DE3643848A1 - Verfahren zur herstellung hochraffinierter essbarer glyceridoele mit einem anteil an ungesaettigten fettsaeuren im triglyceridverband und ihre verwendung - Google Patents
Verfahren zur herstellung hochraffinierter essbarer glyceridoele mit einem anteil an ungesaettigten fettsaeuren im triglyceridverband und ihre verwendungInfo
- Publication number
- DE3643848A1 DE3643848A1 DE19863643848 DE3643848A DE3643848A1 DE 3643848 A1 DE3643848 A1 DE 3643848A1 DE 19863643848 DE19863643848 DE 19863643848 DE 3643848 A DE3643848 A DE 3643848A DE 3643848 A1 DE3643848 A1 DE 3643848A1
- Authority
- DE
- Germany
- Prior art keywords
- oil
- glyceride
- highly refined
- oils
- triglycerides
- 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
- 239000003921 oil Substances 0.000 title claims abstract description 88
- 125000005456 glyceride group Chemical group 0.000 title claims abstract description 61
- 238000000034 method Methods 0.000 title claims abstract description 53
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 235000021122 unsaturated fatty acids Nutrition 0.000 title claims abstract description 10
- 150000004670 unsaturated fatty acids Chemical class 0.000 title claims abstract description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000007670 refining Methods 0.000 claims abstract description 21
- 239000012454 non-polar solvent Substances 0.000 claims abstract description 14
- 235000005911 diet Nutrition 0.000 claims abstract description 6
- 230000000378 dietary effect Effects 0.000 claims abstract description 6
- 235000019198 oils Nutrition 0.000 claims description 83
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 28
- 239000003549 soybean oil Substances 0.000 claims description 25
- 235000012424 soybean oil Nutrition 0.000 claims description 25
- 239000000741 silica gel Substances 0.000 claims description 18
- 229910002027 silica gel Inorganic materials 0.000 claims description 18
- 238000004061 bleaching Methods 0.000 claims description 15
- 235000021323 fish oil Nutrition 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 235000019197 fats Nutrition 0.000 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 235000019486 Sunflower oil Nutrition 0.000 claims description 3
- 239000002600 sunflower oil Substances 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 2
- 235000016311 Primula vulgaris Nutrition 0.000 claims description 2
- 244000028344 Primula vulgaris Species 0.000 claims description 2
- 235000019485 Safflower oil Nutrition 0.000 claims description 2
- 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 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 2
- 235000012343 cottonseed oil Nutrition 0.000 claims description 2
- 239000002385 cottonseed oil Substances 0.000 claims description 2
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 2
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 2
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 2
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 2
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000020778 linoleic acid Nutrition 0.000 claims description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 2
- 229960004488 linolenic acid Drugs 0.000 claims description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 2
- 239000000944 linseed oil Substances 0.000 claims description 2
- 235000021388 linseed oil Nutrition 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 235000005713 safflower oil Nutrition 0.000 claims description 2
- 239000003813 safflower oil Substances 0.000 claims description 2
- 150000003626 triacylglycerols Chemical class 0.000 abstract description 43
- 239000000126 substance Substances 0.000 abstract description 5
- 238000011282 treatment Methods 0.000 description 24
- 238000013016 damping Methods 0.000 description 11
- 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 11
- 239000000203 mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000009874 alkali refining Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229940087168 alpha tocopherol Drugs 0.000 description 5
- 239000008157 edible vegetable oil Substances 0.000 description 5
- 238000010025 steaming Methods 0.000 description 5
- 229960000984 tocofersolan Drugs 0.000 description 5
- 239000002076 α-tocopherol Substances 0.000 description 5
- 235000004835 α-tocopherol Nutrition 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 4
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229940013317 fish oils Drugs 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 229940066595 beta tocopherol Drugs 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 235000010389 delta-tocopherol Nutrition 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 235000010382 gamma-tocopherol Nutrition 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
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 235000019645 odor Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 239000011590 β-tocopherol Substances 0.000 description 2
- 235000007680 β-tocopherol Nutrition 0.000 description 2
- 239000002478 γ-tocopherol Substances 0.000 description 2
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 2
- 239000002446 δ-tocopherol Substances 0.000 description 2
- 241000252203 Clupea harengus Species 0.000 description 1
- 229920000715 Mucilage Polymers 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 241000312370 Sardinella brasiliensis Species 0.000 description 1
