CA2506537C - Lipase-catalysed esterification of marine oil - Google Patents
Lipase-catalysed esterification of marine oil Download PDFInfo
- Publication number
- CA2506537C CA2506537C CA2506537A CA2506537A CA2506537C CA 2506537 C CA2506537 C CA 2506537C CA 2506537 A CA2506537 A CA 2506537A CA 2506537 A CA2506537 A CA 2506537A CA 2506537 C CA2506537 C CA 2506537C
- Authority
- CA
- Canada
- Prior art keywords
- dha
- epa
- lipase
- process according
- ethanol
- 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
- 238000005886 esterification reaction Methods 0.000 title claims description 43
- 230000032050 esterification Effects 0.000 title claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 121
- 108090001060 Lipase Proteins 0.000 claims abstract description 60
- 239000004367 Lipase Substances 0.000 claims abstract description 60
- 102000004882 Lipase Human genes 0.000 claims abstract description 60
- 235000019421 lipase Nutrition 0.000 claims abstract description 60
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- MBMBGCFOFBJSGT-KUBAVDMBSA-N docosahexaenoic acid Natural products 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 claims description 159
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 156
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 127
- 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 126
- 235000021588 free fatty acids Nutrition 0.000 claims description 71
- 235000019441 ethanol Nutrition 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 51
- 235000019198 oils Nutrition 0.000 claims description 42
- 235000021323 fish oil Nutrition 0.000 claims description 38
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 27
- 229930195729 fatty acid Natural products 0.000 claims description 27
- 239000000194 fatty acid Substances 0.000 claims description 27
- 150000004665 fatty acids Chemical class 0.000 claims description 19
- 239000007858 starting material Substances 0.000 claims description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 238000006136 alcoholysis reaction Methods 0.000 claims description 15
- 238000000199 molecular distillation Methods 0.000 claims description 15
- -1 alkyl ester fatty acid Chemical class 0.000 claims description 13
- 125000005907 alkyl ester group Chemical group 0.000 claims description 11
- 125000005456 glyceride group Chemical group 0.000 claims description 11
- 150000003626 triacylglycerols Chemical class 0.000 claims description 9
- 101000968489 Rhizomucor miehei Lipase Proteins 0.000 claims description 6
- 241000223258 Thermomyces lanuginosus Species 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 150000004702 methyl esters Chemical class 0.000 claims description 5
- 241000589774 Pseudomonas sp. Species 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 101001003495 Pseudomonas fluorescens Lipase Proteins 0.000 claims description 3
- 101001064559 Pseudomonas fluorescens Lipase Proteins 0.000 claims description 3
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 3
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 3
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract description 35
- 238000004821 distillation Methods 0.000 abstract description 24
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 48
- 238000011084 recovery Methods 0.000 description 48
- 239000003921 oil Substances 0.000 description 40
- 238000010932 ethanolysis reaction Methods 0.000 description 31
- 125000004494 ethyl ester group Chemical group 0.000 description 16
- 238000000926 separation method Methods 0.000 description 15
- 239000012141 concentrate Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000003026 cod liver oil Substances 0.000 description 10
- 235000012716 cod liver oil Nutrition 0.000 description 10
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 10
- 108090000790 Enzymes Proteins 0.000 description 9
- 102000004190 Enzymes Human genes 0.000 description 9
- 238000000526 short-path distillation Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 241001454694 Clupeiformes Species 0.000 description 7
