JPH0362705B2 - - Google Patents
Info
- Publication number
- JPH0362705B2 JPH0362705B2 JP60097927A JP9792785A JPH0362705B2 JP H0362705 B2 JPH0362705 B2 JP H0362705B2 JP 60097927 A JP60097927 A JP 60097927A JP 9792785 A JP9792785 A JP 9792785A JP H0362705 B2 JPH0362705 B2 JP H0362705B2
- Authority
- JP
- Japan
- Prior art keywords
- soy sauce
- acid ethyl
- fatty acid
- distillation
- ethyl ester
- 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 - Lifetime
Links
- 235000013555 soy sauce Nutrition 0.000 claims description 38
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 25
- 229930195729 fatty acid Natural products 0.000 claims description 25
- 239000000194 fatty acid Substances 0.000 claims description 25
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 230000001877 deodorizing effect Effects 0.000 claims description 4
- 239000003921 oil Substances 0.000 description 22
- 238000004821 distillation Methods 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 235000010469 Glycine max Nutrition 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 230000009965 odorless effect Effects 0.000 description 8
- 239000001058 brown pigment Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 235000021588 free fatty acids Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 240000006439 Aspergillus oryzae Species 0.000 description 2
- 235000002247 Aspergillus oryzae Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 230000002790 anti-mutagenic effect Effects 0.000 description 2
- 238000004042 decolorization Methods 0.000 description 2
- 238000004332 deodorization Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 244000294411 Mirabilis expansa Species 0.000 description 1
- 235000015429 Mirabilis expansa Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000010730 cutting oil Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- FMMOOAYVCKXGMF-MURFETPASA-N ethyl linoleate Chemical group CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC FMMOOAYVCKXGMF-MURFETPASA-N 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 238000009629 microbiological culture Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 235000013536 miso Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Soy Sauces And Products Related Thereto (AREA)
Description
＜産業上の利用分野＞
本発明は、醤油製造に於ける副産物である醤油
油を原料とし、減圧下での蒸留工程と脱色、脱臭
工程の組合せにより醤油油特有の臭いと黒褐色色
素を除去して無色、無臭の脂肪酸エチルエステル
を高純度で製造する方法に関する。
＜従来の技術＞
醤油油は、醤油醸造の副産物として得られ、脂
肪酸エチルエステルを多量に含む特殊な油として
注目され油脂としての性質やその生成過程が解明
されてきた。
また、醤油油の利用に際し、そこに含まれる醤
油様の臭い及び黒褐色色素が問題とされる場合が
多々あることから醤油油を精製改良することも古
くから種々試みられてきた。
これら醤油油の精製、改良に関する研究もしく
は特許出願は、醤油油を直接脱色、脱臭する方
法、あるいは遊離脂肪酸を分離する方法等多岐に
わたつている。
ところで醤油油中の脂肪酸エチルエステルは、
主として原料に由来する脂質が麹菌によつて分離
され、生じた遊離脂肪酸が酵母の作用によつてエ
ステル化されて生成した、言わば天然物である。
しかしながら、この天然物である脂肪酸エチル
エステルのみを雑多な成分を含む醤油油から分離
