JP2014009292A - Method for producing oil and fat composition reduced in amount of 3-chloropropane-1,2-diol fatty acid ester - Google Patents
Method for producing oil and fat composition reduced in amount of 3-chloropropane-1,2-diol fatty acid ester Download PDFInfo
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本発明は、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に関する。 The present invention relates to a method for producing an oil and fat composition in which the amount of 3-chloropropane-1,2-diol fatty acid ester is reduced.
２００７年、ドイツのＢｆＲ（ドイツ連邦リスクアセスメント研究所）は、食用油、食用油使用のマーガリン、調整粉乳等に３−クロロプロパン−１，２−ジオール（３−ＭＣＰＤ）脂肪酸エステルが含まれることを発表した。
３−ＭＣＰＤ脂肪酸エステルの有毒性は不明であるが、遊離の３−ＭＣＰＤは醤油等に含まれ、発癌性や毒性が疑われている（非特許文献１）。したがって、食用油脂中の３−ＭＣＰＤのみならず、体内で３−ＭＣＰＤに変換される可能性のある３−ＭＣＰＤ脂肪酸エステルについても低減することが望まれる。
In 2007, German BfR (German Federal Institute for Risk Assessment) confirmed that 3-chloropropane-1,2-diol (3-MCPD) fatty acid ester was included in edible oil, edible margarine, conditioned milk powder, etc. Announced.
Although toxicity of 3-MCPD fatty acid ester is unknown, free 3-MCPD is contained in soy sauce and the like, and carcinogenicity and toxicity are suspected (Non-patent Document 1). Therefore, it is desired to reduce not only 3-MCPD in edible fats and oils but also 3-MCPD fatty acid esters that may be converted into 3-MCPD in the body.
これまで、３−ＭＣＰＤの量を低減させる方法としては、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の生成を抑制する方法が知られている（特許文献１）。
また、別法として、３−ＭＣＰＤを含み、ジグリセリドを３％以上含有するグリセリド組成物を、１００〜２４０℃の温度条件にて脱臭処理する方法が知られている（特許文献２）。
Until now, as a method of reducing the amount of 3-MCPD, chloropropanols in glyceride fats and oils, characterized by adsorbent treatment and / or alkali treatment before the treatment of heating glyceride fats to 100 ° C. or higher. There is known a method for suppressing the generation of (Patent Document 1).
As another method, a method of deodorizing a glyceride composition containing 3-MCPD and containing 3% or more of diglyceride under a temperature condition of 100 to 240 ° C. is known (Patent Document 2).
しかしながら、特許文献１の方法は、３−ＭＣＰＤや３−ＭＣＰＤ脂肪酸エステルの生成を抑える方法であるため、３−ＭＣＰＤ脂肪酸エステルが多く含まれる油脂から３−ＭＣＰＤ脂肪酸エステル量を低減させたい場合には別の方法を用いる必要があるという問題があった。
また、特許文献２の方法では、油脂中のグリシドール、グリシドールの脂肪酸エステル、３−ＭＣＰＤ、３−ＭＣＰＤの脂肪酸エステルの総量を遊離３−ＭＣＰＤ換算にて算出しているため、１００〜２４０℃の温度条件で脱臭処理することにより量が低減する成分が３−ＭＣＰＤ脂肪酸エステルであるのかが不明であった。本発明者らの研究の結果、１００〜２４０℃の脱臭処理により、３−ＭＣＰＤ脂肪酸エステルの量は当該脱臭処理の前後でほとんど変動しないことが判った。
したがって、３−ＭＣＰＤ脂肪酸エステルが含まれる油脂等の成分中の３−ＭＣＰＤ脂肪酸エステルの量を減らすことのできる新規な方法に対する大きな需要が存在する。
However, since the method of Patent Document 1 is a method of suppressing the production of 3-MCPD and 3-MCPD fatty acid ester, when it is desired to reduce the amount of 3-MCPD fatty acid ester from fats and oils containing a large amount of 3-MCPD fatty acid ester. Had the problem that another method had to be used.
