JP6451447B2 - Method for producing refined palm oil with reduced monochloropropanediol-forming substance content - Google Patents
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本発明は、モノクロロプロパンジオール、モノクロロプロパンジオール脂肪酸エステルから選択される１種以上のモノクロロプロパンジオール生成物質の含有量を低減させた油脂の製造法に関するものである。 The present invention relates to a method for producing fats and oils in which the content of at least one monochloropropanediol-forming substance selected from monochloropropanediol and monochloropropanediol fatty acid ester is reduced.
クロロプロパノールとは、グリセロール骨格に塩素が１つないし２つ結合した化合物である。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 compound in which one or two chlorines are bonded to the glycerol skeleton. It is known that 3-chloropropanediol, which is one of these, is conventionally produced in a small amount as a by-product when mainly producing amino acid solutions such as soy sauce, and in the process of cooking food, It is said that it is generated by the existence of.
近年複数種の食用油脂中から、クロロプロパノールの一種である３−クロロ−１，２−プロパンジオール（３−ＭＣＰＤ）に脂肪酸がエステル結合した ３−ＭＣＰＤ脂肪酸エステル、及びその位置異性体である２−クロロ−１，３−プロパンジオール（２−ＭＣＰＤ）脂肪酸エステルが検出された．３−ＭＣＰＤ脂肪酸エステル及び２−ＭＣＰＤ脂肪酸エステルの存在が確認された油脂の中でも、特にパーム油脂及びパーム油脂を原料とした精製食用油脂にて含有量が比較的高いと報告された（非特許文献１−３）。 In recent years, 3-MCPD fatty acid ester in which fatty acid is ester-bonded to 3-chloro-1,2-propanediol (3-MCPD), which is a kind of chloropropanol, and its positional isomer 2 -Chloro-1,3-propanediol (2-MCPD) fatty acid ester was detected. Among oils and fats in which the presence of 3-MCPD fatty acid esters and 2-MCPD fatty acid esters was confirmed, it was reported that the content was particularly high in refined edible fats and oils using palm oils and palm oils as raw materials (non-patent literature) 1-3).
３−ＭＣＰＤ脂肪酸エステルに関して、ｉｎ ｖｉｔｒｏ における体内での加水分解に関する試験が行われた。その結果、３−ＭＣＰＤ脂肪酸エステルを摂取した場合、体内のリパーゼの作用により加水分解され、３−ＭＣＰＤとなるとされている（非特許文献４）。３−ＭＣＰＤはＦＡＯ／ＷＨＯ合同食品添加物専門家会議（ＪＥＣＦＡ）により，最大耐容１日摂取量（ＰＭＴＤＩ）を体重あたり２μｇと設定されている化合物である（非特許文献５）。これを上回る３−ＭＣＰＤを長年にわたって摂取した場合、腎臓に悪影響を与える可能性があるとされている（非特許文献５）。 The 3-MCPD fatty acid ester was tested for in vivo hydrolysis in vitro. As a result, when 3-MCPD fatty acid ester is ingested, it is said to be hydrolyzed by the action of lipase in the body to become 3-MCPD (Non-patent Document 4). 3-MCPD is a compound whose maximum tolerable daily intake (PMTDI) is set to 2 μg per body weight by the FAO / WHO Joint Food Additives Expert Meeting (JECFA) (Non-patent Document 5). When 3-MCPD exceeding this is taken for many years, it is supposed that it may have a bad influence on a kidney (nonpatent literature 5).
以上の背景を踏まえ、モノクロロプロパンジオール、モノクロロプロパンジオール脂肪酸エステルから選択される１種以上のモノクロロプロパンジオール生成物質の含有量を低減させた油脂の開発が望まれている。 Based on the above background, development of oils and fats in which the content of one or more monochloropropanediol-forming substances selected from monochloropropanediol and monochloropropanediol fatty acid esters is reduced is desired.
モノクロロプロパンジオール生成物質の含有量を低減する方法として、モノクロロプロパンジオール生成物質は脱臭処理中に生成される傾向より、特許文献１にはモノクロロプロパンジオール生成物質であるグリシドール等を含有するグリセリド組成物を、１００〜２４０℃という低温での脱臭処理することにより、グリシドール等を低減する方法が提案されている。また、特許文献２には、同様に１９０〜２３０℃の低温脱臭処理が提案されている。しかし、特許文献１や特許文献２の方法では、脱臭後の精製油酸価の低下が不十分で、かつ精製油風味が油っぽいものになるという問題があった。 As a method for reducing the content of the monochloropropanediol-producing substance, the monochloropropanediol-producing substance tends to be produced during the deodorization treatment. Therefore, Patent Document 1 discloses a glyceride composition containing glycidol, which is a monochloropropanediol-producing substance. A method for reducing glycidol and the like by deodorizing at a low temperature of 100 to 240 ° C. has been proposed. Patent Document 2 similarly proposes a low-temperature deodorization treatment at 190 to 230 ° C. However, the methods of Patent Document 1 and Patent Document 2 have a problem that the refined oil acid value after deodorization is not sufficiently lowered and the refined oil flavor becomes oily.
特許文献３は、上記の問題を解決するべく、２３０〜２６５℃、１５０〜７００Ｐａの真空度で３０〜１８０分間、油脂と水蒸気をトレイ式脱臭装置におけるトレイ中で接触させ、かつ上記水蒸気量が、上記トレイ中の油脂に対して３〜８質量％である油脂の製造方法に関する。本方法によれば、脱臭工程を高温条件下で行っても、脱臭後の油脂中のグリシドール等の増加を抑制できると記載されているが、本発明者らが検証したところ、原料油脂によっては本方法でも満足できるレベルまでモノクロロプロパンジオール生成物質含有量を低減できない場合もあることが判明した。 In Patent Document 3, in order to solve the above-described problem, oil and fat and water vapor are brought into contact with each other in a tray in a tray-type deodorizing apparatus at 230 to 265 ° C. and a vacuum degree of 150 to 700 Pa for 30 to 180 minutes. The present invention relates to a method for producing fats and oils of 3 to 8% by mass with respect to the fats and oils in the tray. According to this method, even if the deodorization step is performed under high temperature conditions, it is described that increase in glycidol and the like in the fat after deodorization can be suppressed, but when the present inventors verified, depending on the raw material fat It has been found that even in this method, the content of the monochloropropanediol-forming substance cannot be reduced to a satisfactory level.
