DE2021530A1 - Verfahren zur Herstellung von Oxyfettsaeureestern - Google Patents
Verfahren zur Herstellung von OxyfettsaeureesternInfo
- Publication number
- DE2021530A1 DE2021530A1 DE19702021530 DE2021530A DE2021530A1 DE 2021530 A1 DE2021530 A1 DE 2021530A1 DE 19702021530 DE19702021530 DE 19702021530 DE 2021530 A DE2021530 A DE 2021530A DE 2021530 A1 DE2021530 A1 DE 2021530A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogenation
- fatty acid
- acid esters
- catalyst
- epoxidized
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 17
- -1 oxy fatty acid esters Chemical class 0.000 title claims description 16
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 13
- 239000000194 fatty acid Substances 0.000 title claims description 13
- 229930195729 fatty acid Natural products 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 34
- 239000003054 catalyst Substances 0.000 claims description 22
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 229910001385 heavy metal Inorganic materials 0.000 claims description 7
- 229910017052 cobalt Inorganic materials 0.000 claims description 6
- 239000010941 cobalt Substances 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 235000009508 confectionery Nutrition 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000005809 transesterification reaction Methods 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- WXBXVVIUZANZAU-UHFFFAOYSA-N 2E-decenoic acid Natural products CCCCCCCC=CC(O)=O WXBXVVIUZANZAU-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- WXBXVVIUZANZAU-CMDGGOBGSA-N trans-2-decenoic acid Chemical compound CCCCCCC\C=C\C(O)=O WXBXVVIUZANZAU-CMDGGOBGSA-N 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- IMYZYCNQZDBZBQ-UHFFFAOYSA-N (+-)-8-(cis-3-octyl-oxiranyl)-octanoic acid Natural products CCCCCCCCC1OC1CCCCCCCC(O)=O IMYZYCNQZDBZBQ-UHFFFAOYSA-N 0.000 description 1
- BITHHVVYSMSWAG-KTKRTIGZSA-N (11Z)-icos-11-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 description 1
- NIONDZDPPYHYKY-SNAWJCMRSA-N (2E)-hexenoic acid Chemical compound CCC\C=C\C(O)=O NIONDZDPPYHYKY-SNAWJCMRSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-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
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- 241000252203 Clupea harengus Species 0.000 description 1
- GZZPOFFXKUVNSW-UHFFFAOYSA-N Dodecenoic acid Natural products OC(=O)CCCCCCCCCC=C GZZPOFFXKUVNSW-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 229940108623 eicosenoic acid Drugs 0.000 description 1
- BITHHVVYSMSWAG-UHFFFAOYSA-N eicosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCC(O)=O BITHHVVYSMSWAG-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000019514 herring Nutrition 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 235000015250 liver sausages Nutrition 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- ADHNUPOJJCKWRT-UHFFFAOYSA-N octadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCCCCC=CC=CC(O)=O ADHNUPOJJCKWRT-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C11C3/12—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
- C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702021530 DE2021530A1 (de) | 1970-05-02 | 1970-05-02 | Verfahren zur Herstellung von Oxyfettsaeureestern |
| NL7104458A NL7104458A (enExample) | 1970-05-02 | 1971-04-02 | |
| US00137968A US3778465A (en) | 1970-05-02 | 1971-04-27 | Process for the production of hydroxy-fatty acid esters |
| CH629271A CH546728A (de) | 1970-05-02 | 1971-04-29 | Verfahren zur herstellung von oxyfettsaeureestern. |
