JP2941046B2 - Fatty acid separation method - Google Patents
Fatty acid separation methodInfo
- Publication number
- JP2941046B2 JP2941046B2 JP2327054A JP32705490A JP2941046B2 JP 2941046 B2 JP2941046 B2 JP 2941046B2 JP 2327054 A JP2327054 A JP 2327054A JP 32705490 A JP32705490 A JP 32705490A JP 2941046 B2 JP2941046 B2 JP 2941046B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- fatty acids
- unsaturated fatty
- polar solvent
- fatty acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は脂肪酸の分離方法に係り、さらに詳しくは飽
和脂肪酸と不飽和脂肪酸の分離と、不飽和結合数に応じ
て不飽和脂肪酸成分の分離が可能な脂肪酸の分離方法に
関する。The present invention relates to a method for separating fatty acids, and more particularly to a method for separating saturated fatty acids and unsaturated fatty acids, and a method for separating unsaturated fatty acid components according to the number of unsaturated bonds. The present invention relates to a method for separating a fatty acid which can be carried out.
中性脂肪、リン脂質および糖脂質に分類される脂質
は、動植物の油脂等の天然物質から抽出生産され、食
用、燃料、医薬品などの他、石けんや化粧品等にも多く
用いられている。脂質の中でも特に炭素数14〜22の中性
脂肪酸の用途は広く、例えば炭素数20の不飽和脂肪酸で
あるエイコサペンタエン酸（EPA）は、魚油等に含ま
れ、血栓溶解作用や血液降下作用があり、医薬品として
の付加価値が高い。Lipids classified as neutral fats, phospholipids and glycolipids are extracted and produced from natural substances such as animal and plant fats and oils, and are widely used in foods, fuels, pharmaceuticals, soaps, cosmetics and the like. Among lipids, neutral fatty acids having 14 to 22 carbon atoms are particularly widely used. For example, eicosapentaenoic acid (EPA), which is an unsaturated fatty acid having 20 carbon atoms, is contained in fish oil and the like, and has a thrombolytic effect and a blood lowering effect. There is a high added value as a pharmaceutical.
いわし等の魚油から抽出された複数の脂肪酸を含む抽
出液からエイコサペンタエン酸を分離する方法として
は、CO2の超臨界流体を用いる抽出分離法が知られてい
る。この方法は、魚油から脂肪酸を抽出した後、CO2の
超臨界流体を移動相としてクロマトグラフィーによりエ
イコサペンタエン酸を分離するが、炭素数18〜22の不飽
和脂肪酸を完全に分離することができず、純度100％の
エイコサペンタエン酸を得ることは困難であった。また
超臨界状態にするために装置を72.9atm以上に保つ必要
があり、装置の耐圧化が必要であった。As a method for separating eicosapentaenoic acid from an extract containing a plurality of fatty acids extracted from fish oil such as sardines, an extraction separation method using a supercritical fluid of CO 2 is known. In this method, eicosapentaenoic acid is separated by chromatography using a supercritical fluid of CO 2 as a mobile phase after extracting fatty acids from fish oil, but unsaturated fatty acids having 18 to 22 carbon atoms can be completely separated. Therefore, it was difficult to obtain eicosapentaenoic acid having a purity of 100%. In addition, it was necessary to maintain the device at 72.9 atm or more in order to attain the supercritical state, and it was necessary to increase the pressure resistance of the device.
一方、飽和脂肪酸と不飽和脂肪酸の分離方法として
は、粘度鉱物の一種であるヘクライトを球状化した担体
に銀を担持させ、これを吸着剤として用い、ｎ−ヘキサ
ンのような非極性溶媒を溶離液としてクロマトグラフィ
ーにより分離する方法が知られている（第33回液体クロ
マトグラフィー研究会講演要旨集、p58（1990））。こ
の方法では、不飽和脂肪酸を担体に吸着させ、飽和脂肪
酸を溶出させることによりこれらの成分を分離できる
が、不飽和結合数（−Ｃ＝Ｃ−の数）に応じた不飽和脂
肪酸成分の分離には適用できなかった。On the other hand, as a method for separating saturated fatty acids and unsaturated fatty acids, silver is supported on a carrier obtained by spheroidizing hectorite, a kind of viscous mineral, and this is used as an adsorbent to elute a non-polar solvent such as n-hexane. A method of separating a liquid by chromatography is known (the 33rd Annual Meeting of the Liquid Chromatography Workshop, p58 (1990)). In this method, these components can be separated by adsorbing unsaturated fatty acids onto a carrier and eluting the saturated fatty acids. However, separation of unsaturated fatty acid components according to the number of unsaturated bonds (the number of -C = C-) is possible. Could not be applied to
本発明の目的は、上記従来技術の問題を解決し、飽和
脂肪酸と不飽和脂肪酸とを分離し、かつ異なる不飽和結
合数の不飽和脂肪酸成分をも分離することができる脂肪
酸の分離方法を提供することにある。An object of the present invention is to solve the above-mentioned problems of the prior art and to provide a method for separating a fatty acid capable of separating a saturated fatty acid and an unsaturated fatty acid and also separating an unsaturated fatty acid component having a different number of unsaturated bonds. Is to do.
