DE2216593C3 - Verfahren zur gelenkten Umesterung von Glyceridgemischen - Google Patents
Verfahren zur gelenkten Umesterung von GlyceridgemischenInfo
- Publication number
- DE2216593C3 DE2216593C3 DE2216593A DE2216593A DE2216593C3 DE 2216593 C3 DE2216593 C3 DE 2216593C3 DE 2216593 A DE2216593 A DE 2216593A DE 2216593 A DE2216593 A DE 2216593A DE 2216593 C3 DE2216593 C3 DE 2216593C3
- Authority
- DE
- Germany
- Prior art keywords
- temperature
- oil
- mixture
- transesterification
- cloud point
- 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
- 239000000203 mixture Substances 0.000 title claims description 57
- 238000005809 transesterification reaction Methods 0.000 title claims description 34
- 238000000034 method Methods 0.000 title claims description 27
- 125000005456 glyceride group Chemical group 0.000 title claims description 23
- 230000008569 process Effects 0.000 title claims description 10
- 230000000737 periodic effect Effects 0.000 claims description 16
- 235000013310 margarine Nutrition 0.000 claims description 11
- 239000003264 margarine Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003921 oil Substances 0.000 description 38
- 235000019198 oils Nutrition 0.000 description 37
- 239000003054 catalyst Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 230000008859 change Effects 0.000 description 10
- 239000003925 fat Substances 0.000 description 10
- 235000019197 fats Nutrition 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 235000019486 Sunflower oil Nutrition 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002574 poison Substances 0.000 description 8
- 231100000614 poison Toxicity 0.000 description 8
- 239000002600 sunflower oil Substances 0.000 description 8
- 239000007790 solid phase Substances 0.000 description 7
- 150000003626 triacylglycerols Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000004665 fatty acids Chemical group 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 235000003441 saturated fatty acids Nutrition 0.000 description 6
- 150000004671 saturated fatty acids Chemical class 0.000 description 6
- 239000000344 soap Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 235000019485 Safflower oil Nutrition 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 235000004626 essential fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 235000005713 safflower oil Nutrition 0.000 description 5
- 239000003813 safflower oil Substances 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000012670 alkaline solution Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000010339 dilation Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 235000020183 skimmed milk Nutrition 0.000 description 3
- 235000002316 solid fats Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 235000015277 pork Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- OYHQOLUKZRVURQ-UHFFFAOYSA-N 9,12-Octadecadienoic Acid Chemical compound CCCCCC=CCC=CCCCCCCCC(O)=O OYHQOLUKZRVURQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- 235000019498 Walnut oil Nutrition 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008169 grapeseed oil Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 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
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000010491 poppyseed oil Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 235000019710 soybean protein Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-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
- 238000001291 vacuum drying Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 235000008939 whole milk Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/10—Ester interchange
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB907871A GB1381721A (en) | 1971-04-08 | 1971-04-08 | Interesterification process |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2216593A1 DE2216593A1 (de) | 1972-11-02 |
