JPS60214757A - 高度不飽和脂肪酸又はそのエステルの濃縮分離方法 - Google Patents
高度不飽和脂肪酸又はそのエステルの濃縮分離方法Info
- Publication number
- JPS60214757A JPS60214757A JP6839384A JP6839384A JPS60214757A JP S60214757 A JPS60214757 A JP S60214757A JP 6839384 A JP6839384 A JP 6839384A JP 6839384 A JP6839384 A JP 6839384A JP S60214757 A JPS60214757 A JP S60214757A
- Authority
- JP
- Japan
- Prior art keywords
- carbon dioxide
- unsaturated fatty
- highly unsaturated
- fatty acid
- 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.)
- Granted
Links
- 235000021122 unsaturated fatty acids Nutrition 0.000 title claims abstract description 20
- 150000004670 unsaturated fatty acids Chemical class 0.000 title claims abstract description 20
- 150000002148 esters Chemical class 0.000 title abstract description 18
- 238000000926 separation method Methods 0.000 title abstract description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 58
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 29
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 29
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000004202 carbamide Substances 0.000 claims abstract description 28
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 24
- 238000000605 extraction Methods 0.000 claims abstract description 24
- 229930195729 fatty acid Natural products 0.000 claims abstract description 24
- 239000000194 fatty acid Substances 0.000 claims abstract description 24
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims abstract description 21
- 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 abstract description 20
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims abstract description 20
- 239000007787 solid Substances 0.000 claims abstract description 16
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims abstract description 13
- -1 alcohol ester Chemical class 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 150000001298 alcohols Chemical class 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 16
- 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 4
- 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 4
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 claims description 4
- 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 abstract description 18
- 229940090949 docosahexaenoic acid Drugs 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 3
- 208000007536 Thrombosis Diseases 0.000 abstract description 2
- 239000012141 concentrate Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000003449 preventive effect Effects 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 25
- 235000019198 oils Nutrition 0.000 description 25
- 239000002994 raw material Substances 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- 150000004702 methyl esters Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000007789 gas Substances 0.000 description 8
- 238000004458 analytical method 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
- 238000010586 diagram Methods 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
- 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
- 241000718541 Tetragastris balsamifera Species 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
- 239000003054 catalyst Substances 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 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
- 238000010438 heat treatment 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
- 235000014593 oils and fats Nutrition 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
- 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 true JPS60214757A (ja) | 1985-10-28 |
| JPH0137387B2 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) |
Cited By (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 |
| JPH02180996A (ja) * | 1989-01-06 | 1990-07-13 | Nippon Suisan Kaisha Ltd | 連続式尿素付加分別法およびその装置 |
| WO2003084907A1 (de) * | 2002-04-11 | 2003-10-16 | Cognis Deutschland Gmbh & Co. Kg | Verfahren zur trennung von über- bzw. nahekritischen gemischen |
| WO2003089399A1 (en) | 2002-04-22 | 2003-10-30 | Industrial Research Limited | Improvements in or relating to separation technology |
| CN107459459A (zh) * | 2016-06-02 | 2017-12-12 | 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
Cited By (10)
| 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 |
| JPH02180996A (ja) * | 1989-01-06 | 1990-07-13 | Nippon Suisan Kaisha Ltd | 連続式尿素付加分別法およびその装置 |
| WO2003084907A1 (de) * | 2002-04-11 | 2003-10-16 | Cognis Deutschland Gmbh & Co. Kg | Verfahren zur trennung von über- bzw. nahekritischen gemischen |
| US7084313B2 (en) | 2002-04-11 | 2006-08-01 | Cognis Deutschland Gmbh & Co. Kg | Three stage processes for the separation of supercritical or near-critical mixtures |
| WO2003089399A1 (en) | 2002-04-22 | 2003-10-30 | Industrial Research Limited | Improvements in or relating to separation technology |
| JP2005523323A (ja) * | 2002-04-22 | 2005-08-04 | インダストリアル リサーチ リミティド | 分離技術における又はそれに関する改良 |
| US7709668B2 (en) | 2002-04-22 | 2010-05-04 | Industrial Research Limited | Separation technology |
| KR100972703B1 (ko) | 2002-04-22 | 2010-07-27 | 인더스트리얼 리서치 리미티드 | 분리 기술의 개선 방법 |
| CN107459459A (zh) * | 2016-06-02 | 2017-12-12 | 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 |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0137387B2 (enrdf_load_stackoverflow) | 1989-08-07 |
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