may be performed, but both are preferably performed.
  • the shape of the solid alkaline substance used in the present invention is not particularly limited as long as it can be contacted in solid form, not in a solution dissolved in a solvent or the like. However, in order to make contact more efficiently, it is in a powder form. More preferably, a fine powder form containing 60 w / w% or more of particles having a particle size of 1.2 mm or less is suitable.
  • the method for contacting the solid alkaline substance is not particularly limited, but the method is to add the solid alkaline substance to the heated glyceride oil and fat, remove the solid alkaline substance by centrifugation after mixing and stirring for about 30 minutes.
  • the method is to add the solid alkaline substance to the heated glyceride oil and fat, remove the solid alkaline substance by centrifugation after mixing and stirring for about 30 minutes.
  • a prescribed amount of sodium methoxide is added to glyceride oil heated to 85 ° C. and reacted under vacuum. After stirring and centrifuging for the purpose of neutralization and washing with water, the oil layer is dehydrated, decolorized, and deodorized to reduce chloropropanols and substances forming the glyceride oil.
  • the glyceride fats and oils obtained by the method of the present invention have a reduced content of 3-chloropropanediol and 3-chloropropanediol fatty acid esters that are chloropropanols, and glycidol fatty acid esters that form the chloropropanols.
  • the content of propanols and glycidol fatty acid esters which are substances forming the propanols is measured by the following method with reference to the following literature. (Determination of total 3-chloropropane-1,2-diol (3-MCPD) in editable oils by cleavage of MCPD esters with sodium method. Eur. J. Lipid Sci.
  • the upper layer is subjected to GS-MS analysis.
  • GC-MS is quantified using molecular ion peaks m / z 196 (3-MCPD) and m / z 201 (3-MCPD-d 5 ).
  • the above method is adopted as a method for measuring 3-chloropropanediol fatty acid ester and glycidol fatty acid ester, which is a forming substance, in Germany (Deutsche Gesellchaft fur Fettsch: DGF). Hydrolyzes 3-chloropropanediol fatty acid ester and its forming substance glycidol fatty acid ester in fats and oils, all 3-chloropropanediol fatty acid ester and its forming substance glycidol fatty acid ester as 3-MCPD Measuring. “With this method, another compounds forming 3-MCPD under the conditions of the anomalous areal and detected three-MCPD esters”. (Ester-bound 3-chloropropane-1,2-diol (3-MCPD esters) and 3-MCPD forming subnets: DGF Standard Methods Section C-Fats / C-III 18 (09))
  • RBD palm olein (iodine value: 67) was added with 2% by weight of white clay, decolorized at 110 ° C. and 20 Torr for 10 minutes, and then deodorized at 250 ° C. and 2 Torr for 90 minutes.
  • the content of chloropropanols and the substances forming the edible palm olein was 6.1 ppm.
  • the SFC% is 25.5% at 20 ° C. (1.0 with respect to the SFC of the fat obtained in Comparative Example 2), and 6.2% at 35 ° C. (the SFC of the fat obtained in Comparative Example 2). 1.0), which was in the range of 0.9 to 1.1.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention porte sur un procédé selon lequel de l'huile ou de la matière grasse glycéridique après l'étape de décoloration et de désodorisation est mise en contact avec une solution aqueuse alcaline puis purifiée, ce qui réduit de cette manière les chloropropanols tels que le 3-chloropropanediol ou les esters d'acides gras et de 3-chloropropanediol et les substances formant du chloropropanol présents dans l'huile ou la matière grasse glycéridique. De façon spécifique, l'invention porte sur un procédé selon lequel lorsque de l'huile ou de la matière grasse glycéridique après l'étape de décoloration et de désodorisation est mise en contact avec une substance alcaline solide en un rapport pondéral de 150-750 ppm puis purifiée, la SFC (teneur en matières grasses solides, à 20˚C et/ou 35˚C) de l'huile ou de la matière grasse devant être obtenue est réglée pour être de 0,9-1,1 par rapport à la SFC (à 20˚C et/ou 35˚C) de l'huile ou de la matière grasse qui est purifiée sans être mise en contact avec la substance alcaline solide. En conséquence, les chloropropanols tels que le 3-chloropropanediol ou les esters d'acides gras et de 3-chloropropanediol et les substances formant du chloropropanol dans l'huile ou la matière grasse glycéridique peuvent être réduits.
PCT/JP2010/069548 2009-11-06 2010-11-04 Procédé de réduction de chloropropanols et de substances formant du chloropropanol dans une huile ou matière grasse glycéridique WO2011055732A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2011539373A JPWO2011055732A1 (ja) 2009-11-06 2010-11-04 グリセリド油脂中のクロロプロパノール類及びその形成物質を低減する方法

