JPH0259199B2 - - Google Patents
Info
- Publication number
- JPH0259199B2 JPH0259199B2 JP58149241A JP14924183A JPH0259199B2 JP H0259199 B2 JPH0259199 B2 JP H0259199B2 JP 58149241 A JP58149241 A JP 58149241A JP 14924183 A JP14924183 A JP 14924183A JP H0259199 B2 JPH0259199 B2 JP H0259199B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oil
- distillate
- deodorized
- reaction
- 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
- 238000000034 method Methods 0.000 claims description 55
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 238000005886 esterification reaction Methods 0.000 claims description 20
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 13
- 230000032050 esterification Effects 0.000 claims description 13
- 238000005243 fluidization Methods 0.000 claims description 11
- 230000001877 deodorizing effect Effects 0.000 claims description 9
- 239000003921 oil Substances 0.000 claims description 9
- 235000021588 free fatty acids Nutrition 0.000 claims description 8
- 239000003925 fat Substances 0.000 claims description 7
- 239000003729 cation exchange resin Substances 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000002253 acid Substances 0.000 description 11
- 239000003456 ion exchange resin Substances 0.000 description 10
- 229920003303 ion-exchange polymer Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000012488 sample solution Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000011732 tocopherol Substances 0.000 description 5
- 229930003799 tocopherol Natural products 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 235000019197 fats Nutrition 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- 235000010384 tocopherol Nutrition 0.000 description 3
- 229960001295 tocopherol Drugs 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
- 235000019482 Palm oil Nutrition 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- 238000004332 deodorization Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 238000009775 high-speed stirring Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 238000000199 molecular distillation Methods 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- 235000019149 tocopherols Nutrition 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 2
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000019774 Rice Bran oil Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000008165 rice bran oil Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229930193551 sterin Natural products 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58149241A JPS6042495A (ja) | 1983-08-17 | 1983-08-17 | 油脂脱臭留出物のメチルエステル化法 |
| GB08402453A GB2145079B (en) | 1983-08-17 | 1984-01-31 | Methyl-esterification of deodorisation distillates of oils |
| MYPI87000866A MY100032A (en) | 1983-08-17 | 1987-06-23 | Method of methyl-esterification of deodorization distillates of oils. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58149241A JPS6042495A (ja) | 1983-08-17 | 1983-08-17 | 油脂脱臭留出物のメチルエステル化法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6042495A JPS6042495A (ja) | 1985-03-06 |
| JPH0259199B2 true JPH0259199B2 (xx) | 1990-12-11 |
Family
ID=15470962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58149241A Granted JPS6042495A (ja) | 1983-08-17 | 1983-08-17 | 油脂脱臭留出物のメチルエステル化法 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS6042495A (xx) |
| GB (1) | GB2145079B (xx) |
| MY (1) | MY100032A (xx) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04128195A (ja) * | 1990-09-14 | 1992-04-28 | Niigata Eng Co Ltd | 混液防止装置 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3500938A1 (de) * | 1985-01-14 | 1986-07-17 | Henkel KGaA, 4000 Düsseldorf | Stabilisierung von palmkernoel und palmkernfettsaeurealkylestern fuer deren verarbeitung zu farbneutralen reaktionsfolgeprodukten |
| DE3501761A1 (de) * | 1985-01-21 | 1986-07-24 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur vorveresterung freier fettsaeuren in rohfetten und/oder -oelen |
| DE4228476C2 (de) * | 1992-08-27 | 2002-05-02 | Cognis Deutschland Gmbh | Verfahren zum Gewinnen von Tocopherol und/oder Sterin |
| ATE213239T1 (de) * | 1993-08-06 | 2002-02-15 | Henkel Corp | Wiedergewinnung von tocopherolen |
| DE19652522C2 (de) * | 1996-12-17 | 2000-10-26 | Cognis Deutschland Gmbh | Verfahren zur Gewinnung von Tocopherolen und/oder Sterinen |
| DE19906551C1 (de) | 1999-02-13 | 2000-06-29 | Cognis Deutschland Gmbh | Verfahren zur Herstellung von Phytosterinen |
| DE19916034C1 (de) * | 1999-04-09 | 2000-08-03 | Cognis Deutschland Gmbh | Verfahren zur Gewinnung von Phytosterinen |
| DE10038442A1 (de) | 2000-08-07 | 2002-02-21 | Cognis Deutschland Gmbh | Verfahren zur Gewinnung von Sterinen aus fettsäurehaltigen Rückständen |
| MY150129A (en) | 2004-04-09 | 2013-11-29 | Archer Daniels Midland Co | Method of preparing fatty acid alkyl esters from waste or recycled fatty acid stock |
| AU2008318000A1 (en) * | 2007-10-30 | 2009-05-07 | Bayer Intellectual Property Gmbh | Method for the heterogenically catalyzed esterification of fatty acids |
| DE102008007431A1 (de) * | 2008-02-01 | 2009-08-13 | Bayer Technology Services Gmbh | Verbessertes Verfahren zur heterogen katalysierten Veresterung von Fettsäuren |
| DE102007052065A1 (de) * | 2007-10-30 | 2009-05-07 | Bayer Technology Services Gmbh | Kontinuierliches Verfahren zur heterogen katalysierten Veresterung von Fettsäuren |
| EP2165998A1 (en) * | 2008-09-15 | 2010-03-24 | Rohm and Haas Company | Method for selective esterification of free fatty acids in triglycerides |
| BR112022005776A2 (pt) | 2019-09-27 | 2022-06-21 | Basf Health And Care Products France S A S | Processo para purificação de fitoesteróis |
| BR112022005715A2 (pt) | 2019-09-27 | 2022-06-21 | Basf Health And Care Products France S A S | Processo para produzir e purificar esteróis |
| WO2021058647A1 (en) | 2019-09-27 | 2021-04-01 | Basf Se | Process for the production of sterols and/or tocopherols with recovery of by-products |
-
1983
- 1983-08-17 JP JP58149241A patent/JPS6042495A/ja active Granted
-
1984
- 1984-01-31 GB GB08402453A patent/GB2145079B/en not_active Expired
-
1987
- 1987-06-23 MY MYPI87000866A patent/MY100032A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04128195A (ja) * | 1990-09-14 | 1992-04-28 | Niigata Eng Co Ltd | 混液防止装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| MY100032A (en) | 1989-04-20 |
| GB2145079B (en) | 1986-11-12 |
| GB2145079A (en) | 1985-03-20 |
| JPS6042495A (ja) | 1985-03-06 |
| GB8402453D0 (en) | 1984-03-07 |
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