WO2010126136A1 - Procédé d'inhibition de la production d'un composé chloropropanol et substance de formation d'un composé chloropropanol dans l'huile et graisse de glycérides - Google Patents

Procédé d'inhibition de la production d'un composé chloropropanol et substance de formation d'un composé chloropropanol dans l'huile et graisse de glycérides Download PDF

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Publication number
WO2010126136A1
WO2010126136A1 PCT/JP2010/057691 JP2010057691W WO2010126136A1 WO 2010126136 A1 WO2010126136 A1 WO 2010126136A1 JP 2010057691 W JP2010057691 W JP 2010057691W WO 2010126136 A1 WO2010126136 A1 WO 2010126136A1
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Prior art keywords
glyceride
treatment
fats
chloropropanols
oil
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PCT/JP2010/057691
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English (en)
Japanese (ja)
Inventor
雅充 栗山
太 横溝
晴康 木田
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不二製油株式会社
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Priority to JP2011511470A priority Critical patent/JPWO2010126136A1/ja
Publication of WO2010126136A1 publication Critical patent/WO2010126136A1/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
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • 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
    • C11B3/003—Refining fats or fatty oils by enzymes or microorganisms, living or dead
    • 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
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B3/00—Refining fats or fatty oils
    • C11B3/10—Refining fats or fatty oils by adsorption
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B3/00—Refining fats or fatty oils
    • C11B3/12—Refining fats or fatty oils by distillation

