DE1216307B - Process for the preparation of nicotinic acid esters of polyhydric alcohols - Google Patents
Process for the preparation of nicotinic acid esters of polyhydric alcoholsInfo
- Publication number
- DE1216307B DE1216307B DEA30629A DEA0030629A DE1216307B DE 1216307 B DE1216307 B DE 1216307B DE A30629 A DEA30629 A DE A30629A DE A0030629 A DEA0030629 A DE A0030629A DE 1216307 B DE1216307 B DE 1216307B
- Authority
- DE
- Germany
- Prior art keywords
- nicotinic acid
- excess
- acid esters
- polyhydric alcohols
- production
- 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
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 12
- 150000005846 sugar alcohols Polymers 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 235000001968 nicotinic acid Nutrition 0.000 claims description 3
- 239000011664 nicotinic acid Substances 0.000 claims description 3
- 229960003512 nicotinic acid Drugs 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960001238 methylnicotinate Drugs 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VVEZBNVPLZZJBI-UHFFFAOYSA-N 5-hydroxypentyl pyridine-3-carboxylate Chemical compound OCCCCCOC(=O)C1=CC=CN=C1 VVEZBNVPLZZJBI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- -1 alkylene glycols Chemical class 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ISADYLURVDPAIP-UHFFFAOYSA-N 2,3-dihydroxypropyl pyridine-3-carboxylate Chemical compound OCC(O)COC(=O)C1=CC=CN=C1 ISADYLURVDPAIP-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- ILPDLILZCXQOPA-UHFFFAOYSA-N propane-1,2,3-triol pyridine-3-carboxylic acid Chemical compound OCC(O)CO.C(C1=CN=CC=C1)(=O)O ILPDLILZCXQOPA-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Nicotinsäureestern mehrwertiger Alkohole Von mehrwertigen Alkoholen, wie Glykol, Glycerin, Pentaerythrit u. a., wurden die durch Umsetzung mit Nicotinsäurechlorid vollständig acylierten Derivate bereits beschrieben. Nicotinsäureester von Polyolen mit einer freien Hydroxylgruppe werden von Z. Ve j d e 1 e k und Mitarbeitern für Alkylenglykole beschrieben (Referate in Chemical Abstracts, 47 [1953], Sp. 8068, i. u: 50 [1956], Sp.7149f.). Sie werden ebenfalls nach der Nicotinsäurechloridmethode dargestellt. Dabei entstehen beim Äthylenglykol Mono- und Diester der Nicotinsäure nebeneinander, während bei längerkettigen Glykolen die Monoester nur mit Ausbeuten von etwa 25°/o der Theorie erhalten wurden. (Ferner zu vergleichen: Chemical Abstracts 1958, Sp. 2933 e.) Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Nicotinsäureestern mehrwertiger Alkohole mit einer oder mehreren freien primären und bzw. oder sekundären Hydroxylgruppen aus einem niederen Alkylester der Nicotinsäure, vorzugsweise dem Methylester, das dadurch gekennzeichnet ist, daß der Ester mit einem zwei oder drei Hydroxylgruppen enthaltenden Alkohol in Dimethylformamid als Lösungsmittel bei Gegenwart von wasserfreiem Kaliumcarbonat als Katalysator bei Temperaturen von 50 bis 80"C umgesetzt wird. Man kann unter einem Vakuum von 30 bis 80 Torr arbeiten. Es entsteht, wenn man den mehrwertigen Alkohol im Überschuß von 200 bis 3000/o über die theoretische Menge anwendet, ein Monoester, während bei Anwendung eines Überschusses von weniger als 5001, über die theoretische Menge Polyester entstehen.Process for the preparation of nicotinic acid esters of polyhydric alcohols Of polyhydric alcohols such as glycol, glycerin, pentaerythritol and others, the derivatives already fully acylated by reaction with nicotinic acid chloride described. Nicotinic acid esters of polyols with a free hydroxyl group can be used described by Z. Ve j d e 1 e k and co-workers for alkylene glycols (Referate in Chemical Abstracts, 47 [1953], Sp. 8068, i. u: 50 [1956], Col. 7149f.). you will be also shown according to the nicotinic acid chloride method. Thereby arise at Ethylene glycol mono- and diesters of nicotinic acid side by side, while with longer-chain Glycols the monoesters were only obtained with yields of about 25% of theory. (Also to be compared: Chemical Abstracts 1958, Col. 2933 e.) Subject matter of the invention is a process for the preparation of nicotinic acid esters of polyhydric alcohols with one or more free primary and / or secondary hydroxyl groups a lower alkyl ester of nicotinic acid, preferably the methyl ester, which thereby is characterized in that the ester with one containing two or three hydroxyl groups Alcohol in dimethylformamide as a solvent in the presence of anhydrous potassium carbonate is reacted as a catalyst at temperatures of 50 to 80 "C. One can under work in a vacuum of 30 to 80 torr. It arises when you look at the multi-valued Alcohol used in excess of 200 to 3000 / o over the theoretical amount Monoester, while using an excess of less than 5001, over the theoretical amount of polyester.