本発明は、従来の方法の問題点を解決し、モノクロロプロパンジオール、モノクロロプロパンジオール脂肪酸エステルから選択される１種以上のモノクロロプロパンジオール生成物質の含有量を満足できるレベルまで低減させた精製パーム油（ＲＢＤＰＯ）の製造方法を提供することを目的とする。 The present invention solves the problems of conventional methods, and refined palm oil in which the content of one or more monochloropropanediol-producing substances selected from monochloropropanediol and monochloropropanediol fatty acid ester is reduced to a satisfactory level An object is to provide a method for producing (RBDPO).
本発明者らは、鋭意研究を重ねた結果、モノクロロプロパンジオール、モノクロロプロパンジオール脂肪酸エステルから選択される１種以上のモノクロロプロパンジオール生成物質を含有する粗パーム油（ＣＰＯ）をモノクロロプロパンジオール生成物質の分圧が１．０×１０−５ｍｍＨｇ以下の条件により脱臭することで、モノクロロプロパンジオール生成物質の含有量を低減することができるという知見を得た。また、粗パーム油（ＣＰＯ）を水および／または有機酸水溶液によって洗浄後、水相を分離して得られる油相を、モノクロロプロパンジオール生成物質の分圧が１．０×１０−５ｍｍＨｇ以下の条件により脱臭することで、さらにモノクロロプロパンジオール生成物質の含有量を低減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。 As a result of intensive research, the present inventors have determined that a crude palm oil (CPO) containing at least one monochloropropanediol fatty acid ester selected from monochloropropanediol and monochloropropanediol fatty acid ester is used as a monochloropropanediol production material. It was found that the content of the monochloropropanediol-producing substance can be reduced by deodorizing under the condition of the partial pressure of 1.0 × 10 −5 mmHg or less. Further, after washing crude palm oil (CPO) with water and / or an organic acid aqueous solution and separating the aqueous phase, the partial pressure of the monochloropropanediol-producing substance is 1.0 × 10 −5 mmHg or less. The inventors have found that the content of the monochloropropanediol-producing substance can be further reduced by deodorizing under the above conditions, and have completed the present invention.
すなわち本発明は、
（１）モノクロロプロパンジオール、モノクロロプロパンジオール脂肪酸エステルから選択される１種以上のモノクロロプロパンジオール生成物質を含有する粗パーム油を、モノクロロプロパンジオール生成物質の分圧が１．０×１０−５ｍｍＨｇ以下の条件で脱臭することを特徴とする、モノクロロプロパンジオール生成物質の含有量を低減させた精製パーム油の製造方法。
（２）粗パーム油が水および／または有機酸水溶液により洗浄後、水相を分離して得られる油相である、（１）記載の精製パーム油の製造方法。
（３）脱臭条件が、脱臭温度２３０〜２６０℃、真空度１〜５ｍｍＨｇ，脱臭温度における吹き込み蒸気量が粗パーム油１００重量％に対し真空度（ｍｍＨｇ）×４〜８重量％である、（１）又は（２）に記載の精製パーム油の製造方法。
（４）精製パーム油のモノクロロプロパンジオール生成物質含有量が２．５ｐｐｍ以下である、（１）〜（３）のいずれか１記載の精製パーム油の製造方法。
である。
That is, the present invention
(1) A crude palm oil containing at least one monochloropropanediol-forming substance selected from monochloropropanediol and monochloropropanediol fatty acid ester is used, and the partial pressure of the monochloropropanediol-forming substance is 1.0 × 10 −5 mmHg. A method for producing a refined palm oil in which the content of a monochloropropanediol-producing substance is reduced, which is characterized by deodorizing under the following conditions.
(2) The method for producing refined palm oil according to (1), wherein the crude palm oil is an oil phase obtained by separating the aqueous phase after washing with water and / or an organic acid aqueous solution.
(3) The deodorization conditions are a deodorization temperature of 230 to 260 ° C., a degree of vacuum of 1 to 5 mmHg, and an amount of blown steam at the deodorization temperature is 100% by weight of crude palm oil (mmHg) × 4 to 8% by weight. The manufacturing method of the refined palm oil as described in 1) or (2).
(4) The method for producing purified palm oil according to any one of (1) to (3), wherein the content of the monochloropropanediol-producing substance in the purified palm oil is 2.5 ppm or less.
It is.
本発明の低減方法により、モノクロロプロパンジオール生成物質であるモノクロロプロパンジオール、モノクロロプロパンジオール脂肪酸エステルの含有量が低減された精製パーム油（ＲＢＤＰＯ）を提供することができる。 According to the reduction method of the present invention, it is possible to provide purified palm oil (RBDPO) in which the contents of monochloropropanediol and monochloropropanediol fatty acid ester, which are monochloropropanediol-forming substances, are reduced.
以下に、本発明を詳細に説明する。 The present invention is described in detail below.
本発明の低減方法は、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において、好ましく適用できる。 The reduction method of the present invention is a refining process such as degumming, deoxidation, decolorization, deodorization, and dewaxing to obtain refined palm oil (RBDPO) from crude palm oil (CPO) obtained by squeezing the pulp of oil palm. It can be preferably applied.
