JP2013199581A - Method of producing refined bleached deodorized palm oil (rbdpo) reduced in content of chloropropanols - Google Patents
Method of producing refined bleached deodorized palm oil (rbdpo) reduced in content of chloropropanols Download PDFInfo
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本発明はクロロプロパノール類の含有量が低減された精製パーム油（ＲＢＤＰＯ）の製造方法に関する。 The present invention relates to a method for producing refined palm oil (RBDPO) having a reduced content of chloropropanols.
クロロプロパノールとは、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 general term for substances in which chlorine is bonded to propanol, but 3-chloropropanediol, which is one of these substances, has traditionally been produced in small quantities as a by-product when producing mainly amino acid solutions such as soy sauce. In addition, it is said that it is formed by the presence of lipids and salt in the process of cooking food.
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 exist in the form of esters in which 3-chloropropanediol is bonded to fatty acids. (Non-Patent Document 1)
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含量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 determined, but in Europe, all the fatty acids that bind to 3-chloropropanediol fatty acid ester are released and 3-chloropropanediol Therefore, it is desirable to develop technology that reduces the content of glyceride oils and fats.
本発明は、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の含有量が低減された精製パーム油（ＲＢＤＰＯ）を提供することを目的とする。 An object of this invention is to provide refine | purified palm oil (RBDPO) in which content of 3-chloropropanediol and 3-chloropropanediol fatty acid ester which are chloropropanols was reduced.
本発明者らは、粗パーム油（ＣＰＯ）の過酸化物価（ＰＯＶ）が精製後のパーム油（ＲＢＤＰＯ）中のクロロプロパノール類の含有量に重大な影響を及ぼすという知見を得た。かかる知見から、上記課題に対し、鋭意研究を重ねた結果、過酸化物価（ＰＯＶ）が２以下の粗パーム油（ＣＰＯ）を精製することにより、クロロプロパノール類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。 The present inventors have found that the peroxide value (POV) of crude palm oil (CPO) has a significant effect on the content of chloropropanols in the refined palm oil (RBDPO). From such knowledge, as a result of intensive research on the above problems, the content of chloropropanols can be reduced by purifying crude palm oil (CPO) having a peroxide value (POV) of 2 or less. As a result, the present invention has been completed.
すなわち本発明は
（１）過酸化物価（ＰＯＶ）が２以下の粗パーム油（ＣＰＯ）を精製することを特徴とする、精製パーム油（ＲＢＤＰＯ）中のクロロプロパノール類の低減方法、
（２）過酸化物価（ＰＯＶ）が２以下の粗パーム油（ＣＰＯ）を精製し、アルカリ脱酸を行わないことを特徴とする、精製パーム油（ＲＢＤＰＯ）中のクロロプロパノール類の低減方法、
（３）（１）又は（２）記載の方法で、クロロプロパノール類を低減することを特徴とする、精製パーム油の製造方法である。
That is, the present invention provides (1) a method for reducing chloropropanols in refined palm oil (RBDPO), wherein the crude palm oil (CPO) having a peroxide value (POV) of 2 or less is refined,
(2) A method for reducing chloropropanols in refined palm oil (RBDPO), wherein the crude palm oil (CPO) having a peroxide value (POV) of 2 or less is purified and alkali deoxidation is not performed.
(3) A method for producing refined palm oil, characterized in that chloropropanols are reduced by the method described in (1) or (2).
本発明の低減方法により、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など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。 By the reduction method of the present invention, purified palm oil (RBDPO) in which the content of chloropropanols such as 3-chloropropanediol and 3-chloropropanediol fatty acid ester is reduced can be provided.
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.
