JPH09176678A - Method of concentration of fat or oil containing highly unsaturated aliphatic acid - Google Patents
Method of concentration of fat or oil containing highly unsaturated aliphatic acidInfo
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- JPH09176678A JPH09176678A JP33457695A JP33457695A JPH09176678A JP H09176678 A JPH09176678 A JP H09176678A JP 33457695 A JP33457695 A JP 33457695A JP 33457695 A JP33457695 A JP 33457695A JP H09176678 A JPH09176678 A JP H09176678A
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- fatty acid
- highly unsaturated
- fat
- extraction
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Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は高度不飽和脂肪酸含
有油脂の濃縮方法に関し、特にアラキドン酸（以下ＡＡ
と略す）、エイコサペンタエン酸（以下ＥＰＡと略
す）、ドコサヘキサエン酸（以下ＤＨＡと略す）等の高
度不飽和脂肪酸を、トリグリセリドの形で簡便かつ効率
よく濃縮できる高度不飽和脂肪酸含有油脂の濃縮方法に
関する。TECHNICAL FIELD The present invention relates to a method for concentrating highly unsaturated fatty acid-containing fats and oils, and more particularly to arachidonic acid (hereinafter referred to as AA).
And a highly unsaturated fatty acid such as eicosapentaenoic acid (hereinafter abbreviated as EPA) and docosahexaenoic acid (hereinafter abbreviated as DHA) in a form of triglyceride can be simply and efficiently concentrated. .
【０００２】[0002]
【従来の技術】魚油などの油脂に含まれるＡＡ、ＥＰ
Ａ、ＤＨＡは、ｎ−６系及びｎ−３系高度不飽和脂肪酸
として、それぞれ生体内で重要な役割をはたしている。
そのため、これら高度不飽和脂肪酸含有油脂類は、健康
食品を始めとする食品全般、さらには医薬品分野など多
岐にわたって使用されている。2. Description of the Related Art AA and EP contained in fats and oils such as fish oil
A and DHA play important roles in the body as n-6 and n-3 polyunsaturated fatty acids, respectively.
Therefore, these highly unsaturated fatty acid-containing oils and fats are widely used in a wide variety of foods including health foods, and further in the pharmaceutical field.
【０００３】一般に、上記高度不飽和脂肪酸は天然物に
おいてはグリゼリドの形で存在しており、その含有量は
さまざまである。このため、グリセリドの中に含まれる
ＡＡ、ＥＰＡ、ＤＨＡなどの分離・精製にあたっては、
これら高度不飽和脂肪酸の低級アルコールエステルを調
製した後、真空蒸留法、分子蒸留法、超臨界抽出法、酸
素法、ウインタリング法（低温分別法または低温溶媒分
別法）、尿素付加法、銀錯体形成法、クロマト法などの
方法によって分離・精製しているのが一般的である。Generally, the above polyunsaturated fatty acids are present in the form of glyceride in natural products, and their contents are various. Therefore, when separating and purifying AA, EPA, DHA, etc. contained in glycerides,
After preparing these lower alcohol esters of highly unsaturated fatty acids, vacuum distillation method, molecular distillation method, supercritical extraction method, oxygen method, wintering method (low temperature fractionation method or low temperature solvent fractionation method), urea addition method, silver complex In general, it is separated and purified by a forming method, a chromatographic method, or the like.
【０００４】[0004]
【発明が解決しようとする課題】しかしながら、上記の
ごとき従来方法にあっては、高度不飽和脂肪酸の低級ア
ルコールエステルを調製した後、真空蒸留法等で分離・
精製するので、工程が複雑で効率が悪く、コスト高にな
るという不具合があった。However, in the conventional method as described above, after the lower alcohol ester of the polyunsaturated fatty acid is prepared, it is separated by a vacuum distillation method or the like.
Since it is purified, there are problems that the process is complicated, the efficiency is low, and the cost is high.
【０００５】そこで、この不具合を回避するために、直
接トリグリセリドの形で特定の高度不飽和脂肪酸を多く
含む画分を濃縮する方法が種々提案されている。Therefore, in order to avoid this problem, various methods have been proposed for directly concentrating a fraction containing a large amount of a specific polyunsaturated fatty acid in the form of triglyceride.