本発明のモノクロロプロパンジオールとは、３−クロロプロパン−１，２−ジオールおよび２−クロロプロパン−１，３−ジオールを意味する。また、モノクロロプロパンジオール脂肪酸エステルとは、３−クロロプロパン−１，２−ジオール脂肪酸エステルおよび２−クロロプロパン−１，３−ジオール脂肪酸エステルを意味する。
本発明の低減方法は、粗パーム油（ＣＰＯ）をモノクロロプロパンジオール生成物質の分圧が１．０×１０−５ｍｍＨｇ以下の条件で脱臭することを特徴とするが、脱臭の前処理としては水分、夾雑物、色素成分などを除去するため、活性白土や活性炭を用い、１００〜１２０℃、減圧下による脱色工程を経るのが好ましい。脱色工程後にろ過された脱色油を、脱臭工程においてモノクロロプロパンジオール生成物質の分圧が１．０×１０−５ｍｍＨｇ以下、好ましくは８．０×１０−６ｍｍＨｇ以下の条件で脱臭する。モノクロロプロパンジオール生成物質の分圧が１．０×１０−５ｍｍＨｇを超えると、脱臭後のモノクロロプロパンジオール生成物質の含有量の低減が不十分となり、好ましくない。
The monochloropropanediol of the present invention means 3-chloropropane-1,2-diol and 2-chloropropane-1,3-diol. Monochloropropanediol fatty acid ester means 3-chloropropane-1,2-diol fatty acid ester and 2-chloropropane-1,3-diol fatty acid ester.
The reduction method of the present invention is characterized in that crude palm oil (CPO) is deodorized under the condition that the partial pressure of the monochloropropanediol-producing substance is 1.0 × 10 −5 mmHg or less. In order to remove moisture, impurities, pigment components, etc., it is preferable to use an activated clay or activated carbon and go through a decoloring step at 100 to 120 ° C. under reduced pressure. The decolorized oil filtered after the decolorization step is deodorized in the deodorization step under the condition that the partial pressure of the monochloropropanediol-forming substance is 1.0 × 10 −5 mmHg or less, preferably 8.0 × 10 −6 mmHg or less. When the partial pressure of the monochloropropanediol-producing substance exceeds 1.0 × 10 −5 mmHg, the content of the monochloropropanediol-producing substance after deodorization is not sufficiently reduced, which is not preferable.
上記分圧を得るためには、脱臭条件としては脱臭温度２３０〜２６０℃、真空度１〜５ｍｍＨｇ，脱臭時間３０〜１８０分、脱臭時の吹き込み水蒸気量は脱臭する油脂１００重量％に対し真空度（ｍｍＨｇ）×４〜８重量％である。上記分圧は、真空度が高い（真空度の数値がより低い）ほど、脱臭時の吹き込み水蒸気量が多いほど、低下する傾向にある。例えば、脱臭温度２５０℃、真空度２ｍｍＨｇの場合の脱臭時の吹き込み水蒸気量は、８〜１６重量％で１．０×１０−５ｍｍＨｇ以下のモノクロロプロパンジオール生成物質の分圧を得ることができる。また、脱臭温度２５０℃、真空度１ｍｍＨｇの場合の脱臭時の吹き込み水蒸気量は４〜８重量％で、前記同分圧を得ることができる。脱臭温度が下限未満であると、酸価の低下が不十分となるとともに脱臭油風味が油っぽいものになる傾向がある。逆に、上限を超えると、脱臭工程中におけるモノクロロプロパンジオール生成物質の生成量が多くなるためか、脱臭後のモノクロロプロパンジオール生成物質含有量の低減が不十分となる傾向がある。真空度は高いほど、モノクロロプロパンジオール生成物質の分圧を低下させることができるが、５ｍｍＨｇを超えると分圧低下が困難となるため、好ましくない。また、吹き込み水蒸気量は真空度に依存するが、真空度（ｍｍＨｇ）×４〜８重量％の下限未満ではモノクロロプロパンジオール生成物質の分圧低下が不十分となるため、好ましくない。上限を超えるのは、脱臭時の真空度保持が困難となるため、やはり好ましくない。 In order to obtain the above partial pressure, the deodorization conditions include a deodorization temperature of 230 to 260 ° C., a degree of vacuum of 1 to 5 mmHg, a deodorization time of 30 to 180 minutes, and the amount of steam blown during deodorization is a degree of vacuum relative to 100% by weight of the oil to be deodorized. (MmHg) × 4 to 8% by weight. The partial pressure tends to decrease as the degree of vacuum is higher (the degree of vacuum is lower) or as the amount of water vapor blown during deodorization is larger. For example, when the deodorization temperature is 250 ° C. and the degree of vacuum is 2 mmHg, the amount of water vapor blown at the time of deodorization is 8 to 16% by weight, and a partial pressure of the monochloropropanediol-producing substance of 1.0 × 10 −5 mmHg or less can be obtained. . In addition, when the deodorization temperature is 250 ° C. and the degree of vacuum is 1 mmHg, the amount of water vapor blown at the time of deodorization is 4 to 8% by weight, and the same partial pressure can be obtained. When the deodorization temperature is less than the lower limit, the acid value is not sufficiently lowered and the deodorized oil flavor tends to be oily. On the other hand, if the upper limit is exceeded, the amount of monochloropropanediol-producing substance produced during the deodorization process increases, or the monochloropropanediol-producing substance content after deodorization tends to be insufficiently reduced. The higher the degree of vacuum, the lower the partial pressure of the monochloropropanediol-producing substance. However, if it exceeds 5 mmHg, it is difficult to lower the partial pressure, which is not preferable. Further, the amount of water vapor blown depends on the degree of vacuum, but if the degree of vacuum (mmHg) × 4 to 8% by weight is less than the lower limit, the partial pressure of the monochloropropanediol-forming substance is insufficient, which is not preferable. Exceeding the upper limit is also not preferable because it is difficult to maintain the degree of vacuum during deodorization.