本発明は、２以上の脂肪酸を含む液を、鉛を担持した
吸着剤を充填した分離カラムに添加し、非極性溶媒また
は非極性溶媒と極性溶媒の混合液によりクロマトグラフ
ィー分離することを特徴とする脂肪酸の分離方法に関す
る。The present invention is characterized in that a liquid containing two or more fatty acids is added to a separation column filled with an adsorbent supporting lead, and chromatographed with a non-polar solvent or a mixture of a non-polar solvent and a polar solvent. The present invention relates to a method for separating fatty acids.
鉛を担持した吸着剤は、飽和脂肪酸と不飽和脂肪酸を
吸着し、特に炭素数16〜22の脂肪酸をほぼ完全に吸着す
る。上記飽和脂肪酸としてはパルミチン酸、ステアリン
酸、アラキジン酸、ベヘン酸、リグノセリン酸などが挙
げられ、不飽和脂肪酸としては、炭素−炭素二重結合数
が１個のパルミトレイン酸、オレイン酸、ガドレイン
酸、２個のリノール酸、３個のリノレン酸、４個のステ
アリドン酸、アラキドン酸、５個のエイコサペンタエン
酸等が挙げられる。The adsorbent loaded with lead adsorbs saturated fatty acids and unsaturated fatty acids, and particularly adsorbs fatty acids having 16 to 22 carbon atoms almost completely. Examples of the saturated fatty acids include palmitic acid, stearic acid, arachidic acid, behenic acid, and lignoceric acid. Examples of the unsaturated fatty acids include palmitoleic acid having one carbon-carbon double bond, oleic acid, gadolinic acid, Two linoleic acids, three linolenic acids, four stearidonic acids, arachidonic acids, five eicosapentaenoic acids, and the like.
上記担体に吸着された飽和脂肪酸は、溶離液として非
極性溶媒または非極性溶媒と極性溶媒の混合液を用いて
も溶離されず、吸着されたまた担体に残る。一方、不飽
和脂肪酸は、上記溶離液により不飽和結合数の少ない不
飽和脂肪酸成分から順に溶離される。これは鉛イオンと
不飽和脂肪酸の二重結合との相互作用に基づくものであ
り、高性能の分離が可能である。The saturated fatty acid adsorbed on the carrier is not eluted even when a non-polar solvent or a mixture of a non-polar solvent and a polar solvent is used as an eluent, and is adsorbed and remains on the carrier. On the other hand, unsaturated fatty acids are sequentially eluted by the eluent from the unsaturated fatty acid component having a small number of unsaturated bonds. This is based on the interaction between the lead ion and the double bond of the unsaturated fatty acid, and enables high-performance separation.
本発明に用いられる鉛を担持した吸着剤は、例えば、
硝酸鉛の水溶液に陽イオン交換樹脂などの担体を添加し
て撹拌し、鉛イオンを担体に吸着させて得られるが、そ
の製法には特に制約はない。Adsorbent carrying lead used in the present invention, for example,
It is obtained by adding a carrier such as a cation exchange resin to an aqueous solution of lead nitrate, stirring the mixture, and adsorbing the lead ions to the carrier, but the production method is not particularly limited.
本発明においては溶離液として、非極性溶媒またはこ
れと極性溶媒の混合液が用いられるが、非極性溶媒とし
てはエーテル、アセトン等が用いられ、極性溶媒として
はアセトニトリル等が用いられる。In the present invention, a non-polar solvent or a mixture of the non-polar solvent and a polar solvent is used as an eluent, but ether or acetone is used as a non-polar solvent, and acetonitrile or the like is used as a polar solvent.
実施例１ 1Mの硝酸鉛の水溶液100mlに陽イオン交換樹脂（MR（M
acro Retcular）樹脂）10mlを添加して一夜撹拌し、Pb
2+を陽イオン交換樹脂に平衡吸着させた。得られた樹脂
を内径8mmで長さ100mmのガラスカラムに充填し、分離カ
ラムとした。Example 1 A cation exchange resin (MR (M
acro Retcular) Resin) Add 10ml and stir overnight, Pb
2+ was adsorbed equilibrium on the cation exchange resin. The obtained resin was packed in a glass column having an inner diameter of 8 mm and a length of 100 mm to form a separation column.