- 235000019513 anchovy Nutrition 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241000252203 Clupea harengus Species 0.000 description 5
- 241001125048 Sardina Species 0.000 description 5
- 235000019514 herring Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 235000019512 sardine Nutrition 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 3
- 238000012746 preparative thin layer chromatography Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000007039 two-step reaction Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 108010048733 Lipozyme Proteins 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001609028 Micromesistius poutassou Species 0.000 description 2
- 241001661345 Moesziomyces antarcticus Species 0.000 description 2
- 241000235403 Rhizomucor miehei Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ACNUVXZPCIABEX-UHFFFAOYSA-N 3',6'-diaminospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(N)C=C1OC1=CC(N)=CC=C21 ACNUVXZPCIABEX-UHFFFAOYSA-N 0.000 description 1
- 241001417902 Mallotus villosus Species 0.000 description 1
- 108010084311 Novozyme 435 Proteins 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000589540 Pseudomonas fluorescens Species 0.000 description 1
- 241000736029 Ruvettus pretiosus Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000009834 vaporization Methods 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
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
-
- 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
- C11B3/00—Refining fats or fatty oils
- C11B3/12—Refining fats or fatty oils by distillation
-
- 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
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
-
- 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
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
- C11C1/025—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by saponification and release of fatty acids
-
- 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
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO20025456 | 2002-11-14 | ||
| NO20025456A NO319194B1 (no) | 2002-11-14 | 2002-11-14 | Lipase-katalysert forestringsfremgangsmate av marine oljer |
| PCT/NO2003/000364 WO2004043894A1 (en) | 2002-11-14 | 2003-10-31 | Lipase-catalysed esterification of marine oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2506537A1 CA2506537A1 (en) | 2004-05-27 |
| CA2506537C true CA2506537C (en) | 2011-02-22 |
Family
ID=19914177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2506537A Expired - Lifetime CA2506537C (en) | 2002-11-14 | 2003-10-31 | Lipase-catalysed esterification of marine oil |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7491522B2 (enExample) |
| EP (2) | EP2602308B1 (enExample) |
| JP (1) | JP2006506483A (enExample) |
| CN (1) | CN100338010C (enExample) |
| AU (1) | AU2003283872A1 (enExample) |
| CA (1) | CA2506537C (enExample) |
| DK (2) | DK2602308T3 (enExample) |
| ES (2) | ES2702273T3 (enExample) |
| NO (1) | NO319194B1 (enExample) |
| WO (1) | WO2004043894A1 (enExample) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2295529B2 (en) | 2002-07-11 | 2022-05-18 | Basf As | Use of a volatile environmental pollutants-decreasing working fluid for decreasing the amount of pollutants in a fat for alimentary or cosmetic use |
| SE0202188D0 (sv) * | 2002-07-11 | 2002-07-11 | Pronova Biocare As | A process for decreasing environmental pollutants in an oil or a fat, a volatile fat or oil environmental pollutants decreasing working fluid, a health supplement, and an animal feed product |
| HRP20020885B1 (en) | 2002-11-11 | 2007-05-31 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | SUBSTITUTED 9a-N-{N'-[4-(SULFONYL)PHENYLCARBAMOYL]}DERIVATIVES 9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERITHROMYCIN A AND 5-O-DESOZAMINYL-9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERITHRONOLIDE A |
| JP2008540394A (ja) * | 2005-05-04 | 2008-11-20 | プロノヴァ バイオファーマ ノルゲ アクティーゼルスカブ | 脂肪酸組成物、即ち、ｄｈａ誘導体の医薬としての使用 |
| EP1891189B1 (en) * | 2005-05-23 | 2020-09-23 | Epax Norway AS | Concentration of fatty acid alkyl esters by enzymatic reactions with glycerol |
