JPH0516478B2 - - Google Patents
Info
- Publication number
- JPH0516478B2 JPH0516478B2 JP22326482A JP22326482A JPH0516478B2 JP H0516478 B2 JPH0516478 B2 JP H0516478B2 JP 22326482 A JP22326482 A JP 22326482A JP 22326482 A JP22326482 A JP 22326482A JP H0516478 B2 JPH0516478 B2 JP H0516478B2
- Authority
- JP
- Japan
- Prior art keywords
- oil
- distillation
- distilled
- thin film
- μtorr
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000003921 oil Substances 0.000 claims description 102
- 235000019198 oils Nutrition 0.000 claims description 102
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Natural products 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 description 35
- 238000004821 distillation Methods 0.000 claims description 30
- 235000021323 fish oil Nutrition 0.000 claims description 28
- HVYWMOMLDIMFJA-UHFFFAOYSA-N 3-cholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 HVYWMOMLDIMFJA-UHFFFAOYSA-N 0.000 claims description 21
- 125000005456 glyceride group Chemical group 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 19
- 239000010409 thin film Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 235000019197 fats Nutrition 0.000 claims description 18
- 238000000199 molecular distillation Methods 0.000 claims description 16
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 14
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 14
- 229930195729 fatty acid Natural products 0.000 claims description 14
- 239000000194 fatty acid Substances 0.000 claims description 14
- 230000009965 odorless effect Effects 0.000 claims description 12
- -1 cholesterin fatty acid esters Chemical class 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000010696 ester oil Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000002994 raw material Substances 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 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 3
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 3
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 239000010775 animal oil Substances 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 239000010408 film Substances 0.000 claims 1
- 150000005846 sugar alcohols Polymers 0.000 claims 1
- 235000019645 odor Nutrition 0.000 description 24
- 239000003925 fat Substances 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 16
- 239000008157 edible vegetable oil Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 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 description 12
- 239000000047 product Substances 0.000 description 11
- 238000004332 deodorization Methods 0.000 description 10
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 10
- 230000001877 deodorizing effect Effects 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 150000004671 saturated fatty acids Chemical class 0.000 description 5
- 238000005809 transesterification reaction Methods 0.000 description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 description 5
- 239000008158 vegetable oil Substances 0.000 description 5
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 240000008415 Lactuca sativa Species 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 235000005687 corn oil Nutrition 0.000 description 4
- 239000002285 corn oil Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 208000019622 heart disease Diseases 0.000 description 4
- 235000013372 meat Nutrition 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 235000012045 salad Nutrition 0.000 description 4
- 241000251468 Actinopterygii Species 0.000 description 3
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 3
- 235000019485 Safflower oil Nutrition 0.000 description 3
- 241001125048 Sardina Species 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000004042 decolorization Methods 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 230000005674 electromagnetic induction Effects 0.000 description 3
- 235000019688 fish Nutrition 0.000 description 3
- 229940013317 fish oils Drugs 0.000 description 3
- 235000020778 linoleic acid Nutrition 0.000 description 3
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 3
- 235000005713 safflower oil Nutrition 0.000 description 3
- 239000003813 safflower oil Substances 0.000 description 3
- 235000019512 sardine Nutrition 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 229930003427 Vitamin E Natural products 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229940090949 docosahexaenoic acid Drugs 0.000 description 2
- 239000011552 falling film Substances 0.000 description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 235000013310 margarine Nutrition 0.000 description 2
- 239000003264 margarine Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 235000019165 vitamin E Nutrition 0.000 description 2
- 229940046009 vitamin E Drugs 0.000 description 2
- 239000011709 vitamin E Substances 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- ATNNLHXCRAAGJS-QZQOTICOSA-N (e)-docos-2-enoic acid Chemical compound CCCCCCCCCCCCCCCCCCC\C=C\C(O)=O ATNNLHXCRAAGJS-QZQOTICOSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- 241000238366 Cephalopoda Species 0.000 description 1
- 241001149724 Cololabis adocetus Species 0.000 description 1
- 241000276498 Pollachius virens Species 0.000 description 1
- 241000269821 Scombridae Species 0.000 description 1
- 238000009874 alkali refining Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 235000020640 mackerel Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000010517 refined sesame oil Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22326482A JPS59113099A (ja) | 1982-12-20 | 1982-12-20 | 高度不飽和油組成物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22326482A JPS59113099A (ja) | 1982-12-20 | 1982-12-20 | 高度不飽和油組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59113099A JPS59113099A (ja) | 1984-06-29 |
| JPH0516478B2 true JPH0516478B2 (de) | 1993-03-04 |
Family
ID=16795379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22326482A Granted JPS59113099A (ja) | 1982-12-20 | 1982-12-20 | 高度不飽和油組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59113099A (de) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59172596A (ja) * | 1983-03-22 | 1984-09-29 | 高尾 正保 | 精製魚油及びその製法 |
| JPH0715108B2 (ja) * | 1986-02-12 | 1995-02-22 | 日清製粉株式会社 | エイコサペンタエン酸のグリセリドを含む食用油脂製品 |
| US4804555A (en) * | 1986-10-21 | 1989-02-14 | General Mills, Inc. | Physical process for simultaneous deodorization and cholesterol reduction of fats and oils |
| GB2218984B (en) * | 1988-05-27 | 1992-09-23 | Renafield Limited | Process for preparing high-concentration mixtures of polyunsaturated fatty acids & their esters and their prophylactic or therapeutic uses |
| US4961939A (en) * | 1989-06-02 | 1990-10-09 | Nabisco Brands, Inc. | Deodorized water-in-oil emulsion containing fish oil |
| US5883273A (en) * | 1996-01-26 | 1999-03-16 | Abbott Laboratories | Polyunsaturated fatty acids and fatty acid esters free of sterols and phosphorus compounds |
| US6063946A (en) * | 1996-01-26 | 2000-05-16 | Eastman Chemical Company | Process for the isolation of polyunsaturated fatty acids and esters thereof from complex mixtures which contain sterols and phosphorus compounds |
| JP4524547B2 (ja) * | 2003-07-16 | 2010-08-18 | 株式会社カネカ | 油脂組成物の製造法、及びこれを用いる油脂組成物 |
| JP2010132631A (ja) * | 2008-11-04 | 2010-06-17 | Bizen Chemical Co Ltd | カンナビノイド受容体のインバースアゴニストおよびアンタゴニスト活性を有する組成物 |
| ES2661234T3 (es) * | 2011-03-08 | 2018-03-28 | Cognis Ip Management Gmbh | Un procedimiento para la destilación de ésteres de ácidos grasos |
| US8258330B1 (en) * | 2012-01-04 | 2012-09-04 | Naturalis, S.A. | Carrier fluid composition comprising fatty acids ethyl esters and process for reducing the concentration of persistent organic pollutants in fish oil |
| TW201516030A (zh) * | 2013-09-26 | 2015-05-01 | Kewpie Corp | 含有低級醇脂肪酸酯化合物之組成物的製造方法及含有低級醇脂肪酸酯化合物之組成物 |
| LU102019B1 (de) * | 2020-08-26 | 2022-02-28 | K D Pharma Bexbach Gmbh | Verfahren zur Herstellung von Öl aus einem Mikroalgenerzeugnis |
-
1982
- 1982-12-20 JP JP22326482A patent/JPS59113099A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59113099A (ja) | 1984-06-29 |
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