DE2250470A1 - Verfahren zum dimerisieren ungesaettigter fettsaeuren und fettsaeureester - Google Patents
Verfahren zum dimerisieren ungesaettigter fettsaeuren und fettsaeureesterInfo
- Publication number
- DE2250470A1 DE2250470A1 DE19722250470 DE2250470A DE2250470A1 DE 2250470 A1 DE2250470 A1 DE 2250470A1 DE 19722250470 DE19722250470 DE 19722250470 DE 2250470 A DE2250470 A DE 2250470A DE 2250470 A1 DE2250470 A1 DE 2250470A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- reaction
- catalysts
- fatty acids
- fatty acid
- 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 18
- -1 FATTY ACID ESTERS Chemical class 0.000 title claims description 9
- 230000000447 dimerizing effect Effects 0.000 title claims 2
- 235000014113 dietary fatty acids Nutrition 0.000 title description 25
- 229930195729 fatty acid Natural products 0.000 title description 25
- 239000000194 fatty acid Substances 0.000 title description 25
- 150000004665 fatty acids Chemical class 0.000 title description 19
- 239000003054 catalyst Substances 0.000 claims description 31
- 239000007858 starting material Substances 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 238000006471 dimerization reaction Methods 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000011148 porous material Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 14
- 239000000539 dimer Substances 0.000 description 11
- 235000010469 Glycine max Nutrition 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 4
- 229960004488 linolenic acid Drugs 0.000 description 4
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 4
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 4
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 4
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- PIFPCDRPHCQLSJ-WYIJOVFWSA-N 4,8,12,15,19-Docosapentaenoic acid Chemical compound CC\C=C\CC\C=C\C\C=C\CC\C=C\CC\C=C\CCC(O)=O PIFPCDRPHCQLSJ-WYIJOVFWSA-N 0.000 description 1
- FKLSONDBCYHMOQ-UHFFFAOYSA-N 9E-dodecenoic acid Natural products CCC=CCCCCCCCC(O)=O FKLSONDBCYHMOQ-UHFFFAOYSA-N 0.000 description 1
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PIFPCDRPHCQLSJ-UHFFFAOYSA-N Clupanodonic acid Natural products CCC=CCCC=CCC=CCCC=CCCC=CCCC(O)=O PIFPCDRPHCQLSJ-UHFFFAOYSA-N 0.000 description 1
- 241001137251 Corvidae Species 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- XZJZNZATFHOMSJ-KTKRTIGZSA-N cis-3-dodecenoic acid Chemical compound CCCCCCCC\C=C/CC(O)=O XZJZNZATFHOMSJ-KTKRTIGZSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 235000021290 n-3 DPA Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002904 solvent 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
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- IWPOSDLLFZKGOW-AATRIKPKSA-N trans-beta-octenoic acid Chemical compound CCCC\C=C\CC(O)=O IWPOSDLLFZKGOW-AATRIKPKSA-N 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 210000001170 unmyelinated nerve fiber Anatomy 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722250470 DE2250470A1 (de) | 1972-10-14 | 1972-10-14 | Verfahren zum dimerisieren ungesaettigter fettsaeuren und fettsaeureester |
| NL7312712A NL7312712A (enExample) | 1972-10-14 | 1973-09-14 | |
| BE136509A BE805877A (fr) | 1972-10-14 | 1973-10-10 | Procede perfectionne pour dimeriser des acides et esters gras insatures |
| IT2995173A IT995740B (it) | 1972-10-14 | 1973-10-10 | Procedimento per dimerizzare acidi grassi insaturi e loro esteri |
| FR7336592A FR2202874B1 (enExample) | 1972-10-14 | 1973-10-12 | |
| GB4776373A GB1430663A (en) | 1972-10-14 | 1973-10-12 | Process for the chemical dimerization of carboxylic acids |
| LU68604D LU68604A1 (enExample) | 1972-10-14 | 1973-10-12 | |
| JP11401273A JPS4974205A (enExample) | 1972-10-14 | 1973-10-12 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722250470 DE2250470A1 (de) | 1972-10-14 | 1972-10-14 | Verfahren zum dimerisieren ungesaettigter fettsaeuren und fettsaeureester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2250470A1 true DE2250470A1 (de) | 1974-04-18 |
Family
ID=5859052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722250470 Pending DE2250470A1 (de) | 1972-10-14 | 1972-10-14 | Verfahren zum dimerisieren ungesaettigter fettsaeuren und fettsaeureester |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4974205A (enExample) |
| BE (1) | BE805877A (enExample) |
| DE (1) | DE2250470A1 (enExample) |
| FR (1) | FR2202874B1 (enExample) |
| GB (1) | GB1430663A (enExample) |
| IT (1) | IT995740B (enExample) |
| LU (1) | LU68604A1 (enExample) |
| NL (1) | NL7312712A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0069405A1 (en) * | 1981-06-25 | 1983-01-12 | Unilever N.V. | Process for the trimerization of unsaturated fatty acids |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140284520A1 (en) * | 2013-03-20 | 2014-09-25 | Elevance Renewable Sciences, Inc. | Acid catalyzed oligomerization of alkyl esters and carboxylic acids |
| CN104817521B (zh) * | 2015-03-03 | 2016-09-28 | 中国林业科学研究院林产化学工业研究所 | 一种环氧二聚脂肪酸甲酯及其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3367952A (en) * | 1964-10-22 | 1968-02-06 | Arizona Chem | Polymerization of unsaturated fatty acids |
| US3661956A (en) * | 1969-05-01 | 1972-05-09 | Wolf Ltd Victor | Polymerised fatty acids and their esters |
-
1972
- 1972-10-14 DE DE19722250470 patent/DE2250470A1/de active Pending
-
1973
- 1973-09-14 NL NL7312712A patent/NL7312712A/xx unknown
- 1973-10-10 BE BE136509A patent/BE805877A/xx unknown
- 1973-10-10 IT IT2995173A patent/IT995740B/it active
- 1973-10-12 GB GB4776373A patent/GB1430663A/en not_active Expired
- 1973-10-12 LU LU68604D patent/LU68604A1/xx unknown
- 1973-10-12 JP JP11401273A patent/JPS4974205A/ja active Pending
- 1973-10-12 FR FR7336592A patent/FR2202874B1/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0069405A1 (en) * | 1981-06-25 | 1983-01-12 | Unilever N.V. | Process for the trimerization of unsaturated fatty acids |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2202874B1 (enExample) | 1976-06-18 |
| BE805877A (fr) | 1974-04-10 |
| NL7312712A (enExample) | 1974-04-16 |
| GB1430663A (en) | 1976-03-31 |
| JPS4974205A (enExample) | 1974-07-17 |
| IT995740B (it) | 1975-11-20 |
| LU68604A1 (enExample) | 1974-05-09 |
| FR2202874A1 (enExample) | 1974-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |