CA1303416C - Concentrat d'huile de poisson raffine et procede pour sa production - Google Patents

Concentrat d'huile de poisson raffine et procede pour sa production

Info

Publication number: CA1303416C
Authority: CA; Canada
Prior art keywords: fatty acid; concentrate; process according; urea; compounds
Prior art date: 1985-12-19
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

Application number

CA000523914A

Other languages

English (en)

Inventor

TORE-ERLING JõRGENSEN

BERNT BõRRETZEN

Harald Breivik

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Norsk Hydro ASA

Original Assignee

Norsk Hydro ASA

Priority date (The priority date 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 date listed.)

1985-12-19

Filing date

1986-11-27

Publication date

1992-06-16

1986-11-27 Application filed by Norsk Hydro ASA filed Critical Norsk Hydro ASA

1992-06-16 Application granted granted Critical

1992-06-16 Publication of CA1303416C publication Critical patent/CA1303416C/fr

2009-06-16 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000012141 concentrate Substances 0.000 title claims abstract description 32
235000021323 fish oil Nutrition 0.000 title claims description 12
238000004519 manufacturing process Methods 0.000 title claims description 7
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 claims abstract description 74
239000000194 fatty acid Substances 0.000 claims abstract description 71
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 67
235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 56
229930195729 fatty acid Natural products 0.000 claims abstract description 56
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 51
239000004202 carbamide Substances 0.000 claims abstract description 38
235000012000 cholesterol Nutrition 0.000 claims abstract description 36
-1 fatty acid esters Chemical class 0.000 claims abstract description 29
JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims abstract description 27
235000020673 eicosapentaenoic acid Nutrition 0.000 claims abstract description 26
229960005135 eicosapentaenoic acid Drugs 0.000 claims abstract description 26
239000000047 product Substances 0.000 claims abstract description 26
239000000203 mixture Substances 0.000 claims abstract description 9
239000002035 hexane extract Substances 0.000 claims abstract description 7
238000000034 method Methods 0.000 claims description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
150000004665 fatty acids Chemical class 0.000 claims description 32
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 26
150000001875 compounds Chemical class 0.000 claims description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 15
235000019197 fats Nutrition 0.000 claims description 12
238000005809 transesterification reaction Methods 0.000 claims description 12
125000005907 alkyl ester group Chemical group 0.000 claims description 10
235000021122 unsaturated fatty acids Nutrition 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
238000001816 cooling Methods 0.000 claims description 7
238000000926 separation method Methods 0.000 claims description 7
238000005886 esterification reaction Methods 0.000 claims description 6
238000000605 extraction Methods 0.000 claims description 6
230000032050 esterification Effects 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
150000004702 methyl esters Chemical class 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
239000002244 precipitate Substances 0.000 claims description 2
238000000638 solvent extraction Methods 0.000 claims 1
229940107161 cholesterol Drugs 0.000 abstract description 34
241000251468 Actinopterygii Species 0.000 abstract description 12
238000001556 precipitation Methods 0.000 abstract description 11
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 abstract description 10
235000020669 docosahexaenoic acid Nutrition 0.000 abstract description 6
239000002699 waste material Substances 0.000 abstract description 6
229940090949 docosahexaenoic acid Drugs 0.000 abstract description 5
239000000706 filtrate Substances 0.000 abstract description 4
238000007670 refining Methods 0.000 abstract description 3
241001565477 Aphyosemion omega Species 0.000 abstract 1
230000005540 biological transmission Effects 0.000 abstract 1
239000000243 solution Substances 0.000 description 17
239000003925 fat Substances 0.000 description 11
235000004626 essential fatty acids Nutrition 0.000 description 9
239000000306 component Substances 0.000 description 8
239000002994 raw material Substances 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
239000000463 material Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
235000019387 fatty acid methyl ester Nutrition 0.000 description 4
125000005456 glyceride group Chemical group 0.000 description 4
235000020777 polyunsaturated fatty acids Nutrition 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
235000021588 free fatty acids Nutrition 0.000 description 3
239000002044 hexane fraction Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
230000000875 corresponding effect Effects 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
229960004488 linolenic acid Drugs 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000000344 soap Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 2
150000004670 unsaturated fatty acids Chemical class 0.000 description 2
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 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
244000228957 Ferula foetida Species 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
206010067482 No adverse event Diseases 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
241000193803 Therea Species 0.000 description 1
QWDCYFDDFPWISL-UHFFFAOYSA-N UNPD207407 Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(=O)OC QWDCYFDDFPWISL-UHFFFAOYSA-N 0.000 description 1
229940022682 acetone Drugs 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
235000020661 alpha-linolenic acid Nutrition 0.000 description 1
DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
230000002785 anti-thrombosis Effects 0.000 description 1
239000003146 anticoagulant agent Substances 0.000 description 1
238000005844 autocatalytic reaction Methods 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000010586 diagram Methods 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
229940013317 fish oils Drugs 0.000 description 1
235000013332 fish product Nutrition 0.000 description 1
239000000727 fraction Substances 0.000 description 1
VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 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
KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
230000007721 medicinal effect Effects 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
235000021313 oleic acid Nutrition 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000004262 preparative liquid chromatography Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
235000003441 saturated fatty acids Nutrition 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000000194 supercritical-fluid extraction Methods 0.000 description 1
UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
230000001732 thrombotic effect Effects 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter

Landscapes

Life Sciences & Earth Sciences (AREA)
Microbiology (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Wood Science & Technology (AREA)
Organic Chemistry (AREA)
Fats And Perfumes (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

CA000523914A 1985-12-19 1986-11-27 Concentrat d'huile de poisson raffine et procede pour sa production Expired - Lifetime CA1303416C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NO855.147		1985-12-19
NO855147A NO157302C (no)	1985-12-19	1985-12-19	Fremgangsmaate for fremstilling av et fiskeoljekonsentrat.

Publications (1)

Publication Number	Publication Date
CA1303416C true CA1303416C (fr)	1992-06-16

Family

ID=19888637

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000523914A Expired - Lifetime CA1303416C (fr)	1985-12-19	1986-11-27	Concentrat d'huile de poisson raffine et procede pour sa production

Country Status (15)

Country	Link
EP (1)	EP0255824B1 (fr)
AR (1)	AR242111A1 (fr)
AU (1)	AU6621186A (fr)
CA (1)	CA1303416C (fr)
DD (1)	DD261805A1 (fr)
DE (1)	DE3668467D1 (fr)
IE (1)	IE59171B1 (fr)
IS (1)	IS1425B6 (fr)
MA (1)	MA20840A1 (fr)
MX (1)	MX168698B (fr)
NO (1)	NO157302C (fr)
NZ (1)	NZ218500A (fr)
PT (1)	PT83991B (fr)
WO (1)	WO1987003899A1 (fr)
ZA (1)	ZA868927B (fr)

