JPS6037110B2 - Tocopherol purification and concentration method - Google Patents
Tocopherol purification and concentration methodInfo
- Publication number
- JPS6037110B2 JPS6037110B2 JP14524074A JP14524074A JPS6037110B2 JP S6037110 B2 JPS6037110 B2 JP S6037110B2 JP 14524074 A JP14524074 A JP 14524074A JP 14524074 A JP14524074 A JP 14524074A JP S6037110 B2 JPS6037110 B2 JP S6037110B2
- Authority
- JP
- Japan
- Prior art keywords
- tocopherol
- alcohol
- purification
- resin
- concentration method
- 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
Links
- 239000011732 tocopherol Substances 0.000 title claims description 23
- 229930003799 tocopherol Natural products 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 8
- 229960001295 tocopherol Drugs 0.000 title description 20
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 title description 19
- 235000010384 tocopherol Nutrition 0.000 title description 19
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 title description 19
- 238000000746 purification Methods 0.000 title 1
- 229920001577 copolymer Polymers 0.000 claims description 5
- 235000019149 tocopherols Nutrition 0.000 claims description 3
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 claims description 3
- 238000004440 column chromatography Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000012535 impurity Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 4
- 230000001877 deodorizing effect Effects 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920001890 Novodur Polymers 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 244000082204 Phyllostachys viridis Species 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 229930003270 Vitamin B Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- -1 isopropylene alcohol Chemical compound 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 210000004894 snout Anatomy 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Pyrane Compounds (AREA)
Description
【発明の詳細な説明】
本発明はスチレンジビニルベンゼン共重合ポーラスポリ
マ−（以下スチレン系樹脂という）を用いてのトコフェ
ロール物質の天然又は合成の粗成トコフヱロールの精製
濃縮法に係る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for purifying and concentrating natural or synthetic crude tocopherol substances using a styrene divinylbenzene copolymer porous polymer (hereinafter referred to as styrenic resin).
今日植物油の脱臭脱酸工程で得られる浮連を用い、これ
を医薬食品等に使用し得る程度の純度のものまで、経済
的かつ高収率で処理する方法はごく限られている。Today, there are only a limited number of economical and high-yield methods for processing the oil obtained from the deodorizing and deoxidizing process of vegetable oils to a purity level that can be used in pharmaceutical foods and the like.
本発明は、天然の状態で多種の不純物を含んでおり、か
つトコフェロール分の極めて低濃度である原料を脱臭脱
酸の後、アルコール系溶媒に溶解し、これを同溶媒を用
いスチレン系樹脂で処理する時■トコフェロール物質、
■ステロイド類、■炭化水素及び高級アルコールの順に
熔出し、色素及びその他の不純物は樹脂上に吸着するこ
とに基く、すなわちアルコール系溶媒に熔解した多くの
不純物を含むトコフェロール物質をスチレン系樹脂で展
開しトコフェロール物質のみを優先的に溶出せしめ、そ
の他吸着した不純物を、アルコール以外の有機溶媒にて
洗浄し、かつ樹脂の再生を同時に行う方法である。In the present invention, a raw material that naturally contains various impurities and has an extremely low concentration of tocopherol is deodorized, deoxidized, dissolved in an alcohol solvent, and then treated with a styrene resin using the same solvent. When processing ■ Tocopherol substances,
■Steroids, ■hydrocarbons, and higher alcohols are dissolved in this order, and pigments and other impurities are adsorbed onto the resin.In other words, tocopherol substances containing many impurities dissolved in an alcohol solvent are developed with a styrene resin. This is a method in which only tocopherol substances are preferentially eluted, other adsorbed impurities are washed with an organic solvent other than alcohol, and the resin is simultaneously regenerated.
ここで述べるトコフェロール物質とは、植物油中に存在
しビタミンＢとしての生理作用を有する天然ｄ−型及び
合成ｄクー型のＱ８ｙ６同族体を意味する。The tocopherol substances mentioned herein refer to natural d-type and synthetic d-cou type Q8y6 homologs that exist in vegetable oils and have physiological effects as vitamin B.
スチレン系樹脂を用いた、カラムクロマトグラフイーで
トコフェロールの分離に、優れた分離を示す溶媒はメタ
ノール、エタノール、ィソプロピ′レアルコール、ｎー
プロピルアルコール、ｎーフ。Solvents that show excellent separation of tocopherol by column chromatography using styrene resin are methanol, ethanol, isopropylene alcohol, n-propyl alcohol, and n-propyl alcohol.