Definitions

  • the present invention relates to a method for inhibiting the production of chloropropanols and their forming substances in glyceride oils and fats.
  • Chloropropanol is a generic name for substances in which chlorine is bonded to propanol.
  • 3-chloropropanediol which is one of these substances, has been conventionally produced in small amounts as a by-product when mainly producing amino acid solutions such as soy sauce. It is known and is said to be produced 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 suppressing the production of chloropropanols such as 3-chloropropanediol and 3-chloropropanediol fatty acid esters, and glycidol fatty acid esters as their forming substances, in glyceride fats and oils.
  • chloropropanols such as 3-chloropropanediol and 3-chloropropanediol fatty acid esters, and glycidol fatty acid esters as their forming substances, in glyceride fats and oils.
  • the present inventors have found that chloropropanols in glyceride oils and their substances are increased by a decolorization process, particularly a deodorization process, which is a normal oil refining process, and heat treatment such as frying and oven cooking. Also gained the knowledge that From this knowledge, as a result of intensive research on the above problems, the glyceride fat is treated with an adsorbent and / or alkali before heat treatment, or the diglyceride content in the fat is reduced. The inventors have found that chloropropanols in glyceride fats and oils and the formation of glycidol fatty acid esters, which are the forming substances thereof, can be suppressed, and have completed the present invention.
  • the present invention provides (1).
  • (2) A method for suppressing the production of chloropropanols and their forming substances in glyceride fats and oils, characterized by subjecting the glyceride fats and oils to an adsorbent treatment and / or an alkali treatment before the treatment in which the glyceride fats are heated to 100 ° C. or higher.
  • the method according to (2) wherein the adsorbent treatment and / or the alkali treatment is performed at a product temperature of the glyceride oil of less than 150 ° C.
  • the method according to (6), wherein the partial glyceride reduction treatment is a method using a partial glyceride-specific lipase.
  • chloropropanols such as 3-chloropropanediol and 3-chloropropanediol fatty acid esters and glycidol fatty acid esters that are their forming substances in glyceride oils.
  • Examples of glyceride oils and fats to which the method of the present invention can be applied include raw materials such as soybean, rapeseed, safflower, corn, sunflower, cottonseed, rice, olive, palm, palm, palm kernel, sesame, cow, pig, and fish. And unrefined fats and oils obtained by squeezing, extracting, crudely refined fats and oils obtained by filtering and centrifuging unrefined fats, and glyceride fats and oils obtained by esterification reaction of fatty acid and glycerin.
  • glyceride oil examples include soybean oil, rapeseed oil, safflower oil, corn oil, sunflower oil, cottonseed oil, rice oil, olive oil, palm oil, coconut oil, palm kernel oil, although it can apply also to edible refined fats and oils, such as sesame oil, beef tallow, pork tallow, and fish oil, among these, it can apply preferably to palm system fats and oils, especially crude palm oil (CPO).
  • the method of the present invention includes a refining process such as degumming, deoxidation, decolorization, deodorization, dewaxing, etc. to obtain refined palm oil (RBDPO) from crude palm oil (CPO) obtained by squeezing oil palm pulp, It can be preferably applied in the step of further purifying the refined palm oil (RBDPO) such as decolorization and deodorization.
  • a refining process such as degumming, deoxidation, decolorization, deodorization, dewaxing, etc.
  • the method of the present invention relates to a method for suppressing the production of chloropropanols in glyceride fats and glycidol fatty acid esters which are the forming substances thereof, but the chloropropanols in glyceride fats and glycidol fatty acid esters which are the forming substances are Since it is considered that oils and fats are produced by being heated at a high temperature, it is necessary to apply the method of the present invention described below before the treatment in which the oils and fats are heated to a high temperature of 100 ° C or higher, particularly 150 ° C or higher. It is.
  • the treatment of heating the glyceride fat to 100 ° C. or higher, further 150 ° C. or higher is a step of decolorization or deodorization when purifying the glyceride fat or oil, or hydrogenating the glyceride fat to harden the fat.
  • Manufacturing processes such as manufacturing, processes for producing transesterified oils and fats using glycerides and fats and chemical catalysts, and cooking processes such as frying, frying, or heating as a spray oil when used for cooking. Is mentioned.
  • the method of the present invention is a chloropropanol and its forming substance by treating a glyceride oil / fat heated to 100 ° C. or higher, particularly 150 ° C. or higher, with an adsorbent treatment of the glyceride oil / fat before the heating treatment.
  • It is characterized by reducing chlorine compounds and diglycerides, which are considered to be causative substances for the formation of glycidol fatty acid esters, from glyceride oils and fats, but as adsorbents, active clay, acidic clay, activated carbon, diatomaceous earth, silica gel, etc.
  • silica gel and coconut shell activated carbon are preferably used.
  • adsorbent treatment As a method of adsorbent treatment, 0.1 to 5% by weight of an adsorbent is added to glyceride oil and fat, and the mixture is heated for 50 to 80 ° C., preferably 50 to 110 ° C., 0.5 to 100 Torr for a certain time. And a method of contacting with stirring under reduced pressure.