本発明の低減方法は、過酸化物価（ＰＯＶ）が２以下の粗パーム油（ＣＰＯ）を精製することを特徴とするが、過酸化物価（ＰＯＶ）は、油脂１ｋｇ中の過酸化物によりヨウ化カリウムから遊離されるヨウ素量のｍｇ数で表され、粗パーム油（ＣＰＯ）の過酸化物価（ＰＯＶ）は、日本油化学協会の基準油脂分析試験法２．４．１２−７１により測定することができる。 The reduction method of the present invention is characterized by refining crude palm oil (CPO) having a peroxide value (POV) of 2 or less. The peroxide value (POV) is reduced by iodine in 1 kg of fats and oils. The peroxide value (POV) of crude palm oil (CPO) is measured by the standard method for analysis of fats and oils of Japan Oil Chemical Association 2.4.12-71. be able to.
本発明の低減方法において、粗パーム油（ＣＰＯ）の過酸化物価（ＰＯＶ）は２以下であり、好ましくは１以下、より好ましくは０．５以下であると、精製パーム油（ＲＢＤＰＯ）中のクロロプロパノール類をより低減することができる。 In the reduction method of the present invention, the peroxide value (POV) of the crude palm oil (CPO) is 2 or less, preferably 1 or less, more preferably 0.5 or less, in the refined palm oil (RBDPO). Chloropropanols can be further reduced.
本発明の低減方法は、過酸化物価（ＰＯＶ）が２以下の粗パーム油（ＣＰＯ）を精製し、アルカリ脱酸を行わないことを特徴とし、過酸化物価（ＰＯＶ）が２以下の粗パーム油（ＣＰＯ）を精製することにより、アルカリ脱酸による精製を行わなくても、精製パーム油（ＲＢＤＰＯ）中のクロロプロパノール類を低減することができる。 The reduction method of the present invention is characterized in that a crude palm oil (CPO) having a peroxide value (POV) of 2 or less is purified and alkali deoxidation is not performed, and the crude palm having a peroxide value (POV) of 2 or less. By refining oil (CPO), chloropropanols in refined palm oil (RBDPO) can be reduced without purification by alkaline deoxidation.
本発明の低減方法によって得られた精製パーム油（ＲＢＤＰＯ）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の含有量が低減されるが、本発明において、クロロプロパノール類の含量は非特許文献１を参考に次のような方法で測定している。 In the refined palm oil (RBDPO) obtained by the reduction method of the present invention, the content of 3-chloropropanediol and 3-chloropropanediol fatty acid ester, which are chloropropanols, is reduced. The content is measured by the following method with reference to Non-Patent Document 1.
まず、油脂０．１ｇをＴＨＦ １ｍｌに溶かし、０．０１８％（ｖ／ｖ）硫酸メタノール溶液１．８ｍｌを加え、４０℃で１６時間静置する。飽和炭酸水素ナトリウム０．５ｍｌ、２０μｇ／ｍｌ内部標準物質（３−ＭＣＰＤ−ｄ５ 酢酸エチル溶液）０．５ｍｌと混和、脱溶剤後、２０％ＮａＣｌ ２ｍｌに溶解する。続いて、ヘキサン ２ｍｌを加え攪拌し、上層を除去する操作を２回行う。２０％（ｗ／ｖ）ＰＢＡ溶液（アセトン：水＝１９：１）０．４ｍｌを加え、９０℃で２０分反応させた後、常温まで放冷し、ヘキサン２ｍｌを加え攪拌し、上層をＧＣ／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 １４７（３−ＭＣＰＤ）、ｍ／ｚ １５０（３−ＭＣＰＤ−ｄ５）を用いて定量する。
First, 0.1 g of fats and oils are dissolved in 1 ml of THF, 1.8 ml of 0.018% (v / v) sulfuric acid methanol solution is added, and the mixture is allowed to stand at 40 ° C. for 16 hours. Mix with 0.5 ml of saturated sodium bicarbonate and 0.5 ml of 20 μg / ml internal standard (3-MCPD-d5 ethyl acetate solution), remove the solvent, and dissolve in 2 ml of 20% NaCl. Subsequently, 2 ml of hexane is added and stirred, and the operation of removing the upper layer is performed twice. After adding 0.4 ml of 20% (w / v) PBA solution (acetone: water = 19: 1) and reacting at 90 ° C. for 20 minutes, the mixture is allowed to cool to room temperature, 2 ml of hexane is added and stirred, and the upper layer is GC / Used for MS analysis.
