WO2010126136A1 - Method for inhibiting production of chloropropanols and chloropropanol-forming substances in glyceride oils and fats - Google Patents

Method for inhibiting production of chloropropanols and chloropropanol-forming substances in glyceride oils and fats Download PDF

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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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glyceride
treatment
fats
chloropropanols
oil
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PCT/JP2010/057691
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French (fr)
Japanese (ja)
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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/en
Publication of WO2010126136A1 publication Critical patent/WO2010126136A1/en

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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.

Abstract

Provided is a method for inhibiting the production of chloropropanols such as 3-chloropropanediol or 3-chloropropanediol fatty acid esters and chloropropanol-forming substances in glyceride oils and fats. It is possible to inhibit the production of chloropropanols such as 3-chloropropanediol or 3-chloropropanediol fatty acid esters and chloropropanol-forming substances in an oil or fat by reducing the partial glyceride content of the oil or fat or treating the oil or fat with an adsorbent or an alkali prior to the heating step for decolorizing or deodorizing the oil or fat in the process for purifying an oil or fat.

Description

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Method for inhibiting the formation of chloropropanols and their forming substances in glyceride oils and fats
本発明は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に関する。 The present invention relates to a method for inhibiting the production of chloropropanols and their forming substances in glyceride oils and fats.
クロロプロパノールは、プロパノールに塩素が結合した物質の総称であるが、これらの一種である、３－クロロプロパンジオールは、従来から、しょうゆなど主にアミノ酸液を製造する際、副産物として少量生成することが知られており、また食品を加熱調理する過程で、脂質と食塩の存在により生成するといわれている。 Chloropropanol is a generic name for substances in which chlorine is bonded to propanol. However, 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.
最近、食用油脂中には、３－クロロプロパンジオールが脂肪酸と結合したエステル体で存在していることが明らかになった。（非特許文献１） Recently, it has been clarified that edible fats and oils contain 3-chloropropanediol in an ester form combined with a fatty acid. (Non-Patent Document 1)
さらに、最近、グリセリド油脂中にクロロプロパノール類が生成される過程において、グリシドール脂肪酸エステルがその形成物質として存在していることも報告されている。（非特許文献２） Furthermore, recently, it has been reported that glycidol fatty acid esters are present as forming substances in the process of producing chloropropanols in glyceride oils. (Non-Patent Document 2)
３－クロロプロパンジオール脂肪酸エステルについては、許容摂取量が定められている、というような規制は無いが、欧州においては、３－クロロプロパンジオール脂肪酸エステルに結合する脂肪酸が全て遊離して、３－クロロプロパンジオールになるとみなし、評価をする動きがあり、グリセリド油脂中の３－クロロプロパンジオール脂肪酸エステルを低減する技術の開発が望ましい。 For 3-chloropropanediol fatty acid ester, there is no regulation that the allowable intake is set, but in Europe, all the fatty acids bound to 3-chloropropanediol fatty acid ester are released and 3-chloropropanediol fatty acid ester is released. Therefore, it is desirable to develop a technology for reducing 3-chloropropanediol fatty acid esters in glyceride oils and fats.
また、グリシドール脂肪酸エステルについても、毒性学的なデータはないが、クロロプロパノール類と同様、グリセリド油脂中のグリシドール脂肪酸エステルを低減する技術の開発が望ましい。 There is no toxicological data for glycidol fatty acid esters, but it is desirable to develop a technique for reducing glycidol fatty acid esters in glyceride fats and oils, as with chloropropanols.
本発明は、グリセリド油脂中のクロロプロパノール類である３－クロロプロパンジオールや３－クロロプロパンジオール脂肪酸エステル及びそれらの形成物質であるグリシドール脂肪酸エステルなどの生成を抑制する方法を提供することを目的とする。 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.
本発明者らは、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は、通常の油脂の精製工程である脱色工程、とりわけ脱臭工程を経ると増加すること、フライ調理やオーブン調理などの加熱処理によっても増加するという知見を得た。かかる知見から、上記課題に対し、鋭意研究を重ねた結果、加熱処理以前に、グリセリド油脂を吸着剤処理及び／又はアルカリ処理しておく、あるいは、油脂中のジグリセリド含量を低減させておくことで、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であるグリシドール脂肪酸エステルなどの生成を抑制することができるという知見を見出し、本発明を完成させるに至った。 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.
