JPH0158240B2 - - Google Patents
Info
- Publication number
- JPH0158240B2 JPH0158240B2 JP7293884A JP7293884A JPH0158240B2 JP H0158240 B2 JPH0158240 B2 JP H0158240B2 JP 7293884 A JP7293884 A JP 7293884A JP 7293884 A JP7293884 A JP 7293884A JP H0158240 B2 JPH0158240 B2 JP H0158240B2
- Authority
- JP
- Japan
- Prior art keywords
- extraction
- fatty acids
- esters
- carbon dioxide
- temperature
- 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
Links
- 238000000605 extraction Methods 0.000 claims description 67
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 54
- 239000001569 carbon dioxide Substances 0.000 claims description 27
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 27
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 21
- 229930195729 fatty acid Natural products 0.000 claims description 21
- 239000000194 fatty acid Substances 0.000 claims description 21
- 150000004665 fatty acids Chemical class 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 238000010992 reflux Methods 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 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 15
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 15
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 15
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 15
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 15
- 239000002994 raw material Substances 0.000 claims description 14
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 14
- 150000001298 alcohols Chemical class 0.000 claims description 11
- 239000004202 carbamide Substances 0.000 claims description 11
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 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
- 150000003672 ureas Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 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 16
- 150000004702 methyl esters Chemical class 0.000 description 13
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 229940090949 docosahexaenoic acid Drugs 0.000 description 8
- 235000021323 fish oil Nutrition 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 5
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000005456 glyceride group Chemical group 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- -1 alcohol ester Chemical class 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000007536 Thrombosis Diseases 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
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- VCDLWFYODNTQOT-UHFFFAOYSA-N docosahexaenoic acid methyl ester Natural products CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)OC VCDLWFYODNTQOT-UHFFFAOYSA-N 0.000 description 1
- XJFYWGIWEYQMPK-UHFFFAOYSA-N ethanol;urea Chemical compound CCO.NC(N)=O XJFYWGIWEYQMPK-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 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
- 235000020778 linoleic acid Nutrition 0.000 description 1
- LUYYTKKXYNRVHQ-UHFFFAOYSA-N methyl docosa-2,4,6,8,10,12-hexaenoate Chemical compound CCCCCCCCCC=CC=CC=CC=CC=CC=CC(=O)OC LUYYTKKXYNRVHQ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 235000014102 seafood Nutrition 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7293884A JPS60217299A (ja) | 1984-04-13 | 1984-04-13 | 高度不飽和脂肪酸又はそのエステルの濃縮分離法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7293884A JPS60217299A (ja) | 1984-04-13 | 1984-04-13 | 高度不飽和脂肪酸又はそのエステルの濃縮分離法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60217299A JPS60217299A (ja) | 1985-10-30 |
| JPH0158240B2 true JPH0158240B2 (enrdf_load_stackoverflow) | 1989-12-11 |
Family
ID=13503807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7293884A Granted JPS60217299A (ja) | 1984-04-13 | 1984-04-13 | 高度不飽和脂肪酸又はそのエステルの濃縮分離法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60217299A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2538753B2 (ja) * | 1993-08-27 | 1996-10-02 | 財団法人地球環境産業技術研究機構 | 脂肪酸の抽出方法 |
-
1984
- 1984-04-13 JP JP7293884A patent/JPS60217299A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60217299A (ja) | 1985-10-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5679809A (en) | Concentrate of polyunsaturated fatty acid ethyl esters and preparation thereof | |
| JPH0159318B2 (enrdf_load_stackoverflow) | ||
| FR2678632A1 (fr) | Procede de preparation de l'insaponifiable d'avocat permettant d'ameliorer sa teneur en l'une de ses fractions dite h. | |
| JPH11236591A (ja) | 高純度エイコサペンタエン酸またはそのエステルの製造方法 | |
| RU2242505C2 (ru) | Способ удаления свободных жирных кислот из жиров и масел биологического происхождения или их паровых дистиллятов (варианты) | |
| KR20020042432A (ko) | 결정화방법을 이용한 고순도 불포화지방산의 분리방법 | |
| JPS63162796A (ja) | 脂肪酸の分画方法 | |
| US7709668B2 (en) | Separation technology | |
| Patil et al. | Microwave-mediated non-catalytic transesterification of algal biomass under supercritical ethanol conditions | |
| JPS649977B2 (enrdf_load_stackoverflow) | ||
| Gunstone et al. | Improved procedures for the isolation of pure oleic, linoleic, and linolenic acids or their methyl esters from natural sources | |
| JPH0796498B2 (ja) | セレノア・レペンスの果実の抽出方法 | |
| JP2010513570A (ja) | Ｄｈａ高濃度化方法 | |
| KR20040104525A (ko) | 데오더라이져 증류물의 처리방법 | |
| JP3678317B2 (ja) | エイコサペンタエン酸含有物の濃縮方法 | |
| JPH0158240B2 (enrdf_load_stackoverflow) | ||
| JP3040136B2 (ja) | エイコサペンタエン酸またはそのエステルの製造方法 | |
| JP3611222B2 (ja) | 高度不飽和脂肪酸類含有油脂の過酸化物低減方法 | |
| JP3344887B2 (ja) | 高度不飽和脂肪酸含有油脂の濃縮方法 | |
| JPH0137387B2 (enrdf_load_stackoverflow) | ||
| JPS588037A (ja) | エイコサペンタエン酸またはそのエステルの製法 | |
| JP2726828B2 (ja) | 高度不飽和脂肪酸またはそのエステルの濃縮分別装置とその濃縮分別法 | |
| JP2004502657A (ja) | スクアレンの製造方法 | |
| JP3005638B2 (ja) | 高濃度エイコサペンタエン酸またはそのエステルの製造方法 | |
| JP2001354991A (ja) | 高度不飽和脂肪酸含有油脂の精製方法 |