In addition, about GC-MS, it quantifies using molecular ion peak m / z 147 (3-MCPD) and m / z 150 (3-MCPD-d5).
本発明の低減方法により、粗パーム油（ＣＰＯ）の精製工程でのクロロプロパノール類の生成を低減でき、得られる精製パーム油（ＲＢＤＰＯ）中のクロロプロパノール類の含量は１ｐｐｍ以下に低減でき、さらには０．５ｐｐｍ以下に低減できる。 According to the reduction method of the present invention, the production of chloropropanols in the purification step of crude palm oil (CPO) can be reduced, and the content of chloropropanols in the obtained refined palm oil (RBDPO) can be reduced to 1 ppm or less, Can be reduced to 0.5 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.
過酸化物価（ＰＯＶ）が１．９７の粗パーム油（ＣＰＯ／酸価＝７．８）に８５％リン酸を対油０．１％、温水を対油２％加え、攪拌、遠心分離し、ガム質を除去した後、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の含量は１．０ｐｐｍであった。 To crude palm oil (CPO / acid value = 7.8) with a peroxide value (POV) of 1.97, add 85% phosphoric acid to oil 0.1% and warm water 2% to oil, and stir and centrifuge. After the gum was removed, decolorization was performed at 1% by weight of white clay, 110 ° C., 20 Torr for 10 minutes, and further deodorized at 250 ° C., 2 Torr for 90 minutes. The content of chloropropanols in the obtained refined palm oil (RBDPO / IV: 52.2, rising melting point: 36.5 ° C.) was 1.0 ppm.
過酸化物価（ＰＯＶ）が０．９８の粗パーム油（ＣＰＯ／酸価＝７．８）に８５％リン酸を対油０．１％、温水を対油２％加え、攪拌、遠心分離し、ガム質を除去した後、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の含量は０．３ｐｐｍであった。 Add 85% phosphoric acid to oil 0.1% and warm water 2% to oil to crude palm oil (CPO / acid value = 7.8) with a peroxide value (POV) of 0.98, and stir and centrifuge. After the gum was removed, decolorization was performed at 1% by weight of white clay, 110 ° C., 20 Torr for 10 minutes, and further deodorized at 250 ° C., 2 Torr for 90 minutes. The content of chloropropanols in the obtained refined palm oil (RBDPO / IV: 52.2, rising melting point: 36.5 ° C.) was 0.3 ppm.
過酸化物価（ＰＯＶ）が０．４９の粗パーム油（ＣＰＯ／酸価＝７．８）に８５％リン酸を対油０．１％、温水を対油２％加え、攪拌、遠心分離し、ガム質を除去した後、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の含量は０．９ｐｐｍであった。 To crude palm oil (CPO / acid value = 7.8) with a peroxide value (POV) of 0.49, add 85% phosphoric acid to oil 0.1% and warm water 2% to oil, and stir and centrifuge. After the gum was removed, decolorization was performed at 1% by weight of white clay, 110 ° C., 20 Torr for 10 minutes, and further deodorized at 250 ° C., 2 Torr for 90 minutes. The content of chloropropanols in the obtained refined palm oil (RBDPO / IV: 52.2, rising melting point: 36.5 ° C.) was 0.9 ppm.
過酸化物価（ＰＯＶ）が０．４の粗パーム油（ＣＰＯ／酸価＝７．８）に８５％リン酸を対油０．１％、温水を対油２％加え、攪拌、遠心分離し、ガム質を除去した後、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の含量は０．１ｐｐｍであった。 Add 85% phosphoric acid to oil 0.1% and warm water 2% to crude palm oil (CPO / acid value = 7.8) with a peroxide value (POV) of 0.4, stir and centrifuge. After the gum was removed, decolorization was performed at 1% by weight of white clay, 110 ° C., 20 Torr for 10 minutes, and further deodorized at 250 ° C., 2 Torr for 90 minutes. The content of chloropropanols in the obtained refined palm oil (RBDPO / IV: 52.2, rising melting point: 36.5 ° C.) was 0.1 ppm.