In the method of Patent Document 2, since the total amount of glycidol in fatty oil, fatty acid ester of glycidol, 3-MCPD, and fatty acid ester of 3-MCPD is calculated in terms of free 3-MCPD, it is 100 to 240 ° C. It was unclear whether the component whose amount was reduced by deodorizing treatment under temperature conditions was 3-MCPD fatty acid ester. As a result of the study by the present inventors, it was found that the amount of 3-MCPD fatty acid ester hardly fluctuated before and after the deodorization treatment by the deodorization treatment at 100 to 240 ° C.
Therefore, there is a great demand for a novel method capable of reducing the amount of 3-MCPD fatty acid ester in components such as fats and oils containing 3-MCPD fatty acid ester.
本発明は、上記課題に鑑みてなされたものであり、３−ＭＣＰＤ脂肪酸エステルの量を低減した油脂を製造する方法を提供することを目的とする。さらに、本発明は、３−ＭＣＰＤ脂肪酸エステルの量を低減させた油脂を含む食品を提供することを目的とする。 This invention is made | formed in view of the said subject, and it aims at providing the method of manufacturing the fats and oils which reduced the quantity of 3-MCPD fatty acid ester. Furthermore, this invention aims at providing the foodstuff containing the fats and oils which reduced the quantity of 3-MCPD fatty acid ester.
本発明者は、鋭意努力の結果、１７０℃以上の温度条件下で３−ＭＣＰＤ脂肪酸エステル含有油脂に空気を吹き込むことにより、３−ＭＣＰＤ脂肪酸エステルの量を減らすことができることを見出し、本発明を完成させるに至った。すなわち、本発明は、以下の構成を有する。 As a result of diligent efforts, the present inventors have found that the amount of 3-MCPD fatty acid ester can be reduced by blowing air into the oil containing 3-MCPD fatty acid ester under a temperature condition of 170 ° C. or higher. It came to complete. That is, the present invention has the following configuration.
（１） ３−クロロプロパン−１，２−ジオール脂肪酸エステルを含む油脂組成物に、１７０℃以上の温度条件にて空気を吹込む工程を含むことを特徴とする、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。
（２） 吹込まれる空気の量が、油脂組成物１ｋｇあたり１〜１００Ｌ／分である、上記（１）に記載の方法。
（３） 温度条件が１７０〜２４０℃である、上記（１）又は（２）に記載の方法。
（４） 上記（１）〜（３）のいずれかに記載の方法で得られた油脂組成物を含む、食品。
(1) A 3-chloropropane-1,2- characterized in that it includes a step of blowing air into an oil and fat composition containing 3-chloropropane-1,2-diol fatty acid ester at a temperature of 170 ° C. or higher. The manufacturing method of the oil-fat composition which reduced the quantity of diol fatty acid ester.
(2) The method according to (1) above, wherein the amount of air blown is 1 to 100 L / min per 1 kg of the fat and oil composition.
(3) The method as described in said (1) or (2) whose temperature conditions are 170-240 degreeC.
(4) Foodstuff containing the oil-fat composition obtained by the method in any one of said (1)-(3).
本発明により、３−ＭＣＰＤ脂肪酸エステルの量が低減された油脂組成物を得ることができる。 According to the present invention, an oil and fat composition in which the amount of 3-MCPD fatty acid ester is reduced can be obtained.
以下、本発明を実施するための形態を説明する。
＜＜３−ＭＣＰＤの量が低減された油脂組成物の製造方法＞＞
本発明の第１の態様は、３−クロロプロパン−１，２−ジオール脂肪酸エステルを含む油脂組成物に、１７０℃以上の温度条件にて空気を吹込む工程を含むことを特徴とする、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である。
Hereinafter, modes for carrying out the present invention will be described.
<< 3-Method for Producing Oil Composition with Reduced Amount of MCPD >>
1st aspect of this invention includes the process of blowing air on the oil-and-fat composition containing 3-chloropropane- 1, 2-diol fatty acid ester on the temperature conditions of 170 degreeC or more, It is characterized by the above-mentioned. This is a method for producing an oil and fat composition in which the amount of chloropropane-1,2-diol fatty acid ester is reduced.