| BE766473A BE766473A (fr) | 1970-05-02 | 1971-04-29 | Procede de preparation d'esters d'hydroxyacides gras |
| FR7115336A FR2090932A5 (enExample) | 1970-05-02 | 1971-04-29 | |
| GB02171/71A GB1300526A (en) | 1970-05-02 | 1971-04-29 | Process for the preparation of hydroxy-fatty acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702021530 DE2021530A1 (de) | 1970-05-02 | 1970-05-02 | Verfahren zur Herstellung von Oxyfettsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2021530A1 true DE2021530A1 (de) | 1971-11-25 |
Family
ID=5770052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702021530 Pending DE2021530A1 (de) | 1970-05-02 | 1970-05-02 | Verfahren zur Herstellung von Oxyfettsaeureestern |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3778465A (enExample) |
| BE (1) | BE766473A (enExample) |
| CH (1) | CH546728A (enExample) |
| DE (1) | DE2021530A1 (enExample) |
| FR (1) | FR2090932A5 (enExample) |
| GB (1) | GB1300526A (enExample) |
| NL (1) | NL7104458A (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3923393A1 (de) * | 1989-07-14 | 1991-01-17 | Henkel Kgaa | Verfahren zur altpapieraufbereitung |
| WO1991006531A1 (de) * | 1989-11-04 | 1991-05-16 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung anionischer tenside mit sulfatstruktur |
| US5914006A (en) * | 1995-04-26 | 1999-06-22 | Henkel Kommanditgesellschaft Auf Aktien | Process for controlling the deposit of adhesive impurities from paper material suspensions |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57117526A (en) * | 1981-01-13 | 1982-07-22 | Takasago Corp | Preparation of polycondensate from omega-oxypentadecanoic acid |
| US4519951A (en) * | 1983-07-05 | 1985-05-28 | Uop Inc. | Selective reduction of fatty materials using a supported group VIII metal in eggshell distribution |
| DE3420226A1 (de) * | 1984-05-30 | 1985-12-05 | Henkel KGaA, 4000 Düsseldorf | Gleitmittel fuer polyvinylchlorid |
| DE3442176A1 (de) * | 1984-11-17 | 1986-05-28 | Henkel KGaA, 4000 Düsseldorf | Polyester als gleitmittel |
| FR2617839B1 (fr) * | 1987-07-06 | 1989-10-27 | Cetiom | Procedes de fabrication catalytique de monohydroxyacides gras satures ou de derives de ceux-ci |
| US5041621A (en) * | 1989-09-27 | 1991-08-20 | Eastman Kodak Company | Process for the preparation of dihydroxy esters |
| US6734315B1 (en) * | 2003-06-27 | 2004-05-11 | The C.P. Hall Company | Thin-film epoxidation of an unsaturated oil or alkyl fatty acid ester |
| MX2010008963A (es) | 2008-02-15 | 2011-02-24 | Union Carbide Chem Plastic | Sistema plastificante de reemplazo para formulaciones plastificadas con ftalato. |
| US8859654B2 (en) | 2009-09-30 | 2014-10-14 | Dow Global Technologies Llc | Heat stabilized polymeric composition with epoxidized fatty acid ester plasticizer |
| JP5841946B2 (ja) | 2009-09-30 | 2016-01-13 | ダウ グローバル テクノロジーズ エルエルシー | ヒマシ油のアセチル化誘導体およびそのエポキシ化脂肪酸エステルとのブレンド |
| KR101978520B1 (ko) | 2009-09-30 | 2019-05-14 | 다우 글로벌 테크놀로지스 엘엘씨 | 12-히드록시스테아르산의 아세틸화 글리세리드 및 에폭시드화 지방산 에스테르와의 블렌드 |
| US8552098B2 (en) * | 2009-09-30 | 2013-10-08 | Dow Global Technologies Llc | Purified acetylated derivatives of castor oil and compositions including same |
| CA2798296C (en) | 2010-05-10 | 2016-12-13 | Dow Global Technologies Llc | Flexible pvc compositions made with plasticizers derived from renewable sources |
| TW201209168A (en) | 2010-07-28 | 2012-03-01 | Dow Global Technologies Llc | Plasticizers made from oil extracted from microorganisms and polar polymeric compositions comprising the same |
| WO2013003225A2 (en) * | 2011-06-29 | 2013-01-03 | Dow Global Technologies Llc | Vegetable-oil derived plasticizer |