すなわち本発明は
（１）．グリセリド油脂が１００℃以上に加熱される処理以前に、吸着剤処理及び／又はアルカリ処理することを特徴とする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
（２）．当該グリセリド油脂の加熱処理温度が１５０℃以上である、（１）記載の方法
（３）．吸着剤処理及び／又はアルカリ処理をグリセリド油脂の品温１５０℃未満で行う、（２）記載の方法
（４）．吸着剤処理及び／又はアルカリ処理をグリセリド油脂の品温６０～９５℃で行う、（３）記載の方法
（５）．吸着剤がシリカゲル及び／又はヤシ殻活性炭である（１）～（５）いずれか１に記載の方法
（６）．グリセリド油脂が１００℃以上に加熱される処理以前に、部分グリセリド低減処理することを特徴とする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
（７）．部分グリセリド低減処理が部分グリセリド特異性リパーゼを使用する方法である（６）記載の方法
（８）．部分グリセリド低減処理により、グリセリド油脂中のジグリセリド含量を２重量％以下にする（６）又は（７）記載の方法
（９）．粗パーム油（ＣＰＯ）を吸着剤処理、アルカリ処理及び部分グリセリド低減処理から選ばれる１種以上の処理の後、精製することを特徴とする精製パーム油（ＲＢＤＰＯ）の製造方法
（１０）．（９）記載の製造方法により得られる、クロロプロパノール類及びその形成物質が３．５ｐｐｍ以下である、ヨウ素価５０～５５、上昇融点３３～３９℃の精製パーム油（ＲＢＤＰＯ）
（１１）．（１０）記載の精製パーム油（ＲＢＤＰＯ）又はそのオレイン画分を加工してなるパーム系油脂
である。 That is, 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 (3) according to (1), wherein the heat treatment temperature of the glyceride fat is 150 ° 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. (5) The method according to (3), wherein the adsorbent treatment and / or alkali treatment is performed at a product temperature of 60 to 95 ° C. of the glyceride oil. The method (6) according to any one of (1) to (5), wherein the adsorbent is silica gel and / or coconut shell activated carbon. (7) A method for suppressing the production of chloropropanols and their forming substances in a glyceride oil or fat, characterized by subjecting the glyceride oil or fat to a partial glyceride reduction treatment before the treatment in which the glyceride oil or fat is heated to 100 ° C. or higher. The method according to (6), wherein the partial glyceride reduction treatment is a method using a partial glyceride-specific lipase. (9) The method according to (6) or (7), wherein the diglyceride content in the glyceride fat is reduced to 2% by weight or less by partial glyceride reduction treatment. A method for producing refined palm oil (RBDPO), characterized in that crude palm oil (CPO) is purified after one or more treatments selected from adsorbent treatment, alkali treatment and partial glyceride reduction treatment (10). (9) Purified palm oil (RBDPO) obtained by the production method according to (9), wherein the chloropropanols and their forming substances are 3.5 ppm or less, the iodine value is 50 to 55, and the melting point is 33 to 39 ° C.
(11). (10) A palm oil or fat obtained by processing the refined palm oil (RBDPO) or its olein fraction.
本発明の方法により、グリセリド油脂中のクロロプロパノール類である３－クロロプロパンジオールや３－クロロプロパンジオール脂肪酸エステル及びそれらの形成物質であるグリシドール脂肪酸エステルなどの生成を抑制することができる。 According to the method of the present invention, it is possible to suppress the production of chloropropanols such as 3-chloropropanediol and 3-chloropropanediol fatty acid esters and glycidol fatty acid esters that are their forming substances in glyceride oils.
以下に、本発明を詳細に説明する。 The present invention is described in detail below.
本発明の方法を適用することができるグリセリド油脂としては、大豆、菜種、サフラワー、コーン、ひまわり、綿実、米、オリーブ、パーム、ヤシ、パーム核、ゴマ、牛、豚、魚などの原料を搾油、抽出して得られる未精製油脂や、未精製油脂をろ過、遠心分離した粗精製油脂、また、脂肪酸とグリセリンとのエステル化反応により得られるグリセリド油脂等が挙げられる。 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.
また、本発明の方法を適用することができるグリセリド油脂としては、大豆油、菜種油、サフラワー油、コーン油、ひまわり油、綿実油、米油、オリーブオイル、パーム油、ヤシ油、パーム核油、ゴマ油、牛脂、豚脂、魚油などの食用精製油脂にも適用することができるが、これらのなかでもパーム系油脂、特に粗パーム油（ＣＰＯ）に対して、好ましく適用できる。 Examples of the glyceride oil to which the method of the present invention can be applied 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).
