JPH0435000B2 - - Google Patents
Info
- Publication number
- JPH0435000B2 JPH0435000B2 JP60102870A JP10287085A JPH0435000B2 JP H0435000 B2 JPH0435000 B2 JP H0435000B2 JP 60102870 A JP60102870 A JP 60102870A JP 10287085 A JP10287085 A JP 10287085A JP H0435000 B2 JPH0435000 B2 JP H0435000B2
- Authority
- JP
- Japan
- Prior art keywords
- alcohol
- bile
- bile acids
- fatty acid
- separating
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 51
- 239000003613 bile acid Substances 0.000 claims description 38
- 238000005886 esterification reaction Methods 0.000 claims description 26
- 238000000926 separation method Methods 0.000 claims description 25
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 24
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 16
- 239000001569 carbon dioxide Substances 0.000 claims description 12
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000002994 raw material Substances 0.000 claims description 9
- -1 fatty acid esters Chemical class 0.000 description 30
- 235000014113 dietary fatty acids Nutrition 0.000 description 22
- 229930195729 fatty acid Natural products 0.000 description 22
- 239000000194 fatty acid Substances 0.000 description 22
- 230000032050 esterification Effects 0.000 description 21
- 238000000605 extraction Methods 0.000 description 16
- 235000021323 fish oil Nutrition 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 210000000941 bile Anatomy 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003815 supercritical carbon dioxide extraction Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Steroid Compounds (AREA)
Description
【発明の詳細な説明】
〔発明の利用分野〕
本発明は胆汁酸を含む原料から胆汁酸を高純度
で分離する方法に係り、特に、超臨界ガスあるい
は液化ガス抽出を利用した上記方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Application of the Invention] The present invention relates to a method for separating bile acids with high purity from raw materials containing bile acids, and particularly to the above-mentioned method using supercritical gas or liquefied gas extraction.
魚油の中には、エーコサペンタエン酸（以下、
EPA）、デコサヘキサエン酸（以下、DHA）等
多くの有価物質が存在する。EPA，DHAは食
効、薬効を有する高級不飽和脂肪酸で、プロスタ
グランジンの前駆物質とされている。魚油の中に
は、脂肪やコレステロールを水溶性化する生理活
性を有する胆汁酸も微量ながら存在する。
Some fish oils contain eicosapentaenoic acid (hereinafter referred to as
There are many valuable substances such as EPA) and decosahexaenoic acid (DHA). EPA and DHA are higher unsaturated fatty acids that have dietary and medicinal effects, and are considered precursors of prostaglandins. Fish oil also contains small amounts of bile acids, which have physiological activity to make fats and cholesterol water-soluble.
EPA，DHAの有価物質の濃縮方法について
は、種々の提案（例えば特開昭57−187397、特開
昭57−149400等）がなされている。一般的には魚
油を低級アルコールエステル化処理し、魚油中の
グリセリドを脂肪酸エステルとし、ついで、この
脂肪酸エステルを前記エステル化処理液から分離
し、蒸留等で分画し、上記EPA，DHAを濃縮す
る方法（参考文献、特開昭57−187397、特開昭58
−8037）がある。上記低級アルコールエステル化
処理およびエステル化処理液からの生成脂肪酸エ
ステルの分離の詳細工程を第５図に示す。この工
程には下記の問題がある。 Various proposals have been made regarding methods for concentrating valuable substances such as EPA and DHA (eg, JP-A-57-187397, JP-A-57-149400, etc.). Generally, fish oil is esterified with a lower alcohol, the glycerides in the fish oil are converted into fatty acid esters, and then the fatty acid esters are separated from the esterification solution and fractionated by distillation etc. to concentrate the EPA and DHA. (References, JP-A-187397, JP-A-58
-8037). The detailed steps of the lower alcohol esterification treatment and the separation of the produced fatty acid ester from the esterification treatment liquid are shown in FIG. This process has the following problems.
