CA2967772C - Solvent-free process for obtaining phospholipids and neutral enriched krill oils using melting and evaporation - Google Patents
Solvent-free process for obtaining phospholipids and neutral enriched krill oils using melting and evaporation Download PDFInfo
- Publication number
- CA2967772C CA2967772C CA2967772A CA2967772A CA2967772C CA 2967772 C CA2967772 C CA 2967772C CA 2967772 A CA2967772 A CA 2967772A CA 2967772 A CA2967772 A CA 2967772A CA 2967772 C CA2967772 C CA 2967772C
- Authority
- CA
- Canada
- Prior art keywords
- krill
- phospholipids
- process according
- minced
- decanter
- 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.)
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Links
- 241000239366 Euphausiacea Species 0.000 title claims abstract description 199
- 150000003904 phospholipids Chemical class 0.000 title claims abstract description 102
- 238000000034 method Methods 0.000 title claims abstract description 64
- 230000008569 process Effects 0.000 title claims abstract description 56
- 230000007935 neutral effect Effects 0.000 title claims abstract description 19
- 238000001704 evaporation Methods 0.000 title claims abstract description 12
- 230000008020 evaporation Effects 0.000 title claims description 10
- 238000002844 melting Methods 0.000 title abstract description 69
- 230000008018 melting Effects 0.000 title abstract description 67
- 239000003921 oil Substances 0.000 title description 13
- 239000007788 liquid Substances 0.000 claims abstract description 55
- 239000007787 solid Substances 0.000 claims abstract description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 48
- 229940106134 krill oil Drugs 0.000 claims abstract description 47
- 150000002632 lipids Chemical class 0.000 claims abstract description 44
- 239000000839 emulsion Substances 0.000 claims abstract description 36
- 238000010793 Steam injection (oil industry) Methods 0.000 claims abstract description 26
- JEBFVOLFMLUKLF-IFPLVEIFSA-N Astaxanthin Natural products CC(=C/C=C/C(=C/C=C/C1=C(C)C(=O)C(O)CC1(C)C)/C)C=CC=C(/C)C=CC=C(/C)C=CC2=C(C)C(=O)C(O)CC2(C)C JEBFVOLFMLUKLF-IFPLVEIFSA-N 0.000 claims abstract description 16
- 235000013793 astaxanthin Nutrition 0.000 claims abstract description 16
- MQZIGYBFDRPAKN-ZWAPEEGVSA-N astaxanthin Chemical compound C([C@H](O)C(=O)C=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C(=O)[C@@H](O)CC1(C)C MQZIGYBFDRPAKN-ZWAPEEGVSA-N 0.000 claims abstract description 16
- 229940022405 astaxanthin Drugs 0.000 claims abstract description 16
- 239000001168 astaxanthin Substances 0.000 claims abstract description 16
- 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 claims description 28
- 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 20
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 20
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 20
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 20
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 17
- 238000010438 heat treatment Methods 0.000 claims description 16
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 14
- 238000003825 pressing Methods 0.000 claims description 13
- 102000004169 proteins and genes Human genes 0.000 claims description 9
- 108090000623 proteins and genes Proteins 0.000 claims description 9
- 238000013019 agitation Methods 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 7
- 230000009471 action Effects 0.000 claims description 6
- 238000000227 grinding Methods 0.000 claims description 6
- 241000251468 Actinopterygii Species 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 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 3
- 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 3
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 claims description 3
- 235000013372 meat Nutrition 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 3
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims description 2
- 238000005191 phase separation Methods 0.000 claims description 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 1
- 235000012054 meals Nutrition 0.000 abstract description 16
- 239000010409 thin film Substances 0.000 abstract description 7
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 abstract description 4
- 229940067631 phospholipid Drugs 0.000 description 93
- 238000012360 testing method Methods 0.000 description 26
- 239000012071 phase Substances 0.000 description 14
- 238000010411 cooking Methods 0.000 description 13
- 238000000605 extraction Methods 0.000 description 11