本発明の低減方法の一態様として、上記の脱色工程の前工程として、粗パーム油（ＣＰＯ）を水および／または有機酸水溶液で洗浄し、水相を分離した油相を前記の脱色及び脱臭工程に供し、モノクロロプロパンジオール生成物質の分圧が１．０×１０−５ｍｍＨｇ以下の条件で脱臭することができる。粗パーム油（ＣＰＯ）の洗浄には水および／または有機酸水溶液が使用できるが、より好ましくは有機酸水溶液である。有機酸としてはクエン酸、シュウ酸、リン酸、アスコルビン酸が例示できる。有機酸水溶液としては、例えば対油０．０１〜１重量％の５０％水溶液のような高濃度水溶液と対油１〜５０重量％の水を混合または別添加して、前記洗浄処理に供することができる。粗パーム油（ＣＰＯ）を水および／または有機酸水溶液で洗浄し、水相を分離した油相を常法通り脱色後、モノクロロプロパンジオール生成物質の分圧が１．０×１０−５ｍｍＨｇ以下の条件で脱臭することにより、最終精製油である精製パーム油のモノクロロプロパンジオール生成物質の含有量を、より低レベル、例えば２．５ｐｐｍ以下まで低減することができる。 As one aspect of the reduction method of the present invention, as a preceding step of the above decolorization step, crude palm oil (CPO) is washed with water and / or an organic acid aqueous solution, and the oil phase separated from the aqueous phase is subjected to the above decolorization and deodorization. It can use for a process and can deodorize on the conditions whose partial pressure of a monochloropropanediol production substance is 1.0 * 10 < -5 > mmHg or less. Water and / or an organic acid aqueous solution can be used for washing crude palm oil (CPO), and an organic acid aqueous solution is more preferable. Examples of the organic acid include citric acid, oxalic acid, phosphoric acid, and ascorbic acid. As the organic acid aqueous solution, for example, a high concentration aqueous solution such as a 50% aqueous solution of 0.01 to 1% by weight of oil and a water of 1 to 50% by weight of oil are mixed or separately added and subjected to the washing treatment. Can do. After washing crude palm oil (CPO) with water and / or an organic acid aqueous solution and decolorizing the oil phase from which the aqueous phase has been separated as usual, the partial pressure of the monochloropropanediol-producing substance is 1.0 × 10 −5 mmHg or less By deodorizing under these conditions, the content of the monochloropropanediol-producing substance in the refined palm oil that is the final refined oil can be reduced to a lower level, for example, 2.5 ppm or less.
本発明において、脱臭時の吹き込み蒸気量におけるモノクロロプロパンジオール生成物質の分圧は、次の要領で算出することができる。 In the present invention, the partial pressure of the monochloropropanediol-producing substance in the amount of steam blown at the time of deodorization can be calculated as follows.
まず、脱臭装置内の気相を構成する化合物は、蒸気、遊離脂肪酸、ＭＣＰＤ生成物質の３種のみと仮定する。ヘンリーの法則より、気体を構成する化合物の分圧比は、その化合物の物質量モル比と一致する。よって、脱臭装置内の気相を構成する化合物（蒸気、遊離脂肪酸、ＭＣＰＤ生成物質）の物質量モル比から、分圧が算出できる。 First, it is assumed that there are only three types of compounds constituting the gas phase in the deodorizing apparatus: steam, free fatty acids, and MCPD-generating substances. According to Henry's law, the partial pressure ratio of the compound constituting the gas coincides with the molar amount ratio of the compound. Therefore, the partial pressure can be calculated from the molar ratio of the compounds (steam, free fatty acid, MCPD product) constituting the gas phase in the deodorizing apparatus.
遊離脂肪酸、蒸気、ＭＣＰＤ生成物質の物質量は、下記の計算式より算出する。
＜遊離脂肪酸算出式＞
脱臭操作前と脱臭操作後の油脂の酸価を測定し、脱臭操作によって減少した酸価から、脱臭装置内の気相に含まれる遊離脂肪酸の物質量を算出した。計算式は下記のようになる。
遊離脂肪酸物質量（ｍｏｌ／ｇ）＝（脱臭操作前の酸価−脱臭操作後の酸価）／５６．１０／１０００
＜蒸気量算出式＞
下記の計算式から、脱臭装置内の気相に含まれる蒸気の物質量を算出する。
吹き込み蒸気物質量（ｍｏｌ／ｇ）＝吹き込み蒸気量（％）／１００／１８
＜ＭＣＰＤ生成物質物質量算出式＞
蒸気を吹き込まない場合に生成するＭＣＰＤ生成物質の物質量と、各吹き込み蒸気量において生成するＭＣＰＤ生成物質の物質量を測定する。吹き込み蒸気量の増加に伴い、減少するＭＣＰＤ生成物質の物質量を用いて、脱臭装置内の気相に含まれるＭＣＰＤ生成物質の物質量を算出する。算出の際は、ＭＣＰＤの生成物質を一価の塩素化合物と仮定する。計算式は下記のようになる。
ＭＣＰＤ生成物物質量（ｍｏｌ／ｇ）＝（（蒸気を吹き込まない場合の２−ＭＣＰＤと３−ＭＣＰＤの含有量合算値（ｐｐｍ））―（蒸気吹き込み後の精製油中の２−ＭＣＰＤと３−ＭＣＰＤの含有量合算値（ｐｐｍ）））／１１０．５／１００００００
The amount of free fatty acid, steam, and MCPD-generating substance is calculated from the following formula.
<Free fatty acid calculation formula>
The acid value of the fats and oils before and after the deodorizing operation was measured, and the amount of free fatty acid contained in the gas phase in the deodorizing apparatus was calculated from the acid value decreased by the deodorizing operation. The calculation formula is as follows.
