JP2006063252A - Manufacturing process of oil highly containing diglyceride - Google Patents

Manufacturing process of oil highly containing diglyceride Download PDF

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JP2006063252A
JP2006063252A JP2004249929A JP2004249929A JP2006063252A JP 2006063252 A JP2006063252 A JP 2006063252A JP 2004249929 A JP2004249929 A JP 2004249929A JP 2004249929 A JP2004249929 A JP 2004249929A JP 2006063252 A JP2006063252 A JP 2006063252A
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fats
oils
diglyceride
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JP4473680B2 (en
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Eizo Maruyama
栄造 丸山
Keiji Shibata
啓二 柴田
Hiroaki Yamaguchi
浩明 山口
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Kao Corp
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Abstract

<P>PROBLEM TO BE SOLVED: To provide an efficient and commercial manufacturing process of an oil with a high content of diglycerides. <P>SOLUTION: The manufacturing process of the oil with a high content of diglycerides comprises adding an aqueous solution containing 50-90 mass% of an organic acid to an oil containing ≥30 mass% of diglycerides in the amount of 0.05-5 mass% of the oil, mixing the mixture continuously for 0.1-10 minutes in a line mixer, washing it with water and deoderizing it. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

本発明は、ジグリセリドを多く含有する油脂の製造方法に関する。   The present invention relates to a method for producing fats and oils containing a large amount of diglycerides.

ジグリセリドには、体脂肪の蓄積を低下させ肥満を防ぐ効果(特許文献1、2)や植物ステロールとあいまって血中コレステロール値を低下させる効果(特許文献3)等が見出されている。このような観点から、ジグリセリド含量の高い油脂が、家庭用食用油として広く使用されるに至っている。   Diglycerides have been found to have an effect of reducing body fat accumulation and preventing obesity (Patent Documents 1 and 2) and an effect of reducing blood cholesterol level together with plant sterols (Patent Document 3). From such a viewpoint, fats and oils having a high diglyceride content have been widely used as domestic cooking oils.

ジグリセリド含量の高い油脂は、脂肪酸とグリセリンとのエステル化反応や油脂とグリセリンとのエステル交換反応等により製造されるため、遊離脂肪酸や金属等の不純物が含まれており、食用油として用いるためには脱酸処理や脱臭処理による精製が必要である。ここで、高純度のジグリセリドは、高温において分解や不均化反応等が生じることによりジグリセリド含量が著しく減少するため、ジグリセリドを高純度に維持するためにはこれらを抑制することが必要である。   Fats and oils with a high diglyceride content are produced by esterification reaction of fatty acids and glycerin, transesterification reaction of fats and oils and glycerin, etc., so they contain impurities such as free fatty acids and metals. Needs to be purified by deoxidation or deodorization. Here, since high-purity diglyceride significantly reduces the diglyceride content due to decomposition, disproportionation reaction, and the like at high temperatures, it is necessary to suppress the diglyceride to maintain high purity.

ジグリセリド含量の高い油脂の精製法としては、当該油脂に有機酸を添加した後、脱臭処理を行う方法が知られている(特許文献4)。
特開平4−300826号公報 特開平10−176181号公報 国際公開第99/48378号パンフレット 特開平4−261497号公報
As a method for purifying fats and oils having a high diglyceride content, a method of performing a deodorizing treatment after adding an organic acid to the fats and oils is known (Patent Document 4).
Japanese Unexamined Patent Publication No. 4-300826 JP-A-10-176181 WO 99/48378 pamphlet JP-A-4-261497

しかし、前記方法においては、油脂に有機酸を添加後減圧で脱水するか、減圧で脱水した後さらに脱色処理した後に、脱臭処理を施す必要があり、工業的な精製法としては問題があった。
従って、本発明の目的は、より簡便な手段で効率良く、風味が良好で食用油として有用な精製ジグリセリド高含有油脂を製造する方法を提供することにある。
However, in the above method, it is necessary to dehydrate under reduced pressure after adding an organic acid to fats or oils, or after decoloring after dehydration under reduced pressure, there is a problem as an industrial purification method .
Accordingly, an object of the present invention is to provide a method for producing a high-purified diglyceride-containing fat and oil that is efficient and simple in flavor and has a good flavor and is useful as an edible oil.