(A) エステル化反応は可逆反応であり、生成エス
テルの収率を高めるため、反応式から得られる
理論アルコール量より過剰のアルコールが必
要、
(B) 余剰アルコール及び触媒である塩基（例えば
NaOH等）と生成脂肪酸エステルは良く溶け
合い、相互分離が困難、
このため、第５図に示すように、本来のエステ
ル化工程の他に、水を導入し、水中に余剰アルコ
ールを溶解させ、脂肪酸エステルとアルコール水
溶液の比重差を利用して、脂肪酸エステルを分離
する工程が余分に必要である。さらに、上記低級
アルコールエステル化処理及び生成脂肪酸エステ
ルの分離工程で、エステル化に要するアルコール
を回収するためには蒸留等によるアルコールと水
の分離が必要となる。(A) The esterification reaction is a reversible reaction, and in order to increase the yield of the produced ester, an excess of alcohol is required compared to the theoretical amount of alcohol obtained from the reaction formula. (B) Excess alcohol and a base as a catalyst (e.g.
NaOH, etc.) and the resulting fatty acid esters dissolve well and are difficult to separate from each other. Therefore, as shown in Figure 5, in addition to the original esterification process, water is introduced, the excess alcohol is dissolved in water, and the fatty acid ester is dissolved in the fatty acid ester. An extra step is required to separate the fatty acid ester by utilizing the difference in specific gravity between the ester and the alcohol aqueous solution. Furthermore, in the lower alcohol esterification process and the separation process of the produced fatty acid ester, it is necessary to separate alcohol and water by distillation or the like in order to recover the alcohol required for esterification.
発明者らは、低級アルコールエステル化処理さ
れた魚油からの脂肪酸エステルとアルコールの分
離に超臨界ガス抽出の適用を種々検討し、下記の
新しい事項を見出し、本発明に至つた。 The inventors have conducted various studies on the application of supercritical gas extraction to the separation of fatty acid esters and alcohols from fish oil that has been subjected to lower alcohol esterification treatment, and have discovered the following new matter, leading to the present invention.
(1) 超臨界ガス抽出により、アルコールを含まな
い脂肪酸エステル及び90％以上のアルコール
を、それぞれ、収率95％以上で分離できる。(1) Supercritical gas extraction can separate alcohol-free fatty acid esters and 90% or more alcohol with a yield of 95% or more.
(2) 分離された上記アルコール中には、胆汁酸エ
ステルが70％以上（アルコール分を除く）の高
濃度で濃縮される。(2) Bile acid esters are concentrated in the separated alcohol at a high concentration of 70% or more (excluding alcohol content).
(3) 胆汁酸エステルはアルコールと常に共存す
る。(3) Bile acid esters always coexist with alcohol.
(4) 分離されたアルコール中で、胆汁酸はすみや
かに結晶化する。(4) Bile acids quickly crystallize in the separated alcohol.
本発明の目的は、胆汁酸を含む原料から胆汁酸
を高純度で分離する方法を提供することにある。
An object of the present invention is to provide a method for separating bile acids with high purity from raw materials containing bile acids.
本発明は胆汁酸を含む原料を、エステル化反応
式から得られる理論アルコール量よりも過剰のア
ルコールと反応させて低級アルコールエステル化
処理し、前記エステル化処理液から超臨界ガス抽
出により、アルコールを分離し、ついで、分離さ
れたアルコールから胆汁酸を分離することを特徴
とする。
In the present invention, a raw material containing bile acid is reacted with alcohol in excess of the theoretical alcohol amount obtained from the esterification reaction formula to esterify a lower alcohol, and the alcohol is extracted from the esterification solution by supercritical gas extraction. separation and then separation of bile acids from the separated alcohol.
以下、図面を用いて本発明の実施例を述べる。 Embodiments of the present invention will be described below with reference to the drawings.