本発明の方法は、とりわけアブラヤシの果肉を搾って得られる粗パーム油（ＣＰＯ）から精製パーム油（ＲＢＤＰＯ）を得るための脱ガム、脱酸、脱色、脱臭、脱ロウなどの精製工程や、精製パーム油（ＲＢＤＰＯ）を更に脱色、脱臭などの精製を行う工程において、好ましく適用できる。 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.
本発明の方法は、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であるグリシドール脂肪酸エステルなどの生成を抑制する方法に関するが、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であるグリシドール脂肪酸エステルなどは、油脂が高温で加熱されることにより生成すると考えられるため、油脂が１００℃以上とりわけ１５０℃以上の高い温度に加熱される処理前に、以下に説明する本発明の方法を適用することが必要である。 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.
本発明の方法において、グリセリド油脂が１００℃以上、さらには１５０℃以上に加熱される処理としては、グリセリド油脂を精製する際の、脱色、脱臭といった工程、又はグリセリド油脂を水素添加し硬化油脂を製造するといった加工工程、あるいはグリセリド油脂を化学触媒を用いエステル交換油脂を製造する際の工程、さらには加熱調理に用いた際の、炒める、揚げる、あるいはスプレー油として用いオーブン加熱するといった調理工程などが挙げられる。 In the method of the present invention, 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.
本発明の方法は、１００℃以上とりわけ１５０℃以上に加熱されるグリセリド油脂に対し、加熱される処理以前に、グリセリド油脂を吸着剤処理しておくことにより、クロロプロパノール類及びその形成物質であるグリシドール脂肪酸エステルなどの生成の原因物質と考えられる塩素化合物やジグリセリド等を、グリセリド油脂中から低減させることを特徴とするが、吸着剤としては、活性白土、酸性白土、活性炭、珪藻土、シリカゲル等を例示することができ、これら吸着剤のなかでも、シリカゲル、ヤシ殻活性炭を用いることが好ましい。また、上記吸着剤として、化学賦活処理を行っていない活性炭を使用することが好ましい。 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. Of these adsorbents, silica gel and coconut shell activated carbon are preferably used. Moreover, it is preferable to use activated carbon which has not been subjected to chemical activation treatment as the adsorbent.
吸着剤処理の方法としては、グリセリド油脂に吸着剤を０．１～５重量％添加し、一定時間、５０～８０℃の加温、好ましくは５０～１１０℃の加温、０．５～１００Ｔｏｒｒの減圧下で、撹拌接触させる方法などが挙げられる。
上記吸着剤処理は、グリセリド油脂の精製工程における脱臭工程前の脱色工程で、脱色処理と同時に吸着剤処理を行うことにより、処理工程を簡略化することができる。 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.
また、本発明の方法は、１００℃以上とりわけ１５０℃以上に加熱されるグリセリド油脂に対し、加熱前に、グリセリド油脂をアルカリ処理しておくことが好ましく、アルカリ剤としては、アルカリ金属若しくはアルカリ土類金属の水酸化物、及び炭酸塩を用いることができ、具体的には、水酸化ナトリウム、水酸化カリウム、水酸化カルシウム、炭酸ナトリウム、炭酸水素ナトリウム等を用いることができる。 In the method of the present invention, 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.
アルカリ処理の方法としては、グリセリド油脂に水酸化ナトリウムを遊離脂肪酸の中和当量の０．８～１．２倍量添加し、攪拌後、遠心分離し、フーツを除去し、さらに水洗し、攪拌後、遠心分離し、水層を除去後、加温減圧下で脱水する方法などが挙げられる。 As an alkali treatment method, 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.
本発明の方法である、吸着剤処理及び／又はアルカリ処理は、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が、高温で生成することから、グリセリド油脂品温が１５０℃未満、より好ましくは１００℃未満、さらに好ましくは６０～９５℃で行うことが好ましい。 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.
さらに、本発明の別の方法は、１００℃以上とりわけ１５０℃以上に加熱されるグリセリド油脂に対し、加熱される処理以前に、グリセリド油脂中のジグリセリド含量を２重量％以下にしておくことが好ましい。グリセリド油脂中のジグリセリド含量が高いと、加熱によりグリセリド油脂中のクロロプロパノール類である３－クロロプロパンジオールや３－クロロプロパンジオール脂肪酸エステル及びそれらの形成物質であるグリシドール脂肪酸エステルなどの生成量がより増加する傾向があるため、好ましくない。 Further, according to another method of the present invention, it is preferable that 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. . When 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.