Free fatty acid substance amount (mol / g) = (acid value before deodorizing operation−acid value after deodorizing operation) /56.10/1000
<Steam calculation formula>
The amount of vapor contained in the gas phase in the deodorizer is calculated from the following formula.
Blowing vapor amount (mol / g) = Blowing vapor amount (%) / 100/18
<MCPD product substance amount calculation formula>
The amount of MCPD-generating substance generated when steam is not blown and the amount of MCPD-generating substance generated at each blowing steam amount are measured. The amount of MCPD-generating substance contained in the gas phase in the deodorizing apparatus is calculated using the amount of MCPD-generating substance that decreases as the amount of blown steam increases. In the calculation, it is assumed that the MCPD product is a monovalent chlorine compound. The calculation formula is as follows.
MCPD product substance amount (mol / g) = ((total content of 2-MCPD and 3-MCPD when steam is not blown (ppm)) − (2-MCPD and 3 in refined oil after steam blown -MCPD content total value (ppm))) / 110.5 / 1000000
脱臭装置内の全圧は脱臭中の真空度（ｍｍＨｇ）であるので、上記で算出した各化合物の物質量と、下記の計算式から、ＭＣＰＤ生成物質の分圧を算出できる。
ＭＣＰＤ生成物質分圧（ｍｍＨｇ）＝真空度×ＭＣＰＤ生成物物質量／（遊離脂肪酸物質量＋吹き込み蒸気物質量）
上記式より、ＭＣＰＤ生成物質分圧は真空度が高い（真空度の数値がより低い）ほど、また吹き込み蒸気量が多いほど、低下することがわかる。すなわち、ＭＣＰＤ生成物質分圧を低減するには、真空度を高くするか、吹き込み水蒸気量を多くする必要がある。
Since the total pressure in the deodorization apparatus is the degree of vacuum during deodorization (mmHg), the partial pressure of the MCPD-generating substance can be calculated from the amount of each compound calculated above and the following calculation formula.
MCPD product substance partial pressure (mmHg) = vacuum degree × MCPD product substance amount / (free fatty acid substance amount + injected steam substance amount)
From the above equation, it can be seen that the MCPD product partial pressure decreases as the degree of vacuum increases (the degree of vacuum is lower) and the amount of blown steam increases. That is, in order to reduce the MCPD product substance partial pressure, it is necessary to increase the degree of vacuum or increase the amount of blown water vapor.
本発明の脱臭工程において、モノクロロプロパンジオール生成物質の分圧が１．０×１０−５ｍｍＨｇ以下の条件とするには、脱臭温度２３０〜２６０℃、真空度１〜５ｍｍＨｇ、脱臭温度における吹き込み蒸気量が粗パーム油１００重量％に対し真空度（ｍｍＨｇ）×４〜８重量％とする必要がある。 In the deodorizing step of the present invention, in order to set the partial pressure of the monochloropropanediol-forming substance to 1.0 × 10 −5 mmHg or less, the blowing steam at a deodorizing temperature of 230 to 260 ° C., a degree of vacuum of 1 to 5 mmHg, and a deodorizing temperature The amount needs to be a degree of vacuum (mmHg) × 4 to 8% by weight with respect to 100% by weight of the crude palm oil.
本発明の低減方法によって得られた精製パーム油（ＲＢＤＰＯ）は、モノクロロプロパンジオール、モノクロロプロパンジオール脂肪酸エステルから選択される１種以上のモノクロロプロパンジオール生成物質の含有量が低減されるが、本発明において、モノクロロプロパンジオール生成物質の含量は次のような方法で測定している。 The refined palm oil (RBDPO) obtained by the reduction method of the present invention has a reduced content of one or more monochloropropanediol-producing substances selected from monochloropropanediol and monochloropropanediol fatty acid ester. The content of the monochloropropanediol-forming substance is measured by the following method.
油脂試料１００ｍｇにイソオクタン０．３ｍＬを加え、油脂試料を溶解する。試験管に９０Ｕ／ｍＬリパーゼ含有臭化ナトリウム溶液３ｍＬ加えて、試験管を振盪機で３０分間振盪する。試験管を８０℃で１０分間加熱後、試験管を室温になるまで放冷又は水冷する。試験管に２．０ μｇ／ｍＬ内標準混合溶液を５０μＬとヘキサン３ｍＬを加えて蓋を閉める。試験管をボルテックスミキサーで撹拌、遠心分離機後、水層をパスツールピペットで新たな試験管に移す。水層を移した試験管に、ヘキサン３ｍＬを加えて蓋を閉め、ボルテックスミキサーで撹拌し、遠心分離機後、有機層を除去する。試験管にフェニルボロン酸溶液２０μＬとヘキサン３ｍＬ加えて蓋を閉める。試験管を振盪機で１０分間振盪する。有機層をパスツールピペットで新たな試験管に移す。新たな試験管中の有機層を窒素ガスで０．５〜０．８ｍＬに濃縮後、ＧＣ−ＭＳにて分析を行う。
なお、ＧＣ−ＭＳについては、分子イオンピークｍ／ｚ １４７（３−ＭＣＰＤ）、ｍ／ｚ １５０（３−ＭＣＰＤ−ｄ５）、ｍ／ｚ １９６（２−ＭＣＰＤ）、ｍ／ｚ、２１０（２−ＭＣＰＤ−ｄ５）を用いて定量する。
Add 0.3 mL of isooctane to 100 mg of an oil and fat sample to dissolve the oil and fat sample. Add 3 mL of sodium bromide solution containing 90 U / mL lipase to the test tube, and shake the test tube for 30 minutes on a shaker. After heating the test tube at 80 ° C. for 10 minutes, the test tube is allowed to cool to room temperature or water-cooled. Add 50 μL of 2.0 μg / mL internal standard mixed solution and 3 mL of hexane to the test tube and close the lid. Stir the test tube with a vortex mixer, centrifuge, and transfer the aqueous layer to a new test tube with a Pasteur pipette. Add 3 mL of hexane to the test tube to which the aqueous layer has been transferred, close the lid, stir with a vortex mixer, remove the organic layer after centrifugation. Add 20 μL of phenylboronic acid solution and 3 mL of hexane to the test tube and close the lid. Shake test tube on shaker for 10 minutes. Transfer the organic layer to a new tube with a Pasteur pipette. The organic layer in a new test tube is concentrated to 0.5 to 0.8 mL with nitrogen gas, and then analyzed by GC-MS.