第１図は本発明の一実施例である胆汁酸の分離
プロセスを示す。本発明は、胆汁酸を含む原料
を、エステル化反応式から得られる理論アルコー
ル量よりも過剰のアルコールと反応させて低級ア
ルコールエステル化処理する工程（ａ）、前記工
程（ａ）から得られるエステル化処理液１０か
ら、アルコールを分離する超臨界炭酸ガス抽出工
程（ｂ）及び前記工程（ｂ）より分離されたアル
コール１１から胆汁酸を結晶化させ固液分離する
工程（ｃ）からなる。 FIG. 1 shows a bile acid separation process according to an embodiment of the present invention. The present invention provides a step (a) of reacting a raw material containing bile acid with alcohol in excess of the theoretical alcohol amount obtained from an esterification reaction formula to esterify a lower alcohol, and an ester obtained from the step (a). The process consists of a supercritical carbon dioxide gas extraction step (b) for separating alcohol from the chemical treatment liquid 10, and a step (c) for crystallizing bile acids from the alcohol 11 separated in step (b) and performing solid-liquid separation.
胆汁酸は多くの脊椎動物の胆汁中に存在する。
魚油中にも微量存在する。原料としては胆汁酸を
含むものであれば良いが、以下、魚油を対象に述
べる。上記工程（ａ）で魚油中のグリセリド及び
胆汁酸は、KOH，NaOH等の触媒の存在下で、
それぞれ、低級アルコールエステル（以下脂肪酸
エステルと呼称）、胆汁酸エステルとなり、相互
に余剰アルコールと溶け合う。特に、遊離の胆汁
酸エステルはアルコールに極めて良く溶け、常に
アルコールと共存する。したがつて、胆汁酸の分
離にはアルコールを共存させることがポイントで
ある。また、一部の胆汁酸あるいは胆汁酸エステ
ルはコレステロール、アルコール等と複化合物を
形成する。工程（ａ）で得られるエステル化処理
液の組成は上記、脂肪酸エステル、アルコール、
胆汁酸エステル、胆汁酸複化合物コレステロール
等及び低級アルコールエステル化反応の結果生じ
るグリセリンで、上記エステル化処理液を静置す
れば、グリセリンとその他のものに二相分離す
る。後段の工程（ｂ）に導入するものは、上記エ
ステル化処理液でも良く、グリセリンを除くその
他のものでも良い。 Bile acids are present in the bile of many vertebrates.
It is also present in trace amounts in fish oil. Any raw material containing bile acid may be used, but fish oil will be described below. In the above step (a), the glycerides and bile acids in the fish oil are treated in the presence of a catalyst such as KOH or NaOH.
They become lower alcohol esters (hereinafter referred to as fatty acid esters) and bile acid esters, respectively, and they mutually dissolve with excess alcohol. In particular, free bile acid esters are extremely soluble in alcohol and always coexist with alcohol. Therefore, it is important to have alcohol present in the separation of bile acids. Furthermore, some bile acids or bile acid esters form complex compounds with cholesterol, alcohol, etc. The composition of the esterification treatment solution obtained in step (a) is as described above, fatty acid ester, alcohol,
Bile acid ester, bile acid complex compound cholesterol, etc., and glycerin produced as a result of the lower alcohol esterification reaction separate into two phases, glycerin and other substances, when the above-mentioned esterification treatment solution is allowed to stand still. What is introduced into the latter step (b) may be the above-mentioned esterification treatment liquid, or may be other liquids other than glycerin.
以下、グリセリンを除くその他のもの（以下、
エステル化処理液と呼称）を対象に説明を続け
る。つぎに、エステル化処理液１０は工程（ｂ）
に導入される。工程（ｂ）の詳細を第２図に示
す。 Other items except glycerin (hereinafter,
The explanation will continue focusing on the esterification treatment liquid. Next, the esterification treatment liquid 10 is processed in step (b).
will be introduced in Details of step (b) are shown in FIG.