- 238000004945 emulsification Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000012545 processing Methods 0.000 description 9
- 235000021588 free fatty acids Nutrition 0.000 description 8
- 235000018102 proteins Nutrition 0.000 description 8
- 239000000203 mixture Substances 0.000 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 description 6
- 235000004213 low-fat Nutrition 0.000 description 6
- 230000001932 seasonal effect Effects 0.000 description 6
- 241000894007 species Species 0.000 description 6
- 241000238424 Crustacea Species 0.000 description 4
- 229930182558 Sterol Natural products 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- 235000003702 sterols Nutrition 0.000 description 4
- DJMUYABFXCIYSC-UHFFFAOYSA-N 1H-phosphole Chemical compound C=1C=CPC=1 DJMUYABFXCIYSC-UHFFFAOYSA-N 0.000 description 3
- 239000002028 Biomass Substances 0.000 description 3
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 230000036541 health Effects 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 239000007764 o/w emulsion Substances 0.000 description 3
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 150000003432 sterols Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241000212918 Euphausia crystallorophias Species 0.000 description 2
- 241000239370 Euphausia superba Species 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000019688 fish Nutrition 0.000 description 2
- 235000003642 hunger Nutrition 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000037351 starvation Effects 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 1
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
- RYCNUMLMNKHWPZ-SNVBAGLBSA-N 1-acetyl-sn-glycero-3-phosphocholine Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C RYCNUMLMNKHWPZ-SNVBAGLBSA-N 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- 241000238366 Cephalopoda Species 0.000 description 1
- 241001346906 Cervimunida johni Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000239368 Euphausia Species 0.000 description 1
- 241001625807 Euphausia frigida Species 0.000 description 1
- 241001472116 Euphausia lucens Species 0.000 description 1
- 241001472118 Euphausia pacifica Species 0.000 description 1
- 241000943459 Euphausia recurva Species 0.000 description 1
- 241001472120 Euphausia similis Species 0.000 description 1
- 241001472122 Euphausia tricantha Species 0.000 description 1
- 241000308443 Exophiala spinifera Species 0.000 description 1
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
- 241001122740 Heterocarpus Species 0.000 description 1
- 241000238070 Pandalus borealis Species 0.000 description 1
- 241001346894 Pleuroncodes Species 0.000 description 1
- -1 Sterol esters Chemical class 0.000 description 1
- 241000430432 Thysanoessa gregaria Species 0.000 description 1
- 241001534900 Thysanoessa inermis Species 0.000 description 1
- 241000212929 Thysanoessa macrura Species 0.000 description 1
- 241000680651 Thysanoessa raschii Species 0.000 description 1
- ATBOMIWRCZXYSZ-XZBBILGWSA-N [1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (9e,12e)-octadeca-9,12-dienoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C\C\C=C\CCCCC ATBOMIWRCZXYSZ-XZBBILGWSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
- 210000003484 anatomy Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000002681 cryosurgery Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000001982 diacylglycerols Chemical class 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- ZGSPNIOCEDOHGS-UHFFFAOYSA-L disodium [3-[2,3-di(octadeca-9,12-dienoyloxy)propoxy-oxidophosphoryl]oxy-2-hydroxypropyl] 2,3-di(octadeca-9,12-dienoyloxy)propyl phosphate Chemical compound [Na+].[Na+].CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COP([O-])(=O)OCC(O)COP([O-])(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC ZGSPNIOCEDOHGS-UHFFFAOYSA-L 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003028 elevating effect Effects 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 1
- 235000020665 omega-6 fatty acid Nutrition 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- 238000011020 pilot scale process Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000003685 thermal hair damage Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 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
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/12—Production of fats or fatty oils from raw materials by melting out
- C11B1/16—Production of fats or fatty oils from raw materials by melting out with steam
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