し、高度に精製することは、その用途があまり知
られていなかつたためか、充分には検討されず、
醤油油より無色、無臭で純度90％以上の天然脂肪
酸エチルエステルを工業的に製造する具体的な方
法は未だ提案されていない。
なお、現在市販されている脂肪酸エチルエステ
ルはすべて合成品であり、その製法は、工業的に
は油脂、脂肪酸にエチルアルコールを添加して反
応させる直接エステル化法、グリセリドを原料と
してエステル交換によつてエチルエステルを生成
させるアルコリシス法等の合成法によつて得られ
ている。
＜発明が解決しようとする問題点＞
醤油油には脂肪酸のエチルエステルと遊離の脂
肪酸が主成分として含まれているが、他に未分解
のトリグリセリド、原料由来のステロイド、サポ
ニン類及び醸造中に麹菌、乳酸菌、酵母等各種微
生物の菌体内で生産された脂質成分を含んでい
る。
また醤油油は、醤油様の香気成分や黒褐色の色
素を含んでいるため、その用途は通常の油に比べ
制限されている。
これを精製改良することは、前途の如く古くか
ら種々試みられ特許出願もなされたが、殆ど実施
されていないのが現状である。現在では醤油油は
主として切削油、脂肪酸原料、微生物培養基等に
利用されているにとどまつている。
一方、最近味噌中の抗変異原性物質として脂肪
酸エチルエステルが報告され、注目されている。
これとは別に本発明者等は、醤油油を有効利用す
ることを目的とし、脂肪酸エチルエステルの用途
開発の研究に着手した。
そこで問題点として浮かび上がつてきたのは、
脂肪酸エチルエステルの純度である。即ち、無
色、無臭で純度100％に近いものが製造できれば、
天然脂肪酸エチルエステルとして、従来の遊離脂
肪酸にはない新しい付加価値の高い用途がいくつ
かあることが判明した。
＜問題点を解決するための手段＞
本発明者等は、従来醤油様の特有の臭いと黒褐
色色素を持つていいるためその用途が制限されて
いる醤油油を原料として無色、無臭、高純度の天
然脂肪酸エチルエステルを工業的に製造する方法
を鋭意検討した結果、醤油油を減圧下に蒸留して
主留分のみを厳密な条件で分取し、これを脱色、
脱臭することにより目的の脂肪酸エチルエステル
が得られることを知見し、本発明を完成した。
即ち、本発明は、醤油油を減圧下に蒸留して主
留分を分取し該主留分を脱色、脱臭することを特
徴とする脂肪酸エチルエステルの製造法である。
以下、本発明を詳細に説明する。
本発明に於いて用いられる醤油油は、通常の発
酵過程を経た醤油諸味を圧搾して得た醤油の表面
に浮遊してくる油脂分の総称であつて、醤油製造
における副産物として得られるものである。また
醤油油は丸大豆あるいは脱脂大豆から由来するい
ずれの醤油油を用いてもよいが、極端に古いもの
は成分の酸化劣化が進んでいるのでなるべく新鮮
な醤油を用いるのがよい。
次に醤油油を減圧下に蒸留するのであるが、本
発明に於いて用いることができる蒸留は、減圧下
で行なうのであれば、例えば水蒸気蒸留法、エタ
ノール蒸気蒸留法、減圧蒸留法、分子蒸留法等い
ずれも用いることができるが、好ましくは、減圧
蒸留法が精製効果及び製造コストの点から望まし
い。
減圧は60mmHg以下、好ましくは４mmHg以下の
高度の減圧下とし、醤油油を加温もしくは加熱し
つつ、場合によつては醤油油中に水蒸気、エタノ
ール蒸気等を吹き込んで蒸留を行ない、出てくる
蒸気を冷却して凝縮させ留出液を得る。
この際、蒸留温度が高い程、得られる脂肪酸エ
チルエステルが分解し回収率が低下すること、ま
た蒸留時の減圧度が不足すると１回の蒸留で目的
の精製度に達せず再留が必要となること等を考慮
し、要は上記した60mmHg以下、好ましくは４mm
Hg以下の蒸留圧力で蒸留を行う。
次に主留分のみ分取するのであるが、まず留出
液の初留には、醤油油のもつている醤油様のフレ
ーバーが留出されるのでこの初留液を少なくとも
仕込醤油油量の３％（Ｖ／Ｖ）、好ましくは、10
％（Ｖ／Ｖ）前後採取する。この醤油様のフレー
バーを含む初留液は、本発明の対象ではないので
留去する。
そして仕込醤油油量の３％（Ｖ／Ｖ）目より採
取を開始し75％（Ｖ／Ｖ）目迄、特に好ましくは
10％（Ｖ／Ｖ）目から65％（Ｖ／Ｖ）目迄の主留
分を採取して蒸留を終了する。
このようにして得られた主留分は、なお微弱の
醤油様の臭いをもち、淡褐色の色を有する。なお
残留分には刺激臭、黒褐色色素、遊離の脂肪酸等
を含有する。
次に上記主留液を脱色、脱臭処理する。この脱
色、脱臭処理は、活性炭、白土、イオン交換樹脂
等を用いることができる。例えば、活性炭を用い
る場合は、得られた主留分に適量の活性炭を添加
し、20℃前後で２時間以上、好ましくは10時間以
上攪拌しながら放置する。そしてこれを濾過する
ことにより、無色、無臭の精製された脂肪酸エチ
ルエステルを90％以上の純度で得ることができ
る。
本発明で得られる脂肪酸エチルエステルは、そ
のままあるいはさらに単一の脂肪酸エチルエステ
ルに単離して、化粧品、食品、医薬品等各種の原
料又は添加剤として用いることができ、産業上有
用である。
＜実施例＞
以下、本発明の実施例を示してさらに詳細に説
明する。
実施例 １
仕込後８カ月を経た醤油諸味を圧搾して分離し
た醤油油100を、圧力４mmHg、品温168〜178℃
の条件で減圧蒸留を行い、初留８、主留52、
残留分38を得た。
この主留分の47に対し、活性炭〔武田薬品工
業(株)製〕2.3Kgを加え、20℃で20時間攪拌したの
ち、濾過して微黄色、殆ど無臭の脂肪酸エチルエ
ステル41を得た。
本品の分析値は、第１〜３表の通りであつた。