エステル化処理液１０は抽出槽１に導入され、
ここで超臨界炭酸ガス２０と接触し、エステル化
処理液中の脂肪酸エステル、アルコール及び遊離
胆汁酸エステルが優先的に超臨界炭酸ガス中に溶
解する。ついで、同抽出槽で、エステル化処理液
と超臨界炭酸ガスを比重差により分離し、超臨界
炭酸ガス２０′を第１段分離槽２に導入し、ここ
で臨界炭酸ガスの密度を低下し、超臨界炭酸ガス
から脂肪酸エステル１２を優先的に分離する。つ
ぎに、炭酸ガス２１を第１段分離槽２から取出
し、第２段分離槽３に導入する。ここで、密度を
さらに低下し、アルコール１１及び遊離胆汁酸エ
ステル１４を分離する。上記工程（ｂ）におい
て、抽出圧力を200，150，100atg.の３種、抽出
温度55℃、第１段分離圧力を60atg.，第１段分離
温度50℃、第２段分離圧力を30atg.第２段分離温
度15℃とした場合の第１段分離槽から得られる第
１段抽出液及び第２段分離槽から得られる第２段
抽出液の組成を、それぞれ、第３図、第４図に示
す。いずれも、横軸は第１段抽出液の回収率で、
第１段抽出液流出量とエステル化処理液流入量の
比（回分処理では、第１段抽出液量とエステル化
処理液の抽出槽仕込量の比）である。図中、記号
○・は抽出圧力200atg.，記号○｜は150atg.，記号
は100atg.の場合の抽出結果を示すが、抽出液の
組成は抽出圧力によらず、抽出液の回収率に依存
することが分る。すなわち、エステル化処理液中
に存在する脂肪酸エステルの割合（本実施例では
82.5％）以下の回収率で運転することにより、第
１段分離槽からはアルコールを含まないほぼ98％
以上の脂肪酸エステルが得られ、第２段分離槽か
らはすくなくとも90％以上のアルコールが、いず
れも95％以上の収率で得られる。アルコールの未
回収分約５％は、胆汁酸複化合物の構成物質とし
て、抽出槽に残留し、ここから残留物１３として
取出される。なお、胆汁酸エステルは分析上、脂
肪酸エステルの濃度の中に含まれ、第４図中、脂
肪酸エステル濃度を示す記号の内黒ヌリの記号
は、その濃度の中に胆汁酸エステル分も含むこと
を示す。第４図中、斜線の部分は第２段抽出液中
の脂肪酸エステルの割合を示すが、この内の70％
は胆汁酸エステルである。 The esterification treatment liquid 10 is introduced into the extraction tank 1,
Here, it comes into contact with the supercritical carbon dioxide gas 20, and the fatty acid ester, alcohol, and free bile acid ester in the esterification treatment liquid are preferentially dissolved in the supercritical carbon dioxide gas. Next, in the same extraction tank, the esterification treatment liquid and the supercritical carbon dioxide gas are separated based on the difference in specific gravity, and the supercritical carbon dioxide gas 20' is introduced into the first stage separation tank 2, where the density of the critical carbon dioxide gas is reduced. , preferentially separates fatty acid ester 12 from supercritical carbon dioxide gas. Next, carbon dioxide gas 21 is taken out from the first stage separation tank 2 and introduced into the second stage separation tank 3. Here, the density is further reduced and alcohol 11 and free bile acid ester 14 are separated. In the above step (b), the extraction pressure is 200, 150, and 100 atg. The extraction temperature is 55°C, the first stage separation pressure is 60 atg., the first stage separation temperature is 50°C, and the second stage separation pressure is 30 atg. The compositions of the first-stage extract obtained from the first-stage separation tank and the second-stage extract obtained from the second-stage separation tank when the second-stage separation temperature is 15°C are shown in Figures 3 and 4, respectively. As shown in the figure. In both cases, the horizontal axis is the recovery rate of the first stage extract;
This is the ratio of the outflow amount of the first-stage extract to the inflow amount of the esterification treatment liquid (in batch processing, the ratio of the amount of the first-stage extraction liquid to the amount of the esterification treatment liquid charged in the extraction tank). In the figure, the symbol ○ indicates the extraction result when the extraction pressure is 200atg., the symbol ○｜ is 150atg., and the symbol is 100atg. However, the composition of the extract does not depend on the extraction pressure, but depends on the recovery rate of the extract. I know what to do. In other words, the proportion of fatty acid ester present in the esterification treatment solution (in this example,
By operating at a recovery rate of 82.5% or less, approximately 98% of alcohol is removed from the first stage separation tank.