In addition, about GC-MS, molecular ion peak m / z 147 (3-MCPD), m / z 150 (3-MCPD-d5), m / z 196 (2-MCPD), m / z, 210 (2 Quantify using MCPD-d5).
本発明の低減方法により、粗パーム油（ＣＰＯ）の精製工程でのモノクロロプロパンジオール生成物質の生成を低減でき、得られる精製パーム油（ＲＢＤＰＯ）中のモノクロロプロパンジオール生成物質含有量を３．５ｐｐｍ以下、より好ましくは２．５ｐｐｍ以下，最も好ましくは２ｐｐｍ以下に低減することができる。 According to the reduction method of the present invention, it is possible to reduce the production of monochloropropanediol-producing substance in the purification step of crude palm oil (CPO), and the content of monochloropropanediol-producing substance in the obtained refined palm oil (RBDPO) is 3.5 ppm. Hereinafter, it can be reduced to more preferably 2.5 ppm or less, and most preferably 2 ppm or less.
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.
実施例１
粗パーム油（ＣＰＯ、酸価８．６３））を白土１．５重量％、１１０℃、２０ｍｍＨｇで１０分間脱色し、ろ過して得られた脱色油をさらに２５０℃、２ｍｍＨｇで９０分間脱臭処理を行った。脱臭温度における吹き込み蒸気量は、油脂１００％に対し１０．９％であった。得られた精製パーム油（ＲＢＤＰＯ）の２−ＭＣＰＤの含量は１．２３ｐｐｍ、３−ＭＣＰＤの含量は２．１９ｐｐｍであり、モノクロロプロパンジオール生成物質含有量は３．４２ｐｐｍであった。脱臭処理の際のモノクロロプロパンジオール生成物質分圧は、実施例１と比較参考例１のモノクロロプロパンジオール生成物質含有量から算出して、８．６×１０−６ｍｍＨｇであった。
Example 1
Crude palm oil (CPO, acid value 8.63)) is decolorized at 1.5% by weight of white clay at 110 ° C. and 20 mmHg for 10 minutes, and the decolorized oil obtained by filtration is further deodorized at 250 ° C. and 2 mmHg for 90 minutes. Went. The amount of steam blown at the deodorizing temperature was 10.9% with respect to 100% of fats and oils. The obtained refined palm oil (RBDPO) had a 2-MCPD content of 1.23 ppm, a 3-MCPD content of 2.19 ppm, and a monochloropropanediol-producing substance content of 3.42 ppm. The monochloropropanediol-producing substance partial pressure during the deodorization treatment was 8.6 × 10 −6 mmHg calculated from the monochloropropanediol-producing substance content of Example 1 and Comparative Reference Example 1.
比較例１
実施例１で用いたものと同じ粗パーム油を白土１．５重量％、１１０℃、２０ｍｍＨｇで１０分間脱色し、ろ過して得られた脱色油をさらに２５０℃、２ｍｍＨｇで９０分間脱臭処理を行った。脱臭温度における吹き込み蒸気量は、油脂１００％に対し３．５％であった。得られた精製パーム油（ＲＢＤＰＯ）の２−ＭＣＰＤの含量は１．５７ｐｐｍ、３−ＭＣＰＤの含量は３．４０ｐｐｍであり、モノクロロプロパンジオール生成物質含有量は４．９７ｐｐｍであった。脱臭処理の際のモノクロロプロパンジオール生成物質の分圧は、比較例１と比較参考例１のモノクロロプロパンジオール生成物質含有量から算出して、１．２×１０−５ｍｍＨｇであった。
Comparative Example 1
The same crude palm oil as used in Example 1 was decolorized at 1.5% by weight of white clay at 110 ° C. and 20 mmHg for 10 minutes, and the decolorized oil obtained by filtration was further deodorized at 250 ° C. and 2 mmHg for 90 minutes. went. The amount of steam blown at the deodorizing temperature was 3.5% with respect to 100% of fats and oils. The resulting refined palm oil (RBDPO) had a 2-MCPD content of 1.57 ppm, a 3-MCPD content of 3.40 ppm, and a monochloropropanediol-producing substance content of 4.97 ppm. The partial pressure of the monochloropropanediol-forming substance during the deodorization treatment was 1.2 × 10 −5 mmHg, calculated from the monochloropropanediol-forming substance content in Comparative Example 1 and Comparative Reference Example 1.
比較例２
実施例１で用いたものと同じ粗パーム油（ＣＰＯ）を白土１．５重量％、１１０℃、２０ｍｍＨｇで１０分間脱色し、ろ過して得られた脱色油をさらに２５０℃、２ｍｍＨｇで９０分間脱臭処理を行った。脱臭温度における吹き込み蒸気量は、油脂１００％に対し７．２％であった。得られた精製パーム油（ＲＢＤＰＯ）の２−ＭＣＰＤの含量は１．２５ｐｐｍ、３−ＭＣＰＤの含量は２．４９ｐｐｍであり、モノクロロプロパンジオール生成物質含有量は３．７４ｐｐｍであった。脱臭処理の際のモノクロロプロパンジオール生成物質の分圧は、比較例２と比較参考例１のモノクロロプロパンジオール生成物質含有量から算出して、１．１×１０−５ｍｍＨｇであった。
Comparative Example 2
The same crude palm oil (CPO) as used in Example 1 was decolorized at 1.5% by weight of white clay, 110 ° C., 20 mmHg for 10 minutes, and the decolorized oil obtained by filtration was further 250 ° C., 2 mmHg for 90 minutes. Deodorization treatment was performed. The amount of steam blown at the deodorizing temperature was 7.2% with respect to 100% of fats and oils. The obtained refined palm oil (RBDPO) had a 2-MCPD content of 1.25 ppm, a 3-MCPD content of 2.49 ppm, and a monochloropropanediol-producing substance content of 3.74 ppm. The partial pressure of the monochloropropanediol-producing substance during the deodorization treatment was 1.1 × 10 −5 mmHg, calculated from the monochloropropanediol-producing substance content in Comparative Example 2 and Comparative Reference Example 1.