グリセリド油脂中のジグリセリド含量を低減させる方法としては、蒸留、クロマトグラフィーによる分離、リパーゼ処理などの方法があるが、本発明はこられのなかでも、ジグリセリドなどの部分グリセリドに特異的に作用するリパーゼなどの酵素処理により、ジグリセリド含量を低減させる方法が簡便であり、かつ高い温度に晒される加熱工程を経ないため好ましく、特開昭６２‐６１５９０号公報に記載の方法が好ましく適用できる。 Methods for reducing the diglyceride content in glyceride fats and oils include distillation, chromatographic separation, and lipase treatment. Among these, 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.
グリセリド油脂は通常の精製工程において、脱色工程や、とりわけ脱臭工程中に、油脂は８０～２７０℃の高い温度で加熱されるため、油脂中のクロロプロパノール類及びその形成物質が増加しやすいことが分かっており、本発明の方法は、１００℃以上とりわけ１５０℃以上に加熱される、上記脱色工程及び／又は脱臭工程の前に行っておくことで、油脂中のクロロプロパノール類及びその形成物質であるグリシドール脂肪酸エステルの生成を抑制することができる。 Since 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.
本発明の方法によって得られたグリセリド油脂は、クロロプロパノール類である３－クロロプロパンジオールや３－クロロプロパンジオール脂肪酸エステル及びそれらの形成物質であるグリシドール脂肪酸エステルの生成が抑制されるが、本発明において、クロロプロパノール類及びその形成物質であるグリシドール脂肪酸エステルの含量は以下の文献を参考に次のような方法で測定している。
（Ｄｅｔｅｒｍｉｎａｔｉｏｎ　ｏｆ　ｔｏｔａｌ　３－ｃｈｌｏｒｏｐｒｏｐａｎｅ－１，２－ｄｉｏｌ　（３－ＭＣＰＤ）　ｉｎ　ｅｄｉｂｌｅ　ｏｉｌｓ　ｂｙ　ｃｌｅａｖａｇｅ　ｏｆ　ＭＣＰＤ　ｅｓｔｅｒｓ　ｗｉｔｈ　ｓｏｄｉｕｍ　ｍｅｔｈｏｘｉｄｅ．　Ｅｕｒ．　Ｊ．　Ｌｉｐｉｄ　Ｓｃｉ．　Ｔｅｃｈｎｏｌ．　２００８，　１１０，：１８３－１８６） In the glyceride oil obtained by the method of the present invention, 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.
まず、油脂　０．１ｇをｔ－ブチルメチルエーテル　１ｍｌに溶かし、２０μｇ／ｍｌ内部標準物質（３－ＭＣＰＤ－ｄ５　酢酸エチル溶液）２５０μｌを加え、ＮａＯＣＨ３　溶液（０．５ｍｏｌ／ｌ　ＮａＯＣＨ３　ｉｎ　ＭｅＯＨ）１ｍｌと混和後、室温で１０分静置する。続いて、ヘキサン　３ｍｌ、ＮａＣｌ　溶液（ＮａＣｌ　２００ｇ／水１ｌ）３ｍｌ、氷酢酸　０．１ｍｌを添加し、攪拌後、上層を除去する。さらに、ヘキサン　３ｍｌを添加、攪拌後、上層を除去する。そして、フェニルボロン酸溶液（フェニルボロン酸１ｇをアセトン：水＝１９：１　４ｍｌに溶解）を添加、攪拌後、８０℃、２０分放置し、室温に放冷後、ヘキサン　２ｍｌを添加、攪拌し、上層をＧＳ－ＭＳ分析に供する。
なお、ＧＣ－ＭＳについては、分子イオンピークｍ／ｚ　１９６（３－ＭＣＰＤ）、ｍ／ｚ　２０１（３－ＭＣＰＤ－ｄ５）を用いて定量する。 First, 0.1 g of fat / oil is dissolved in 1 ml of t-butyl methyl ether, 250 μl of 20 μg / 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. Further, 3 ml of hexane is added, and after stirring, the upper layer is removed. Then, a phenylboronic acid solution (1 g of phenylboronic acid was dissolved in acetone: water = 19: 1, 4 ml) was added, stirred, allowed to stand at 80 ° C. for 20 minutes, allowed to cool to room temperature, and then added with 2 ml of hexane and stirred. 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 ).