The above fatty acid esters are obtained, and at least 90% or more alcohol is obtained from the second stage separation tank, with a yield of 95% or more. Approximately 5% of the unrecovered alcohol remains in the extraction tank as a constituent of the bile acid complex, from which it is taken out as residue 13. In addition, bile acid esters are included in the concentration of fatty acid esters in analysis, and in Figure 4, the symbol with a black square inside the symbol indicating the concentration of fatty acid esters indicates that the concentration also includes bile acid esters. shows. In Figure 4, the shaded area indicates the proportion of fatty acid ester in the second stage extract, of which 70%
is a bile acid ester.
第１図に戻つて、上記第２段抽出液１１は工程
（Ｃ）に導入される。ここで、アルコール中の胆
汁酸エステルはすみやかに結晶化し、前記アルコ
ールから固液分離される。ここで分離された胆汁
酸エステルは１分子の結晶アルコールを有する
が、この結晶アルコールは130℃に加熱すれば除
かれ、極めて高純度の胆汁酸が得られる。 Returning to FIG. 1, the second stage extract 11 is introduced into step (C). Here, the bile acid ester in the alcohol quickly crystallizes and is separated into solid and liquid from the alcohol. The bile acid ester separated here has one molecule of crystalline alcohol, but this crystallized alcohol is removed by heating to 130°C, yielding an extremely pure bile acid.
以上、魚油を対象とした本発明を述べたが、上
述したごとく、胆汁酸を含む原料であれば良く、
さらには、脊椎動物体内で胆汁がつくられる肝臓
や胆汁が貯えられる胆のうあるいはこれらをすり
つぶしたものを原料とすればさらに良い。 The present invention has been described above for fish oil, but as mentioned above, any raw material containing bile acid may be used.
It is even better to use the liver, where bile is produced in the vertebrate body, the gallbladder, where bile is stored, or the ground material of these materials.
本発明により、胆汁酸が微量にしか存在しない
原料から高純度の胆汁酸が容易に分離できる他、
原料を魚油とすれば、上記胆汁酸の他に、アルコ
ールを含まない脂肪酸エステル及び90％以上のア
ルコールがそれぞれ95％以上の収率で分離回収で
きる。
According to the present invention, high purity bile acids can be easily separated from raw materials containing only trace amounts of bile acids, and
If fish oil is used as the raw material, in addition to the above-mentioned bile acids, alcohol-free fatty acid esters and 90% or more alcohol can be separated and recovered at a yield of 95% or more.
なお、本発明について、超臨界ガスとはそのガ
スの臨界圧力以上かつ臨界温度以上の圧力、温度
条件下にあるものである。 In the present invention, a supercritical gas is a gas under pressure and temperature conditions that are higher than the critical pressure and higher than the critical temperature of the gas.
第１図は本発明の一実施例である胆汁酸の分離
プロセスを示すフロー図、第２図は本発明の一実
施例である胆汁酸の分離プロセスの内、超臨界炭
酸ガス抽出工程の詳細フロー図、第３図Ａ，Ｂ，
Ｃ及び第４図は本発明の実施データ例、第５図は
従来の低級アルコールエステル化工程及び生成脂
肪酸エステルの分離工程を示すフロー図である。
１……抽出槽、２……第１段分離槽、３……第
２段分離槽、１０……エステル化処理液、１１…
…アルコール、１２……脂肪酸エステル、１３…
…残留物、１４……胆汁酸エステル、２０……超
臨界炭酸ガス、２０′……超臨界炭酸ガス、２１，
２１′……炭酸ガス。
Figure 1 is a flow diagram showing a bile acid separation process that is an embodiment of the present invention, and Figure 2 is a detailed diagram of the supercritical carbon dioxide extraction step in the bile acid separation process that is an embodiment of the present invention. Flow diagram, Figure 3 A, B,
C and FIG. 4 are examples of practical data of the present invention, and FIG. 5 is a flow diagram showing a conventional lower alcohol esterification process and a separation process of the produced fatty acid ester. DESCRIPTION OF SYMBOLS 1...Extraction tank, 2...1st stage separation tank, 3...2nd stage separation tank, 10...Esterification treatment liquid, 11...
...Alcohol, 12...Fatty acid ester, 13...