Das erfindungsgemäße Verfahren hat außer dem Vorteil, daß wahlweise Mono- oder Polyester als leicht isolierbare Hauptprodukte entstehen, vor allem noch den Vorteil, daß das Verfahren einfacher als die bekannten Verfahren und die Ausbeute etwa doppelt so hoch, teilweise auch beträchtlich höher ist. The inventive method has the advantage that optionally Mono- or polyester emerge as easily isolable main products, especially still the advantage that the process is simpler than the known processes and the yield is about twice as high, in some cases considerably higher.
Die nach dem erfindungsgemäßen Verfahren hergestellten Nicotinsäureester mehrwertiger Alkohole mit freien Hydroxylgruppen sind therapeutisch wertvoll; sie haben gefäßerweiternde Wirkung und sind zum Teil sehr gut wasserlöslich. The nicotinic acid esters produced by the process according to the invention Polyhydric alcohols with free hydroxyl groups are therapeutically valuable; she have a vasodilating effect and some of them are very soluble in water.
Beispiele 1. Glycerin--mononicotinat 20 g Nicotinsäuremethylester (0,15 Mol), 54 g wasserfreies Glycerin (0,6 Mol) (Überschuß: 30001o) und 3 g wasserfreies Kaliumcarbonat werden in 250 ml Dimethylformamid gelöst bzw: suspendiert und 24 Stunden auf 65"C bei einem Vakuum von 50 bis 60 mm Hg erwärmt. Über eine kleine Kolonne mit angesetztem Kühler destilliert während dieser Zeit der gebildete Methylalkohol ab. Man entfernt das Lösungsmittel im Vakuum, extrahiert den Rückstand erschöpfend mit Aceton und entfernt auch das Aceton im Vakuum. Der zurückbleibende Acetonextrakt wird mehrmals mit siedendem Xylol oder Toluol digeriert, aus dem beim Abkühlen Glycerina-mononicotinat kristallin erhalten wird. Examples 1. Glycerol mononicotinate 20 g of methyl nicotinate (0.15 mol), 54 g of anhydrous glycerine (0.6 mol) (excess: 300010) and 3 g of anhydrous Potassium carbonate are dissolved or suspended in 250 ml of dimethylformamide and 24 Heated to 65 "C under a vacuum of 50 to 60 mm Hg. About a small Column with With the cooler attached, the methyl alcohol formed distills during this time away. The solvent is removed in vacuo and the residue is exhaustively extracted with acetone and also removes the acetone in vacuo. The remaining acetone extract is digested several times with boiling xylene or toluene, from which glycerine mononicotinate on cooling is obtained crystalline.
Schmelzpunkt: 78"C. Ausbeute: 80 bis 8501, der Theorie. Melting point: 78 "C. Yield: 80 to 8501, the theory.