なお、上記方法は、ドイツ（Ｄｅｕｔｓｃｈｅ　Ｇｅｓｅｌｌｓｃｈａｆｔ　ｆｕｒ　Ｆｅｔｔｗｉｓｓｅｎｓｃｈａｆｔ：ＤＧＦ）の、３－クロロプロパンジオール脂肪酸エステル及びその形成物質であるグリシドール脂肪酸エステルの測定方法として採用されているものであるが、この方法では、グリセリド油脂中の３－クロロプロパンジオール脂肪酸エステル及びその形成物質であるグリシドール脂肪酸エステルを加水分解し、グリセリド油脂中に存在する３－クロロプロパンジオール脂肪酸エステル及びその形成物質であるグリシドール脂肪酸エステルを全て３－ＭＣＰＤとして測定している。
「Ｗｉｔｈ　ｔｈｉｓ　ｍｅｔｈｏｄ，　ｏｔｈｅｒ　ｃｏｍｐｏｕｎｄｓ　ｆｏｒｍｉｎｇ　３－ＭＣＰＤ　ｕｎｄｅｒ　ｔｈｅ　ｃｏｎｄｉｔｉｏｎｓ　ｏｆ　ａｎａｌｙｓｉｓ　ａｒｅ　ａｌｓｏ　ｄｅｔｅｃｔｅｄ．　Ｔｈｅ　ｍｏｓｔ　ｉｍｐｏｒｔａｎｔ　３－ＭＣＰＤ　ｅｓｔｅｒｓ　ｆｏｒｍｉｎｇ　ｃｏｍｐｏｕｎｄｓ　ｉｓ　ｇｌｙｃｉｄｏｌ　（ｏｘｉｒａｎｅ－２－ｍｅｔｈａｎｏｌ）．」（Ｅｓｔｅｒ－ｂｏｕｎｄ　３－ｃｈｌｏｒｏｐｒｏｐａｎｅ－１，２－ｄｉｏｌ（３－ＭＣＰＤ　ｅｓｔｅｒｓ）　ａｎｄ　３－ＭＣＰＤ　ｆｏｒｍｉｎｇ　ｓｕｂｓｔａｎｃｅｓ：ＤＧＦ　Ｓｔａｎｄａｒｄ　Ｍｅｔｈｏｄｓ　Ｓｅｃｔｉｏｎ　Ｃ－Ｆａｔｓ／Ｃ－ＩＩＩ　１８（０９）） 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 Fettwissenschaft: 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. The most important 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))
本発明の方法により、グリセリド油脂の精製工程でのクロロプロパノール類及びその形成物質の生成が効果的に抑制され、ＣＰＯ（粗パーム油）を脱ガム、脱色、脱臭処理して得られる、ヨウ素価５０～５５、上昇融点３３～３９℃であるＲＢＤＰＯ（精製パーム油）中のクロロプロパノール類及びその形成物質の含量は３．５ｐｐｍ以下に抑えることができ、さらには３ｐｐｍ以下に抑えることができる。 According to the method of the present invention, 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.
本発明の方法により、得られた精製パーム油（ＲＢＤＰＯ）又は、さらに分別して得られるオレイン画分を加工して得られたパーム系油脂は、クロロプロパノール類及びその形成物質の含量が少なく、また、フライ油として使用した際に、加熱調理などの加熱工程に晒されても、クロロプロパノール類及びその形成物質の生成を抑えることができる。 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.
以下、実施例を示し、本発明をさらに具体的に説明する。なお、例中の％は重量基準を意味する。 Hereinafter, the present invention will be described more specifically with reference to examples. In addition,% in an example means a basis of weight.
粗パーム油（ＣＰＯ／酸価＝７．８）を脱ガム処理した原料パーム油に微粉末シリカを３重量％添加し、７０℃、２０Ｔｏｒｒで１０分間攪拌することにより、吸着剤処理を行った。吸着剤処理後、白土１重量％添加し、１１０℃、２０Ｔｏｒｒで１０分間脱色し、さらに２５０℃、２Ｔｏｒｒで９０分間脱臭処理を行った。得られた精製パーム油（ＲＢＤＰＯ／ＩＶ：５２．２、上昇融点：３６．５℃）のクロロプロパノール類及びその形成物質の含量は３．５ｐｐｍであった。 Adsorbent treatment was performed by adding 3% by weight of fine powder silica to raw palm oil obtained by degumming crude palm oil (CPO / acid value = 7.8) and stirring at 70 ° C. and 20 Torr for 10 minutes. . After the adsorbent treatment, 1% by weight of white clay was added, decolorized at 110 ° C. and 20 Torr for 10 minutes, and further deodorized at 250 ° C. and 2 Torr for 90 minutes. 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.
