NO314788B1 - Framgangsmåte for utvinning av en eller flere forbindelser fra en blanding - Google Patents
Framgangsmåte for utvinning av en eller flere forbindelser fra en blanding Download PDFInfo
- Publication number
- NO314788B1 NO314788B1 NO19954099A NO954099A NO314788B1 NO 314788 B1 NO314788 B1 NO 314788B1 NO 19954099 A NO19954099 A NO 19954099A NO 954099 A NO954099 A NO 954099A NO 314788 B1 NO314788 B1 NO 314788B1
- Authority
- NO
- Norway
- Prior art keywords
- mixture
- solvent
- compounds
- sorbent
- extraction
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 39
- 239000000203 mixture Substances 0.000 title claims description 33
- 238000000034 method Methods 0.000 title claims description 19
- 239000002904 solvent Substances 0.000 claims description 30
- 238000000605 extraction Methods 0.000 claims description 28
- 239000002594 sorbent Substances 0.000 claims description 26
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 12
- 239000000194 fatty acid Substances 0.000 claims description 12
- 229930195729 fatty acid Natural products 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 9
- -1 fatty acid compounds Chemical class 0.000 claims description 8
- 150000004665 fatty acids Chemical class 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 7
- 230000005526 G1 to G0 transition Effects 0.000 claims description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 6
- 239000001569 carbon dioxide Substances 0.000 claims description 6
- 238000004090 dissolution Methods 0.000 claims description 6
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 4
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003574 free electron Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 2
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 description 14
- 239000002253 acid Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- 239000003026 cod liver oil Substances 0.000 description 4
- 235000012716 cod liver oil Nutrition 0.000 description 4
- 230000000750 progressive effect Effects 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 3
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 3
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 3
- 235000021323 fish oil Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000004237 preparative chromatography Methods 0.000 description 3
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000004458 analytical method Methods 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000021294 Docosapentaenoic acid Nutrition 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 229910018503 SF6 Inorganic materials 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 1
- 229940090949 docosahexaenoic acid Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
- 229960000909 sulfur hexafluoride Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/007—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids using organic solvents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/14—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to the introduction of the feed to the apparatus
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
- B01D15/18—Selective adsorption, e.g. chromatography characterised by constructional or operational features relating to flow patterns
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
- C11B1/104—Production of fats or fatty oils from raw materials by extracting using super critical gases or vapours
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
- B01D15/08—Selective adsorption, e.g. chromatography
- B01D15/26—Selective adsorption, e.g. chromatography characterised by the separation mechanism
- B01D15/40—Selective adsorption, e.g. chromatography characterised by the separation mechanism using supercritical fluid as mobile phase or eluent
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Extraction Or Liquid Replacement (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4440694 | 1994-11-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO954099D0 NO954099D0 (no) | 1995-10-13 |
| NO954099L NO954099L (no) | 1996-05-20 |
| NO314788B1 true NO314788B1 (no) | 2003-05-26 |
Family
ID=6533320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19954099A NO314788B1 (no) | 1994-11-15 | 1995-10-13 | Framgangsmåte for utvinning av en eller flere forbindelser fra en blanding |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8293932B2 (un) |
| EP (1) | EP0712651B1 (un) |
| JP (1) | JP4501088B2 (un) |
| DE (1) | DE59507736D1 (un) |
| NO (1) | NO314788B1 (un) |
| ZA (1) | ZA959161B (un) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1125914A1 (en) | 2000-02-14 | 2001-08-22 | Nisshin Flour Milling Co., Ltd. | Process for separating and purifying eicosapentaenoic acid or its ester |
| FR2894772B1 (fr) * | 2005-12-20 | 2008-03-14 | Pierre Fabre Medicament Sa | Procede d'enrichissement en dha |
| DE102007061436A1 (de) * | 2007-12-20 | 2009-06-25 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verfahren zur Gewinnung von Fettbegleitstoffen aus Kraftstoffen und Verwendung dieses Verfahrens |
| KR102117725B1 (ko) | 2012-05-14 | 2020-06-01 | 닛폰 스이산 가부시키가이샤 | 환경 오염 물질을 저감시킨 고도 불포화 지방산 또는 고도 불포화 지방산 에틸에스테르 및 그 제조 방법 |
| ES2670473T3 (es) | 2015-12-04 | 2018-05-30 | Evonik Degussa Gmbh | Procedimiento mejorado para la extracción de sustancias aromatizantes a partir de fases líquidas grasas y/o acuosas |
| KR20190113520A (ko) | 2017-02-09 | 2019-10-08 | 에스.엘.에이. 파르마 에이지 | 유리지방산으로서 고도로 정제된 에이코사펜타엔산의 궤양성 대장염 환자의 분변 칼프로텍틴 레벨의 감소 및 임상 재발 방지 |
| WO2018150257A1 (en) | 2017-02-14 | 2018-08-23 | S.L.A. Pharma Ag | Treatment with highly purified eicosapentaenoic acid as free fatty acid improves inflammation, affects colonic differentiation markers and microbiota in patients with ulcerative colitis |
| US11607623B2 (en) | 2019-08-08 | 2023-03-21 | Cornerstone Technologies Llc | Dynamic interface system and its application in supercritical fluid extraction and chromatography |
| EP4125856A1 (en) | 2020-03-23 | 2023-02-08 | S.L.A. Pharma AG | Highly purified eicosapentaenoic acid, as free fatty acid for treatment of coronaviruses and specifically novel coronavirus-19 (covid-19) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2726828B2 (ja) * | 1988-03-31 | 1998-03-11 | 宮城県 | 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 |
| DE3831516A1 (de) * | 1988-09-16 | 1990-03-22 | Henkel Kgaa | Verfahren zum anreichern von oelsaeure und/oder elaidinsaeure |
| CS276379B6 (en) * | 1988-11-22 | 1992-05-13 | Tessek Sdruzeni | Sorbent based on cyclodextrin |
| DE4206539A1 (de) | 1992-03-02 | 1993-09-09 | K D Pharma Gmbh | Verfahren zum gewinnen ungesaettigter fettsaeuren |
| CN1040690C (zh) * | 1992-09-03 | 1998-11-11 | 惠普公司 | 一种色谱用的固相提取柱 |
-
1995
- 1995-10-13 NO NO19954099A patent/NO314788B1/no not_active IP Right Cessation
- 1995-10-30 ZA ZA959161A patent/ZA959161B/xx unknown
- 1995-11-06 DE DE59507736T patent/DE59507736D1/de not_active Expired - Lifetime
- 1995-11-06 EP EP95117439A patent/EP0712651B1/de not_active Expired - Lifetime
- 1995-11-09 JP JP32495595A patent/JP4501088B2/ja not_active Expired - Fee Related
-
2006
- 2006-06-30 US US11/479,538 patent/US8293932B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US8293932B2 (en) | 2012-10-23 |
| DE59507736D1 (de) | 2000-03-09 |
| ZA959161B (en) | 1996-05-27 |
| EP0712651A1 (de) | 1996-05-22 |
| US20060247455A1 (en) | 2006-11-02 |
| EP0712651B1 (de) | 2000-02-02 |
| NO954099D0 (no) | 1995-10-13 |
| JP4501088B2 (ja) | 2010-07-14 |
| JPH08224405A (ja) | 1996-09-03 |
| NO954099L (no) | 1996-05-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1K | Patent expired |