チルアルコール等炭素数１〜４個の低級１価のアルコー
ル及び、そのの混合溶媒であるが、その他塩化メチレン
、塩化エチレン、クロロホルム、四塩化炭素等の溶媒に
ても分離が可能である。トコフェロールを分離した後カ
ラム内に残った脂肪酸色素等種々の不純物は、ｎーヘキ
サン、ｎーヘプタン等の炭化水素類アセトン、メチルヱ
チルケトン等のケトン類にて樹脂の洗浄再生を行う。こ
こで述べるスチレンジビニルベンゼン共重合体ポーラス
ポリマーとは一般的には孔径５０〜１２０Ａ、比表面積
１００〜４００の／ｇ、粒子径３０〜２００仏ｍで、好
ましくは、孔径５０〜８０Ａ、比表面積２００〜２５０
力／ｇ、粒子径６０〜１００ｒｍであるスチレンとジビ
ニルベンゼンからなる共重合体のポーラスポリマーが用
いられる。■ スチレン系樹脂は、ポーラス型であるた
め処理量が大きく又、■ 酸アルカリ類を用いないため
分離のトコフェロールに後処理の必要かないこと。Separation is possible using lower monohydric alcohols having 1 to 4 carbon atoms such as methyl alcohol, and mixed solvents thereof, but other solvents such as methylene chloride, ethylene chloride, chloroform, and carbon tetrachloride can also be used. Various impurities such as fatty acid pigments remaining in the column after tocopherol separation are removed by washing and regenerating the resin with hydrocarbons such as n-hexane and n-heptane, acetone, and ketones such as methyl ethyl ketone. The styrene divinylbenzene copolymer porous polymer described here generally has a pore size of 50 to 120 A, a specific surface area of 100 to 400 m/g, and a particle size of 30 to 200 French m, preferably a pore size of 50 to 80 A and a specific surface area of 200-250
A porous copolymer of styrene and divinylbenzene having a force/g and a particle size of 60 to 100 rm is used. ■ Styrenic resin is porous, so it can be processed in a large amount, and ■ Since no acids and alkalis are used, there is no need for post-treatment of separated tocopherol.
■ 樹脂の再生が容易であり、この樹脂は半永久的に使
用できる。■ The resin can be easily recycled and can be used semi-permanently.
等のことから本方法は、トコフェロール類を工業的、経
済的に精製濃縮する方法として、大変優れていると思わ
れる。For these reasons, the present method is considered to be very excellent as a method for industrially and economically purifying and concentrating tocopherols.
実施例 １
大豆油の、脱臭脱酸により得られたトコフェロール濃度
３１．８％の濃縮物６腿を６０の【のアルコールに溶か
し、これをスチレンジピニルベンゼン共重合体ポーラス
型球状樹脂日立ゲル３０１９（平均孔径６０Ａ、比表面
積２４０で／ｇ、平均粒子径６０仏ｍ：日立製作所製）
を使用し、直径６０助長さ５０物帆のガラスカラム中に
３００側の高さに充填したものを用い、アルコールを溶
媒として、流速２の‘／ｍｉｎで展開溶出し始めた直後
の１００の‘を初溜として除き、この後の溜分３００地
を分取この溜分を減圧下に濃縮、トコフェロール純度７
２．６％の濃縮物１７．衣を得た。Example 1 Six pieces of a concentrate with a tocopherol concentration of 31.8% obtained by deodorizing and deoxidizing soybean oil were dissolved in 60% alcohol and mixed into styrene dipinylbenzene copolymer porous spherical resin Hitachi Gel. 3019 (average pore size 60A, specific surface area 240/g, average particle size 60 French m: manufactured by Hitachi, Ltd.)
A glass column with a diameter of 60 mm and a length of 50 mm was packed at a height of 300 mm. was removed as the first distillation, and the subsequent 300 fractions were collected. This fraction was concentrated under reduced pressure, and the purity of tocopherol was 7.
2.6% concentrate17. I got clothes.
実施例 ２
大豆油の脱臭脱酸後のトコフェロール濃度３８．８％の
濃縮物６０ｇを６０叫のイソプロピルアルコ−ル、メタ
ノール（１：２）の混合溶媒で溶解したものを、直径６
物吻、高さ３０物肋‘こ充填した前出日立ゲル３０１９
に同溶媒を用い展開し、その主溜分３００の‘を分取濃
縮後、トコフェロール純度９９．８％の濃縮物１４．艇
が得られた。Example 2 60g of a concentrate with a tocopherol concentration of 38.8% after deodorizing and deoxidizing soybean oil was dissolved in a mixed solvent of 60% isopropyl alcohol and methanol (1:2), and a solution of
Hitachi Gel 3019 filled with snout, height 30mm
was developed using the same solvent, and after preparative concentration of the main fraction 300', a concentrate with tocopherol purity of 99.8% 14. A boat was obtained.
実施例 ３
合成により得られた純度６０％のｄぞ−Ｑートコフェロ
ール６雌をインプロピルアルコール、メタノール（１：
２）の混合溶媒６０の【‘こ溶かし、実施例２と同様の
カラム条件で展開主溜分を濃縮後、トコフヱロール純度
９４．２％のｄ〆−Ｑ−トコフェロール３２．笹を得た
。Example 3 dzo-Q tocopherol 6 female with a purity of 60% obtained by synthesis was mixed with inpropyl alcohol and methanol (1:
After dissolving 60% of the mixed solvent of 2) and concentrating the developed main fraction under the same column conditions as in Example 2, d〆-Q-tocopherol with a tocopherol purity of 94.2% was obtained. I got bamboo.
実施例 ４
大豆油を脱臭脱酸後得られた純度３８．８％の濃縮トコ
フエロ−ル６０ｇを、６０のとのインプロピルアルコー
ル、メタノール（１：２）の混合溶媒に溶かし、これを
実施例１〜３と同条件で展開溶出した、溶媒を各フラク
ション１００の上を１単位として、分取それぞれを濃縮
後、淡黄色オイル状トコフェロール濃縮物を得た、これ
をガスクロマトグラフィ‐（ＯＥＳＥ−３０、１．５％
カラム）で分析したところフラクション１はＱ体を全く
含まない８ｙ６体とトコフェロールが認められフラクシ
ョン２、３、４と純次Ｑ体の濃度の増加が見られた。Example 4 60 g of concentrated tocopherol with a purity of 38.8% obtained after deodorizing and deoxidizing soybean oil was dissolved in a mixed solvent of 60% inpropyl alcohol and methanol (1:2), and this was dissolved in Example 4. The solvent was developed and eluted under the same conditions as 1 to 3. After concentrating each fraction of the solvent, the top 100 of each fraction was concentrated to obtain a pale yellow oily tocopherol concentrate, which was subjected to gas chromatography (OESE-30 , 1.5%
When analyzed using a column), fraction 1 contained 8y6 isomer and tocopherol, which did not contain any Q isomer, and an increase in the concentration of pure Q isomer was observed in fractions 2, 3, and 4.
Claims (1)
ビニルベンゼン共重合体ポーラスポリマーを充填したカ
ラムで処理することを特徴とするカラムクロマトグラフ
イーによるトコフエロールの精製濃縮法。1. A method for purifying and concentrating tocopherols by column chromatography, which comprises treating natural or synthetic crude tocopherols in a column packed with a porous styrene divinylbenzene copolymer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14524074A JPS6037110B2 (en) | 1974-12-18 | 1974-12-18 | Tocopherol purification and concentration method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14524074A JPS6037110B2 (en) | 1974-12-18 | 1974-12-18 | Tocopherol purification and concentration method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5175074A JPS5175074A (en) | 1976-06-29 |
| JPS6037110B2 true JPS6037110B2 (en) | 1985-08-24 |
Family
ID=15380557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14524074A Expired JPS6037110B2 (en) | 1974-12-18 | 1974-12-18 | Tocopherol purification and concentration method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6037110B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5251305A (en) * | 1975-10-20 | 1977-04-25 | Nisshin Flour Milling Co Ltd | Proces for purification of isoprene |
| US7640620B2 (en) * | 2004-05-10 | 2010-01-05 | Stockton John H | Retractable hose extension for a vacuum |
| GB2416138A (en) * | 2004-07-15 | 2006-01-18 | Stegram Pharmaceuticals Ltd | Chromatographic separation of trilostane mixture |
-
1974
- 1974-12-18 JP JP14524074A patent/JPS6037110B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5175074A (en) | 1976-06-29 |
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