（比較例１）
過酸化物価（ＰＯＶ）が１０．５５の粗パーム油（ＣＰＯ／酸価＝７．８）に８５％リン酸を対油０．１％、温水を対油２％加え、攪拌、遠心分離し、ガム質を除去した後、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の含量は２．８ｐｐｍであった。
(Comparative Example 1)
Add 85% phosphoric acid to oil 0.1% and warm water 2% to crude palm oil (CPO / acid value = 7.8) with a peroxide value (POV) of 10.55, and stir and centrifuge. After the gum was removed, decolorization was performed at 1% by weight of white clay, 110 ° C., 20 Torr for 10 minutes, and further deodorized at 250 ° C., 2 Torr for 90 minutes. The content of chloropropanols in the obtained refined palm oil (RBDPO / IV: 52.2, rising melting point: 36.5 ° C.) was 2.8 ppm.
（比較例２）
過酸化物価（ＰＯＶ）が４．３２の粗パーム油（ＣＰＯ／酸価＝７．８）に８５％リン酸を対油０．１％、温水を対油２％加え、攪拌、遠心分離し、ガム質を除去した後、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の含量は１．４ｐｐｍであった。
(Comparative Example 2)
Add 85% phosphoric acid to oil 0.1% and warm water 2% to crude palm oil (CPO / acid value = 7.8) with a peroxide value (POV) of 4.32, and stir and centrifuge. After the gum was removed, decolorization was performed at 1% by weight of white clay, 110 ° C., 20 Torr for 10 minutes, and further deodorized at 250 ° C., 2 Torr for 90 minutes. The content of chloropropanols in the obtained refined palm oil (RBDPO / IV: 52.2, rising melting point: 36.5 ° C.) was 1.4 ppm.
（比較例３）
過酸化物価（ＰＯＶ）が４．３２の粗パーム油（ＣＰＯ／酸価＝７．８）に８５％リン酸を対油０．１％、温水を対油２％加え、攪拌、遠心分離し、ガム質を除去した後、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％、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の含量は０．９ｐｐｍであった。
(Comparative Example 3)
Add 85% phosphoric acid to oil 0.1% and warm water 2% to crude palm oil (CPO / acid value = 7.8) with a peroxide value (POV) of 4.32, and stir and centrifuge. After removing the gum, 6.7% by weight of sodium hydroxide was added, stirred at 3000 rpm for 3 minutes, centrifuged, and after removing the foots, 20% by weight of water was added and stirred at 3000 rpm for 3 minutes. Thereafter, the mixture was centrifuged and the aqueous layer was removed, followed by dehydration treatment at 110 ° C. and 20 Torr for 10 minutes.
After the alkali treatment, decolorization was performed at 1% by weight of white clay, 110 ° C., 20 Torr for 10 minutes, and further, deodorization treatment was performed at 250 ° C., 2 Torr for 90 minutes. The content of chloropropanols in the obtained refined palm oil (RBDPO / IV: 52.2, rising melting point: 36.5 ° C.) was 0.9 ppm.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2010050449A1 (en) * | 2008-10-28 | 2010-05-06 | 日清オイリオグループ株式会社 | Palm oil, deodorized distillates and manufacturing methods therefor |
| WO2012006950A1 (en) * | 2010-07-16 | 2012-01-19 | 丰益(上海)生物技术研发中心有限公司 | Method of controlling level of 3-chloro-1,2-propanediol or esters thereof in oils and fats |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021079989A1 (en) * | 2019-10-25 | 2021-04-29 | 株式会社Adeka | Method for producing refined fat/oil |
| CN114761524A (en) * | 2019-10-25 | 2022-07-15 | 株式会社Adeka | Method for producing purified oil or fat |
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