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GB8819110D0 (en) *	1988-08-11	1988-09-14	Norsk Hydro As	Antihypertensive drug & method for production
US5336792A (en) *	1990-03-12	1994-08-09	Einar Sola	Process for enrichment of fat with regard to polyunsaturated fatty acids and phospholipids, and application of such enriched fat
SE9303446D0 (sv) *	1993-10-20	1993-10-20	Trikonex Ab	A novel urea fractionation process
GB9404483D0 (en) *	1994-03-08	1994-04-20	Norsk Hydro As	Refining marine oil compositions
TW425285B (en)	1996-06-10	2001-03-11	Viva America Marketing Inc	Fish oil and garlic nutritive supplement
US6313167B1 (en)	1997-06-16	2001-11-06	Nippon Suisan Kaisha Ltd.	Composition having capability of removing risk factor during exercise
NO309795B1 (no) *	1998-07-01	2001-04-02	Norsk Hydro As	FremgangsmOte for O stabilisere oljer samt anvendelse derav, fremgangsmOte for O stabilisere pigmenter, og fremgangsmOte for fremstilling av for
IT1308613B1 (it)	1999-02-17	2002-01-09	Pharmacia & Upjohn Spa	Acidi grassi essenziali nella prevenzione di eventi cardiovascolari.
NO311041B1 (no) *	1999-12-22	2001-10-01	Norsk Hydro As	Stabilisering av pigmenter og flerumettede oljer og oljekonsentrater
US6395778B1 (en)	2000-01-11	2002-05-28	Omegatech, Inc.	Process for making an enriched mixture of polyunsaturated fatty acid esters
AT414205B (de)	2000-06-20	2006-10-15	Vis Vitalis Lizenz & Handels	Verfahren zur herstellung von ungesättigtem fettsäure-trockenkonzentrat
ITMI20010129A1 (it)	2001-01-25	2002-07-25	Pharmacia & Upjohn Spa	Acidi grassi essenziali nella terapia di insufficienza cardiaca e scompenso cardiaco
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
EP2295529B2 (fr)	2002-07-11	2022-05-18	Basf As	Procédé de diminution des polluants environnementaux dans une huile ou une graisse et produit d'alimentation pour poissons
ITMI20032247A1 (it) *	2003-11-19	2005-05-20	Tiberio Bruzzese	Interazione di derivati polari di composti insaturi con substrati inorganici
DK2447356T3 (en)	2005-06-07	2016-06-06	Dsm Nutritional Products Ag	Eukaryotic MICROORGANISMS FOR PRODUCTION OF LIPIDS AND ANTIOXIDANTS
ITMI20051560A1 (it) *	2005-08-10	2007-02-11	Tiberio Bruzzese	Composizione di acidi grassi n-3 con elevata concentrazione di epa e-o dha e contenente acidi grassi n-6
WO2008129358A2 (fr)	2006-08-01	2008-10-30	Ocean Nutrition Canada Ltd.	Microbes produisant des huiles et procedes de modification associes
CA2873141C (fr)	2009-12-30	2018-05-29	Adam Kelliher	Procede de separation chromatographique en lit mobile simule
ITMI20102297A1 (it)	2010-12-15	2012-06-16	Prime Europ Therapeuticals	Procedimento per stabilizzare acidi grassi poliinsaturi per mezzo di idruri metallici
US8889895B2 (en) *	2011-03-08	2014-11-18	Cognis Ip Management Gmbh	Process for the distillation of fatty acid esters
GB201111589D0 (en)	2011-07-06	2011-08-24	Equateq Ltd	New modified process
GB201111591D0 (en)	2011-07-06	2011-08-24	Equateq Ltd	Further new process
GB201111601D0 (en)	2011-07-06	2011-08-24	Equateq Ltd	New process
GB201111594D0 (en)	2011-07-06	2011-08-24	Equateq Ltd	New improved process
GB201111595D0 (en)	2011-07-06	2011-08-24	Equateq Ltd	Improved process
GB201300354D0 (en)	2013-01-09	2013-02-20	Basf Pharma Callanish Ltd	Multi-step separation process
EP2970926B1 (fr)	2013-03-13	2018-01-31	DSM Nutritional Products AG	Modification génétique de micro-organismes
US9428711B2 (en)	2013-05-07	2016-08-30	Groupe Novasep	Chromatographic process for the production of highly purified polyunsaturated fatty acids
EP2883860B1 (fr)	2013-12-11	2016-08-24	Novasep Process	Procédé chromatographique de production d'acides gras polyinsaturés
JP6303017B2 (ja)	2014-01-07	2018-03-28	ノヴァセププロセスＮｏｖａｓｅｐＰｒｏｃｅｓｓ	芳香族アミノ酸を精製する方法
US9163198B2 (en) *	2014-01-17	2015-10-20	Orochem Technologies, Inc.	Process for purification of EPA (eicosapentanoic acid) ethyl ester from fish oil
WO2016028235A1 (fr) *	2014-08-18	2016-02-25	Chiang Mai University	Système et procédé d'extraction et/ou de concentration
CN107666904B (zh)	2015-03-26	2022-02-01	提贝托·布鲁泽塞	多不饱和脂肪酸的纯化组合物、其制备方法及其用途
AR104042A1 (es)	2015-03-26	2017-06-21	Mara Renewables Corp	Producción de alta densidad de biomasa y aceite utilizando glicerol en bruto
HRP20201965T1 (hr)	2015-05-13	2021-02-05	Epax Norway As	Polinezasićene masne kiseline vrlo dugog lanca iz prirodnih ulja
AU2016293487B2 (en)	2015-07-13	2021-07-01	MARA Renewables Corporation	Enhancing microalgal metabolism of xylose
US10851395B2 (en)	2016-06-10	2020-12-01	MARA Renewables Corporation	Method of making lipids with improved cold flow properties
WO2019053744A1 (fr)	2017-09-14	2019-03-21	Fermenta Biotech Limited	Processus amélioré d'extraction de cholestérol à partir de résidus de déchets d'huile de poisson
US10196586B1 (en) *	2018-02-14	2019-02-05	Golden Omega S.A.	Feed ingredient