そこで本発明者は、ジグリセリド含量の高い油脂に有機酸を50〜90質量%の高濃度で含む水溶液として極少量を添加し、その撹拌をタンク中でなくラインミキサーで連続して行えば、脱水工程を必要とせず、極めて短時間の処理であるにもかかわらずその後の脱臭操作においてジグリセリドの純度低下が抑制できることを見出した。さらに、かかる処理をし、水洗後脱臭処理した油脂は風味も良好であることを見出した。   Therefore, the present inventor added a very small amount as an aqueous solution containing an organic acid at a high concentration of 50 to 90% by mass to fats and oils having a high diglyceride content, and the stirring was continuously performed in a line mixer instead of in a tank. It has been found that a decrease in the purity of diglyceride can be suppressed in the subsequent deodorizing operation despite the fact that the process is not required and the treatment is extremely short. Furthermore, it discovered that the fats and oils which carried out this process, and which were deodorized after washing with water also had favorable flavor.

すなわち、本発明は、ジグリセリドを30質量%以上含む油脂に有機酸を50〜90質量%含む水溶液を油脂に対し0.05〜5質量%添加し、ラインミキサーで連続して0.1〜10分混合した後、水洗し、次いで脱臭処理する、ジグリセリド高含有油脂の製造方法を提供するものである。   That is, in the present invention, 0.05 to 5% by mass of an aqueous solution containing 50 to 90% by mass of an organic acid is added to oils and fats containing 30% by mass or more of diglyceride, and 0.1 to 10 continuously by a line mixer. A method for producing an oil and fat with a high diglyceride content is provided which is mixed and then washed with water and then deodorized.

本発明の製造方法によれば、ジグリセリドの純度低下が抑制され、かつ簡便な操作で風味が良好な、ジグリセリド含量の高い油脂が効率良く得られる。従って、本発明の方法によれば、工業的に大量に連続してジグリセリド含量の高い食用油脂が得られる。   According to the production method of the present invention, a decrease in the purity of diglyceride is suppressed, and an oil and fat having a high diglyceride content with good flavor and simple operation can be obtained efficiently. Therefore, according to the method of the present invention, an edible fat with a high diglyceride content can be obtained industrially in large quantities.

本発明方法に用いられる油脂は、ジグリセリドを30質量%以上含む油脂であるが、ジグリセリドを35質量%以上、さらに50質量%以上、さらに70質量%以上、特に80〜95質量%含む油脂が好ましい。   The fats and oils used in the method of the present invention are fats and oils containing 30% by mass or more of diglycerides, but fats and oils containing 35% by mass or more, further 50% by mass or more, further 70% by mass or more, and particularly 80 to 95% by mass of diglyceride are preferable. .

当該油脂の構成脂肪酸は特に限定されないが、生理効果の点から50質量%以上、特に80質量%以上不飽和脂肪酸を含むことが好ましい。また、構成脂肪酸の炭素数は14〜24、特に16〜22であるのが生理効果の点で好ましい。   The constituent fatty acid of the fat is not particularly limited, but preferably contains 50% by mass or more, particularly 80% by mass or more of unsaturated fatty acid from the viewpoint of physiological effects. Moreover, it is preferable from the point of the physiological effect that carbon number of a constituent fatty acid is 14-24, especially 16-22.

