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
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- 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 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3218456B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6538164B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN107105692B (cg-RX-API-DMAC7.html) |
| AU (1) | AU2015347014B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2967772C (cg-RX-API-DMAC7.html) |
| CL (1) | CL2017001224A1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL252261B (cg-RX-API-DMAC7.html) |
| WO (1) | WO2016075669A1 (cg-RX-API-DMAC7.html) |
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 |
| PL3660135T3 (pl) | 2018-11-30 | 2025-04-28 | Alfa Laval Corporate Ab | Metoda wytwarzania produktu niskotłuszczowego oraz układ do wytwarzania produktu niskotłuszczowego |
| CA3129365C (en) | 2019-02-12 | 2023-01-03 | Acasti Pharma, Inc. | Process of producing concentrated therapeutic phospholipid composition from krill extracts containing high level of 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 |
| WO2007080514A2 (en) * | 2006-01-13 | 2007-07-19 | Krill A/S | A method for the extraction of lipid fractions from krill |
| EP2144618B2 (en) | 2007-03-28 | 2024-11-20 | Aker Biomarine Antarctic As | Bioeffective krill oil compositions |
| AU2014100737B4 (en) * | 2007-03-28 | 2014-09-25 | Aker Biomarine Antarctic As | Processes and products thereof |
| EP2732709A1 (en) * | 2007-08-29 | 2014-05-21 | Aker BioMarine AS | A new method for making krill meal |
| US20100226977A1 (en) * | 2007-08-29 | 2010-09-09 | Aker Biomarine Asa | Low viscosity phospholipid compositions |
| US8784921B2 (en) * | 2008-09-26 | 2014-07-22 | Nippon Suisan Kaisha, Ltd. | Method for concentrating lipids |
| WO2010097701A1 (en) * | 2009-02-26 | 2010-09-02 | Aker Biomarine Asa | Low viscosity phospholipid compositions |
| JP5735521B2 (ja) | 2009-10-30 | 2015-06-17 | タロス・リミテッドＴｈａｒｏｓ Ｌｔｄ． | リン脂質および中性脂質が強化されたオキアミ油を得る無溶媒の方法 |
| 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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| EP3218456B1 (en) | 2024-12-18 |
| CN107105692A (zh) | 2017-08-29 |
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| AU2015347014B2 (en) | 2019-01-17 |
| US10059904B2 (en) | 2018-08-28 |
| AU2015347014A1 (en) | 2017-06-15 |
| US20170313956A1 (en) | 2017-11-02 |
| CA2967772A1 (en) | 2016-05-19 |
| CL2017001224A1 (es) | 2017-12-11 |
| EP3218456C0 (en) | 2024-12-18 |
| IL252261A0 (en) | 2017-07-31 |
| JP6538164B2 (ja) | 2019-07-03 |
| JP2018500011A (ja) | 2018-01-11 |
| CN107105692B (zh) | 2021-04-27 |
| IL252261B (en) | 2020-01-30 |
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