JPS59118740A - エイコサペンタエン酸またはその低級アルコ−ルエステルの製造方法 - Google Patents
エイコサペンタエン酸またはその低級アルコ−ルエステルの製造方法Info
- Publication number
- JPS59118740A JPS59118740A JP22702182A JP22702182A JPS59118740A JP S59118740 A JPS59118740 A JP S59118740A JP 22702182 A JP22702182 A JP 22702182A JP 22702182 A JP22702182 A JP 22702182A JP S59118740 A JPS59118740 A JP S59118740A
- Authority
- JP
- Japan
- Prior art keywords
- lower alcohol
- urea
- alcohol ester
- acid
- ester
- 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.)
- Granted
Links
- -1 alcohol ester Chemical class 0.000 title claims abstract description 41
- 235000020673 eicosapentaenoic acid Nutrition 0.000 title claims abstract description 33
- 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 title claims abstract description 16
- 229960005135 eicosapentaenoic acid Drugs 0.000 title claims abstract description 16
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 title claims abstract description 16
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 105
- 239000004202 carbamide Substances 0.000 claims abstract description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 37
- 229930195729 fatty acid Natural products 0.000 claims abstract description 37
- 239000000194 fatty acid Substances 0.000 claims abstract description 37
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 35
- 239000003960 organic solvent Substances 0.000 claims abstract description 26
- 239000010775 animal oil Substances 0.000 claims abstract description 24
- 238000011276 addition treatment Methods 0.000 claims abstract description 19
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 15
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 14
- 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 abstract description 12
- 239000003377 acid catalyst Substances 0.000 claims abstract description 9
- 239000003513 alkali Substances 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 3
- 238000007127 saponification reaction Methods 0.000 claims description 9
- 150000001298 alcohols Chemical class 0.000 claims description 8
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 4
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000003672 ureas Chemical class 0.000 claims 2
- 239000003921 oil Substances 0.000 abstract description 14
- 238000006136 alcoholysis reaction Methods 0.000 abstract description 6
- 208000007536 Thrombosis Diseases 0.000 abstract description 5
- 235000019512 sardine Nutrition 0.000 abstract description 5
- 241001465754 Metazoa Species 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 230000003449 preventive effect Effects 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 2
- 241001125046 Sardina pilchardus Species 0.000 abstract 1
- 238000011282 treatment Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 70
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 63
- 238000000034 method Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 150000004702 methyl esters Chemical class 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- 238000000622 liquid--liquid extraction Methods 0.000 description 10
- 238000000638 solvent extraction Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
- 239000010935 stainless steel Substances 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 3
- NMZKLLJQNNTBRJ-OIXZZONUSA-N TXA3 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)C\C=C/CC)O[C@@H]2O[C@H]1C2 NMZKLLJQNNTBRJ-OIXZZONUSA-N 0.000 description 3
- QWDCYFDDFPWISL-UHFFFAOYSA-N UNPD207407 Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(=O)OC QWDCYFDDFPWISL-UHFFFAOYSA-N 0.000 description 3
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 description 3
- 229960001123 epoprostenol Drugs 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 208000019622 heart disease Diseases 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- 241000251468 Actinopterygii Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 241000238366 Cephalopoda Species 0.000 description 2
- 206010008132 Cerebral thrombosis Diseases 0.000 description 2
- 241000555825 Clupeidae Species 0.000 description 2
- 241000238557 Decapoda Species 0.000 description 2
- 229920000064 Ethyl eicosapentaenoic acid Polymers 0.000 description 2
- 241000276438 Gadus morhua Species 0.000 description 2
- 201000001429 Intracranial Thrombosis Diseases 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- 241001125048 Sardina Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 206010008118 cerebral infarction Diseases 0.000 description 2
