JPH0137387B2 - - Google Patents
Info
- Publication number
- JPH0137387B2 JPH0137387B2 JP6839384A JP6839384A JPH0137387B2 JP H0137387 B2 JPH0137387 B2 JP H0137387B2 JP 6839384 A JP6839384 A JP 6839384A JP 6839384 A JP6839384 A JP 6839384A JP H0137387 B2 JPH0137387 B2 JP H0137387B2
- Authority
- JP
- Japan
- Prior art keywords
- fatty acids
- carbon dioxide
- highly unsaturated
- unsaturated fatty
- extraction
- 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
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 50
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 25
- 239000004202 carbamide Substances 0.000 claims description 25
- 239000001569 carbon dioxide Substances 0.000 claims description 25
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 25
- 150000004665 fatty acids Chemical class 0.000 claims description 24
- 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 claims description 23
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 23
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 23
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 23
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 23
- 229930195729 fatty acid Natural products 0.000 claims description 23
- 239000000194 fatty acid Substances 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 21
- 238000000605 extraction Methods 0.000 claims description 20
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 18
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 13
- 150000001298 alcohols Chemical class 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- -1 alcohol ester Chemical class 0.000 claims description 6
- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 claims description 5
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 claims description 5
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 claims description 5
- 239000003921 oil Substances 0.000 description 28
- 235000019198 oils Nutrition 0.000 description 28
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 26
- 150000002148 esters Chemical class 0.000 description 16
- 239000002994 raw material Substances 0.000 description 16
- 229940090949 docosahexaenoic acid Drugs 0.000 description 13
- 150000004702 methyl esters Chemical class 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 9
- 239000007789 gas Substances 0.000 description 8
- 238000000926 separation method Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 235000021323 fish oil Nutrition 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QWDCYFDDFPWISL-UHFFFAOYSA-N UNPD207407 Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(=O)OC QWDCYFDDFPWISL-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- VCDLWFYODNTQOT-UHFFFAOYSA-N docosahexaenoic acid methyl ester Natural products CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)OC VCDLWFYODNTQOT-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000000998 batch distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 235000014102 seafood Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Extraction Or Liquid Replacement (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6839384A JPS60214757A (ja) | 1984-04-07 | 1984-04-07 | 高度不飽和脂肪酸又はそのエステルの濃縮分離方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6839384A JPS60214757A (ja) | 1984-04-07 | 1984-04-07 | 高度不飽和脂肪酸又はそのエステルの濃縮分離方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60214757A JPS60214757A (ja) | 1985-10-28 |
| JPH0137387B2 true JPH0137387B2 (enrdf_load_stackoverflow) | 1989-08-07 |
Family
ID=13372412
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6839384A Granted JPS60214757A (ja) | 1984-04-07 | 1984-04-07 | 高度不飽和脂肪酸又はそのエステルの濃縮分離方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60214757A (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01294649A (ja) * | 1988-05-21 | 1989-11-28 | Agency Of Ind Science & Technol | スケトウタラ精巣よりドコサへキサエン酸およびエイコサペンタエン酸を高濃度で抽出する方法 |
| JPH07107158B2 (ja) * | 1989-01-06 | 1995-11-15 | 日本水産株式会社 | 連続式尿素付加分別法およびその装置 |
| DE10215862A1 (de) | 2002-04-11 | 2003-10-30 | Cognis Deutschland Gmbh | Verfahren zur Trennung von über- bzw. nahekritischen Gemischen |
| NZ518504A (en) | 2002-04-22 | 2005-05-27 | Ind Res Ltd | Use of near-critical fluids in the separation of saturated and mono-unsaturated fatty acids from urea-containing solutions |
| CN107459459B (zh) * | 2016-06-02 | 2020-08-11 | 中国石化扬子石油化工有限公司 | 一种从硬脂酸苯甲酰甲烷残液中提取硬脂酸甲酯的方法 |
-
1984
- 1984-04-07 JP JP6839384A patent/JPS60214757A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60214757A (ja) | 1985-10-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5840944A (en) | Method to produce highly pure eicosapentaenoic acid or its ester | |
| KR100972703B1 (ko) | 분리 기술의 개선 방법 | |
| JPS649977B2 (enrdf_load_stackoverflow) | ||
| JPH0137387B2 (enrdf_load_stackoverflow) | ||
| JP2003506423A (ja) | 尿素付加物からのポリ不飽和脂肪酸の回収 | |
| JPH1180083A (ja) | エイコサペンタエン酸エステルの製造方法 | |
| JP3678317B2 (ja) | エイコサペンタエン酸含有物の濃縮方法 | |
| JPH1095744A (ja) | 高度不飽和脂肪酸又はそのアルキルエステルの製造方法 | |
| JPH04243849A (ja) | 高度不飽和脂肪酸類の精製方法 | |
| GB2160874A (en) | A process for producing carotene from oils and fats | |
| JP2003171376A (ja) | トコフェロール類及びトコトリエノール類濃縮物、その製造方法 | |
| JPH0140817B2 (enrdf_load_stackoverflow) | ||
| JP2726828B2 (ja) | 高度不飽和脂肪酸またはそのエステルの濃縮分別装置とその濃縮分別法 | |
| JP2742569B2 (ja) | ω３位及びω６位に２重結合を有する高度不飽和脂肪酸エステルの分離方法 | |
| JPS588037A (ja) | エイコサペンタエン酸またはそのエステルの製法 | |
| JPH09302380A (ja) | エイコサペンタエン酸又はそのエステルの精製方法 | |
| US3720696A (en) | Process for the extraction of 9-hexadecenoic acid | |
| Nadenicek et al. | Preparation of pure polyunsaturated fatty acids 1. Linolenic acid | |
| KR0139006B1 (ko) | 에이코사펜타엔산과 그 에스테르화물의 제조방법 | |
| JPS61176597A (ja) | フオスフアチジルコリンの精製法 | |
| SU641963A1 (ru) | Способ получени арахидоновой и эйкозатриеновой кислот | |
| JPH0158240B2 (enrdf_load_stackoverflow) | ||
| JPH051090A (ja) | シヨ糖脂肪酸エステルの分離・精製方法 | |
| JPS635073A (ja) | カロチン含有濃縮物の製造方法 | |
| JPH06248288A (ja) | 高度不飽和脂肪酸類を分別回収する方法 |