＜温度条件＞
本発明の方法では、１７０℃以上の温度条件で空気吹込み工程を行う。温度の下限値は、好ましくは１８０℃であり、より好ましくは１９０℃であり、さらにより好ましくは２００℃である。
温度が上記下限値以上であると、存在する３−ＭＣＰＤ脂肪酸エステルの量を減らすことができる。
一方、本発明の方法は、温度が高い程３−ＭＣＰＤ脂肪酸エステルの量を減らす傾向にあるため、温度の上限値を具体的に限定する必要はない。ただし、高温条件下では油脂が発火する危険性があるため、安全面からは２４０℃以下であることが好ましく、２３０℃以下であることがより好ましく、２２０℃以下であることがさらにより好ましい。
<Temperature conditions>
In the method of the present invention, the air blowing step is performed under a temperature condition of 170 ° C. or higher. The lower limit of the temperature is preferably 180 ° C, more preferably 190 ° C, and even more preferably 200 ° C.
If the temperature is equal to or higher than the lower limit, the amount of 3-MCPD fatty acid ester present can be reduced.
On the other hand, since the method of the present invention tends to reduce the amount of 3-MCPD fatty acid ester as the temperature increases, it is not necessary to specifically limit the upper limit of the temperature. However, since there is a risk that oils and fats may ignite under high temperature conditions, it is preferably 240 ° C. or lower, more preferably 230 ° C. or lower, and even more preferably 220 ° C. or lower from the viewpoint of safety.
＜空気の吹込み速度＞
本発明の方法では、吹込まれる空気の量が、油脂１ｋｇにつき１分あたり１〜１００Ｌ（１〜１００Ｌ／分／ｋｇ油脂）であることが好ましく、油脂１ｋｇにつき１分あたり２〜８０Ｌであることがより好ましく、油脂１ｋｇにつき１分あたり３〜５０Ｌであることがさらにより好ましく、油脂１ｋｇにつき１分あたり５〜３０Ｌであることが特に好ましい。
吹込み速度が上記範囲内であると、油脂中に含まれる３−ＭＣＰＤの量を顕著に低下させることができる。
<Air blowing speed>
In the method of the present invention, the amount of air blown is preferably 1 to 100 L per minute per 1 kg of fat (1 to 100 L / min / kg fat), and 2 to 80 L per kg of fat. More preferably, the amount is 3 to 50 L per minute per 1 kg of fat and oil, and particularly preferably 5 to 30 L per 1 kg of fat and oil.
If the blowing speed is within the above range, the amount of 3-MCPD contained in the fat can be significantly reduced.
＜攪拌速度＞
攪拌速度は油脂組成物の油温が均一になる速度であれば特に制限はなく、空気の吹込み量や吹込み時間、温度条件に合わせて調整すればよい。例えば１〜１０００ｒｐｍ、５〜８００ｒｐｍ、又は１０〜８００ｒｐｍで攪拌することが出来る。
<Agitation speed>
The stirring speed is not particularly limited as long as the oil temperature of the oil and fat composition becomes uniform, and may be adjusted according to the amount of air blown, the blowing time, and the temperature conditions. For example, it can stir at 1-1000 rpm, 5-800 rpm, or 10-800 rpm.
＜油脂の種類＞
本発明の方法における原料油脂組成物は、３−ＭＣＰＤ脂肪酸エステルを含む油脂を含む限り、特に制限なく用いることができる。３−ＭＣＰＤ脂肪酸エステルを含む油脂としては、パーム油、サフラワー油、グランドナッツ油、コーン油、オリーヴ油、綿実油、米油などが挙げられる。これらの中でも、３−ＭＣＰＤ脂肪酸エステルはパーム系油脂に多く含まれるため、パーム油の適用が好ましい。
上記原料油脂組成物に含まれる油脂は、上記油脂１種類を単独で用いてもよく、３−ＭＣＰＤ脂肪酸エステルを含んでいる油脂を２種類以上組み合わせて用いてもよく、３−ＭＣＰＤ脂肪酸エステルを含んでいる油脂と含んでいない油脂とを組み合わせて用いてもよい。
また、上記原料油脂組成物は、油脂のみから構成されていてもよく、他の成分が油脂とともに含まれていてもよい。
<Types of fats and oils>
The raw material fat composition in the method of the present invention can be used without particular limitation as long as it contains a fat containing 3-MCPD fatty acid ester. Examples of fats and oils containing 3-MCPD fatty acid esters include palm oil, safflower oil, ground nut oil, corn oil, olive oil, cottonseed oil, and rice oil. Among these, since 3-MCPD fatty acid ester is contained abundantly in palm oil fat, application of palm oil is preferable.