  • the adsorbent treatment is a decolorization step before the deodorization step in the glyceride fat refining step, and the treatment step can be simplified by performing the adsorbent treatment simultaneously with the decolorization treatment.
  • glyceride oils and fats heated to 100 ° C. or higher, particularly 150 ° C. or higher are preferably subjected to alkali treatment before heating, and the alkali agent may be an alkali metal or alkaline earth.
  • Metal hydroxides and carbonates can be used. Specifically, sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, sodium hydrogen carbonate, and the like can be used.
  • sodium hydroxide is added to glyceride fats and oils in an amount of 0.8 to 1.2 times the neutralization equivalent of free fatty acid, and after stirring, centrifuged to remove the foots, and further washed with water and stirred. Thereafter, a method of centrifuging, removing the aqueous layer, and dehydrating under heating and reduced pressure can be used.
  • the adsorbent treatment and / or alkali treatment which is the method of the present invention, generates chloropropanols and their forming substances in glyceride fats and oils at high temperatures, so that the temperature of glyceride fats is less than 150 ° C., more preferably 100. It is preferable to carry out the reaction at a temperature lower than 0 ° C., more preferably 60 to 95 ° C.
  • the diglyceride content in the glyceride oil or fat is set to 2% by weight or less before the heating treatment with respect to the glyceride oil or fat heated to 100 ° C or higher, particularly 150 ° C or higher. .
  • the diglyceride content in glyceride fats and oils is high, the amount of 3-chloropropanediol and 3-chloropropanediol fatty acid esters that are chloropropanols and glycidol fatty acid esters that form them in the glyceride fats and oils increases by heating. Since there is a tendency, it is not preferable.
  • Methods for reducing the diglyceride content in glyceride fats and oils include distillation, chromatographic separation, and lipase treatment.
  • the present invention is a lipase that specifically acts on partial glycerides such as diglycerides.
  • a method for reducing the diglyceride content by an enzyme treatment such as the above is preferable because it is simple and does not go through a heating step that is exposed to a high temperature, and the method described in JP-A No. 62-61590 can be preferably applied.
  • glyceride oils and fats are heated at a high temperature of 80 to 270 ° C. in the normal refining process, in the decolorization process, and in particular in the deodorization process, chloropropanols and their forming substances in the oils and fats are likely to increase. It is known that the method of the present invention is carried out before the above decolorization step and / or deodorization step, which is heated to 100 ° C. or higher, particularly 150 ° C. or higher, so that The production of certain glycidol fatty acid esters can be suppressed.
  • the production of 3-chloropropanediol and 3-chloropropanediol fatty acid esters which are chloropropanols and glycidol fatty acid esters which are their forming substances is suppressed.
  • the content of chloropropanols and glycidol fatty acid ester which is a forming substance thereof 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.
  • 0.1 g of fat / oil is dissolved in 1 ml of t-butyl methyl ether, 250 ⁇ l of 20 ⁇ g / ml internal standard substance (3-MCPD-d 5 ethyl acetate solution) is added, and NaOCH 3 solution (0.5 mol / l NaOCH 3 in MeOH) is added. ) Mix with 1 ml and let stand at room temperature for 10 minutes. Subsequently, 3 ml of hexane, 3 ml of NaCl solution (NaCl 200 g / 1 l of water) and 0.1 ml of glacial acetic acid are added, and after stirring, the upper layer is removed.
  • 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 thereof, 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, other compounds forming 3-MCPD under the conditions of analysis are also detected.
  • 3-MCPD esters forming compounds is glycidol (oxirane-2-methanol)." (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))
  • the production of chloropropanols and their forming substances in the glyceride oil refining step is effectively suppressed, and the iodine value obtained by degumming, decolorizing and deodorizing CPO (crude palm oil).
  • the content of chloropropanols and their forming substances in RBDPO (refined palm oil) having a melting point of 50 to 55 and a rising melting point of 33 to 39 ° C. can be suppressed to 3.5 ppm or less, and further can be suppressed to 3 ppm or less.
  • the palm oil obtained by processing the refined palm oil (RBDPO) obtained by the method of the present invention or the olein fraction obtained by further fractionation has a low content of chloropropanols and its forming substances, When used as a frying oil, even if it is exposed to a heating process such as cooking, the production of chloropropanols and their forming substances can be suppressed.
  • % in an example means a basis of weight.
  • the obtained refined palm oil (RBDPO / IV: 52.2, ascending melting point: 36.5 ° C.) had a content of chloropropanols and its forming substances of 3.5 ppm.
  • the obtained refined palm oil (RBDPO / IV: 52.2, rising melting point: 36.5 ° C.) had a content of 2.9 ppm of chloropropanols and its forming substance.
  • the obtained refined palm oil (RBDPO / IV: 52.2, rising melting point: 36.5 ° C.) had a content of 3.9 ppm of chloropropanols and its forming substances.
  • the obtained refined palm oil (RBDPO / IV: 52.2, ascending melting point: 36.5 ° C.) had a content of chloropropanols and its forming substances of 4.8 ppm.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Fats And Perfumes (AREA)
  • Edible Oils And Fats (AREA)
  • Treatment Of Liquids With Adsorbents In General (AREA)