2. Glykolmononicotinat 27,5 g Nicotinsäuremethylester (0,2 Mol) 50 g Äthylenglykol, wasserfrei (0,8 Mol) (Überschuß: 3000/o) und 3 g wasserfreies Kaliumcarbonat werden, wie im Beispiel 1 in 250 ml Dimethylformamid umgesetzt. Nach der Entfernung des Lösungsmittels nimmt man den Rückstand in gesättigter Kochsalzlösung auf und extrahiert erschöpfend mit Chloroform. Man entfernt das Lösungsmittel und destilliert im Hochvakuum. Glykolmononicotinat destilliert als farbloses Ö1 vom Kp.0,005 138 bis 140"C. Die Verbindung ist stark hygroskopisch, wird aber im verschlossenen Gefäß über P205 fest. 2. Glycol mononicotinate 27.5 g of methyl nicotinate (0.2 mol) 50 g ethylene glycol, anhydrous (0.8 mol) (excess: 3000 / o) and 3 g anhydrous potassium carbonate are implemented as in Example 1 in 250 ml of dimethylformamide. After removal of the solvent, the residue is taken up in saturated sodium chloride solution and extracted exhaustively with chloroform. The solvent is removed and the mixture is distilled in a high vacuum. Glycol mononicotinate distilled as a colorless oil with a boiling point of 0.005 138 up to 140 "C. The connection is strongly hygroscopic, but becomes in the closed vessel via P205.
Ausbeute: 7301o der Theorie. Yield: 73010 of theory.
3. 2,2-Diäthylpropandiol-(1,3)-mononicotinat 20 g Nicotinsäuremethylester (0,15 Mol) 60 g 2,2-Diäthylpropandiol-(1,3) (0,45 Mol) (Überschuß: 200 0/o) und 3 g wasserfreies Kaliumcarbonat werden in 250 ml Dimethylformamid nach Beispiell umgesetzt. Man filtriert vom Kaliumcarbonat ab, entfernt das Lösungsmittel und den größten Teil des Diolüberschusses im Vakuum und nimmt den Rückstand mit 2 n-HCl auf. Die saure Lösung wird mit Chloroform extrahiert. 3. 2,2-Diethylpropanediol- (1,3) -mononicotinate 20 g of methyl nicotinate (0.15 mol) 60 g of 2,2-diethylpropanediol- (1,3) (0.45 mol) (excess: 200 0 / o) and 3 g of anhydrous potassium carbonate are in 250 ml of dimethylformamide according to example implemented. The potassium carbonate is filtered off, the solvent and the most of the excess diol in vacuo and takes the residue with 2N HCl on. The acidic solution is extracted with chloroform.
Aus dem Extrakt kann der überschüssige Alkohol zurückgewonnen werden. Die wäßrige, saure Phase wird mit Soda alkalisiert und erneut mit Chloroform extrahiert. Man trocknet die Chloroformlösung über wasserfreiem Natriumsulfat, destilliert das Lösungsmittel ab und fraktioniert den Rückstand im Hochvakuum. Das 2,2-Diäthylpropandiol-(1,3-mononicotinat destilliert als farbloses Öl vom Kpo,ool 130 bis 140"C Ausbeute: 55°/0 der Theorie.The excess alcohol can be recovered from the extract. The aqueous, acidic phase is made alkaline with soda and extracted again with chloroform. The chloroform solution is dried over anhydrous sodium sulphate and this is distilled Solvent from and fractionated the residue in a high vacuum. The 2,2-diethylpropanediol- (1,3-mononicotinat distilled as a colorless oil from Kpo, ool 130 to 140 "C Yield: 55% of theory.
4. Glycerin-1,3-dinicotinat 27,5 g Nicotinsäuremethylester (0,2 Mol) 14 g wasserfreies Glycerin (0,15 Mol) (Überschuß: 500/o) und 3 g wasserfreies Kaliumcarbonat werden in 250 ml Dimethylformamid, wie oben, umgesetzt. Nach der Entfernung des - Lösungsmittels wird der Rückstand snit Wasser aufgenommen, die Lösung mit Kochsalz gesättigt und mit Chloroform extrahiert. Man wäscht mit wenig gesättigter Kochsalzlösung, trocknet mit Natriumsulfat und entfernt das Lösungsmittel. Der Rückstand wird nach kurzer Zeit fest und wird aus Alkohol umkristallisiert. Glycerindinicotinat schmilzt bei 115"C. 4.glycerin-1,3-dinicotinate 27.5 g nicotinic acid methyl ester (0.2 mol) 14 g of anhydrous glycerol (0.15 mol) (excess: 500 / o) and 3 g of anhydrous potassium carbonate are reacted in 250 ml of dimethylformamide as above. After removing the - Solvent, the residue is taken up with water, the solution with sodium chloride saturated and extracted with chloroform. Wash with a little saturated saline solution, dries with sodium sulfate and removes the solvent. The residue is after solid for a short time and is recrystallized from alcohol. Glycerine dinicotinate melts at 115 "C.