【０００６】例えば、（１）冷却によって析出する固体
部を除去することにより、相対的に不飽和脂肪酸含有量
の高い魚油を得るウインタリング法（低温分別法または
低温溶媒分別法）、（２）ある種のリパーゼを用いて、
トリグリセリド中の高度不飽和脂肪酸以外の構成脂肪酸
のエステル結合を選択的に加水分解し、除去することに
より、高度不飽和脂肪酸含有グリセリドを濃縮する酵素
法、（３）銀イオンが二重結合を多く持つ化合物と錯体
を形成することを利用して、高度不飽和脂肪酸含有トリ
グリセリドを選択的に濃縮する銀錯体形成法、等であ
る。For example, (1) a wintering method (a low temperature fractionation method or a low temperature solvent fractionation method) for obtaining a fish oil having a relatively high unsaturated fatty acid content by removing a solid portion precipitated by cooling, (2) With some kind of lipase,
Enzymatic method for concentrating polyunsaturated fatty acid-containing glyceride by selectively hydrolyzing and removing ester bonds of constituent fatty acids other than highly unsaturated fatty acid in triglyceride, (3) silver ion has many double bonds It is a silver complex forming method in which a highly unsaturated fatty acid-containing triglyceride is selectively concentrated by utilizing the formation of a complex with a compound possessed by the compound.
【０００７】しかし、これらの方法でも技術上あるいは
コスト面において問題が多く、高度不飽和脂肪酸をトリ
グリセリドの形のままで濃縮するための実用的有効手段
は知られていないのが現状である。However, these methods also have many problems in terms of technology and cost, and at present, there is no known practical effective means for concentrating highly unsaturated fatty acids in the form of triglycerides.
【０００８】本発明は、上記のごとき従来の課題に鑑み
てなされたもので、その目的とするところは、高度不飽
和脂肪酸をトリグリセリドの形のままで、簡便かつ効率
よく濃縮できる高度不飽和脂肪酸含有油脂の濃縮方法を
提供することにある。The present invention has been made in view of the conventional problems as described above, and an object thereof is to provide a highly unsaturated fatty acid which can be simply and efficiently concentrated in the form of triglyceride. It is to provide a method for concentrating contained oils and fats.
【０００９】[0009]
【課題を解決するための手段】本発明は、上記目的を達
成するために、高度不飽和脂肪酸含有油脂から、高度不
飽和脂肪酸含有量の多い画分を取得するに当たり、原料
油脂を二酸化炭素を抽剤とした超臨界流体抽出により、
高度不飽和脂肪酸の少ない画分等を不純物として除去
し、高度不飽和脂肪酸の多い製品を得るようにしたもの
である。Means for Solving the Problems In order to achieve the above object, the present invention uses carbon dioxide as a raw material oil and fat in obtaining a fraction having a high polyunsaturated fatty acid content from a highly unsaturated fatty acid-containing oil and fat. By extracting the supercritical fluid as an extractant,
A product containing a large amount of highly unsaturated fatty acids is obtained by removing a fraction containing a small amount of highly unsaturated fatty acids as an impurity.
【００１０】超臨界流体抽出は、よく知られているよう
に高沸点あるいは不揮発性の物質を超臨界状態のガスを
用いて抽出するもので、本発明では抽剤として二酸化炭
素を使用しているため、溶媒除去などの後処理がいらな
いこと、また他の方法と比べて品質的、コスト的に有利
であることなどの利点を有している。As is well known, the supercritical fluid extraction is to extract a substance having a high boiling point or a non-volatile substance by using a gas in a supercritical state. In the present invention, carbon dioxide is used as an extractant. Therefore, it has advantages such as not requiring post-treatment such as solvent removal, and being advantageous in quality and cost as compared with other methods.
【００１１】以下、その詳細を述べる。The details will be described below.