本発明に使用されるジグリセリド含量の高い油脂の起源としては、植物性、動物性油脂のいずれでもよい。具体的な原料としては、菜種油、ひまわり油、とうもろこし油、大豆油、米油、紅花油、綿実油、牛脂等を挙げることができる。またこれらの油脂を分別、混合したもの、水素添加や、エステル交換反応などにより脂肪酸組成を調整したものも原料として利用できる。
本発明に使用されるジグリセリド含量の高い油脂は、上述した油脂由来の脂肪酸とグリセリンとのエステル化反応、油脂とグリセリンとのエステル交換反応等により得ることができる。反応により生成した過剰のモノアシルグリセリンは分子蒸留法又はクロマトグラフィー法により除去することができる。これらの反応はアルカリ触媒等を用いた化学反応でも行うことができるが、1,3−位選択的リパーゼ等を用いて酵素的に温和な条件で反応を行うのが風味等の点で優れており好ましい。
The origin of fats and oils with a high diglyceride content used in the present invention may be vegetable or animal fats. Specific examples of the raw material include rapeseed oil, sunflower oil, corn oil, soybean oil, rice oil, safflower oil, cottonseed oil, and beef tallow. In addition, those obtained by separating and mixing these oils and fats, those obtained by adjusting the fatty acid composition by hydrogenation, transesterification, or the like can be used as raw materials.
The fats and oils having a high diglyceride content used in the present invention can be obtained by the esterification reaction between fatty acids derived from fats and oils and glycerin, the transesterification reaction between fats and fats and glycerin, and the like. Excess monoacylglycerol produced by the reaction can be removed by molecular distillation or chromatography. These reactions can also be carried out by chemical reactions using an alkali catalyst or the like, but it is excellent in terms of flavor and the like to carry out the reaction under mild conditions enzymatically using a 1,3-position selective lipase or the like. It is preferable.

本発明においては、有機酸としてはクエン酸、コハク酸、マレイン酸、シュウ酸、特にクエン酸が好ましい。まず、前記油脂に有機酸を50〜90質量%含む水溶液を油脂に対して0.05〜5質量%添加する。有機酸水溶液の濃度が50質量%未満では、有機酸添加による効果が十分でなく、また風味改善効果も十分でない。また90質量%を超えると、液物性が悪化し作業性が低下する。また、有機酸水溶液を油脂に対して、5質量%を超えて添加すると、混合後減圧脱水が必要になる。また、0.05質量%未満では、有機酸添加による効果が十分でない。かかる有機酸水溶液の添加温度は0〜100℃、さらに25〜90℃が好ましい。添加手段は、有機酸水溶液が少量なので分割して添加する必要はなく、一括して添加できる。   In the present invention, the organic acid is preferably citric acid, succinic acid, maleic acid, oxalic acid, particularly citric acid. First, 0.05 to 5% by mass of an aqueous solution containing 50 to 90% by mass of an organic acid is added to the oil or fat. When the concentration of the organic acid aqueous solution is less than 50% by mass, the effect of adding the organic acid is not sufficient, and the effect of improving the flavor is not sufficient. Moreover, when it exceeds 90 mass%, a liquid physical property will deteriorate and workability | operativity will fall. Moreover, when organic acid aqueous solution is added exceeding 5 mass% with respect to fats and oils, pressure reduction dehydration will be needed after mixing. Moreover, if it is less than 0.05 mass%, the effect by organic acid addition is not enough. The addition temperature of the organic acid aqueous solution is preferably 0 to 100 ° C, more preferably 25 to 90 ° C. The adding means is a small amount of the organic acid aqueous solution, so it is not necessary to add it in portions, and it can be added all at once.

次に、少量の有機酸水溶液を添加した前記油脂をラインミキサー中で連続して0.1〜10分間混合する。好ましくは、0.2〜5分間混合する。ここでラインミキサーとは、管路中に設けた邪魔板、機械的攪拌機によって流体を流しながら混合する装置をいう。
ラインミキサーを使用することにより、ミキサー中を通過させることにより連続して混合され、油脂をタンクに滞留させる必要がなく、工業的に有利である。混合時間が0.1分未満では十分なジグリセリドの純度低下抑制効果が得られず、10分を超えると装置が大型化し、また水洗後脱臭処理した油脂の風味改善効果が低減する。ここで、混合時間とは、ラインミキサー中の油脂の平均滞留時間をいう。
また、混合は機械的撹拌混合により行うことが好ましく、混合機の撹拌翼の先端周速度を1〜20m/s、特に2〜10m/sとすることが、ジグリセリドの純度低下抑制効果、電力消費量の低減の点から好ましい。
Next, the said fats and oils which added a small amount of organic acid aqueous solution are continuously mixed in a line mixer for 0.1 to 10 minutes. Preferably, mixing is performed for 0.2 to 5 minutes. Here, the line mixer refers to a device that mixes while flowing a fluid using a baffle plate or a mechanical stirrer provided in a pipe.
The use of the line mixer is industrially advantageous because it is continuously mixed by passing through the mixer and the oil and fat do not need to stay in the tank. If the mixing time is less than 0.1 minutes, a sufficient diglyceride purity-inhibiting effect cannot be obtained, and if it exceeds 10 minutes, the apparatus becomes large, and the flavor improving effect of the oil and fat deodorized after washing is reduced. Here, mixing time means the average residence time of the fats and oils in a line mixer.
Further, the mixing is preferably performed by mechanical stirring and mixing, and the tip peripheral speed of the mixing blade of the mixer is set to 1 to 20 m / s, particularly 2 to 10 m / s. It is preferable from the viewpoint of reducing the amount.

