WO1993014060A1 - Procede de fabrication d'acides gras oligomeres - Google Patents
Procede de fabrication d'acides gras oligomeres Download PDFInfo
- Publication number
- WO1993014060A1 WO1993014060A1 PCT/EP1993/000041 EP9300041W WO9314060A1 WO 1993014060 A1 WO1993014060 A1 WO 1993014060A1 EP 9300041 W EP9300041 W EP 9300041W WO 9314060 A1 WO9314060 A1 WO 9314060A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- molar ratio
- fatty acids
- carbon atoms
- esters
- Prior art date
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 25
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 25
- 239000000194 fatty acid Substances 0.000 title claims abstract description 25
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims description 18
- -1 unsaturated fatty acid esters Chemical class 0.000 claims abstract description 15
- 238000007142 ring opening reaction Methods 0.000 claims abstract description 12
- 150000002440 hydroxy compounds Chemical class 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 229920005862 polyol Polymers 0.000 claims description 8
- 150000003077 polyols Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229960003656 ricinoleic acid Drugs 0.000 claims description 5
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000539 dimer Substances 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 238000006735 epoxidation reaction Methods 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 3
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 125000000466 oxiranyl group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- XKGDWZQXVZSXAO-ADYSOMBNSA-N Ricinoleic Acid methyl ester Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC XKGDWZQXVZSXAO-ADYSOMBNSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- XKGDWZQXVZSXAO-UHFFFAOYSA-N ricinoleic acid methyl ester Natural products CCCCCCC(O)CC=CCCCCCCCC(=O)OC XKGDWZQXVZSXAO-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Classifications
-
- 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
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
Definitions
- the invention relates to a process for the production of oligomeric fatty acids by reacting epoxidized fatty acid esters with hydroxy compounds and subsequent saponification of the resulting bridged reaction products and dimer fatty acids based on epoxidized fatty acid esters and ricinoleic acid esters.
- Oligomeric fatty acids i.e. H. technical mixtures of acyclic and z. T. also cyclic di-, tri- and oligocarboxylic acids are important products which are used for the production of adhesives, paints, fibers, corrosion inhibitors and lubricants.
- oligomeric fatty acids dimer fatty acids are of particular importance. Such substances are usually obtained by oligomerizing unsaturated fatty acids at temperatures from 180 to 250 ° C. in the presence of clays, for example montmorillonites [fats, soaps, Anstrichstoff, T2, SSI (1970)].
- clays for example montmorillonites [fats, soaps, Anstrichstoff, T2, SSI (1970)].
- the process has the disadvantage that achieving satisfactory yields in the oligomerization requires not only comparatively high catalyst concentrations, but also drastic reaction conditions which are associated with high energy expenditure.
- German patent application DE 33 18 596 A1 reports that bridged species form as undesirable by-products when epoxidized fatty acid esters are reacted with excess polyhydroxy compounds. This publication does not, however, show how a process for the selective production of these substances has to be designed.
- the invention relates to a process for the preparation of oligomeric fatty acids, which is characterized in that epoxidation products of unsaturated fatty acid esters of the formula (I)
- R ⁇ CO for an aliphatic acyl radical with 16 to 22 carbon atoms and 1 to 5 double bonds
- R 2 is a linear or branched alkyl radical having 1 to 4 carbon atoms
- oligomeric, in particular dimeric fatty acids with high selectivity and in good yields can be obtained if, when opening epoxy esters with polyols, the molar conditions are chosen so that at least one oxirane group is available for each hydroxyl group of the polyol.
- Epoxidized fatty acid esters are known substances that can be obtained by the relevant methods of preparative organic chemistry. For their preparation, one can start, for example, from mono- or polyunsaturated fatty acid esters which are known in a manner known per se, e.g. B. be epoxidized by the in situ performic acid process.
- the unsaturated fatty acid esters can be completely or partially, for example 50 to 95 mol%, epoxidized.
- Suitable hydroxy compounds are polyols or lower alkyl ricinoleic acid esters.
- Polyols are understood to mean compounds which have 2 to 15, preferably 2 to 6 carbon atoms and 2 to 4 hydroxyl groups. Typical examples are ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,4-butanediol, glycerol, diglycerol, trimethylolpropane, pentaerythritol and bisphenol A.
- Typical examples of lower alkyl ricinoleic esters are esters of ricinoleic acid with linear or branched C1-C4 alcohols. Ricinoleic acid methyl ester is preferred.
- the molar ratio between epoxy compound and hydroxy compound can be 1: 1 to 10: 1.
- a molar ratio of 2: 1 to 5: 1 is preferred.
- the use ratio is selected within the limits specified so that at least one oxirane group is available for each hydroxyl group of the polyol used.
- Typical mineral acids or lower organic carboxylic acids come into consideration as acid catalysts for the ring opening reaction. Typical examples are sulfuric acid, phosphoric acid, formic acid and / or acetic acid.
- the acidic catalysts can be used in concentrations of 0.1 to 5% by weight, based on the starting materials.
- the ring opening reaction can be carried out at temperatures of 80 to 120, preferably 90 to 100 ° C. over a period of 1 to 10, preferably 3 to 6 hours. It is then advantageous to neutralize the catalyst acid with a base, for example sodium hydroxide or sodium methylate.
- a base for example sodium hydroxide or sodium methylate.
- the saponification of the ring opening products can be carried out in a manner known per se. It is recommended that at least for every mole of ester groups present in the crude product Use 1, preferably 1.1 to 2 mol of a base, for example sodium hydroxide solution and carry out the reaction under reflux over a period of 1 to 5 hours.