【００１２】本発明で原料として用いる高度不飽和脂肪
酸含有油脂としては、構成脂肪酸中に高度不飽和脂肪酸
を含んでいる限り特に制約はないが、一般には、魚油、
藻類脂質などの水産油脂類、その他の動植物油脂類、微
生物油脂類などの、ＡＡ、ＥＰＡ、ＤＨＡなどをトリグ
リセリドの形で含有する、全ての一般的な油脂を使用す
ることが可能である。The polyunsaturated fatty acid-containing fat or oil used as a raw material in the present invention is not particularly limited as long as the constituent fatty acids contain polyunsaturated fatty acids, but generally, fish oil,
It is possible to use all common fats and oils containing AA, EPA, DHA and the like in the form of triglycerides, such as marine fats and oils such as algal lipids, other animal and vegetable fats and oils, microbial fats and oils.
【００１３】上記原料油脂を使用するに際しては、脱ガ
ム、脱酸処理などし、不純物を低減した精製油脂とする
ことが望ましいが、必ずしも本発明の必要条件ではな
い。When using the above-mentioned raw material fats and oils, it is desirable to degrease and deoxidize them to obtain refined fats and oils with reduced impurities, but this is not necessarily a necessary condition of the present invention.
【００１４】本発明における超臨界流体抽出は、通常の
抽出槽、または分離能を高めるために、ラシヒリング、
ディクソン、ヘリパック等の充填剤を内部に充填し、下
部から上部に温度を段階的に上昇させることで温度勾配
を設けた精留機能を有する抽出塔などに、連続的に原料
を供給する。そして、抽出槽または抽出塔の上部から取
り出した超臨界流体を減圧して、抽出された高度不飽和
脂肪酸が少ない画分を分離し、下部から抽出残分を採取
することによって、容易に特定の高度不飽和脂肪酸をト
リグリセリドの形で濃縮分離するものである。The supercritical fluid extraction according to the present invention is carried out by a conventional extraction tank, or Raschig ring, in order to enhance the separation ability.
A packing material such as Dickson or Helipack is filled inside, and the raw material is continuously supplied to an extraction column or the like having a rectification function in which a temperature gradient is provided by gradually increasing the temperature from the lower part to the upper part. Then, the supercritical fluid taken out from the upper part of the extraction tank or the extraction column is decompressed to separate the fraction containing a small amount of the highly unsaturated fatty acid extracted, and the extraction residue is collected from the lower part to easily identify the specific residue. Polyunsaturated fatty acid is concentrated and separated in the form of triglyceride.
【００１５】必要ならば、得られた抽出残分を再び超臨
界流体抽出することで更に精製し、特定の脂肪酸の濃縮
を行っても良い。また、分離能を高めるため、エントレ
ーナなどを使用することも可能である。If necessary, the obtained extraction residue may be further purified by subjecting it to supercritical fluid extraction again to concentrate a specific fatty acid. It is also possible to use an entrainer or the like in order to enhance the resolution.
【００１６】抽出槽または抽出塔の温度は臨界温度以上
の温度に設定することが必要であり、超臨界流体として
二酸化炭素を使用する場合には３１．１℃以上であり、
また、高度不飽和脂肪酸の変質を防止するために１５０
℃以下とすることが好ましい。It is necessary to set the temperature of the extraction tank or the extraction tower to a temperature above the critical temperature, and when carbon dioxide is used as the supercritical fluid, it is above 31.1 ° C.,
Also, in order to prevent alteration of highly unsaturated fatty acids, 150
It is preferable that the temperature is set to not more than ° C.
【００１７】圧力は臨界圧以上であり、超臨界流体とし
て二酸化炭素を使用する場合には７８ｋｇ／ｃｍ2 以上
とすることが必要である。The pressure is above the critical pressure, and when carbon dioxide is used as the supercritical fluid, it is necessary to set above 78 kg / cm 2 .
【００１８】操作上安定な超臨界状態とするために、温
度は４０℃以上、圧力は８０ｋｇ／ｃｍ2 以上とするこ
とが望ましいが、特に望ましくは、温度は４０〜１１０
℃、圧力は２００〜３５０ｋｇ／ｃｍ2 である。The temperature is preferably 40 ° C. or more and the pressure is 80 kg / cm 2 or more in order to obtain a stable supercritical state in operation, but the temperature is preferably 40 to 110.
The temperature and pressure are 200 to 350 kg / cm 2 .