The fats and oils contained in the raw material fats and oils composition may be used alone or in combination of two or more fats and oils containing 3-MCPD fatty acid esters. You may use combining the fats and oils which contain and the fats and oils which do not contain.
Moreover, the said raw material fat composition may be comprised only from fats and oils, and the other component may be contained with fats and oils.
本発明の方法は、既に加熱処理（一般的な油脂の精製過程）され、３−ＭＣＰＤ脂肪酸エステルが生成した油脂を用いて行うことができる。３−ＭＣＰＤ脂肪酸エステルは、加熱処理（一般的な油脂の精製過程）の過程で生成されるため、上記処理後の油脂は、処理前に比べて３−ＭＣＰＤ脂肪酸エステル濃度が非常に高くなっている。したがって、本発明の方法により、増大した３−ＭＣＰＤ脂肪酸エステル濃度を顕著に低減させることができる。 The method of the present invention can be carried out using fats and oils that have already been heat-treated (general fat and oil purification process) to produce 3-MCPD fatty acid esters. Since 3-MCPD fatty acid ester is produced in the process of heat treatment (general oil refining process), the fat after the treatment has a much higher 3-MCPD fatty acid ester concentration than before the treatment. Yes. Therefore, the increased 3-MCPD fatty acid ester concentration can be significantly reduced by the method of the present invention.
また、空気吹込み後に、再度脱色処理及び／又は脱臭処理を施してもよい。再度脱色処理及び／又は脱臭処理を施すことにより、油脂の品質を高めることが出来る。なお、１度目の脱色処理及び／又は脱臭処理の過程で３−ＭＣＰＤ脂肪酸エステルを生成する原料（モノグリセリド、ジグリセリド、塩素）が消費及び／又は除去されるため、空気吹込み後に再度脱色処理及び／又は脱臭処理を行ったとしても、３−ＭＣＰＤ脂肪酸エステルの量はほとんど増大しない。 Moreover, you may perform a decoloring process and / or a deodorizing process again after blowing in air. By performing decolorization treatment and / or deodorization treatment again, the quality of fats and oils can be improved. In addition, since the raw material (monoglyceride, diglyceride, chlorine) which produces | generates 3-MCPD fatty acid ester in the process of the first decoloring process and / or deodorizing process is consumed and / or removed, decoloring process and / or again after air blowing Or even if it performs a deodorizing process, the quantity of 3-MCPD fatty acid ester hardly increases.
上記の他、空気吹込み工程の後に行う工程の例としては、硬化、エステル交換、分別などの加工工程が挙げられる。 In addition to the above, examples of the steps performed after the air blowing step include processing steps such as curing, transesterification and fractionation.
＜用途＞
本発明の方法で得られた３−ＭＣＰＤ脂肪酸エステルの低減された油脂組成物は、発癌性や毒性が低下しており安全であるため、幅広い用途に用いることができる。用途としては、油脂を含むあらゆる食品が対象となり、例えば、調味油、マーガリン、ファットスプレット、ドレッシング、クリーム、チョコレートなどが挙げられる。本発明の方法により得られた油脂組成物を用いて、安心して提供することのできる食品を製造することが出来る。
<Application>
Since the oil-and-fat composition with reduced 3-MCPD fatty acid ester obtained by the method of the present invention is safe with reduced carcinogenicity and toxicity, it can be used in a wide range of applications. Applications include all foods including fats and oils, such as seasoning oil, margarine, fat spread, dressing, cream, chocolate and the like. Using the oil and fat composition obtained by the method of the present invention, a food that can be provided with confidence can be produced.