...residue, 14...bile acid ester, 20...supercritical carbon dioxide, 20'...supercritical carbon dioxide, 21,
21'... Carbon dioxide gas.
Claims (1)
得られる理論アルコール量よりも過剰のアルコー
ルと反応させて低級アルコールエステル化処理
し、前記エステル化処理液から超臨界ガス抽出に
よりアルコールを分離し、ついで、分離されたア
ルコールから胆汁酸を分離することを特徴とする
胆汁酸の分離方法。 ２ 分離されたアルコールから胆汁酸を結晶化さ
せ、固液分離することを特徴とする特許請求の範
囲第１項記載の胆汁酸の分離方法。 ３ 超臨界ガスが超臨界炭酸ガスであることを特
徴とする特許請求の範囲第１項又は第２項記載の
胆汁酸の分離方法。[Claims] 1. A raw material containing bile acid is reacted with alcohol in excess of the theoretical amount of alcohol obtained from the esterification reaction formula to esterify a lower alcohol, and the esterified solution is extracted with supercritical gas. 1. A method for separating bile acids, which comprises separating alcohol and then separating bile acids from the separated alcohol. 2. The method for separating bile acids according to claim 1, which comprises crystallizing the bile acids from the separated alcohol and performing solid-liquid separation. 3. The method for separating bile acids according to claim 1 or 2, wherein the supercritical gas is supercritical carbon dioxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60102870A JPS61260097A (en) | 1985-05-15 | 1985-05-15 | How to separate bile acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60102870A JPS61260097A (en) | 1985-05-15 | 1985-05-15 | How to separate bile acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61260097A JPS61260097A (en) | 1986-11-18 |
| JPH0435000B2 true JPH0435000B2 (en) | 1992-06-09 |
Family
ID=14338933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60102870A Granted JPS61260097A (en) | 1985-05-15 | 1985-05-15 | How to separate bile acids |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61260097A (en) |
-
1985
- 1985-05-15 JP JP60102870A patent/JPS61260097A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61260097A (en) | 1986-11-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6395778B1 (en) | Process for making an enriched mixture of polyunsaturated fatty acid esters | |
| US3691211A (en) | Process for preparing sterols from tall oil pitch | |
| US3840570A (en) | Process for preparing sterols from tall oil pitch | |
| JP2003500082A (en) | Concentration and purification of polyunsaturated fatty acid esters by a combination of distillation-enzymatic transesterification | |
| US7709668B2 (en) | Separation technology | |
| AU670723B2 (en) | A process for separating lipophilic compounds | |
| JPH1180083A (en) | Production of eicosapentaenoic ester | |
| CN109369397B (en) | A kind of method for Ag+-short-chain polyol coupling extraction and separation of methyl linolenic acid | |
| JP6234908B2 (en) | Method for producing eicosapentaenoic acid and / or docosahexaenoic acid-containing composition | |
| JP2003506423A (en) | Recovery of polyunsaturated fatty acids from urea adduct | |
| JPH04243849A (en) | Purification of highly unsaturated fatty acid and its derivative | |
| JPH0435000B2 (en) | ||
| US2841601A (en) | Separation of dicarboxylic and monocarboxylic acids | |
| EP1751173B1 (en) | Process for the recovery of sterols from organic material | |
| US8013175B2 (en) | Method of refining episesamin | |
| JPS61261398A (en) | Fish oil refining method | |
| JP3227006B2 (en) | Method for producing fatty acid ester | |
| WO1994021766A1 (en) | Process for separating docosahexaenoic acid or ester thereof from marine microalgae | |
| EP1226156B1 (en) | Process for producing phytosterols by saponification in an alcohol/water solvent | |
| WO2020196749A1 (en) | Eicosapentaenoic acid alkyl ester-containing composition and method for producing same | |
| US2249525A (en) | Purification of vitamin a esters | |
| JPH024212B2 (en) | ||
| WO2023170706A1 (en) | A process for the recovery and separation of fatty acids | |
| JPS6112657A (en) | Method for producing carotene-containing concentrate | |
| JPH02214798A (en) | Method for deacidification |