0.1〜10分混合された油脂は、連続して水洗する。脱水操作や吸着操作を行う必要はない。水洗は、油脂を水とよく混合し、その後水を分離することにより行うのが好ましい。なお、この水洗に用いる水には0.01〜10質量%程度のエタノール、イソプロパノール等の低級アルコールを含んでいてもよい。ここで1回の水洗に用いる水の量は、油脂に対し5〜200質量%、さらに10〜50質量%が好ましい。水洗の温度は25〜95℃が好ましい。水洗は1〜5回行われる。   Oils and fats mixed for 0.1 to 10 minutes are continuously washed with water. There is no need to perform dehydration or adsorption. Washing with water is preferably carried out by mixing the fats and oils with water and then separating the water. In addition, the water used for this water washing may contain lower alcohols, such as about 0.01-10 mass% ethanol and isopropanol. Here, the amount of water used for one washing is preferably 5 to 200% by mass and more preferably 10 to 50% by mass with respect to the fats and oils. The washing temperature is preferably 25 to 95 ° C. Washing with water is performed 1 to 5 times.

水洗された油脂は、脱臭処理する。脱臭処理としては水蒸気蒸留が好ましい。水蒸気蒸留は、ジグリセリドの純度低下抑制、風味改善の点から、240℃以下の条件で行うのが好ましい。用いる水蒸気量は、油脂に対して0.5〜20質量%、特に1〜10質量%が好ましい。   Oil and fat washed with water is deodorized. As the deodorizing treatment, steam distillation is preferable. The steam distillation is preferably performed under conditions of 240 ° C. or less from the viewpoint of suppressing the decrease in the purity of diglyceride and improving the flavor. The amount of water vapor to be used is preferably 0.5 to 20% by mass, particularly 1 to 10% by mass with respect to the fat and oil.

本発明方法により得られる精製ジグリセリド高含有油脂は、ジグリセリドの純度低下が抑制されていることから、ジグリセリド含量が高く、かつ風味も良好であり、高い生理効果を有する食用油脂として有用である。   The refined diglyceride-rich fats and oils obtained by the method of the present invention are useful as edible fats and oils that have high diglyceride content and good flavor and high physiological effects because the decrease in diglyceride purity is suppressed.

実施例1
菜種油および大豆油由来の脂肪酸とグリセリンとのエステル化により得られたエステル化物を分子蒸留により、脂肪酸、モノグリセライドを除去した。さらにこの油脂に90℃で50%クエン酸水溶液を0.4%添加後速やかにラインミキサー(先端周速度6.4m/s)で混合した。この油脂に水を油脂に対して10%添加混合後、油水分離を行う操作を三回繰り返し行った。さらに240℃で2時間水蒸気蒸留による脱臭処理を行った。ジグリセリド含量の測定は、ガスクロマトグラフィーにより行った。また、風味の評価は、下記基準にて官能評価により行った。結果を表1に示す。
○:風味が良好。
△:風味がやや劣る。
×:風味が劣る。
Example 1
Fatty acid and monoglyceride were removed from the esterified product obtained by esterification of rapeseed oil and soybean oil-derived fatty acid with glycerin by molecular distillation. Further, 0.4% of a 50% aqueous citric acid solution was added to the oil and fat at 90 ° C., and then immediately mixed with a line mixer (tip peripheral speed 6.4 m / s). The operation of oil / water separation was repeated three times after adding 10% water to the oil / fat and mixing. Furthermore, the deodorizing process by steam distillation was performed at 240 degreeC for 2 hours. The diglyceride content was measured by gas chromatography. Moreover, evaluation of flavor was performed by sensory evaluation according to the following criteria. The results are shown in Table 1.
○: Flavor is good.
Δ: Slightly inferior in flavor
X: Flavor is inferior.