- 208000026106 cerebrovascular disease Diseases 0.000 description 2
- 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 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 235000019688 fish Nutrition 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000000199 molecular distillation Methods 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 208000023516 stroke disease Diseases 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- SJIWUNNSRFWATG-UHFFFAOYSA-N 4-[2-(2-hydroxyethoxy)ethoxy]-4-oxobutanoic acid Chemical compound OCCOCCOC(=O)CCC(O)=O SJIWUNNSRFWATG-UHFFFAOYSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 208000014644 Brain disease Diseases 0.000 description 1
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 241000252203 Clupea harengus Species 0.000 description 1
- 241001149724 Cololabis adocetus Species 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000239366 Euphausiacea Species 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 241000237852 Mollusca Species 0.000 description 1
- 241000238413 Octopus Species 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000269821 Scombridae Species 0.000 description 1
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 235000019516 cod Nutrition 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000001595 contractor effect Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- SSQPWTVBQMWLSZ-AAQCHOMXSA-N ethyl (5Z,8Z,11Z,14Z,17Z)-icosapentaenoate Chemical compound CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC SSQPWTVBQMWLSZ-AAQCHOMXSA-N 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000019514 herring Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 235000020978 long-chain polyunsaturated fatty acids Nutrition 0.000 description 1
- 235000020640 mackerel Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22702182A JPS59118740A (ja) | 1982-12-27 | 1982-12-27 | エイコサペンタエン酸またはその低級アルコ−ルエステルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22702182A JPS59118740A (ja) | 1982-12-27 | 1982-12-27 | エイコサペンタエン酸またはその低級アルコ−ルエステルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59118740A true JPS59118740A (ja) | 1984-07-09 |
| JPH0347259B2 JPH0347259B2 (enrdf_load_stackoverflow) | 1991-07-18 |
Family
ID=16854267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22702182A Granted JPS59118740A (ja) | 1982-12-27 | 1982-12-27 | エイコサペンタエン酸またはその低級アルコ−ルエステルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59118740A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6121065A (ja) * | 1984-07-10 | 1986-01-29 | Akira Kitano | 栄養補助食品 |
| JPS6143143A (ja) * | 1984-08-03 | 1986-03-01 | Nisshin Flour Milling Co Ltd | エイコサペンタエン酸のグリセリンエステルおよびその製法 |
| JPS63162796A (ja) * | 1986-12-17 | 1988-07-06 | ソシエテ デ プロデユイ ネツスル ソシエテ アノニム | 脂肪酸の分画方法 |
| JPS6448898A (en) * | 1987-08-20 | 1989-02-23 | Nisshin Flour Milling Co | Production of eicosapentaenoic acid or ester thereof and docosahexaenoic acid or ester thereof |
| JPS6470439A (en) * | 1987-05-28 | 1989-03-15 | Innoba D Ridorufui Furoola E C | Extraction of polyunsaturated fatty acid from fish oil and medicine and/or feed composition containing same ester |
| JPS6483043A (en) * | 1987-09-24 | 1989-03-28 | Harima Chemicals Inc | Fractional extraction of highly unsaturated fatty acid |
| CN106753812A (zh) * | 2013-06-19 | 2017-05-31 | 阿根特能源（英国）有限公司 | 用于生产生物柴油和相关产品的工艺 |
-
1982
- 1982-12-27 JP JP22702182A patent/JPS59118740A/ja active Granted
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6121065A (ja) * | 1984-07-10 | 1986-01-29 | Akira Kitano | 栄養補助食品 |
| JPS6143143A (ja) * | 1984-08-03 | 1986-03-01 | Nisshin Flour Milling Co Ltd | エイコサペンタエン酸のグリセリンエステルおよびその製法 |
| JPS63162796A (ja) * | 1986-12-17 | 1988-07-06 | ソシエテ デ プロデユイ ネツスル ソシエテ アノニム | 脂肪酸の分画方法 |
| JPS6470439A (en) * | 1987-05-28 | 1989-03-15 | Innoba D Ridorufui Furoola E C | Extraction of polyunsaturated fatty acid from fish oil and medicine and/or feed composition containing same ester |
| JPS6448898A (en) * | 1987-08-20 | 1989-02-23 | Nisshin Flour Milling Co | Production of eicosapentaenoic acid or ester thereof and docosahexaenoic acid or ester thereof |
| JPS6483043A (en) * | 1987-09-24 | 1989-03-28 | Harima Chemicals Inc | Fractional extraction of highly unsaturated fatty acid |
| CN106753812A (zh) * | 2013-06-19 | 2017-05-31 | 阿根特能源（英国）有限公司 | 用于生产生物柴油和相关产品的工艺 |
| CN106753812B (zh) * | 2013-06-19 | 2020-09-22 | 阿根特能源（英国）有限公司 | 用于生产生物柴油和相关产品的工艺 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0347259B2 (enrdf_load_stackoverflow) | 1991-07-18 |
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