| ES2559959T3 (es) | 2005-06-16 | 2016-02-16 | Dsm Nutritional Products Ag | Enzimas inmovilizadas y métodos para usar las mismas |
| ES2292341B1 (es) * | 2006-03-13 | 2009-03-16 | Universidad De Almeria | "procedimiento para la purificacion de acido eicosapentaenoico (epa)". |
| EP2084175B1 (en) | 2006-10-10 | 2010-12-29 | Medivir AB | Hcv nucleoside inhibitor |
| KR101438177B1 (ko) | 2006-11-01 | 2014-09-05 | 프로노바 바이오파마 너지 에이에스 | 페록시솜 증식자-활성화 수용체의 활성자 또는 조절자인 알파-치환된 오메가-3 지질 |
| EP1978102B1 (de) | 2007-04-02 | 2010-07-07 | Cognis IP Management GmbH | Ein Gemisch enthaltend Fettsäureglyceride |
| EP1978101A1 (de) | 2007-04-02 | 2008-10-08 | Cognis IP Management GmbH | Verfahren zur Anreicherung mehrfach ungesättigter Fettsäuren |
| EP2147088A4 (en) * | 2007-04-26 | 2010-05-05 | Patrick Adlercreutz | FERTILIZED MILK OILS COMPRISING MULTIPLE-UNSATURATED FATTY ACIDS, COMPRISING EICOSAPENTAIC ACID (EPA) AND DOCOSAHEXAIC ACID (DHA), AND MANUFACTURING METHOD THEREFOR |
| CL2008002020A1 (es) * | 2007-07-12 | 2008-11-14 | Ocean Nutrition Canada Ltd | Metodo de modificacion de un aceite, que comprende hidrolizar gliceridos con una solucion de lipasa thermomyces lanuginosus, separar la fraccion de acido graso saturado de la fraccion de glicerido hidrolizado y esterificar los gliceridos hidrolizados en la presencia de candida antarctica lipasa b; y composicion de aceite. |
| WO2009017102A1 (ja) * | 2007-07-30 | 2009-02-05 | Nippon Suisan Kaisha, Ltd. | Epa濃縮油およびdha濃縮油の製造方法 |
| KR101034458B1 (ko) * | 2008-03-03 | 2011-05-17 | 고려대학교 산학협력단 | 피놀레닌산 고함유 δ5-지방산의 제조방법 |
| KR101357298B1 (ko) * | 2008-06-20 | 2014-01-28 | 에이케이 앤 엠엔 바이오팜 주식회사 | 오메가-3계 고도불포화 지방산의 고순도 정제방법 |
| CA2742227C (en) | 2008-10-31 | 2017-01-24 | Lipid Pharmaceuticals Ehf. | The use of fatty acid compositions as laxatives |
| CL2009001343A1 (es) * | 2009-06-02 | 2009-07-10 | Golden Omega S A | Proceso de obtencion concentrado de esteres de epa y dha a partir de aceite marino, que comprende agregar al aceite alcali y agua a menos de 100 grados celsius, agregar solvente, separar fase de refinado, agregar acido, separar la fase no acuosa y agregar alcohol y un catalizador a menos de 150 grados celsius, desolventilizar y destilar. |
| PE20130491A1 (es) | 2009-12-30 | 2013-05-02 | Basf Pharma Callanish Ltd | Proceso simulado de separacion cromatografica de lecho movil para la purificacion de acidos grasos poliinsaturados |
| US9476008B2 (en) | 2010-06-25 | 2016-10-25 | Epax As | Process for separating polyunsaturated fatty acids from long chain unsaturated or less saturated fatty acids |
| US20120184760A1 (en) * | 2011-01-14 | 2012-07-19 | Pharma Marine As | Removal of monoglycerides from fatty acid concentrates |
| JP5416861B2 (ja) | 2011-03-03 | 2014-02-12 | 日本水産株式会社 | リパーゼによる高度不飽和脂肪酸含有油脂の製造方法 |
| AU2012224893B2 (en) * | 2011-03-08 | 2015-07-23 | Cognis Ip Management Gmbh | A process for the distillation of fatty acid esters |
| GB201107039D0 (en) * | 2011-04-26 | 2011-06-08 | Syngenta Ltd | Formulation component |
| GB201111591D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | Further new process |
| GB201111594D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | New improved process |
| GB201111601D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | New process |
| GB201111595D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | Improved process |
| GB201111589D0 (en) | 2011-07-06 | 2011-08-24 | Equateq Ltd | New modified process |
| US20140205650A1 (en) | 2011-09-06 | 2014-07-24 | Lipid Pharmaceuticals Ehf. | Coated suppositories |
| US8258330B1 (en) * | 2012-01-04 | 2012-09-04 | Naturalis, S.A. | Carrier fluid composition comprising fatty acids ethyl esters and process for reducing the concentration of persistent organic pollutants in fish oil |
| SG11201403805WA (en) | 2012-01-06 | 2014-08-28 | Omthera Pharmaceuticals Inc | Dpa-enriched compositions of omega-3 polyunsaturated fatty acids in free acid form |
| AR095182A1 (es) | 2012-05-07 | 2015-09-30 | Omthera Pharmaceuticals Inc | Composiciones de estatinas y ácidos grasos omega-3 |