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JP2009-255352 2009-11-06
JP2009255352 2009-11-06
JP2009278246 2009-12-08
JP2009-278246 2009-12-08

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011147436A (ja) * 2010-01-19 2011-08-04 Cj Cheiljedang Corp ３−ｍｃｐｄ−ｆｓが低減化された食用油脂の製造方法
JP2014501808A (ja) * 2010-11-19 2014-01-23 ロダース・クロックラーン・ビー・ブイ 精製された植物油を製造する方法
JP2015105354A (ja) * 2013-12-02 2015-06-08 花王株式会社 精製魚油の製造方法
JP2015142529A (ja) * 2014-01-31 2015-08-06 花王株式会社 油脂組成物
JP2016123330A (ja) * 2014-12-26 2016-07-11 ミヨシ油脂株式会社 食用油脂中のクロロプロパノール類を低減する方法
EP2874501B1 (fr) 2012-07-18 2016-07-20 Aak Ab Réduction de composés de mcpd dans l'huile végétale raffinée pour aliments
JP2016169391A (ja) * 2011-07-29 2016-09-23 日清オイリオグループ株式会社 パーム系油脂
EP2611767B1 (fr) 2010-09-03 2017-10-25 Stepan Specialty Products, LLC Élimination des espèces organohalogénées et oxiranes dans les courants d'ester d'acide carboxylique
JP2018095758A (ja) * 2016-12-15 2018-06-21 日清オイリオグループ株式会社 油脂組成物
JPWO2018043701A1 (ja) * 2016-09-02 2019-06-24 太陽油脂株式会社 育児用調製粉乳に用いるための油脂組成物
EP3385360B1 (fr) 2011-02-10 2021-03-31 Cargill, Incorporated Procédé de réduction de la teneur en 3-mcpd dans des huiles raffinées

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JPS61278595A (ja) * 1985-06-03 1986-12-09 不二製油株式会社 油脂中のジグリセリド成分除去法
WO2009075278A1 (fr) * 2007-12-12 2009-06-18 Fuji Oil Company, Limited Graisse ou huile raffinée à base de palme et leur procédé de production

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JP2999232B2 (ja) * 1990-07-31 2000-01-17 マルハ株式会社 蛋白質加水分解物の製造方法
JP5688207B2 (ja) * 2009-03-03 2015-03-25 日清オイリオグループ株式会社 食用油の製造方法及び該方法により製造された食用油

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WO2009075278A1 (fr) * 2007-12-12 2009-06-18 Fuji Oil Company, Limited Graisse ou huile raffinée à base de palme et leur procédé de production

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011147436A (ja) * 2010-01-19 2011-08-04 Cj Cheiljedang Corp ３−ｍｃｐｄ−ｆｓが低減化された食用油脂の製造方法
USRE48861E1 (en) 2010-09-03 2021-12-28 Stepan Specialty Products, Llc Elimination of organohalo and oxirane species in carboxylic acid ester streams
EP2611767B1 (fr) 2010-09-03 2017-10-25 Stepan Specialty Products, LLC Élimination des espèces organohalogénées et oxiranes dans les courants d'ester d'acide carboxylique
JP2014501808A (ja) * 2010-11-19 2014-01-23 ロダース・クロックラーン・ビー・ブイ 精製された植物油を製造する方法
EP3385360B1 (fr) 2011-02-10 2021-03-31 Cargill, Incorporated Procédé de réduction de la teneur en 3-mcpd dans des huiles raffinées
JP2016169391A (ja) * 2011-07-29 2016-09-23 日清オイリオグループ株式会社 パーム系油脂
CN108669240A (zh) * 2012-07-18 2018-10-19 Aak股份有限公司 食品用精炼植物油中mcpd-化合物的减少
EP2874501B1 (fr) 2012-07-18 2016-07-20 Aak Ab Réduction de composés de mcpd dans l'huile végétale raffinée pour aliments
JP2015105354A (ja) * 2013-12-02 2015-06-08 花王株式会社 精製魚油の製造方法
JP2015142529A (ja) * 2014-01-31 2015-08-06 花王株式会社 油脂組成物
WO2015115584A1 (fr) * 2014-01-31 2015-08-06 花王株式会社 Composition de graisse ou d'huile
JP2016123330A (ja) * 2014-12-26 2016-07-11 ミヨシ油脂株式会社 食用油脂中のクロロプロパノール類を低減する方法
JPWO2018043701A1 (ja) * 2016-09-02 2019-06-24 太陽油脂株式会社 育児用調製粉乳に用いるための油脂組成物
JP2018095758A (ja) * 2016-12-15 2018-06-21 日清オイリオグループ株式会社 油脂組成物
EP3556833A4 (fr) * 2016-12-15 2020-05-20 The Nisshin OilliO Group, Ltd. Composition d'huile/graisse

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