実施例2
クエン酸水溶液の濃度を80%とした以外は、実施例1と同じ操作を行った。ただし、添加量は油脂に対してクエン酸量が同量となるようにした。結果を表1に示す。
Example 2
The same operation as in Example 1 was performed except that the concentration of the citric acid aqueous solution was 80%. However, the addition amount was set so that the amount of citric acid was the same as that of the oil. The results are shown in Table 1.

比較例1
クエン酸水溶液の濃度を2%とした以外は、実施例1と同じ操作を行った。ただし、添加量は油脂に対してクエン酸量が同量となるようにした。結果を表1に示す。
Comparative Example 1
The same operation as in Example 1 was performed except that the concentration of the citric acid aqueous solution was 2%. However, the addition amount was set so that the amount of citric acid was the same as that of the oil. The results are shown in Table 1.

比較例2
菜種油および大豆油由来の脂肪酸とグリセリンとのエステル化により得られたエステル化物を分子蒸留により、脂肪酸、モノグリセライドを除去した。さらにこの油脂に20%クエン酸水溶液を油脂に対して1%添加後、攪拌層中で90℃、60分間混合(先端周速度5m/s)した後、90℃、2Torrで60分間脱水し、この油脂に水を油脂に対して10%添加混合後、油水分離を行う操作を三回繰り返し行った。240℃で2時間水蒸気蒸留による脱臭を行った。表1に結果を示す。
Comparative Example 2
Fatty acid and monoglyceride were removed from the esterified product obtained by esterification of rapeseed oil and soybean oil-derived fatty acid with glycerin by molecular distillation. Furthermore, after adding 1% of a 20% aqueous citric acid solution to this fat and oil, mixing in a stirring layer at 90 ° C. for 60 minutes (tip peripheral speed 5 m / s), followed by dehydration at 90 ° C. and 2 Torr for 60 minutes, The operation of oil / water separation was repeated three times after adding 10% water to the oil / fat and mixing. Deodorization was performed by steam distillation at 240 ° C. for 2 hours. Table 1 shows the results.

Figure 2006063252
Figure 2006063252

Claims (2)

ジグリセリドを30質量%以上含む油脂に有機酸を50〜90質量%含む水溶液を油脂に対し0.05〜5質量%添加し、ラインミキサーで連続して0.1〜10分混合した後、水洗し、次いで脱臭処理する、精製ジグリセリド高含有油脂の製造方法。   An aqueous solution containing 50 to 90% by mass of an organic acid to an oil or fat containing 30% by mass or more of diglyceride is added to the oil and fat in an amount of 0.05 to 5% by mass and continuously mixed with a line mixer for 0.1 to 10 minutes, followed by washing with water. And then deodorizing, a method for producing a refined diglyceride-rich oil and fat. 脱臭処理が、水蒸気蒸留である請求項1記載の製造方法。   The production method according to claim 1, wherein the deodorizing treatment is steam distillation.
JP2004249929A 2004-08-30 2004-08-30 Production method of fats and oils with high diglyceride content Expired - Fee Related JP4473680B2 (en)

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EP2548942A1 (en) * 2010-03-17 2013-01-23 Kao Corporation Method for producing refined oils and fats
EP2548942A4 (en) * 2010-03-17 2014-03-12 Kao Corp Method for producing refined oils and fats
WO2011114863A1 (en) * 2010-03-17 2011-09-22 花王株式会社 Method for producing refined oils and fats
CN102782108B (en) * 2010-03-17 2015-03-18 花王株式会社 Method for producing refined oils and fats
US9006474B2 (en) 2010-03-17 2015-04-14 Kao Corporation Method for producing refined a fat or oil
JP2011213856A (en) * 2010-03-31 2011-10-27 Kao Corp Oil and fat composition
WO2011122184A1 (en) * 2010-03-31 2011-10-06 花王株式会社 Oil and fat composition

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