<Industrial Application Field> The present invention uses soy sauce oil, which is a byproduct of soy sauce production, as a raw material, and removes the odor and dark brown pigment peculiar to soy sauce oil by combining a distillation process under reduced pressure, decolorization, and deodorization process. This invention relates to a method for producing colorless and odorless fatty acid ethyl ester with high purity. <Prior Art> Soy sauce oil is obtained as a byproduct of soy sauce brewing, and has attracted attention as a special oil containing a large amount of fatty acid ethyl ester, and its properties as an oil and fat and its production process have been elucidated. Furthermore, when using soy sauce oil, the soy sauce-like odor and dark brown pigment contained therein are often problematic, so various attempts have been made to refine and improve soy sauce oil for a long time. Research or patent applications related to the purification and improvement of soy sauce oil cover a wide range of topics, including methods for directly decolorizing and deodorizing soy sauce oil, and methods for separating free fatty acids. By the way, fatty acid ethyl ester in soy sauce is
It is a natural product that is produced by separating lipids mainly derived from raw materials using Aspergillus oryzae and esterifying the resulting free fatty acids through the action of yeast. However, separating only this natural product, fatty acid ethyl ester, from soy sauce containing miscellaneous components and refining it to a high degree has not been fully investigated, perhaps because its uses were not well known.
No specific method has yet been proposed for industrially producing natural fatty acid ethyl ester that is colorless, odorless, and has a purity of 90% or more than soy sauce. All fatty acid ethyl esters currently on the market are synthetic products, and their manufacturing methods include direct esterification, in which ethyl alcohol is added to fats and oils and fatty acids, and transesterification using glyceride as a raw material. It is obtained by a synthetic method such as the alcoholysis method in which ethyl ester is produced. <Problems to be solved by the invention> Soy sauce oil contains ethyl esters of fatty acids and free fatty acids as its main components, but it also contains undecomposed triglycerides, steroids derived from raw materials, saponins, and during brewing. Contains lipid components produced within the cells of various microorganisms such as koji mold, lactic acid bacteria, and yeast. Furthermore, because soy sauce oil contains soy sauce-like aromatic components and dark brown pigments, its uses are more limited than that of regular oils. Various attempts have been made to purify and improve this for a long time, and patent applications have been filed, but at present very little has been carried out. At present, soy sauce oil is mainly used as cutting oil, fatty acid raw material, microbial culture medium, etc. On the other hand, fatty acid ethyl esters have recently been reported as anti-mutagenic substances in miso, and are attracting attention.