【００１９】抽出槽または抽出塔より流出した超臨界炭
酸ガスは、臨界圧力以下に減圧することにより、抽出物
と二酸化炭素に分離ができ、必要ならばその二酸化炭素
を精製後、再び超臨界炭酸ガスとして利用することもで
きる。The supercritical carbon dioxide gas flowing out from the extraction tank or the extraction tower can be separated into an extract and carbon dioxide by reducing the pressure to below the critical pressure, and if necessary, the carbon dioxide is purified and then again supercritical carbon dioxide. It can also be used as gas.
【００２０】得られた製品は、濃縮前の油脂と比較し
て、高度不飽和脂肪酸の含有量が高くなっているととも
に、ＤＨＡ／ＥＰＡ比などそれぞれの高度不飽和脂肪酸
間の比率なども変化している点が特徴として挙げられ
る。The obtained product has a higher content of polyunsaturated fatty acids as compared with the fats and oils before concentration, and the ratio between the respective polyunsaturated fatty acids such as DHA / EPA ratio also changes. This is one of the features.
【００２１】[0021]
【発明の実施の形態】以下、本発明の実施の形態を実施
例に基づいて説明する。DESCRIPTION OF THE PREFERRED EMBODIMENTS Embodiments of the present invention will be described below based on examples.
【００２２】[0022]
【実施例１】方法 未精製イワシ油を定法（安田耕作他：油脂製品の知識、
Ｐ６３〜８５、幸書房、１９７７）に準拠して、脱ガ
ム、脱酸処理し、本実施例で用いる試料、すなわち精製
イワシ油を調製した。分析値は表１に示す通りである。
この精製イワシ油１００ｇを原料とし、抽出槽に温度勾
配を設けた超臨界抽出装置を用いて、抽出分と抽出残分
に分離し、それぞれの脂肪酸組成を分析した。[Example 1] Method Unrefined sardine oil was standardized (Kosaku Yasuda et al .: Knowledge of oil and fat products,
P63-85, Koshoubo, 1977), and degumming and deoxidizing treatments were performed to prepare a sample used in this example, that is, a refined sardine oil. The analytical values are as shown in Table 1.
Using 100 g of this refined sardine oil as a raw material, a supercritical extraction device having a temperature gradient in the extraction tank was used to separate into an extract and an extract residue, and the fatty acid composition of each was analyzed.
【００２３】装置 装置は、図１に示す超臨界抽出装置を使用した。以下に
その具体的構成を示す。 Apparatus The apparatus used was the supercritical extraction apparatus shown in FIG. The specific configuration is shown below.
【００２４】まず、ボンベなどの二酸化炭素貯槽１に貯
留してある二酸化炭素を加圧装置２に供給して加圧・加
温し、二酸化炭素を超臨界状態とし、この超臨界状態と
された二酸化炭素を抽出塔３の下部より供給する。First, carbon dioxide stored in a carbon dioxide storage tank 1 such as a cylinder is supplied to a pressurizing device 2 to pressurize and heat it to bring the carbon dioxide into a supercritical state. Carbon dioxide is supplied from the lower part of the extraction tower 3.
【００２５】抽出塔３は、内径４０ｍｍ、高さ３ｍで、
内部には充填物６として直径３ｍｍのディクソンが充填
してあり、周囲には任意の温度に調整可能な加熱ヒータ
ー７が４個配設されている。ここで、４個の加熱ヒータ
ー７は下方のヒーターから上方のヒーターにいくにした
がって設定温度が高くなるよう調節され、４個の加熱ヒ
ーター７の設定温度を調節することにより所望の温度勾
配を抽出塔３内に設定できる。これによって、抽出塔３
内に二酸化炭素濃度の異なる領域が形成され、精留機能
を有することができる。The extraction tower 3 has an inner diameter of 40 mm and a height of 3 m.
Dickson with a diameter of 3 mm is filled as the filling 6 inside, and four heaters 7 that can adjust the temperature to any temperature are arranged around it. Here, the four heating heaters 7 are adjusted so that the set temperature becomes higher from the lower heater to the upper heater, and the desired temperature gradient is extracted by adjusting the set temperature of the four heating heaters 7. It can be set in the tower 3. By this, the extraction tower 3
Regions having different carbon dioxide concentrations are formed in the inside, and can have a rectification function.