比較参考例１
実施例１用いたものと同じ粗パーム油（ＣＰＯ）を白土１．５重量％、１１０℃、２０ｍｍＨｇで１０分間脱色し、さらに２５０℃、２ｍｍＨｇで９０分間脱臭処理を行った。この時の吹き込み蒸気量は対油脂重量０％であった。得られた精製パーム油（ＲＢＤＰＯ）の２−ＭＣＰＤの含量は２．３０ｐｐｍ、３−ＭＣＰＤの含量は４．０６ｐｐｍであり、モノクロロプロパンジオール生成物質含有量は６．３６ｐｐｍであった。
った。
Comparative Reference Example 1
The same crude palm oil (CPO) as used in Example 1 was decolorized at 1.5% by weight of white clay, 110 ° C., 20 mmHg for 10 minutes, and further deodorized at 250 ° C., 2 mmHg for 90 minutes. The amount of steam blown at this time was 0% by weight of fats and oils. The obtained refined palm oil (RBDPO) had a 2-MCPD content of 2.30 ppm, a 3-MCPD content of 4.06 ppm, and a monochloropropanediol-producing substance content of 6.36 ppm.
It was.
表１に、実施例１、比較例1〜２で調製した精製パーム油の分析結果を示す。
表１
Table 1
表1に示すように、同真空度（２ｍｍＨｇ）で脱臭処理した精製パーム油のＭＣＰＤ生成物質含量は、ＭＣＰＤ生成物質分圧が低いほど低減される傾向にあり、ＭＣＰＤ生成物質分圧が１．０×１０−５ｍｍＨｇ以下で、吹き込み水蒸気量が真空度×４〜８％である実施例１は比較例1及び２に対して、ＭＣＰＤ生成物質含有量はより低減されていた。 As shown in Table 1, the content of MCPD-producing substance in refined palm oil deodorized at the same degree of vacuum (2 mmHg) tends to decrease as the MCPD-producing substance partial pressure is lower. In Example 1 in which the amount of water vapor blown in was 0 × 10 −5 mmHg or less and the degree of vacuum was 4 to 8%, the MCPD-producing substance content was further reduced as compared with Comparative Examples 1 and 2.
実施例２
粗パーム油（ＣＰＯ、酸価８．６３）に５０％クエン酸水溶液を対油０．１％、温水を対油２０％加え、攪拌、遠心分離し、ガム質を除去して得られた油相を、白土１．５重量％、１１０℃、２０ｍｍＨｇで１０分間脱色し、ろ過して得られた脱色油をさらに２５０℃、２ｍｍＨｇで９０分間脱臭処理を行った。脱臭温度における吹き込み蒸気量は、油脂１００％に対し１１．２％であった。脱臭後に得られた精製パーム油（ＲＢＤＰＯ）の２−ＭＣＰＤの含量は０．３８ｐｐｍ、３−ＭＣＰＤの含量は０．９４ｐｐｍであり、モノクロロプロパンジオール生成物質含有量は１．３２ｐｐｍであった。脱臭処理の際のモノクロロプロパンジオール生成物質の推定分圧は、実施例２と比較参考例２のモノクロロプロパンジオール生成物質含有量から算出して、６．８×１０−６ｍｍＨｇであった。
Example 2
Oil obtained by adding 50% citric acid aqueous solution to oil 0.1% and warm water 20% to oil to crude palm oil (CPO, acid value 8.63), stirring and centrifuging to remove gum The phase was decolorized at 1.5% by weight of white clay, 110 ° C., 20 mmHg for 10 minutes, and the decolorized oil obtained by filtration was further deodorized at 250 ° C., 2 mmHg for 90 minutes. The amount of steam blown at the deodorizing temperature was 11.2% with respect to 100% of fats and oils. The refined palm oil (RBDPO) obtained after deodorization had a 2-MCPD content of 0.38 ppm, a 3-MCPD content of 0.94 ppm, and a monochloropropanediol-producing substance content of 1.32 ppm. The estimated partial pressure of the monochloropropanediol-producing substance during the deodorization treatment was 6.8 × 10 −6 mmHg calculated from the monochloropropanediol-producing substance content in Example 2 and Comparative Reference Example 2.