| KR102024408B1 (ko) | 2012-02-08 | 2019-09-23 | 다우 글로벌 테크놀로지스 엘엘씨 | 가소제 조성물 및 가소제 조성물의 제조 방법 |
| BR112014027887B1 (pt) | 2012-06-22 | 2021-01-05 | Dow Global Technologies Llc | composição polimérica e condutor revestido |
| CA2872524C (en) | 2012-06-26 | 2021-02-16 | Dow Global Technologies Llc | Plasticizers and plasticized polymeric compositions |
| EP2909261B1 (en) | 2012-10-18 | 2019-04-03 | Dow Global Technologies LLC | Epoxidized fatty acid alkyl ester plasticizers and methods for making epoxidized fatty acid alkyl ester plasticizers |
| KR102012540B1 (ko) | 2012-11-12 | 2019-08-20 | 다우 글로벌 테크놀로지스 엘엘씨 | 에폭시화 지방산 알킬 에스테르의 제조 방법 |
| JP6192733B2 (ja) | 2012-11-12 | 2017-09-06 | ダウ グローバル テクノロジーズ エルエルシー | エポキシ化脂肪酸アルキルエステル可塑剤およびエポキシ化脂肪酸アルキルエステル可塑剤を作製するための方法 |
| WO2022098824A1 (en) * | 2020-11-04 | 2022-05-12 | The United States Of America, As Represented By The Secretary Of Agriculture | Hydroxy fatty acid synthesis |
-
1970
- 1970-05-02 DE DE19702021530 patent/DE2021530A1/de active Pending
-
1971
- 1971-04-02 NL NL7104458A patent/NL7104458A/xx unknown
- 1971-04-27 US US00137968A patent/US3778465A/en not_active Expired - Lifetime
- 1971-04-29 GB GB02171/71A patent/GB1300526A/en not_active Expired
- 1971-04-29 BE BE766473A patent/BE766473A/xx unknown
- 1971-04-29 FR FR7115336A patent/FR2090932A5/fr not_active Expired
- 1971-04-29 CH CH629271A patent/CH546728A/xx not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3923393A1 (de) * | 1989-07-14 | 1991-01-17 | Henkel Kgaa | Verfahren zur altpapieraufbereitung |
| WO1991006531A1 (de) * | 1989-11-04 | 1991-05-16 | Henkel Kommanditgesellschaft Auf Aktien | Verfahren zur herstellung anionischer tenside mit sulfatstruktur |
| US5914006A (en) * | 1995-04-26 | 1999-06-22 | Henkel Kommanditgesellschaft Auf Aktien | Process for controlling the deposit of adhesive impurities from paper material suspensions |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7104458A (enExample) | 1971-11-04 |
| BE766473A (fr) | 1971-10-29 |
| US3778465A (en) | 1973-12-11 |
| GB1300526A (en) | 1972-12-20 |
| CH546728A (de) | 1974-03-15 |
| FR2090932A5 (enExample) | 1972-01-14 |
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| DE2021530A1 (de) | Verfahren zur Herstellung von Oxyfettsaeureestern | |
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| DE2838529C2 (enExample) | ||
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| EP0511986B1 (de) | Olefinisch ungesättigte addukte von ethylen an mehrfach ungesättigte fettsäuren bzw. fettsäureester und verfahren zu ihrer herstellung | |
| DE4002009A1 (de) | Gesaettigte, verzweigte fettsaeuren mit 21 bis 28 kohlenstoffatomen bzw. ester derselben mit c(pfeil abwaerts)1(pfeil abwaerts)-c(pfeil abwaerts)3(pfeil abwaerts)(pfeil abwaerts)6(pfeil abwaerts)-alkanolen, verfahren zu ihrer herstellung und ihre vrwendung | |
| EP0785929B1 (de) | Verfahren zur herstellung von epoxidgruppen enthaltenden organischen verbindungen | |
| DE10248159A1 (de) | Verfahren zur kontinuierlichen Hydrierung | |
| DE2106244A1 (enExample) | ||
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| DE4012873A1 (de) | Verfahren zur herstellung von einfach ungesaettigten fettsaeuren bzw. derivaten derselben durch katalytische hydrierung von mehrfach ungesaettigten fettsaeuren bzw. derivaten derselben | |
| DE1266295B (de) | Verfahren zur kontinuierlichen Herstellung von Fettalkoholen durch Hydrierung von Fettsaeuren | |
| AT331772B (de) | Verfahren zur herstellung von vorwiegend geradkettigen aldehyden |