| DE2216593B2 DE2216593B2 (de) | 1981-07-30 |
| DE2216593C3 true DE2216593C3 (de) | 1982-05-19 |
Family
ID=9864939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2216593A Expired DE2216593C3 (de) | 1971-04-08 | 1972-04-06 | Verfahren zur gelenkten Umesterung von Glyceridgemischen |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5121410B1 (enExample) |
| AT (1) | AT324102B (enExample) |
| AU (1) | AU462615B2 (enExample) |
| BE (1) | BE781844A (enExample) |
| CA (1) | CA954874A (enExample) |
| CH (1) | CH572972A5 (enExample) |
| DE (1) | DE2216593C3 (enExample) |
| ES (1) | ES401554A1 (enExample) |
| FR (1) | FR2136271A5 (enExample) |
| GB (1) | GB1381721A (enExample) |
| IE (1) | IE36259B1 (enExample) |
| NL (1) | NL145279B (enExample) |
| NO (1) | NO139267C (enExample) |
| SE (1) | SE383530B (enExample) |
| ZA (1) | ZA722306B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE870481A (nl) | 1978-09-14 | 1979-01-02 | Vandemoortele Nv | Werkwijze voor het gericht heresteren van een triglyceride-olie of -oliemengsel en triglyceride-olie of -oliemengsel aldus heresterd |
| NZ199915A (en) * | 1981-03-11 | 1985-07-12 | Unilever Plc | Treating edible oils to raise melting point thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2442531A (en) * | 1944-11-06 | 1948-06-01 | Procter & Gamble | Process for treating fats and fatty oils |
| US2442533A (en) * | 1945-11-30 | 1948-06-01 | Procter & Gamble | Treatment of glycerides |
| FR1133498A (fr) * | 1954-07-15 | 1957-03-27 | Procter & Gamble | Perfectionnements à l'interestérification dirigée des corps gras |
| US2733251A (en) * | 1954-09-02 | 1956-01-31 | Molecular rearrangement process | |
| DE1117986B (de) * | 1955-12-17 | 1961-11-23 | Procter & Gamble | Verfahren zur Herstellung eines plastischen, ueberwiegend aus Schweineschmalz bestehenden Fettes |
-
1971
- 1971-04-08 GB GB907871A patent/GB1381721A/en not_active Expired
-
1972
- 1972-04-05 ZA ZA722306A patent/ZA722306B/xx unknown
- 1972-04-05 AU AU40778/72A patent/AU462615B2/en not_active Expired
- 1972-04-06 NL NL727204637A patent/NL145279B/xx not_active IP Right Cessation
- 1972-04-06 IE IE442/72A patent/IE36259B1/xx unknown
- 1972-04-06 CA CA139,026A patent/CA954874A/en not_active Expired
- 1972-04-06 DE DE2216593A patent/DE2216593C3/de not_active Expired
- 1972-04-07 SE SE7204557A patent/SE383530B/xx unknown
- 1972-04-07 FR FR7212345A patent/FR2136271A5/fr not_active Expired
- 1972-04-07 NO NO1195/72A patent/NO139267C/no unknown
- 1972-04-07 CH CH516372A patent/CH572972A5/xx not_active IP Right Cessation
- 1972-04-07 BE BE781844A patent/BE781844A/xx not_active IP Right Cessation
- 1972-04-07 ES ES401554A patent/ES401554A1/es not_active Expired
- 1972-04-08 JP JP7235672A patent/JPS5121410B1/ja active Pending
- 1972-04-10 AT AT308072A patent/AT324102B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2136271A5 (enExample) | 1972-12-22 |
| NL145279B (nl) | 1975-03-17 |
| JPS5121410B1 (enExample) | 1976-07-02 |
| CH572972A5 (enExample) | 1976-02-27 |
| ZA722306B (en) | 1973-11-28 |
| AT324102B (de) | 1975-08-11 |
| AU462615B2 (en) | 1975-06-06 |
| IE36259L (en) | 1972-10-08 |
| GB1381721A (en) | 1975-01-29 |
| NL7204637A (enExample) | 1972-10-10 |
| SE383530B (sv) | 1976-03-15 |
| DE2216593B2 (de) | 1981-07-30 |
| ES401554A1 (es) | 1975-10-16 |
| AU4077872A (en) | 1973-10-11 |
| NO139267C (no) | 1979-01-31 |
| DE2216593A1 (de) | 1972-11-02 |
| BE781844A (fr) | 1972-10-09 |
| NO139267B (no) | 1978-10-23 |
| IE36259B1 (en) | 1976-09-29 |
| CA954874A (en) | 1974-09-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: KOHLER, M., DIPL.-CHEM. DR.RER.NAT., 8000 MUENCHEN GLAESER, J., DIPL.-ING., PAT.-ANW., 2000 HAMBURG |
|
| 8339 | Ceased/non-payment of the annual fee |