【００２６】次に、濃縮分離する原料４は、加圧装置５
に供給されて抽出塔３内の圧力と同等にまで加圧され、
抽出塔３の下から１ｍのところから供給する。Next, the raw material 4 to be concentrated and separated is the pressurizing device 5.
And is pressurized to a pressure equal to that in the extraction tower 3,
It is supplied from the place 1 m from the bottom of the extraction tower 3.
【００２７】抽出塔３の塔頂部からは抽出分を含む超臨
界流体が取り出され、減圧弁８によって３０ｋｇ／ｃｍ
2 に減圧されて分離槽９に移され、そこで抽出物１０と
二酸化炭素に分離される。分離された二酸化炭素は減圧
弁１１によってさらに減圧され、気体処理装置１２によ
って再生されて、再度濃縮分離工程において用いられ
る。The supercritical fluid containing the extracted matter is taken out from the top of the extraction tower 3, and the decompression valve 8 is operated at 30 kg / cm.
It is depressurized to 2 and transferred to a separation tank 9, where it is separated into an extract 10 and carbon dioxide. The separated carbon dioxide is further decompressed by the decompression valve 11, regenerated by the gas treatment device 12, and used again in the concentration and separation step.
【００２８】一方、塔底部よりは、連続的に目的の抽出
残分１３が得られる。On the other hand, the target extraction residue 13 is continuously obtained from the bottom of the column.
【００２９】なお、さらに精製する場合は、抽出残分１
３を三方弁１４を切り替えることにより、異なる条件に
て再度超臨界流体抽出し、目的の物質を得ることができ
る。In the case of further purification, the extraction residue 1
By switching the three-way valve 14 to 3, the supercritical fluid extraction can be performed again under different conditions to obtain the target substance.
【００３０】 分離条件 抽出塔温度 加熱ヒーター７の温度を上部から順に５８，５４， ５０，４６℃に設定 抽出塔圧力 ２５０ｋｇ／ｃｍ2 原料供給速度 ６０ｇ／ｈ 二酸化炭素供給速度 １６ｋｇ／ｈ Separation conditions Extraction tower temperature The temperature of the heater 7 is set to 58, 54, 50, 46 ° C. from the top in order Extraction tower pressure 250 kg / cm 2 Raw material supply rate 60 g / h Carbon dioxide supply rate 16 kg / h
【００３１】分析方法 脂肪酸組成はガスクロマトグラフィーにより、キャピラ
リーカラムを用いて面積％として求めた。（参考文献：
ＡＣＫＭＡＮ Ｒ．Ｇ．；Ａｃｔａ Ｍｅｄ．Ｓｃａ
ｎ，２２２，９９−１０３，１９８７） 酸価（ＡＶ）は１９９４年版基準油脂分析試験法２．
４．１−８３（日本油化学協会編）に準拠して分析し
た。 Analytical method The fatty acid composition was determined by gas chromatography as an area% using a capillary column. (References:
ACKMAN R. G. FIG. Acta Med. Sca
(n, 222, 99-103, 1987) Acid value (AV) is 1994 edition standard oil analysis test method 2.
It analyzed based on 4.1-83 (Japan Oil Chemists' Society edition).
【００３２】結果及び考察 表１に示すように、抽出物と抽出残分に分かれ、大略下
記事項が確認された。 １．分子量の小さい脂肪酸（炭素数１８以下）から構成
された油脂（トリグリセリド）は抽出物の側に多く、分
子量の大きい脂肪酸（炭素数２０以上）の油脂は抽出残
分に分画された。即ち、高度不飽和脂肪酸から構成され
た油脂は抽出物に少なく、抽出残分に多く分画された。 ２．得られた抽出残分のＡＶは減少した。 Results and Discussion As shown in Table 1, the following items were confirmed by being divided into an extract and an extraction residue. 1. A large amount of fats and oils (triglycerides) composed of fatty acids with a low molecular weight (18 or less carbon atoms) were present on the extract side, and fats and oils of fatty acids with a high molecular weight (20 or more carbon atoms) were fractionated in the extraction residue. That is, the amount of fats and oils composed of highly unsaturated fatty acids was small in the extract and large in the extraction residue. 2. The AV of the obtained extraction residue was reduced.