- 241000269821 Scombridae Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000012443 analytical study Methods 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 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 1
- 238000004332 deodorization Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000019514 herring Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 235000020640 mackerel Nutrition 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000010734 process oil Substances 0.000 description 1
- 229940119224 salmon oil Drugs 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 235000021081 unsaturated fats Nutrition 0.000 description 1
- -1 unsaturated fatty acids triglycerides Chemical class 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
- C11B3/10—Refining fats or fatty oils by adsorption
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863643848 DE3643848A1 (de) | 1986-12-22 | 1986-12-22 | Verfahren zur herstellung hochraffinierter essbarer glyceridoele mit einem anteil an ungesaettigten fettsaeuren im triglyceridverband und ihre verwendung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863643848 DE3643848A1 (de) | 1986-12-22 | 1986-12-22 | Verfahren zur herstellung hochraffinierter essbarer glyceridoele mit einem anteil an ungesaettigten fettsaeuren im triglyceridverband und ihre verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3643848A1 true DE3643848A1 (de) | 1988-09-01 |
| DE3643848C2 DE3643848C2 (enrdf_load_stackoverflow) | 1989-09-28 |
Family
ID=6316836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19863643848 Granted DE3643848A1 (de) | 1986-12-22 | 1986-12-22 | Verfahren zur herstellung hochraffinierter essbarer glyceridoele mit einem anteil an ungesaettigten fettsaeuren im triglyceridverband und ihre verwendung |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3643848A1 (enrdf_load_stackoverflow) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0395569A1 (en) * | 1989-04-27 | 1990-10-31 | Jon Katborg | A fatty product and a process for the production of same |
| AT398779B (de) * | 1988-08-11 | 1995-01-25 | Norsk Hydro As | Fettsäurezusammensetzung, verfahren zu ihrer herstellung, ihre verwendung und pharmazeutische zusammensetzung, die sie enthält |
| WO2000044862A1 (en) * | 1999-01-29 | 2000-08-03 | Atlantis Marine Inc. | Process of converting rendered triglyceride oil from marine sources into bland, stable oil |
| EP0304115B2 (en) † | 1987-08-05 | 2001-04-18 | Unilever N.V. | Marine/vegetable oil blend and products made therefrom |
| ES2212913A1 (es) * | 2001-11-07 | 2004-08-01 | Jeronimo Diaz Rivas | Mejoras introducidas en la patente de invencion n.200102447 por "aceite procedente de frutos y semillas vegetales". |
| DE102008060059A1 (de) * | 2008-12-02 | 2010-06-10 | Süd-Chemie AG | Verfahren zur Reduzierung des 3-MCPD-Gehalts in raffinierten Pflanzenölen |
| CZ303281B6 (cs) * | 2010-10-27 | 2012-07-11 | Vysoká škola chemicko-technologická v Praze | Zpusob zabránení vzniku acylderivátu monochlorpropandiolu pri vysokoteplotních úpravách oleju a tuku |
| US11672258B2 (en) | 2015-08-25 | 2023-06-13 | Dsm Ip Assets B.V. | Refined oil compositions and methods for making |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2440111B2 (de) * | 1973-08-24 | 1980-01-31 | Unilever N.V., Rotterdam (Niederlande) | Verfahren zur Behandlung von eßbaren Glyceridölen |
-
1986
- 1986-12-22 DE DE19863643848 patent/DE3643848A1/de active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2440111B2 (de) * | 1973-08-24 | 1980-01-31 | Unilever N.V., Rotterdam (Niederlande) | Verfahren zur Behandlung von eßbaren Glyceridölen |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0304115B2 (en) † | 1987-08-05 | 2001-04-18 | Unilever N.V. | Marine/vegetable oil blend and products made therefrom |
| AT398779B (de) * | 1988-08-11 | 1995-01-25 | Norsk Hydro As | Fettsäurezusammensetzung, verfahren zu ihrer herstellung, ihre verwendung und pharmazeutische zusammensetzung, die sie enthält |
| EP0395569A1 (en) * | 1989-04-27 | 1990-10-31 | Jon Katborg | A fatty product and a process for the production of same |
| WO1990012510A1 (en) * | 1989-04-27 | 1990-11-01 | Jon Katborg | A fatty product and a process for the production of same |
| WO2000044862A1 (en) * | 1999-01-29 | 2000-08-03 | Atlantis Marine Inc. | Process of converting rendered triglyceride oil from marine sources into bland, stable oil |
| US7179491B1 (en) | 1999-01-29 | 2007-02-20 | Ted Mag | Process of converting rendered triglyceride oil from marine sources into bland, stable oil |
| ES2212913A1 (es) * | 2001-11-07 | 2004-08-01 | Jeronimo Diaz Rivas | Mejoras introducidas en la patente de invencion n.200102447 por "aceite procedente de frutos y semillas vegetales". |
| ES2212913B1 (es) * | 2001-11-07 | 2005-04-01 | Nutrinnova Mediterranea S.L. | Mejoras introducidas en la patente de invencion n.200102447 por "aceite procedente de frutos y semillas vegetales". |
| DE102008060059A1 (de) * | 2008-12-02 | 2010-06-10 | Süd-Chemie AG | Verfahren zur Reduzierung des 3-MCPD-Gehalts in raffinierten Pflanzenölen |
| CZ303281B6 (cs) * | 2010-10-27 | 2012-07-11 | Vysoká škola chemicko-technologická v Praze | Zpusob zabránení vzniku acylderivátu monochlorpropandiolu pri vysokoteplotních úpravách oleju a tuku |
| US11672258B2 (en) | 2015-08-25 | 2023-06-13 | Dsm Ip Assets B.V. | Refined oil compositions and methods for making |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3643848C2 (enrdf_load_stackoverflow) | 1989-09-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: SGS GERMANY GMBH, 20095 HAMBURG, DE |
|
| 8339 | Ceased/non-payment of the annual fee |