Ausbeute: 480/o der Theorie. Yield: 480 / o of theory.
5. Pentamethylenglykolmononicotinat 20 g Nicotinsäuremethylester (0,15 Mol), 60 g Pentamethylenglykol (0,6 Mol) (Überschuß: 3000/o) und 3 g wasserfreies Kaliumcarbonat werden in 250 nil Dimethylformamid nach Beispiel 1 umgesetzt. Man filtriert vom Kaliumcarbonat ab, entfernt das Lösungsmittel und etwa 20 bis 30 g des Pentandiols (Kp.,,l 85 bis 90"C. Dann nimmt man mit Wasser auf und extrahiert erschöpfend mit Äther. Der Ätherextrakt wird getrocknet und eingedampft. Auf dem Rückstand erhält man durch fraktionierte, Hochvakuumdestil- lation bei 0,001 mm und 157"C das Pentamethylenglykolmononicotinat. 5. Pentamethylene glycol mononicotinate 20 g of methyl nicotinate (0.15 mol), 60 g of pentamethylene glycol (0.6 mol) (excess: 3000 / o) and 3 g of anhydrous Potassium carbonate are converted into 250 nil dimethylformamide according to Example 1. Man filtered from the potassium carbonate, removed the solvent and about 20 to 30 g of pentanediol (boiling point "85 to 90" C. It is then taken up with water and extracted exhausting with ether. The ether extract is dried and evaporated. On the Residue is obtained by fractionated, high vacuum distillation lation at 0.001 mm and 157 "C the pentamethylene glycol mononicotinate.
Ausbeute: 70°/0 der Theorie. Das Pikrat schmilzt bei 195"C. Yield: 70% of theory. The picrate melts at 195 "C.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA30629A DE1216307B (en) | 1958-10-30 | 1958-10-30 | Process for the preparation of nicotinic acid esters of polyhydric alcohols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA30629A DE1216307B (en) | 1958-10-30 | 1958-10-30 | Process for the preparation of nicotinic acid esters of polyhydric alcohols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1216307B true DE1216307B (en) | 1966-05-12 |
Family
ID=6927276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA30629A Pending DE1216307B (en) | 1958-10-30 | 1958-10-30 | Process for the preparation of nicotinic acid esters of polyhydric alcohols |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1216307B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2054618A1 (en) * | 1969-07-07 | 1971-04-23 | Mar Pha Etu Expl Marques | |
| FR2457684A1 (en) * | 1979-06-01 | 1980-12-26 | Ferrokemia Ipari | COMPOSITIONS FOR USE AS COSMETICS AND PROCESS FOR THE PREPARATION OF THEIR ACTIVE INGREDIENTS |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2831854A (en) * | 1955-05-24 | 1958-04-22 | Procter & Gamble | Method for preparing fatty esters of non-reducing oligosaccharides in the presence of an amide |
-
1958
- 1958-10-30 DE DEA30629A patent/DE1216307B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2831854A (en) * | 1955-05-24 | 1958-04-22 | Procter & Gamble | Method for preparing fatty esters of non-reducing oligosaccharides in the presence of an amide |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2054618A1 (en) * | 1969-07-07 | 1971-04-23 | Mar Pha Etu Expl Marques | |
| FR2457684A1 (en) * | 1979-06-01 | 1980-12-26 | Ferrokemia Ipari | COMPOSITIONS FOR USE AS COSMETICS AND PROCESS FOR THE PREPARATION OF THEIR ACTIVE INGREDIENTS |
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