【００３３】以上の結果から、精製イワシ油（原料）を
超臨界流体抽出することにより、抽出残分として、ＥＰ
Ａ，ＤＨＡなどの高度不飽和脂肪酸が濃縮された製品を
得ることを目的とした本発明の意図が実証された。From the above results, by extracting the refined sardine oil (raw material) with a supercritical fluid, the EP
The intent of the present invention aimed at obtaining a product enriched in polyunsaturated fatty acids such as A, DHA has been demonstrated.
【００３４】[0034]
【表１】 [Table 1]
【００３５】[0035]
【実施例２】未精製カツオ油を実施例１に準拠して精製
し、精製カツオ油（原料）を調整した。分析値は表２に
示すとおりである。Example 2 Unrefined skipjack oil was refined according to Example 1 to prepare refined skipjack oil (raw material). The analytical values are as shown in Table 2.
【００３６】精製カツオ油（原料）１００ｇを用いて、
実施例１と同様な装置を用いて、抽出物と抽出残分に分
画し、それぞれの脂肪酸組成等を分析した。Using 100 g of refined skipjack oil (raw material),
Using the same device as in Example 1, the extract and the extraction residue were fractionated, and the fatty acid composition and the like of each was analyzed.
【００３７】分離条件は以下に示すとおりである。 抽出塔温度 加熱ヒーター７の温度を上部から順に５８，５４， ５０，４６℃に設定 抽出塔圧力 ２５０ｋｇ／ｃｍ2 原料供給速度 ５０ｇ／ｈ 二酸化炭素供給速度 １８ｋｇ／ｈThe separation conditions are as shown below. Extraction tower temperature Set the temperature of the heater 7 from the top to 58, 54, 50, 46 ° C in sequence Extraction tower pressure 250 kg / cm 2 Raw material supply rate 50 g / h Carbon dioxide supply rate 18 kg / h
【００３８】その結果、表２に示すとおり、大略実施例
１と同様の結果が得られた。As a result, as shown in Table 2, the same results as in Example 1 were obtained.
【００３９】以上の結果から、精製カツオ油（原料）を
超臨界流体抽出することにより、抽出残分として、ＤＨ
Ａなどの高度不飽和脂肪酸が濃縮された製品を得ること
を目的とした本発明の意図が実証された。From the above results, by extracting the refined skipjack oil (raw material) with a supercritical fluid, DH was obtained as an extraction residue.
The intent of the present invention aimed at obtaining a product enriched in polyunsaturated fatty acids such as A was demonstrated.
【００４０】[0040]
【表２】 [Table 2]
【００４１】[0041]
【実施例３】オゴノリ（Ｇｒａｃｉｌａｒｉａ ｖｅｒ
ｒｕｃｏｓａ）原油は、オゴノリの凍結乾燥品をｎ−ヘ
キサンによって抽出し、溶媒除去後、実施例１に準拠し
て精製し、精製オゴノリ油（原料）を調製した。分析値
は表３に示すとおりである。[Example 3] Gracilaria ver
As a crude oil, a lyophilized product of R. gonorrhoeae was extracted with n-hexane, the solvent was removed, and then refined according to Example 1 to prepare a refined R. gonorrhoeae oil (raw material). The analytical values are as shown in Table 3.
【００４２】精製オゴノリ油（原料）１００ｇを用い
て、実施例１と同様な装置を用いて、抽出物と抽出残分
に分画し、それぞれの脂肪酸組成等を分析した。Using 100 g of refined gogonoli oil (raw material), an extract and an extraction residue were fractionated using the same apparatus as in Example 1, and the fatty acid composition and the like of each was analyzed.
【００４３】分離条件は以下に示すとおりである。 抽出塔温度 加熱ヒーター７の温度を上部から順に６２，５８， ５４，５０℃に設定 抽出塔圧力 ２４０ｋｇ／ｃｍ2 原料供給速度 ６０ｇ／ｈ 二酸化炭素供給速度 １６ｋｇ／ｈThe separation conditions are as follows. Extraction tower temperature Set the temperature of the heater 7 to 62, 58, 54, 50 ° C from the top in order Extraction tower pressure 240 kg / cm 2 Raw material supply rate 60 g / h Carbon dioxide supply rate 16 kg / h
【００４４】その結果、表３に示すとおり、大略実施例
１と同様の効果が得られた。As a result, as shown in Table 3, the same effect as in Example 1 was obtained.