- A23D7/0053—Compositions other than spreads
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/01—Other fatty acid esters, e.g. phosphatides
- A23D7/011—Compositions other than spreads
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides
- A23D9/013—Other fatty acid esters, e.g. phosphatides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings or cooking oils characterised by the production or working-up
- A23D9/04—Working-up
-
- 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
- C11B1/02—Pretreatment
-
- 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
- C11B1/02—Pretreatment
- C11B1/04—Pretreatment of vegetable raw material
-
- 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
- C11B1/06—Production of fats or fatty oils from raw materials by pressing
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Meat, Egg Or Seafood Products (AREA)
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462079864P | 2014-11-14 | 2014-11-14 | |
| US62/079,864 | 2014-11-14 | ||
| PCT/IB2015/058789 WO2016075669A1 (en) | 2014-11-14 | 2015-11-13 | Solvent-free process for obtaining phospholipids and neutral enriched krill oils using melting and evaporation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2967772A1 CA2967772A1 (en) | 2016-05-19 |
| CA2967772C true CA2967772C (en) | 2021-08-10 |
Family
ID=55069021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2967772A Active CA2967772C (en) | 2014-11-14 | 2015-11-13 | Solvent-free process for obtaining phospholipids and neutral enriched krill oils using melting and evaporation |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10059904B2 (enExample) |
| EP (1) | EP3218456B1 (enExample) |
| JP (1) | JP6538164B2 (enExample) |
| CN (1) | CN107105692B (enExample) |
| AU (1) | AU2015347014B2 (enExample) |
| CA (1) | CA2967772C (enExample) |
| CL (1) | CL2017001224A1 (enExample) |
| IL (1) | IL252261B (enExample) |
| WO (1) | WO2016075669A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108373943A (zh) * | 2018-03-29 | 2018-08-07 | 浙江海力生生物科技股份有限公司 | 一种制备低砷无氟磷虾油的方法 |
| CN109207247A (zh) * | 2018-09-25 | 2019-01-15 | 深圳先进技术研究院 | 南极磷虾油的制备方法、脱腥南极磷虾油及其应用、食品 |
| ES3016834T3 (en) * | 2018-11-30 | 2025-05-09 | Alfa Laval Corp Ab | Method of producing a low-fat product and a system for producing a low-fat product |
| EP3923966A4 (en) | 2019-02-12 | 2023-01-04 | Acasti Pharma Inc. | PROCESS FOR PREPARING A CONCENTRATED THERAPEUTIC PHOSPHOLIPID COMPOSITION FROM KRILL EXTRACTS HIGH IN FREE FATTY ACIDS |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007080515A1 (en) | 2006-01-13 | 2007-07-19 | Aker Biomarine Asa | Thrombosis preventing krill extract |
| AR059659A1 (es) * | 2006-01-13 | 2008-04-23 | Alfa Copenhagen S S | Metodo para la extraccion |
| AU2014100737B4 (en) * | 2007-03-28 | 2014-09-25 | Aker Biomarine Antarctic As | Processes and products thereof |
| FI2144618T4 (fi) | 2007-03-28 | 2025-02-13 | Aker Biomarine Antarctic As | Biovaikuttavat krilliöljykoostumukset |
| RU2460309C2 (ru) * | 2007-08-29 | 2012-09-10 | Акер Биомарине Аса | Новый способ изготовления крилевой муки |
| US20100226977A1 (en) * | 2007-08-29 | 2010-09-09 | Aker Biomarine Asa | Low viscosity phospholipid compositions |
| JP5703022B2 (ja) * | 2008-09-26 | 2015-04-15 | 日本水産株式会社 | 脂質の製造方法 |
| WO2010097701A1 (en) * | 2009-02-26 | 2010-09-02 | Aker Biomarine Asa | Low viscosity phospholipid compositions |
| CA2779334C (en) * | 2009-10-30 | 2017-05-30 | Tharos Ltd. | Solvent-free process for obtaining phospholipids and neutral enriched krill oils |
| CN102311868B (zh) | 2011-04-29 | 2017-05-24 | 塞拉斯有限责任公司 | 一种无溶剂提取富含磷脂和中性油脂的磷虾油的方法 |
| CN102876444A (zh) | 2012-09-18 | 2013-01-16 | 中国水产科学研究院东海水产研究所 | 一种虾类油脂的无溶剂制备方法 |
| WO2014060847A1 (en) * | 2012-09-24 | 2014-04-24 | Aker Biopharma As | Use of long chain polyunsaturated fatty acid derivatives to treat sickle cell disease |
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| CN107105692B (zh) | 2021-04-27 |
| EP3218456A1 (en) | 2017-09-20 |
| JP2018500011A (ja) | 2018-01-11 |
| US20170313956A1 (en) | 2017-11-02 |
| IL252261A0 (en) | 2017-07-31 |
| JP6538164B2 (ja) | 2019-07-03 |
| CN107105692A (zh) | 2017-08-29 |
| WO2016075669A1 (en) | 2016-05-19 |
| EP3218456C0 (en) | 2024-12-18 |
| US10059904B2 (en) | 2018-08-28 |
| AU2015347014B2 (en) | 2019-01-17 |
| AU2015347014A1 (en) | 2017-06-15 |
| EP3218456B1 (en) | 2024-12-18 |
| IL252261B (en) | 2020-01-30 |
| CL2017001224A1 (es) | 2017-12-11 |
| CA2967772A1 (en) | 2016-05-19 |
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