| GB201300354D0 (en) | 2013-01-09 | 2013-02-20 | Basf Pharma Callanish Ltd | Multi-step separation process |
| CN104130860B (zh) * | 2013-05-03 | 2020-03-31 | 丰益(上海)生物技术研发中心有限公司 | 利用固定化疏棉状嗜热丝孢菌脂肪酶富集长链多不饱和脂肪酸的方法 |
| US9428711B2 (en) | 2013-05-07 | 2016-08-30 | Groupe Novasep | Chromatographic process for the production of highly purified polyunsaturated fatty acids |
| US8802880B1 (en) | 2013-05-07 | 2014-08-12 | Group Novasep | Chromatographic process for the production of highly purified polyunsaturated fatty acids |
| JP6302310B2 (ja) * | 2013-08-30 | 2018-03-28 | 備前化成株式会社 | 高純度オメガ３系脂肪酸エチルエステルの生産方法 |
| EP3118186B1 (fr) | 2013-12-11 | 2022-02-09 | Novasep Process | Installation chromatographique de production d acides gras polyinsatures |
| WO2015104464A1 (fr) | 2014-01-07 | 2015-07-16 | Novasep Process | Procédé de purification d'acides aminés aromatiques |
| US9163198B2 (en) | 2014-01-17 | 2015-10-20 | Orochem Technologies, Inc. | Process for purification of EPA (eicosapentanoic acid) ethyl ester from fish oil |
| CN104031950B (zh) * | 2014-05-07 | 2017-06-16 | 威海博宇食品有限公司 | 一种制备富含n‑3多不饱和脂肪酸磷脂的方法 |
| CN105779140A (zh) * | 2014-12-23 | 2016-07-20 | 浙江医药股份有限公司新昌制药厂 | 一种高含量epa乙酯型鱼油的制备方法 |
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| EP4663725A2 (en) * | 2015-10-05 | 2025-12-17 | DSM IP Assets B.V. | Oil compositions and methods of making |
| CN105349587B (zh) * | 2015-11-10 | 2019-05-31 | 浙江工业大学 | 一种提高甘油酯型鱼油中epa和dha含量的方法 |
| PE20191498A1 (es) | 2016-12-19 | 2019-10-22 | Trans Bio Diesel Ltd | ENRIQUECIMIENTO ENZIMATICO DE ACIDOS GRASOS n-3 EN FORMA DE GLICERIDOS |
| CN108265090B (zh) * | 2016-12-30 | 2021-06-15 | 中粮集团有限公司 | 南极磷虾油替代物的制备方法 |
| EP3666082B1 (en) | 2018-12-12 | 2022-05-04 | Nippon Suisan Kaisha, Ltd. | A composition containing highly unsaturated fatty acid or alkyl ester thereof and a method for producing the same |
| CN110029133B (zh) * | 2019-03-12 | 2021-03-19 | 自然资源部第三海洋研究所 | 一种分离dha藻油中饱和脂肪酸和不饱和脂肪酸的方法 |
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| CN114057574A (zh) * | 2021-12-03 | 2022-02-18 | 浙江工商大学 | 一种制备高纯度epa乙酯的方法 |
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| GB9404483D0 (en) * | 1994-03-08 | 1994-04-20 | Norsk Hydro As | Refining marine oil compositions |
| DE4425987A1 (de) | 1994-07-22 | 1996-01-25 | Bosch Gmbh Robert | Verfahren und Vorrichtung zur Ansteuerung eines elektromagnetischen Verbrauchers |
| WO1996037587A1 (en) | 1995-05-24 | 1996-11-28 | Loders Croklaan B.V. | Production of materials high in long chain polyunsaturated fatty acids |
| JP3785467B2 (ja) * | 1996-07-10 | 2006-06-14 | 旭電化工業株式会社 | 油脂組成物の製造方法 |
| JP3773315B2 (ja) * | 1996-11-22 | 2006-05-10 | 大阪市 | ω−３系高度不飽和脂肪酸エステルの精製方法 |
| JP3734905B2 (ja) * | 1996-12-18 | 2006-01-11 | 大阪市 | ω−３系高度不飽和脂肪酸の精製方法 |
| NO312973B1 (no) * | 1999-02-17 | 2002-07-22 | Norsk Hydro As | Lipase-katalysert forestring av marine oljer |
| CA2273570A1 (en) * | 1999-05-31 | 2000-11-30 | Jfs Envirohealth Ltd. | Concentration and purification of polyunsaturated fatty acid esters by distillation-enzymatic transesterification coupling |
| GB2350610A (en) * | 1999-06-01 | 2000-12-06 | Jfs Envirohealth Ltd | Preparation of pure unsaturated fatty acids |
| JP4210437B2 (ja) * | 2000-09-27 | 2009-01-21 | 池田食研株式会社 | 食品用ステロール脂肪酸エステルの製造方法 |
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- 2003-10-31 AU AU2003283872A patent/AU2003283872A1/en not_active Abandoned
- 2003-10-31 CA CA2506537A patent/CA2506537C/en not_active Expired - Lifetime
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| EP2602308A3 (en) | 2014-04-02 |
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| ES2477584T3 (es) | 2014-07-17 |
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| JP2006506483A (ja) | 2006-02-23 |
| EP1560803B1 (en) | 2014-04-23 |
| ES2702273T3 (es) | 2019-02-28 |
| US20060148047A1 (en) | 2006-07-06 |
| DK1560803T3 (da) | 2014-06-23 |
| EP2602308A2 (en) | 2013-06-12 |
| CN1726181A (zh) | 2006-01-25 |
| NO319194B1 (no) | 2005-06-27 |
| CN100338010C (zh) | 2007-09-19 |
| EP2602308B1 (en) | 2018-10-03 |
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