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1176916B (it) *	1984-10-10	1987-08-18	Elvira Pistolesi	Composizione farmaceutica o dietetica ad elevata attivita' antitrombotica e antiarteriosclerotica

1985
- 1985-12-19 NO NO855147A patent/NO157302C/no not_active IP Right Cessation
1986
- 1986-11-21 WO PCT/NO1986/000077 patent/WO1987003899A1/fr not_active Ceased
- 1986-11-21 IS IS3159A patent/IS1425B6/is unknown
- 1986-11-21 EP EP86906964A patent/EP0255824B1/fr not_active Expired - Lifetime
- 1986-11-21 DE DE8686906964T patent/DE3668467D1/de not_active Expired - Lifetime
- 1986-11-21 AU AU66211/86A patent/AU6621186A/en not_active Withdrawn
- 1986-11-21 IE IE306486A patent/IE59171B1/en not_active IP Right Cessation
- 1986-11-25 ZA ZA868927A patent/ZA868927B/xx unknown
- 1986-11-27 CA CA000523914A patent/CA1303416C/fr not_active Expired - Lifetime
- 1986-12-03 NZ NZ218500A patent/NZ218500A/xx unknown
- 1986-12-08 MX MX004578A patent/MX168698B/es unknown
- 1986-12-17 DD DD86297792A patent/DD261805A1/de not_active IP Right Cessation
- 1986-12-19 AR AR86306258A patent/AR242111A1/es active
- 1986-12-19 MA MA21072A patent/MA20840A1/fr unknown
- 1986-12-19 PT PT83991A patent/PT83991B/pt not_active IP Right Cessation

Also Published As

Publication number	Publication date
ZA868927B (en)	1987-08-26
AR242111A1 (es)	1993-03-31
NO855147L (no)	1987-06-22
NZ218500A (en)	1989-03-29
IE59171B1 (en)	1994-01-12
IS3159A7 (is)	1987-06-20
MA20840A1 (fr)	1987-07-01
NO157302C (no)	1988-02-24
PT83991A (en)	1987-01-01
PT83991B (pt)	1989-01-17
EP0255824B1 (fr)	1990-01-24
IE863064L (en)	1987-06-19
WO1987003899A1 (fr)	1987-07-02
AU6621186A (en)	1987-07-15
DE3668467D1 (de)	1990-03-01
NO157302B (no)	1987-11-16
DD261805A1 (de)	1988-11-09
IS1425B6 (is)	1990-03-28
MX168698B (es)	1993-06-04
EP0255824A1 (fr)	1988-02-17

Legal Events

Date	Code	Title	Description
2001-06-18	MKLA	Lapsed

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