粗パーム油（ＣＰＯ／酸価＝７．８）を脱ガム処理した原料パーム油にヤシ殻活性炭を３重量％添加し、７０℃、２０Ｔｏｒｒで１０分間攪拌することにより、吸着剤処理を行った。吸着剤処理後、白土１重量％添加し、１１０℃、２０Ｔｏｒｒで１０分間脱色し、さらに２５０℃、２Ｔｏｒｒで９０分間脱臭処理を行った。得られた精製パーム油（ＲＢＤＰＯ／ＩＶ：５２．２、上昇融点：３６．５℃）のクロロプロパノール類及びその形成物質の含量は２．９ｐｐｍであった。 Adsorbent treatment was performed by adding 3% by weight of coconut shell activated carbon to raw palm oil obtained by degumming crude palm oil (CPO / acid value = 7.8) and stirring at 70 ° C. and 20 Torr for 10 minutes. . After the adsorbent treatment, 1% by weight of white clay was added, decolorized at 110 ° C. and 20 Torr for 10 minutes, and further deodorized at 250 ° C. and 2 Torr for 90 minutes. 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.
粗パーム油（ＣＰＯ／酸価＝７．８）を脱ガム処理した原料パーム油に水酸化ナトリウムを６．７重量％添加し、３０００ｒｐｍで３分間攪拌後、遠心分離し、フーツを除去後、さらに水を２０重量％添加し、３０００ｒｐｍで３分間攪拌後、遠心分離し、水層を除去後、１１０℃、２０Ｔｏｒｒで１０分間脱水処理を行った。アルカリ処理後、白土１重量％添加し、１１０℃、２０Ｔｏｒｒで１０分間脱色し、さらに２５０℃、２Ｔｏｒｒで９０分間脱臭処理を行った。得られた精製パーム油（ＲＢＤＰＯ／ＩＶ：５２．２、上昇融点：３６．５℃）のクロロプロパノール類及びその形成物質の含量は２ｐｐｍであった。 After adding 6.7% by weight of sodium hydroxide to raw palm oil obtained by degumming crude palm oil (CPO / acid value = 7.8), stirring at 3000 rpm for 3 minutes, centrifuging, removing foots, Further, 20% by weight of water was added, and the mixture was stirred at 3000 rpm for 3 minutes and then centrifuged. After removing the aqueous layer, dehydration treatment was performed at 110 ° C. and 20 Torr for 10 minutes. After alkali treatment, 1% by weight of white clay was added, decolorized at 110 ° C. and 20 Torr for 10 minutes, and further deodorized at 250 ° C. and 2 Torr for 90 minutes. The resulting refined palm oil (RBDPO / IV: 52.2, rising melting point: 36.5 ° C.) had a content of 2 ppm of chloropropanols and its forming substances.
粗パーム油（ＣＰＯ／酸価＝７．８）を脱ガム処理した原料パーム油に水を１０重量％、リパーゼ（リパーゼＧ「アマノ」５０［天野エンザイム株式会社製］）を１重量％添加し４３℃、３時間攪拌し反応させた。リパーゼ処理後のジグリセリド含量は０．４％であった。リパーゼ処理後、白土１重量％添加し、１１０℃、２０Ｔｏｒｒで１０分間脱色し、さらに２５０℃、２Ｔｏｒｒで９０分間脱臭処理を行った。得られた精製パーム油（ＲＢＤＰＯ／ＩＶ：５２．２、上昇融点：３６．５℃）のクロロプロパノール類及びその形成物質の含量は３．１ｐｐｍであった。 10% by weight of water and 1% by weight of lipase (lipase G “Amano” 50 [manufactured by Amano Enzyme Co., Ltd.]) are added to raw palm oil degummed with crude palm oil (CPO / acid value = 7.8). The reaction was stirred at 43 ° C. for 3 hours. The diglyceride content after lipase treatment was 0.4%. After the lipase treatment, 1% by weight of white clay was added, decolorized at 110 ° C. and 20 Torr for 10 minutes, and further deodorized at 250 ° C. and 2 Torr for 90 minutes. The obtained refined palm oil (RBDPO / IV: 52.2, ascending melting point: 36.5 ° C.) had a content of chloropropanols and the forming substances thereof of 3.1 ppm.