比較例３
実施例２で用いたものと同じ粗パーム油（ＣＰＯ）に５０％クエン酸水溶液を対油０．１％、温水を対油２０％加え、攪拌、遠心分離し、ガム質を除去して得られた油相を、白土１．５重量％、１１０℃、２０ｍｍＨｇで１０分間脱色し、ろ過して得られた脱色油をさらに２５０℃、２ｍｍＨｇで９０分間脱臭処理を行った。脱臭温度における吹き込み蒸気量は、油脂１００％に対し４．５％であった。得られた精製パーム油（ＲＢＤＰＯ）の２−ＭＣＰＤの含量は０．６４ｐｐｍ、３−ＭＣＰＤの含量は１．４８ｐｐｍであり、モノクロロプロパンジオール生成物質含有量は２．１２ｐｐｍであった。脱臭処理の際のクロロプロパノール類の前駆物質である塩素化合物の推定分圧は比較例３と比較参考例２のモノクロロプロパンジオール生成物質含有量から算出して、１．１×１０−５ｍｍＨｇであった。
Comparative Example 3
The same crude palm oil (CPO) used in Example 2 was obtained by adding 50% aqueous citric acid solution to oil 0.1% and warm water 20% oil, stirring and centrifuging to remove gum. The obtained oil phase was decolorized at 1.5% by weight of white clay, 110 ° C. and 20 mmHg for 10 minutes, and the decolorized oil obtained by filtration was further deodorized at 250 ° C. and 2 mmHg for 90 minutes. The amount of steam blown at the deodorizing temperature was 4.5% with respect to 100% of fats and oils. The obtained refined palm oil (RBDPO) had a 2-MCPD content of 0.64 ppm, a 3-MCPD content of 1.48 ppm, and a monochloropropanediol-producing substance content of 2.12 ppm. The estimated partial pressure of the chlorine compound, which is a precursor of chloropropanols during the deodorization treatment, is calculated from the monochloropropanediol-forming substance content of Comparative Example 3 and Comparative Reference Example 2, and is 1.1 × 10 −5 mmHg. there were.
比較参考例２
実施例２で用いたものと同じ粗パーム油（ＣＰＯ）に、５０％クエン酸水溶液を対油０．１％、温水を対油２０％加え、攪拌、遠心分離し、ガム質を除去して得られた油相を、白土１．５重量％、１１０℃、２０ｍｍＨｇで１０分間脱色し、さらに２５０℃、２ｍｍＨｇで９０分間脱臭処理を行った。この時の吹き込み蒸気量は対油脂重量０％であった。得られた精製パーム油（ＲＢＤＰＯ）の２−ＭＣＰＤの含量は１．０５ｐｐｍ、３−ＭＣＰＤの含量は２．６６ｐｐｍであり、モノクロロプロパンジオール生成物質含有量は３．７１ｐｐｍであった。
Comparative Reference Example 2
To the same crude palm oil (CPO) used in Example 2, add 50% citric acid aqueous solution to oil 0.1% and warm water 20% to oil, and stir and centrifuge to remove gum. The obtained oil phase was decolorized at 1.5% by weight of white clay, 110 ° C. and 20 mmHg for 10 minutes, and further deodorized at 250 ° C. and 2 mmHg for 90 minutes. The amount of steam blown at this time was 0% by weight of fats and oils. The obtained refined palm oil (RBDPO) had a 2-MCPD content of 1.05 ppm, a 3-MCPD content of 2.66 ppm, and a monochloropropanediol-producing substance content of 3.71 ppm.
表２に、実施例２及び比較例３で調製した精製パーム油の分析結果を示す。
表２
Table 2
表２示すように、同真空度（２ｍｍＨｇ）で脱臭処理した精製パーム油のＭＣＰＤ生成物質含量は、ＭＣＰＤ生成物質分圧が低いほど低減される傾向にあり、ＭＣＰＤ生成物質分圧が１．０×１０−５ｍｍＨｇ以下で、吹き込み水蒸気量が真空度×４〜８％である実施例２は比較例３に対して、ＭＣＰＤ生成物質含有量はより低減されていた。また、ＣＰＯ洗浄の効果により、実施例２は実施例１よりも、より効果的にモノクロロプロパンジオール生成物質含有量を低減されていた。 As shown in Table 2, the MCPD-producing substance content of the refined palm oil deodorized at the same degree of vacuum (2 mmHg) tends to decrease as the MCPD-producing substance partial pressure is lower, and the MCPD-producing substance partial pressure is 1.0. In Example 2 in which the blown water vapor amount was a degree of vacuum x 4 to 8% at x 10 −5 mmHg or less, the MCPD-producing substance content was further reduced as compared with Comparative Example 3. Further, due to the effect of CPO cleaning, the content of the monochloropropanediol-producing substance in Example 2 was more effectively reduced than that in Example 1.
本発明を利用することにより、人の健康に悪影響を及ぼす恐れのあるモノクロロプロパンジオール生成物質含有量を低減させた精製パーム油を製造することが出来る。 By using the present invention, it is possible to produce a refined palm oil in which the content of a monochloropropanediol-forming substance that may adversely affect human health is reduced.
Claims (4)
なお、本発明において、下記の計算式から、脱臭装置内の気相に含まれる蒸気の物質量、及びモノクロロプロパンジオール（ＭＣＰＤ）生成物質の分圧を算出できる。
吹き込み蒸気物質量（ｍｏｌ／ｇ）＝吹き込み蒸気量（％）／１００／１８
ＭＣＰＤ生成物質分圧（ｍｍＨｇ）＝真空度×ＭＣＰＤ生成物物質量／（遊離脂肪酸物質量＋吹き込み蒸気物質量） A crude palm oil containing at least one monochloropropanediol-forming substance selected from monochloropropanediol and monochloropropanediol fatty acid ester is subjected to a decolorization step under reduced pressure at 100 to 120 ° C. using activated clay and / or activated carbon. After that, the amount of steam blown at the deodorization temperature is 100% by weight of the crude palm oil, the degree of vacuum (mmHg) × 4 to 8% by weight, and the partial pressure of the monochloropropanediol-producing substance is 1.0 × 10 −5 mmHg or less. A method for producing a refined palm oil in which the content of a monochloropropanediol-producing substance is reduced, characterized by deodorizing under conditions.
In the present invention, the amount of vapor contained in the gas phase in the deodorizer and the partial pressure of the monochloropropanediol (MCPD) product can be calculated from the following calculation formula.
Blowing vapor amount (mol / g) = Blowing vapor amount (%) / 100/18
MCPD product substance partial pressure (mmHg) = vacuum degree × MCPD product substance amount / (free fatty acid substance amount + injected steam substance amount)
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