Abstract

La présente invention vise à inhiber la production de 3-chloropropanediol ou d'un ester d'acide gras et de 3-chloropropanediol qui est un composé chloropropanol et d'une substance capable de former le composé chloropropanol dans une huile et graisse de glycérides. Dans un procédé de purification d'une huile et graisse, l'huile et graisse est traitée par un adsorbant ou un alcali ou est réduite en teneur en glycérides partiels avant une étape de chauffage pour décolorer ou désodoriser l'huile et graisse. De cette manière, la production de 3-chloropropanediol ou d'un ester d'acide gras et de 3-chloropropanediol qui est un composé chloropropanol et d'une substance capable de former le composé chloropropanol dans l'huile et graisse peut être inhibée.
PCT/JP2010/057691 2009-04-30 2010-04-30 Procédé d'inhibition de la production d'un composé chloropropanol et substance de formation d'un composé chloropropanol dans l'huile et graisse de glycérides WO2010126136A1 (fr)

Priority Applications (1)

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JP2011511470A JPWO2010126136A1 (ja) 2009-04-30 2010-04-30 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の生成を抑制する方法

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JP2009-110448 2009-04-30
JP2009110448 2009-04-30
JP2009-229055 2009-09-30
JP2009229055 2009-09-30

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WO2011009841A1 (fr) * 2009-07-21 2011-01-27 Nestec S.A. Huile ou graisse alimentaire désodorisée présentant de faibles niveaux de mcpd liés et procédé de fabrication par purification sur carboxyméthylcellulose et/ou résine
JP2011174091A (ja) * 2011-06-01 2011-09-08 Showa Sangyo Co Ltd 遊離塩素を除去する工程を設けたパーム油の製造方法
WO2011138957A1 (fr) * 2010-05-07 2011-11-10 株式会社Adeka Procédé de purification d'huile ou de matière grasse comestible
WO2012173281A1 (fr) 2011-06-15 2012-12-20 Kao Corporation Procédé de fabrication de graisses et huiles raffinées
WO2013018412A1 (fr) * 2011-07-29 2013-02-07 日清オイリオグループ株式会社 Composition glycéridique purifiée et son procédé de production
JP2014009292A (ja) * 2012-06-29 2014-01-20 Taiyo Yushi Kk ３−クロロプロパン−１，２−ジオール脂肪酸エステルの量を低減させた油脂組成物の製造方法
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
CN103857776A (zh) * 2011-11-30 2014-06-11 日清奥利友集团株式会社 油脂的制造方法
JP2015034259A (ja) * 2013-08-09 2015-02-19 花王株式会社 油脂組成物
JP2015045023A (ja) * 2009-09-07 2015-03-12 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
JP2015105354A (ja) * 2013-12-02 2015-06-08 花王株式会社 精製魚油の製造方法
WO2015174822A1 (fr) * 2014-05-16 2015-11-19 Sime Darby Malaysia Berhad Procédé de raffinage d'un produit d'huile de fruit de palmier brute
US9217120B2 (en) 2011-12-23 2015-12-22 Loders Croklann B.V. Method of treating a vegetable oil
JP2016084353A (ja) * 2010-09-03 2016-05-19 ステパン スペシャルティー プロダクツ、エルエルシー カルボン酸エステル流中の有機ハロ及びオキシラン種の除去
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
JP2016124963A (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
JP2016132714A (ja) * 2015-01-19 2016-07-25 日清オイリオグループ株式会社 精製油脂の製造方法及び精製油脂の製造管理方法
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
JP6369586B1 (ja) * 2017-03-22 2018-08-08 不二製油株式会社 食用シアオレインおよびその製造法
JP2018135490A (ja) * 2017-02-23 2018-08-30 不二製油株式会社 シアオレインおよびその製造法
WO2018155490A1 (fr) * 2017-02-23 2018-08-30 不二製油グループ本社株式会社 Oléine de karité et son procédé de préparation
JP2018157820A (ja) * 2018-04-24 2018-10-11 不二製油株式会社 食用シアオレインおよびその製造法
WO2019139533A1 (fr) * 2018-01-09 2019-07-18 Aak Ab Procédé de raffinage physique de l'huile de palme
CN111330539A (zh) * 2018-12-19 2020-06-26 丰益(上海)生物技术研发中心有限公司 一种复合型固体吸附剂以及一种纯化油脂的方法
CN112592761A (zh) * 2020-09-30 2021-04-02 天津南侨食品有限公司 用于降低牛油中3-氯丙醇酯含量的控制方法
JP2021195471A (ja) * 2020-06-16 2021-12-27 日本水産株式会社 油脂中の３−ｍｃｐｄ含有量を低減させる方法
CN115197776A (zh) * 2022-07-05 2022-10-18 华南理工大学 一种酶法降低植物油中氯丙醇酯和缩水甘油酯的精炼工艺
WO2022249110A1 (fr) * 2021-05-25 2022-12-01 Sabic Global Technologies B.V. Systèmes et procédés pour traiter des acides gras
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Cited By (48)

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US8653288B2 (en) 2009-07-21 2014-02-18 Nestec S.A. Deodorized edible oil or fat with low levels of bound MCPD and process of making by carboxymethyl cellulose and/or resin purification
WO2011009841A1 (fr) * 2009-07-21 2011-01-27 Nestec S.A. Huile ou graisse alimentaire désodorisée présentant de faibles niveaux de mcpd liés et procédé de fabrication par purification sur carboxyméthylcellulose et/ou résine
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