粗パーム油（ＣＰＯ／酸価＝７．８）を脱ガム処理した原料パーム油に、白土１重量％、微粉末シリカ０．５重量％添加し、１１０℃、２０Ｔｏｒｒで１０分間、脱色と同時に吸着剤処理を行い、さらに２５０℃、２Ｔｏｒｒで９０分間脱臭処理を行った。得られた精製パーム油（ＲＢＤＰＯ／ＩＶ：５２．２、上昇融点：３６．５℃）のクロロプロパノール類及びその形成物質の含量は３．９ｐｐｍであった。 Crude palm oil (CPO / acid value = 7.8) was degummed with raw palm oil, 1% by weight of white clay and 0.5% by weight of finely divided silica were added, and at 110 ° C. and 20 Torr for 10 minutes, simultaneously with decolorization. An adsorbent treatment was performed, and a deodorization treatment was further performed at 250 ° C. and 2 Torr for 90 minutes. 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.
粗パーム油（ＣＰＯ／酸価＝７．８）を脱ガム処理した原料パーム油に、白土１重量％、微粉末シリカ０．１重量％添加し、１１０℃、２０Ｔｏｒｒで１０分間、脱色と同時に吸着剤処理を行い、さらに２５０℃、２Ｔｏｒｒで９０分間脱臭処理を行った。得られた精製パーム油（ＲＢＤＰＯ／ＩＶ：５２．２、上昇融点：３６．５℃）のクロロプロパノール類及びその形成物質の含量は４．８ｐｐｍであった。 Crude palm oil (CPO / acid value = 7.8) is degummed to raw palm oil, 1% by weight of white clay and 0.1% by weight of finely divided silica are added, and at 110 ° C. and 20 Torr for 10 minutes, simultaneously with decolorization An adsorbent treatment was performed, and a deodorization treatment was further performed at 250 ° C. and 2 Torr for 90 minutes. 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.
粗パーム油（ＣＰＯ／酸価＝７．８）を脱ガム処理した原料パーム油に水を１０重量％、リパーゼ（リパーゼＧ「アマノ」５０［天野エンザイム株式会社製］）を１重量％添加し４３℃、３時間攪拌し反応させた。リパーゼ処理後のジグリセリド含量は０．３％であった。リパーゼ処理後、白土１重量％、微粉末シリカ３重量％添加し、１１０℃、２０Ｔｏｒｒで１０分間、脱色と同時に吸着剤処理を行い、さらに２５０℃、２Ｔｏｒｒで９０分間脱臭処理を行った。得られた精製パーム油（ＲＢＤＰＯ／ＩＶ：５２．２、上昇融点：３６．５℃）のクロロプロパノール類及びその形成物質の含量は２．０ｐｐｍであった。 10% by weight of water and 1% by weight of lipase (lipase G “Amano” 50 [manufactured by Amano Enzyme Co., Ltd.]) are added to raw palm oil degummed with crude palm oil (CPO / acid value = 7.8). The reaction was stirred at 43 ° C. for 3 hours. The diglyceride content after lipase treatment was 0.3%. After the lipase treatment, 1% by weight of white clay and 3% by weight of fine silica were added, adsorbent treatment was performed simultaneously with decolorization at 110 ° C. and 20 Torr for 10 minutes, and deodorization treatment was further performed at 250 ° C. and 2 Torr for 90 minutes. The resulting refined palm oil (RBDPO / IV: 52.2, ascending melting point: 36.5 ° C.) had a content of chloropropanols and the forming substances thereof of 2.0 ppm.
（比較例１）
粗パーム油（ＣＰＯ／酸価＝７．８）を脱ガム処理した原料パーム油に、白土１重量％、１１０℃、２０Ｔｏｒｒで１０分間脱色し、さらに２５０℃、２Ｔｏｒｒで９０分間脱臭処理を行った。得られた精製パーム油（ＲＢＤＰＯ／ＩＶ：５２．２、上昇融点：３６．５℃）のクロロプロパノール類及びその形成物質の含量は６．０ｐｐｍであった。 (Comparative Example 1)
Crude palm oil (CPO / acid value = 7.8) was degummed and decolorized for 10 minutes at 1% by weight of white clay, 110 ° C, 20 Torr, and then deodorized at 250 ° C, 2 Torr for 90 minutes. It was. The resulting refined palm oil (RBDPO / IV: 52.2, ascending melting point: 36.5 ° C.) had a content of chloropropanols and the forming substances thereof of 6.0 ppm.