脱色処理及び脱臭処理を施したパーム分別油軟質部（以下、ＲＢＤ ＰＩＬと略記することがある。）を用いて、以下の試験を行った。 The following tests were performed using the palm fractionated oil soft part (Hereinafter, it may abbreviate as RBD PIL.) Which performed the decoloring process and the deodorizing process.
＜試験方法＞
＜比較例１＞
ＲＢＤ ＰｌＬ（１６ｋｇ）を脱臭機に投入し、加熱した。２００℃達温後、減圧（４Ｔｏｒｒ（約０．５３ｋＰａ））、蒸気吹込み（８ｇ／分（油脂１ｋｇあたり約０．５ｇ／分））を開始し、０、１２０分後の３−ＭＣＰＤ脂肪酸エステル量を求めた。その結果を表１に示す。
<Test method>
<Comparative Example 1>
RBD PlL (16 kg) was put into a deodorizer and heated. After reaching a temperature of 200 ° C., decompression (4 Torr (about 0.53 kPa)) and steam blowing (8 g / min (about 0.5 g / min per 1 kg of fats and oils)) were started, and 0, 120 minutes later 3-MCPD fatty acid The amount of ester was determined. The results are shown in Table 1.
＜実施例１〜３、比較例２〜５＞
ＲＢＤ ＰｌＬ（１．４ｋｇ）を４つ口フラスコにとり、常圧下、撹拌速度３０ｒｐｍで加熱・撹拌を行った。表１に記載の温度に達した後、空気吹込み（２０Ｌ／分（油脂１ｋｇあたり約１４．３Ｌ／分））を開始した。空気吹込み開始から０、３０、６０、９０、１２０分後の３-ＭＣＰＤ脂肪酸エステル量を求めた。その結果を表１に示す。
<Examples 1-3, Comparative Examples 2-5>
RBD PlL (1.4 kg) was placed in a four-necked flask, and heated and stirred under normal pressure and a stirring speed of 30 rpm. After reaching the temperature shown in Table 1, air blowing (20 L / min (about 14.3 L / min per 1 kg of fat) was started. The amount of 3-MCPD fatty acid ester after 0, 30, 60, 90, 120 minutes from the start of air blowing was determined. The results are shown in Table 1.
＜比較例６＞
ＲＢＤ ＰｌＬ（１．４ｋｇ）を４つ口フラスコにとり、撹拌速度７００ｒｐｍで加熱・撹拌を行った。表１に記載の温度に達温後、０．５ＫＰａまで減圧し、０、６０分後の３-ＭＣＰＤ脂肪酸エステル量を求めた。その結果を表１に示す。
<Comparative Example 6>
RBD PlL (1.4 kg) was placed in a four-necked flask and heated and stirred at a stirring speed of 700 rpm. After reaching the temperature shown in Table 1, the pressure was reduced to 0.5 KPa, and the amount of 3-MCPD fatty acid ester after 0 and 60 minutes was determined. The results are shown in Table 1.
＜比較例７＞
ＲＢＤ ＰｌＬ（１．４ｋｇ）を４つ口フラスコにとり、常圧下、撹拌速度７００ｒｐｍで加熱・撹拌を行った。表１に記載の温度に達した後、窒素吹込み（２Ｌ／分（油脂１ｋｇあたり約１．４３Ｌ／分））を開始した。窒素吹込み開始から０、６０分後の３-ＭＣＰＤ脂肪酸エステル量を調べた。その結果を表１に示す。
<Comparative Example 7>
RBD PlL (1.4 kg) was placed in a four-necked flask, and heated and stirred at a stirring speed of 700 rpm under normal pressure. After reaching the temperature shown in Table 1, nitrogen blowing (2 L / min (about 1.43 L / min per 1 kg of fat) was started. The amount of 3-MCPD fatty acid ester 0, 60 minutes after the start of nitrogen blowing was examined. The results are shown in Table 1.