【００４５】以上の結果から、精製オゴノリ油（原料）
を超臨界流体抽出することにより、抽出残分として、Ａ
Ａなどの高度不飽和脂肪酸が濃縮された製品を得ること
を目的とした本発明の意図が実証された。From the above results, refined sardine oil (raw material)
By extracting the supercritical fluid with
The intent of the present invention aimed at obtaining a product enriched in polyunsaturated fatty acids such as A was demonstrated.
【００４６】[0046]
【表３】 [Table 3]
【００４７】[0047]
【実施例４】実施例１で得られた抽出残分６０ｇを用
い、実施例１と同様な装置を用いて、抽出物と抽出残分
に区画し、それぞれの脂肪酸組成等を分析した。Example 4 Using 60 g of the extraction residue obtained in Example 1, the same apparatus as in Example 1 was used to partition into an extract and an extraction residue, and the fatty acid composition of each was analyzed.
【００４８】分離条件は以下に示すとおりである。 抽出塔温度 加熱ヒーター７の温度を上部から順に５４，５０， ４６，４２℃に設定 抽出塔圧力 ２６０ｋｇ／ｃｍ2 原料供給速度 ２０ｇ／ｈ 二酸化炭素供給速度 １８ｋｇ／ｈThe separation conditions are as shown below. Extraction tower temperature The temperature of the heater 7 is set to 54, 50, 46, 42 ° C from the top in order Extraction tower pressure 260 kg / cm 2 Raw material supply rate 20 g / h Carbon dioxide supply rate 18 kg / h
【００４９】その結果、表４に示すとおり、ＤＨＡなど
の分子量の特に大きい脂肪酸以外がほぼ抽出されたこと
が分かった。As a result, as shown in Table 4, it was found that almost all fatty acids such as DHA other than those having a particularly large molecular weight were extracted.
【００５０】以上の結果から、抽出残分を超臨界流体抽
出することにより、抽出物として、ＥＰＡが更に濃縮さ
れた製品を得ることができ、本発明の意図が実証され
た。From the above results, by extracting the extraction residue with a supercritical fluid, a product in which EPA was further concentrated could be obtained as an extract, demonstrating the intent of the present invention.
【００５１】[0051]
【表４】 [Table 4]
【００５２】[0052]
【発明の効果】以上説明したように、本発明では、高度
不飽和脂肪酸含有油脂から高度不飽和脂肪酸含有量の多
い画分を取得するに当たり、原料油脂を超臨界流体抽出
することにより高度不飽和脂肪酸の少ない画分等を不純
物として除去し、高度不飽和脂肪酸含量の多い製品を得
るようにしたので、高度不飽和脂肪酸をトリグリセリド
の形のままで、簡便かつ効率よく濃縮できる。INDUSTRIAL APPLICABILITY As described above, according to the present invention, when obtaining a fraction having a high content of highly unsaturated fatty acids from a highly unsaturated fatty acid-containing oil or fat, the raw oil or fat is extracted by supercritical fluid to obtain highly unsaturated Since the fraction containing a small amount of fatty acid was removed as an impurity to obtain a product having a high polyunsaturated fatty acid content, the polyunsaturated fatty acid can be simply and efficiently concentrated in the form of triglyceride.
【００５３】また、本発明では、通常の超臨界抽出装置
を用いることができるので、工業的規模で高度不飽和脂
肪酸含量の多い製品を得ることができ、低コストにこの
種製品を得ることができる。Further, in the present invention, since a conventional supercritical extraction apparatus can be used, a product having a high content of highly unsaturated fatty acids can be obtained on an industrial scale, and this kind of product can be obtained at a low cost. it can.
【図１】本発明の抽出分離に使用する超臨界抽出装置の
概略構成図。FIG. 1 is a schematic configuration diagram of a supercritical extraction apparatus used for extraction and separation of the present invention.