この分離カラムに、メチルエステル化したステアリン
酸とオレイン酸の混合物を添加し、５重量％のアセトニ
トリルを含むアセトン混合液を溶離液としてクロマトグ
ラフィー分離を行った。このときのカラム温度は30℃、
溶離液の流速は1ml/minであった。えられたクロマトグ
ラムを第１図に示したが、ステアリン酸（飽和脂肪酸）
とオレイン酸（不飽和脂肪酸）を完全に分離することが
できた。A mixture of methylesterified stearic acid and oleic acid was added to the separation column, and chromatographic separation was performed using an acetone mixture containing 5% by weight of acetonitrile as an eluent. The column temperature at this time was 30 ° C,
The flow rate of the eluent was 1 ml / min. The obtained chromatogram is shown in FIG. 1 and shows that stearic acid (saturated fatty acid)
And oleic acid (unsaturated fatty acid) were completely separated.
実施例２ 実施例１において、メチルエステル化したステアリン
酸、リノール酸およびエイコサペンタエン酸の混合物を
用いた以外は実施例１と同様にしてクロマトグラフィー
分離を行った。得られたクロマトグラムを第２図に示し
たが、飽和脂肪酸（ステアリン酸）と不飽和脂肪酸（リ
ノール酸、エイコサペンタエン酸）の分離だけでなく、
不飽和脂肪酸の２成分を完全に分離することができた。Example 2 Chromatographic separation was carried out in the same manner as in Example 1, except that a mixture of methylesterified stearic acid, linoleic acid and eicosapentaenoic acid was used. The resulting chromatogram is shown in FIG. 2, which shows not only the separation of saturated fatty acids (stearic acid) and unsaturated fatty acids (linoleic acid, eicosapentaenoic acid),
The two components of unsaturated fatty acids could be completely separated.
実施例３ 実施例１において、メチルエステル化したオレイン
酸、リノール酸、γ−リノレン酸およびエイコサペンタ
エン酸の混合物を用いた以外は実施例１と同様にしてク
ロマトグラフィー分離を行った。得られたクロマトグラ
ムを第３図に示したが、上記不飽和脂肪酸の４成分を完
全に分離することができた。Example 3 Chromatographic separation was carried out in the same manner as in Example 1 except that a mixture of oleic acid, linoleic acid, γ-linolenic acid and eicosapentaenoic acid which had been methylesterified was used. The obtained chromatogram is shown in FIG. 3, and the four components of the unsaturated fatty acids were completely separated.
実施例４ 実施例１において、メチルエステル化したパルミチン
酸、ステアリン酸、アラキジン酸およびリノール酸の混
合物を用いた以外は実施例１と同様にしてクロマトグラ
フィー分離を行った。得られたクロマトグラムを第４図
に示したが、飽和脂肪酸である３成分と不飽和脂肪酸
（リノール酸）を完全に分離することができた。Example 4 Chromatographic separation was performed in the same manner as in Example 1 except that a mixture of methyl esterified palmitic acid, stearic acid, arachidic acid and linoleic acid was used. The obtained chromatogram is shown in FIG. 4, and it was possible to completely separate the three components that are saturated fatty acids and the unsaturated fatty acid (linoleic acid).
比較例１ 実施例１において、硝酸鉛水溶液の代わりに硝酸銀水
溶液を用いた以外は実施例１と同様にして分離カラムを
調製した。この分離カラムに、メチルエステル化したオ
レイン酸、リノール酸、γ−リノレン酸およびエイコサ
ペンタエン酸の混合物を添加し、25重量％のアセトニト
リルを含むアセトン混合液を溶離液とし、カラム温度25
℃、溶離液流速0.5ml/minでクロマトグラフィー分離を
行ったが、上記不飽和脂肪酸の４成分の相互分離はでき
なかった。Comparative Example 1 A separation column was prepared in the same manner as in Example 1, except that an aqueous silver nitrate solution was used instead of the aqueous lead nitrate solution. To this separation column, a mixture of methylesterified oleic acid, linoleic acid, γ-linolenic acid and eicosapentaenoic acid was added, and an acetone mixture containing 25% by weight of acetonitrile was used as an eluent.
Chromatographic separation was performed at a temperature of 0.5 ° C. and an eluent flow rate of 0.5 ml / min, but the above-mentioned four components of unsaturated fatty acids could not be separated from each other.
本発明によれば、担体に鉛を担持させた吸着剤を充填
剤として用い、液体クロマトグラフィー分離することに
より、飽和脂肪酸と不飽和脂肪酸の分離だけでなく、不
飽和脂肪酸（特に炭素数16〜22の不飽和脂肪酸）を不飽
和結合数に応じて完全に分離することができる。また従
来のイオン交換樹脂を用いることができるため、特別な
装置や操作を必要とせず、簡便に脂肪酸を分離すること
ができる。According to the present invention, not only separation of saturated fatty acids and unsaturated fatty acids, but also unsaturated fatty acids (particularly 16 to 22 unsaturated fatty acids) can be completely separated according to the number of unsaturated bonds. In addition, since a conventional ion exchange resin can be used, a fatty acid can be easily separated without requiring a special device or operation.