＜効果の評価基準＞
実施例１〜３及び比較例１〜７における３−ＭＣＰＤ脂肪酸エステル低減効果は、以下の基準で評価した。
◎： １２０分後の３−ＭＣＰＤ量（ｐｐｍ）が、０分後の３−ＭＣＰＤ量（ｐｐｍ）に比べて３０％以上減少していた（１２０分後の結果がない場合、６０分後の３−ＭＣＰＤ量（ｐｐｍ）が、０分後の３−ＭＣＰＤ量（ｐｐｍ）に比べて１５％以上減少していた）。
○： １２０分後の３−ＭＣＰＤ量（ｐｐｍ）が、０分後の３−ＭＣＰＤ量（ｐｐｍ）に比べて２０％以上減少していた（１２０分後の結果がない場合、６０分後の３−ＭＣＰＤ量（ｐｐｍ）が、０分後の３−ＭＣＰＤ量（ｐｐｍ）に比べて１０％以上減少していた）。
×： １２０分後の３−ＭＣＰＤ量（ｐｐｍ）が、０分後の３−ＭＣＰＤ量（ｐｐｍ）に比べて増加していた或いは２０％未満しか減少していなかった（１２０分後の結果がない場合、６０分後の３−ＭＣＰＤ量（ｐｐｍ）が、０分後の３−ＭＣＰＤ量（ｐｐｍ）に比べて増加していた或いは１０％未満しか減少していなかった）。
<Evaluation criteria for effects>
The effects of reducing 3-MCPD fatty acid esters in Examples 1 to 3 and Comparative Examples 1 to 7 were evaluated according to the following criteria.
A: The amount of 3-MCPD (ppm) after 120 minutes was reduced by 30% or more compared to the amount of 3-MCPD (ppm) after 0 minutes (if there is no result after 120 minutes, 60 minutes after The amount of 3-MCPD (ppm) was reduced by 15% or more compared to the amount of 3-MCPD (ppm) after 0 minutes).
○: The 3-MCPD amount (ppm) after 120 minutes was reduced by 20% or more compared to the 3-MCPD amount (ppm) after 0 minutes (if there is no result after 120 minutes, 60 minutes later) The amount of 3-MCPD (ppm) was reduced by 10% or more compared to the amount of 3-MCPD (ppm) after 0 minutes).
X: The amount of 3-MCPD (ppm) after 120 minutes was increased or decreased by less than 20% compared to the amount of 3-MCPD (ppm) after 0 minutes (the result after 120 minutes If not, the amount of 3-MCPD (ppm) after 60 minutes was increased or decreased by less than 10% compared to the amount of 3-MCPD (ppm) after 0 minutes).
＜３−ＭＣＰＤ（３−クロロ−１，２−プロパンジオール）量の分析＞
全ての実施例及び比較例において、油脂組成物中の３−ＭＣＰＤ，３−ＭＣＰＤ脂肪酸エステルの定量は、ドイツ公定法（ＤＧＦ Ｓｔａｎｄａｒｄ Ｍｅｔｈｏｄｓ Ｓｅｃｔｉｏｎ Ｃ Ｆａｔｓ Ｃ−ＶＩ １８ （１０）に準拠して行った。具体的には、以下の通りである。
（定量方法）
１）試料１００ｍｇをとり、ｄ５−３−ＭＣＰＤ−１，２−ｐａｌｍｉｔｏｙｌ ｅｓｔｅｒ標準溶液（約４０ｐｐｍ）を１００μＬおよびｔ−ブチルメチルエーテルを１００μＬ添加し、試料を溶解する。
２）ナトリウムメトキシド−メタノール溶液を２００μＬ加え攪拌後、室温にて３．５〜５．５分静置する。
３）酸性臭化ナトリウム水溶液を６００μＬを加え、メチルエステル化反応をストップさせる。
４）ヘキサン６００μＬを加え、攪拌後、ヘキサン層を除去した。
５）さらにヘキサン６００μＬを加え攪拌後、ヘキサン層（上層）を除去する。
６）残った水層に、ジエチルエーテル／酢酸エチル（６：４）を６００μＬ加え、攪拌した後、溶媒層を回収する。
７）溶媒層に誘導体化試薬を１００μＬ添加し、誘導体化後、溶媒を乾固させる。
８）イソオクタン１ｍＬに再溶解し、フィルターろ過した後にＧＣ／ＭＳ分析に供する。
こうして得られたクロマトグラムから３−ＭＣＰＤの面積値をサロゲートの面積値で除した内標比に、サロゲート添加量を乗じて検液中３−ＭＣＰＤ量を算出する。
検液中３−ＭＣＰＤ量［ｎｇ／ｍＬ］＝（３−ＭＣＰＤ面積値／サロゲート面積値）／サロゲート添加量
<Analysis of 3-MCPD (3-chloro-1,2-propanediol) amount>
In all the examples and comparative examples, the quantification of 3-MCPD and 3-MCPD fatty acid ester in the oil and fat composition was performed according to the German official method (DGF Standard Methods Section C Fats C-VI 18 (10)). Specifically, it is as follows.
(Quantitative method)
1) Take 100 mg of sample, add 100 μL of d5-3-MCPD-1,2-palmitoyester standard solution (about 40 ppm) and 100 μL of t-butyl methyl ether, and dissolve the sample.
2) 200 μL of sodium methoxide-methanol solution is added and stirred, and then allowed to stand at room temperature for 3.5 to 5.5 minutes.
3) Add 600 μL of acidic sodium bromide aqueous solution to stop the methyl esterification reaction.
4) 600 μL of hexane was added, and after stirring, the hexane layer was removed.
5) Further, 600 μL of hexane is added and stirred, and then the hexane layer (upper layer) is removed.
6) Add 600 μL of diethyl ether / ethyl acetate (6: 4) to the remaining aqueous layer and stir, then recover the solvent layer.
7) Add 100 μL of the derivatization reagent to the solvent layer, and after derivatization, dry the solvent.
8) Redissolve in 1 mL of isooctane, filter, and subject to GC / MS analysis.
The amount of 3-MCPD in the test solution is calculated by multiplying the internal standard ratio obtained by dividing the 3-MCPD area value by the surrogate area value from the chromatogram thus obtained and the surrogate addition amount.
Amount of 3-MCPD in test solution [ng / mL] = (3-MCPD area value / surrogate area value) / surrogate addition amount
上記の式より算出した値を試料採取量で除して、以下の式により試料中濃度を求める。
３−ＭＣＰＤ量［ｍｇ／ｋｇ］＝検液中３−ＭＣＰＤ量［ｎｇ／ｍＬ］／試料採取量［ｍｇ］
The value calculated from the above equation is divided by the amount of sample collected, and the concentration in the sample is obtained by the following equation.
3-MCPD amount [mg / kg] = 3-MCPD amount in test solution [ng / mL] / sampled amount [mg]
（装置・分析条件）
装置：ＧＣ／ＭＳ（Ａｇｉｌｅｎｔ製５９７５Ｃ／７８９０Ａ）
カラム：ＤＢ−１７ＭＳ，内径０．２５ｍｍ×３０ｍ，膜厚０．２５μｍ
注入量：２μＬ
注入口温度：２４０℃
スプリットレス時間：１．５分
スプリット流量：２０ｍＬ／ｍｉｎ
キャリアガス：ヘリウム，１．２ ｍＬ／ｍｉｎ，定流量
オーブン温度：８５℃（０．５分）→（６℃／分昇温）→１５０℃→（１２℃／分昇温）→１８０℃→（２５℃／分昇温）→２８０℃（７分）
イオン化：ＥＩ（ｐｏｓｉｔｉｖｅ）
測定イオン：３−ＭＣＰＤｍ／ｚ＝１４７（定量用），１４６，１９６，１９８（確認用）
３−ＭＣＰＤ−ｄ５ｍ／ｚ＝１５０（サロゲート）１４９，２０１，２０３（確認用）
イオン源温度：２５０℃
四重極：１５０℃
(Equipment and analysis conditions)
Apparatus: GC / MS (Agilent 5975C / 7890A)
Column: DB-17MS, inner diameter 0.25 mm × 30 m, film thickness 0.25 μm
Injection volume: 2 μL
Inlet temperature: 240 ° C
Splitless time: 1.5 minutes Split flow rate: 20 mL / min
Carrier gas: helium, 1.2 mL / min, constant flow oven temperature: 85 ° C. (0.5 minutes) → (6 ° C./minute temperature increase) → 150 ° C. → (12 ° C./minute temperature increase) → 180 ° C. → (25 ° C / minute temperature increase) → 280 ° C (7 minutes)
Ionization: EI (positive)
Measurement ions: 3-MCPDm / z = 147 (for quantification), 146, 196, 198 (for confirmation)
3-MCPD-d5m / z = 150 (surrogate) 149, 201, 203 (for confirmation)