１ 二酸化炭素貯槽 ２ 加圧装置 ３ 抽出塔 ４ 原料 ５ 加圧装置 ６ 充填物 ７ 加熱装置 ８ 減圧弁 ９ 分離槽 １０ 抽出物 １１ 減圧弁 １２ 気体処理装置 １３ 製品（抽出残分） １４ 三方弁 1 carbon dioxide storage tank 2 pressurizing device 3 extraction tower 4 raw material 5 pressurizing device 6 packing 7 heating device 8 pressure reducing valve 9 separation tank 10 extract 11 pressure reducing valve 12 gas treatment device 13 product (extraction residue) 14 three-way valve
Claims (3)
和脂肪酸含有量の多い画分を取得するに当たり、原料油
脂を超臨界流体抽出することにより高度不飽和脂肪酸の
少ない画分等を不純物として除去し、高度不飽和脂肪酸
含量の多い製品を得ることを特徴とする高度不飽和脂肪
酸含有油脂の濃縮方法。1. When obtaining a fraction having a high polyunsaturated fatty acid content from a fat or oil containing a polyunsaturated fatty acid, the raw fat or oil is subjected to supercritical fluid extraction to remove the fraction having a low polyunsaturated fatty acid as an impurity. A method for concentrating highly unsaturated fatty acid-containing fats and oils, characterized in that a product having a high content of highly unsaturated fatty acids is obtained.
油脂が、トリグリセリドであり、かつアラキドン酸、エ
イコサペンタエン酸、ドコサヘキサエン酸から選ばれる
少なくとも１種類以上の高度不飽和脂肪酸を含有してい
ることを特徴とする請求項１に記載の高度不飽和脂肪酸
含有油脂の濃縮方法。2. A polyunsaturated fatty acid-containing oil or fat used as a raw material is a triglyceride and contains at least one highly unsaturated fatty acid selected from arachidonic acid, eicosapentaenoic acid and docosahexaenoic acid. The method for concentrating a highly unsaturated fatty acid-containing oil or fat according to claim 1.
酸化炭素を用い、抽出槽温度が３１．１〜１５０℃、圧
力が７８〜７５０ｋｇ／ｃｍ2 で処理されることを特徴
とする請求項１に記載の高度不飽和脂肪酸含有油脂の濃
縮方法。3. In the supercritical fluid extraction, carbon dioxide is used as an extractant and the treatment is performed at an extraction tank temperature of 31.1 to 150 ° C. and a pressure of 78 to 750 kg / cm 2. The method for concentrating a highly unsaturated fatty acid-containing oil or fat according to 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP33457695A JP3344887B2 (en) | 1995-12-22 | 1995-12-22 | Method for concentrating fats and oils containing highly unsaturated fatty acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP33457695A JP3344887B2 (en) | 1995-12-22 | 1995-12-22 | Method for concentrating fats and oils containing highly unsaturated fatty acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH09176678A true JPH09176678A (en) | 1997-07-08 |
| JP3344887B2 JP3344887B2 (en) | 2002-11-18 |
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ID=18278950
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|---|---|---|---|
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| Country | Link |
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| US8697138B2 (en) | 2007-03-28 | 2014-04-15 | Aker Biomarine As | Methods of using krill oil to treat risk factors for cardiovascular, metabolic, and inflammatory disorders |
| ES2415684T3 (en) | 2007-03-28 | 2013-07-26 | Aker Biomarine As | Biologically effective krill oil compositions |
| US8372812B2 (en) | 2009-02-26 | 2013-02-12 | Aker Biomarine Asa | Phospholipid and protein tablets |
| AU2014203179C1 (en) | 2013-06-14 | 2017-05-04 | Aker Biomarine Antarctic As | Lipid extraction processes |
| GB201400431D0 (en) | 2014-01-10 | 2014-02-26 | Aker Biomarine As | Phospholipid compositions and their preparation |
| RU2718983C2 (en) | 2015-02-11 | 2020-04-15 | Акер Биомарин Антарктик Ас | Lipid compositions |
| EP3256003B1 (en) | 2015-02-11 | 2022-11-09 | Aker Biomarine Antarctic AS | Lipid extraction processes |
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| JP3344887B2 (en) | 2002-11-18 |
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