（比較例２）
粗パーム油（ＣＰＯ／酸価＝７．８）を脱ガム処理した原料パーム油に、白土１重量％、１１０℃、２０Ｔｏｒｒで１０分間脱色し、さらに２５０℃、２Ｔｏｒｒで９０分間脱臭処理を行った。得られた精製パーム油に、微粉末シリカを３重量％添加し、７０℃、２０Ｔｏｒｒで１０分間攪拌し、吸着剤処理を行った。得られた吸着剤処理後の精製パーム油（ＲＢＤＰＯ／ＩＶ：５２．２、上昇融点：３６．５℃）のクロロプロパノール類及びその形成物質の含量は４．４ｐｐｍであった。 (Comparative Example 2)
Crude palm oil (CPO / acid value = 7.8) was degummed and decolorized for 10 minutes at 1% by weight of white clay, 110 ° C, 20 Torr, and then deodorized at 250 ° C, 2 Torr for 90 minutes. It was. To the resulting refined palm oil, 3% by weight of fine powder silica was added, and the mixture was stirred at 70 ° C. and 20 Torr for 10 minutes to perform the adsorbent treatment. The obtained refined palm oil (RBDPO / IV: 52.2, ascending melting point: 36.5 ° C.) after the treatment with the adsorbent had a content of chloropropanols and its forming substances of 4.4 ppm.
実施例１～４及び比較例１、２の結果を表に示す。 The results of Examples 1 to 4 and Comparative Examples 1 and 2 are shown in the table.
表
Figure JPOXMLDOC01-appb-I000001
table
Figure JPOXMLDOC01-appb-I000001

Claims (11)

  1. グリセリド油脂が１００℃以上に加熱される処理以前に、吸着剤処理及び／又はアルカリ処理することを特徴とする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。 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 of heating the glyceride fats to 100 ° C. or higher.
  2. 当該グリセリド油脂の加熱処理温度が１５０℃以上である、請求項１記載の方法。 The method of Claim 1 that the heat processing temperature of the said glyceride fats and oils is 150 degreeC or more.
  3. 吸着剤処理及び／又はアルカリ処理をグリセリド油脂の品温１５０℃未満で行う、請求項２記載の方法。 The method according to claim 2, wherein the adsorbent treatment and / or the alkali treatment is performed at a product temperature of glyceride fat of less than 150 ° C.
  4. 吸着剤処理及び／又はアルカリ処理をグリセリド油脂の品温６０～９５℃で行う、請求項３記載の方法。 The method according to claim 3, wherein the adsorbent treatment and / or alkali treatment is performed at a product temperature of 60 to 95 ° C of the glyceride oil.
  5. 吸着剤がシリカゲル及び／又はヤシ殻活性炭である請求項１～５いずれか１項に記載の方法。 The method according to any one of claims 1 to 5, wherein the adsorbent is silica gel and / or coconut shell activated carbon.
  6. グリセリド油脂が１００℃以上に加熱される処理以前に、部分グリセリド低減処理することを特徴とする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。 A method for suppressing the production of chloropropanols and their forming substances in glyceride fats and oils, wherein partial glyceride reduction treatment is performed before the treatment of heating the glyceride fats to 100 ° C. or higher.
  7. 部分グリセリド低減処理が部分グリセリド特異性リパーゼを使用する方法である請求項６記載の方法。 The method according to claim 6, wherein the partial glyceride reduction treatment is a method using a partial glyceride-specific lipase.
  8. 部分グリセリド低減処理により、グリセリド油脂中のジグリセリド含量を２重量％以下にする請求項６又は７記載の方法。 The method according to claim 6 or 7, wherein the diglyceride content in the glyceride fat is reduced to 2% by weight or less by the partial glyceride reduction treatment.
  9. 粗パーム油（ＣＰＯ）を吸着剤処理、アルカリ処理及び部分グリセリド低減処理から選ばれる１種以上の処理の後、精製することを特徴とする精製パーム油（ＲＢＤＰＯ）の製造方法。 A method for producing refined palm oil (RBDPO), comprising purifying crude palm oil (CPO) after one or more treatments selected from adsorbent treatment, alkali treatment and partial glyceride reduction treatment.
  10. 請求項９記載の製造方法により得られる、クロロプロパノール類及びその形成物質が３．５ｐｐｍ以下である、ヨウ素価５０～５５、上昇融点３３～３９℃の精製パーム油（ＲＢＤＰＯ）。 A refined palm oil (RBDPO) obtained by the production method according to claim 9, wherein the chloropropanols and the substances forming the chloropropanol are 3.5 ppm or less, the iodine value is 50 to 55, and the rising melting point is 33 to 39 ° C.
  11. 請求項１０記載の精製パーム油（ＲＢＤＰＯ）又はそのオレイン画分を加工してなるパーム系油脂。 The palm oil fat which processes refined palm oil (RBDPO) of Claim 10, or its olein fraction.
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