- the base should then be neutralized by adding a mineral acid, for example sulfuric acid.
- the invention further relates to dimer fatty acids which are obtained by reacting epoxidized fatty acid esters of the formula (I) in the presence of acidic catalysts with lower alkyl ricinoleic acid in a molar ratio of 1: 1 to 1.5: 1 and the resulting bridged ring ⁇ opening products then saponified in a manner known per se.
- the oligomeric fatty acids obtainable by the process according to the invention have pour point-lowering properties and are suitable, for example, for the production of lubricants in which they are present in amounts of 1 to 50, preferably 10 to 25% by weight, based on the composition ⁇ can be hold.
- Tab. 1 Ring opening of 9,10-epoxystearic acid methyl ester Theoretical key figures in () "
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epoxy Compounds (AREA)
Abstract
Des acides gras oligomères sont fabriqués de façon sélective et avec de bons rendements en faisant réagir des produits d'époxydation d'esters d'acides gras insaturés de formule (I): R1CO-OR2, dans laquelle R1CO désigne un reste acyle aliphatique de 16 à 22 atomes de carbone et de 1 à 5 doubles liaisons, et R2 désigne un reste alkyle linéaire ou ramifié de 1 à 4 atomes de carbone, en présence de catalyseurs acides, avec des composés hydroxy, dans un rapport molaire de 1:1 à 10:1, et en saponifiant ensuite, de façon connue en soi, les produits d'ouverture de cycle pontés résultants.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4201343.7 | 1992-01-20 | ||
| DE19924201343 DE4201343A1 (de) | 1992-01-20 | 1992-01-20 | Verfahren zur herstellung oligomerer fettsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1993014060A1 true WO1993014060A1 (fr) | 1993-07-22 |
Family
ID=6449845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1993/000041 WO1993014060A1 (fr) | 1992-01-20 | 1993-01-11 | Procede de fabrication d'acides gras oligomeres |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE4201343A1 (fr) |
| WO (1) | WO1993014060A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007006550A3 (fr) * | 2005-07-11 | 2007-05-18 | Plt Patent & Licence Trading L | Oligomeres d'acides gras a chaines lineaires et non ramifies, et medicaments renfermant des composes |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004031787A1 (de) | 2004-07-01 | 2006-01-26 | Cognis Deutschland Gmbh & Co. Kg | Viskositätssenker für hochviskose Polyole |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3066159A (en) * | 1960-11-29 | 1962-11-27 | Petrolite Corp | Reaction product of polyols and epoxidized fatty compounds |
| EP0113797A1 (fr) * | 1982-12-16 | 1984-07-25 | Henkel Kommanditgesellschaft auf Aktien | Compositions de résines alkydes comprenant des produits obtenus par ouverture de cycle d'alcools gras ou de dérivés d'acides gras époxydés comme composés à groupements hydroxyles |
| EP0127810A1 (fr) * | 1983-05-21 | 1984-12-12 | Henkel Kommanditgesellschaft auf Aktien | Acides hydroxyalkoxycarboxyliques et leurs sels, leurs procédés de préparation ainsi que leur utilisation |
| EP0353012A1 (fr) * | 1988-07-26 | 1990-01-31 | Nabisco Brands, Inc. | Polyesters pontés par une liaison éther |
| WO1991011424A1 (fr) * | 1990-01-26 | 1991-08-08 | Henkel Kommanditgesellschaft Auf Aktien | Composes alcoxyles prepares a partir de derives d'acide carboxylique epoxydes |
-
1992
- 1992-01-20 DE DE19924201343 patent/DE4201343A1/de not_active Withdrawn
-
1993
- 1993-01-11 WO PCT/EP1993/000041 patent/WO1993014060A1/fr active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3066159A (en) * | 1960-11-29 | 1962-11-27 | Petrolite Corp | Reaction product of polyols and epoxidized fatty compounds |
| EP0113797A1 (fr) * | 1982-12-16 | 1984-07-25 | Henkel Kommanditgesellschaft auf Aktien | Compositions de résines alkydes comprenant des produits obtenus par ouverture de cycle d'alcools gras ou de dérivés d'acides gras époxydés comme composés à groupements hydroxyles |
| EP0127810A1 (fr) * | 1983-05-21 | 1984-12-12 | Henkel Kommanditgesellschaft auf Aktien | Acides hydroxyalkoxycarboxyliques et leurs sels, leurs procédés de préparation ainsi que leur utilisation |
| EP0353012A1 (fr) * | 1988-07-26 | 1990-01-31 | Nabisco Brands, Inc. | Polyesters pontés par une liaison éther |
| WO1991011424A1 (fr) * | 1990-01-26 | 1991-08-08 | Henkel Kommanditgesellschaft Auf Aktien | Composes alcoxyles prepares a partir de derives d'acide carboxylique epoxydes |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007006550A3 (fr) * | 2005-07-11 | 2007-05-18 | Plt Patent & Licence Trading L | Oligomeres d'acides gras a chaines lineaires et non ramifies, et medicaments renfermant des composes |
| EP2216319A3 (fr) * | 2005-07-11 | 2010-11-24 | PLT Patent & Licence Trading Ltd. | Oligomères d'acides gras à chaines linéaires et non ramifiés, et médicaments les renfermant |
| US7964640B2 (en) | 2005-07-11 | 2011-06-21 | Plt Patent & License Trading Ltd. | Oligomers of straight-chain and unbranched fatty acids and drugs containing these |
Also Published As
| Publication number | Publication date |
|---|---|
| DE4201343A1 (de) | 1993-07-22 |
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