Separately, the present inventors have begun research into developing uses for fatty acid ethyl esters with the aim of effectively utilizing soy sauce. The problem that emerged was that
Purity of fatty acid ethyl ester. In other words, if we can produce something colorless, odorless, and close to 100% pure,
It has been discovered that natural fatty acid ethyl esters have several new and high value-added uses not found in conventional free fatty acids. <Means for Solving the Problems> The present inventors have developed a colorless, odorless, and highly pure soy sauce oil, which has a characteristic soy sauce-like odor and dark brown pigment, which has limited its use as a raw material. As a result of intensive research into a method for industrially producing natural fatty acid ethyl ester, we distilled soy sauce oil under reduced pressure, separated only the main fraction under strict conditions, and decolorized it.
The present invention was completed based on the finding that the desired fatty acid ethyl ester could be obtained by deodorizing it. That is, the present invention is a method for producing fatty acid ethyl ester, which is characterized by distilling soy sauce oil under reduced pressure, separating the main fraction, and decolorizing and deodorizing the main fraction. The present invention will be explained in detail below. The soy sauce oil used in the present invention is a general term for the fats and oils that float on the surface of soy sauce obtained by pressing soy sauce moromi that has undergone a normal fermentation process, and is obtained as a by-product in soy sauce production. be. Also, any soy sauce derived from whole soybeans or defatted soybeans may be used, but it is better to use as fresh a soy sauce as possible, as extremely old soy sauce has advanced oxidative deterioration of its components. Next, the soy sauce oil is distilled under reduced pressure. Distillation that can be used in the present invention includes, for example, steam distillation, ethanol steam distillation, vacuum distillation, and molecular distillation. Although any method can be used, the vacuum distillation method is preferably used from the viewpoint of purification effect and manufacturing cost. The pressure is reduced to a high level of 60 mmHg or less, preferably 4 mmHg or less, and while heating or heating the soy sauce, steam, ethanol vapor, etc. are blown into the soy sauce to perform distillation. The vapor is cooled and condensed to obtain a distillate. At this time, the higher the distillation temperature, the more the fatty acid ethyl ester obtained will decompose and the recovery rate will decrease. Also, if the degree of vacuum during distillation is insufficient, the desired degree of purification will not be achieved in one distillation and re-distillation will be necessary. In short, the above-mentioned 60mmHg or less, preferably 4mm
Distillation is carried out at a distillation pressure of Hg or less. Next, only the main distillate is separated, but first, the soy sauce-like flavor of soy sauce is distilled out in the first distillate, so this first distillate is used at least as much as the amount of soy sauce to be prepared. 3% (V/V), preferably 10
Sample around % (V/V). This first distillate containing a soy sauce-like flavor is not subject to the present invention and is therefore distilled off. Then, start collecting from 3% (V/V) of the amount of soy sauce and collect until 75% (V/V), particularly preferably.
Distillation is completed by collecting the main fraction from 10% (V/V) to 65% (V/V). The main fraction thus obtained still has a faint soy sauce-like odor and a light brown color. The residue contains a pungent odor, dark brown pigment, free fatty acids, etc. Next, the main distillate is decolorized and deodorized. For this decolorization and deodorization treatment, activated carbon, clay, ion exchange resin, etc. can be used. For example, when using activated carbon, an appropriate amount of activated carbon is added to the obtained main fraction, and the mixture is left stirring at around 20° C. for 2 hours or more, preferably 10 hours or more. By filtering this, colorless and odorless purified fatty acid ethyl ester can be obtained with a purity of 90% or more. The fatty acid ethyl ester obtained in the present invention can be used as it is or further isolated into a single fatty acid ethyl ester and used as a raw material or additive for various cosmetics, foods, pharmaceuticals, etc., and is industrially useful. <Examples> Hereinafter, examples of the present invention will be shown and explained in more detail. Example 1 Soy sauce oil 100, which was separated by pressing soy sauce moromi 8 months after preparation, was heated to a pressure of 4 mmHg and a product temperature of 168 to 178°C.
Distillation under reduced pressure was carried out under the following conditions, and the first distillate was 8, the main distillate was 52,
A residue of 38 was obtained. To this main fraction 47, 2.3 kg of activated carbon (manufactured by Takeda Pharmaceutical Co., Ltd.) was added, stirred at 20°C for 20 hours, and then filtered to obtain slightly yellow, almost odorless fatty acid ethyl ester 41. The analytical values of this product were as shown in Tables 1 to 3.
【表】【table】
【表】【table】
【表】【table】
【表】
実施例 ２
仕込後７カ月を経た醤油諸味を圧搾し分離して
得られた醤油油100を、圧力２mmHg、品温152
〜157℃の条件で減圧蒸留し、初留12、主留47
、残留分36を得た。
この主留分47に対し、活性炭〔武田薬品工業
(株)製〕2.4Kgを加え、20℃で20時間攪拌したのち、
濾過して無色、無臭の脂肪酸エチルエステル42
を得た。 本品の分析値は、第４〜６表の通りで
あつた。なお、各分析値は実施例１と同様に行つ
た。[Table] Example 2 Soy sauce oil 100% obtained by squeezing and separating soy sauce moromi 7 months after preparation was heated at a pressure of 2 mmHg and a product temperature of 152 cm.
Distilled under reduced pressure at ~157°C, with an initial distillation of 12 and a main distillation of 47.
, a residue of 36 was obtained. For this main distillate 47, activated carbon [Takeda Pharmaceutical Co., Ltd.
Co., Ltd.] 2.4 kg and stirred at 20℃ for 20 hours.
Filtered colorless, odorless fatty acid ethyl ester 42
I got it. The analytical values of this product were as shown in Tables 4 to 6. Note that each analytical value was determined in the same manner as in Example 1.
【表】【table】
【表】【table】
【表】
＜発明の効果＞
本発明は従来醤油様の臭いや黒褐色色素を持つ
ているため、その用途が限られていた醤油油の有
効利用並びに最近抗変異原性が強いと報告された
リノール酸エチルエステル、リノレイン酸エチル
エステルを含む脂肪酸エチルエステルを合成法に
よることなく、天然物資源より得ることを目的と
し、醤油油を厳密な蒸留条件による蒸留工程と脱
色、脱臭工程の組み合わせにより醤油様の臭いと
黒褐色色素を効率良く除去して無色、無臭の脂肪
酸エチルエステルを高純度で得るものである。[Table] <Effects of the Invention> The present invention enables the effective use of soy sauce, which has been limited in its use due to its soy sauce-like odor and dark brown pigment, as well as linole, which has recently been reported to have strong antimutagenic properties. The aim is to obtain fatty acid ethyl esters, including acid ethyl esters and linoleic acid ethyl esters, from natural resources without using synthetic methods. This method efficiently removes the odor and dark brown pigment to obtain colorless and odorless fatty acid ethyl ester with high purity.
Claims (1)
該主留分を脱色、脱臭することを特徴とする脂肪
酸エチルエステルの製造法。1 Distill soy sauce oil under reduced pressure and separate the main fraction,
A method for producing fatty acid ethyl ester, which comprises decolorizing and deodorizing the main fraction.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60097927A JPS61257945A (en) | 1985-05-10 | 1985-05-10 | Production of ethyl ester of fatty acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60097927A JPS61257945A (en) | 1985-05-10 | 1985-05-10 | Production of ethyl ester of fatty acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61257945A JPS61257945A (en) | 1986-11-15 |
| JPH0362705B2 true JPH0362705B2 (en) | 1991-09-26 |
Family
ID=14205309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60097927A Granted JPS61257945A (en) | 1985-05-10 | 1985-05-10 | Production of ethyl ester of fatty acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61257945A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01316344A (en) * | 1988-03-23 | 1989-12-21 | Yoshitomi Pharmaceut Ind Ltd | Removal of dyestuff substance |
| DE10302299A1 (en) * | 2003-01-22 | 2004-07-29 | Cognis Deutschland Gmbh & Co. Kg | Deodorization of oils comprises treatment with a polymeric adsorbent in addition to distillation with steam or a carrier gas |
| CN112979466B (en) * | 2021-03-02 | 2023-08-25 | 江西益普生药业有限公司 | A kind of usage method of the refining device of medicinal ethyl oleate |
-
1985
- 1985-05-10 JP JP60097927A patent/JPS61257945A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61257945A (en) | 1986-11-15 |
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