Ion source temperature: 250 ° C
Quadrupole: 150 ° C
＜結果＞
表１から明らかなように、減圧条件下で水蒸気を吹き込む従来の脱臭処理では、３−ＭＣＰＤ脂肪酸エステルの量はほとんど低減しなかった（比較例１）。
また、１６０℃以下の温度条件下で空気を吹き込んでも、油脂組成物中に含まれる３−ＭＣＰＤ脂肪酸エステルの量はほとんど低減しなかった（比較例３〜５）。
一方、１８０℃以上の温度条件下で空気を吹き込んだ場合には、油脂組成物中に含まれる３−ＭＣＰＤ脂肪酸エステルの量を顕著に低減することができた（実施例１〜３）。
減圧条件下で行った場合や、空気の代わりに窒素を吹込んだ場合には、３−ＭＣＰＤ脂肪酸エステル量がほとんど低減しなかったことから（比較例６、７）、本発明の効果を得るには、空気吹込みと１７０℃以上の温度条件が重要であることが判る。
<Result>
As is clear from Table 1, the amount of 3-MCPD fatty acid ester was hardly reduced by the conventional deodorization treatment in which water vapor was blown under reduced pressure (Comparative Example 1).
Moreover, even if air was blown in under the temperature conditions of 160 ° C. or less, the amount of 3-MCPD fatty acid ester contained in the oil and fat composition was hardly reduced (Comparative Examples 3 to 5).
On the other hand, when air was blown under a temperature condition of 180 ° C. or higher, the amount of 3-MCPD fatty acid ester contained in the oil and fat composition could be significantly reduced (Examples 1 to 3).
When carried out under reduced pressure conditions or when nitrogen was blown in place of air, the amount of 3-MCPD fatty acid ester was hardly reduced (Comparative Examples 6 and 7), and thus the effects of the present invention were obtained. It can be seen that air blowing and a temperature condition of 170 ° C. or higher are important.
本発明により、３−ＭＣＰＤ脂肪酸エステルの量が低減された油脂組成物を得ることができる。したがって、産業上、極めて有用である。 According to the present invention, an oil and fat composition in which the amount of 3-MCPD fatty acid ester is reduced can be obtained. Therefore, it is very useful industrially.
Claims (4)
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| JP2011147435A (en) * | 2010-01-19 | 2011-08-04 | Cj Cheiljedang Corp | Method for producing edible oil-and-fat reduced in 3-mcpd-fs |
| JP2011174091A (en) * | 2011-06-01 | 2011-09-08 | Showa Sangyo Co Ltd | Method for producing palm oil having step of removing free chlorine |
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| JP2001152181A (en) * | 1999-11-26 | 2001-06-05 | Kao Corp | Purification method for fatty acid |
| WO2010126136A1 (en) * | 2009-04-30 | 2010-11-04 | 不二製油株式会社 | Method for inhibiting production of chloropropanols and chloropropanol-forming substances in glyceride oils and fats |
| JP2011074358A (en) * | 2009-09-07 | 2011-04-14 | Nisshin Oillio Group Ltd | Glyceride composition and method for producing the same |
| JP2011147436A (en) * | 2010-01-19 | 2011-08-04 | Cj Cheiljedang Corp | Method for producing edible oil-and-fat reduced in 3-mcpd-fs |
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