第１図、第２図、第３図および第４図は、それぞれ実施
例１、２、３および４で得られたクロマトグラムを示す
図である。 １……オレイン酸、２……リノール酸、３……γ−リノ
レン酸、４……エイコサペンタエン酸。FIG. 1, FIG. 2, FIG. 3, and FIG. 4 are diagrams showing the chromatograms obtained in Examples 1, 2, 3, and 4, respectively. 1 ... oleic acid, 2 ... linoleic acid, 3 ... γ-linolenic acid, 4 ... eicosapentaenoic acid.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.6，ＤＢ名) C11C 1/08 C11B 7/00 C11B 3/10 C07C 51/47 ──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int. Cl. 6 , DB name) C11C 1/08 C11B 7/00 C11B 3/10 C07C 51/47
Claims (1)
吸着剤を充填した分離カラムに添加し、非極性溶媒また
は非極性溶媒と極性溶媒の混合液によりクロマトグラフ
ィー分離することを特徴とする脂肪酸の分離方法。A liquid containing two or more fatty acids is added to a separation column filled with an adsorbent supporting lead, and chromatographed with a non-polar solvent or a mixture of a non-polar solvent and a polar solvent. Method for separating fatty acids.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2327054A JP2941046B2 (en) | 1990-11-28 | 1990-11-28 | Fatty acid separation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2327054A JP2941046B2 (en) | 1990-11-28 | 1990-11-28 | Fatty acid separation method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04198397A JPH04198397A (en) | 1992-07-17 |
| JP2941046B2 true JP2941046B2 (en) | 1999-08-25 |
Family
ID=18194791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2327054A Expired - Fee Related JP2941046B2 (en) | 1990-11-28 | 1990-11-28 | Fatty acid separation method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2941046B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69724629T2 (en) * | 1996-06-03 | 2004-07-29 | Croda International Plc., Goole | COMPOSITIONS AND THEIR USE |
-
1990
- 1990-11-28 JP JP2327054A patent/JP2941046B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04198397A (en) | 1992-07-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5719302A (en) | Processes for chromatographic fractionation of fatty acids and their derivatives | |
| ES2459951T3 (en) | Simulated mobile bed chromatographic separation process for the purification of polyunsaturated fatty acids | |
| US10723973B2 (en) | Multi-step separation process | |
| US5777141A (en) | Process for recovering unsaturated fatty acids and derivatives thereof | |
| CA2815296C (en) | Smb process | |
| US9260677B2 (en) | SMB process | |
| US9234157B2 (en) | SMB process | |
| Dillon et al. | Purification of omega-3 polyunsaturated fatty acids from fish oil using silver-thiolate chromatographic material and high performance liquid chromatography | |
| CA2633509A1 (en) | Method of preparing a composition using argentation chromatography | |
| KR970002037B1 (en) | PROCESS FOR PREPARING Ñß-LINOLEIC ACID FROM PERILLA | |
| Fagan et al. | Rapid isolation of omega‐3 long‐chain polyunsaturated fatty acids using monolithic high performance liquid chromatography columns | |
| Latyshev et al. | Concentration and purification of polyunsaturated fatty acids from squid liver processing wastes | |
| Demirbüker et al. | Separation of triacylglycerols by supercritical-fluid argentation chromatography | |
| Higashidate et al. | Enrichment of eicosapentaenoic acid and docosahexaenoic acid esters from esterified fish oil by programmed extraction-elution with supercritical carbon dioxide | |
| Choo et al. | Separation of crude palm oil components by semipreparative supercritical fluid chromatography | |
| JP2941046B2 (en) | Fatty acid separation method | |
| Liao et al. | Silver (I)-dimercaptotriazine functionalized silica: A highly selective liquid chromatography stationary phase targeting unsaturated molecules | |
| JPS61192797A (en) | Concentration of highly unsaturated acid | |
| Ottenstein et al. | Column types for the chromatographic analysis of oleochemicals | |
| Kleiner‐Shuhler et al. | Purification of stearidonic acid from modified soybean oil by argentation silica gel column chromatography | |
| JPS62277496A (en) | Concentration of highly unsaturated fatty acid-containing triglyceride | |
| Guo et al. | Purification of α-linolenic acid from flaxseed oil by silver-silica gel chromatography column | |
| David et al. | Oils, fats and waxes: supercritical fluid chromatography | |
| Sebedio | High Performance liquid chromatography of fatty acids | |
| Van der Meeren et al. | PREPARAT I VE HI GH-PERF ORMAN CE LIQUID CHROMATOGRAPHY OF LIPIDS |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |