CH234588A - Process for the production of nicotinic acid. - Google Patents
Process for the production of nicotinic acid.Info
- Publication number
- CH234588A CH234588A CH234588DA CH234588A CH 234588 A CH234588 A CH 234588A CH 234588D A CH234588D A CH 234588DA CH 234588 A CH234588 A CH 234588A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- nicotinic acid
- pressure
- acid
- methyl
- Prior art date
Links
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
- C07D213/803—Processes of preparation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung von Nicotinsäure. Es wurde gefunden, dass man 2-Methyl- 5-äthylpyridin auf sehr einfache Weise in Nicotinsäure überführen kann, wenn man dieses bei erhöhter Temperatur unter Druck mit verdünnter Salpetersäure behandelt.
Man verwendet zweckmässig 5 bis 40 % ige, mit Vorteil etwa 20 % ige Säure. Die Seiten letten werden bei der Oxydation zunächst zu Carboxylgrüppen abgebaut, bei weiterem Erhitzen, beispielsweise auf 180 bis 220 , wird die in a-Stellung zum Stickstoffatom stehende Carboxylgruppe abgespalten. Durch Zusatz oxydationsbeschleunigender Katalysa toren, wie Eisen-, Mangan-, Kupfer- oder Vanadinverbindungen, kann die Umsetzungs temperatur herabgesetzt werden.
Man kann das Verfahren diskontinuierlich durchführen; vorteilhaft arbeitet man aber kontinuierlich, indem man beispielsweise das Reaktionsgut unter Druck durch ein be heiztes, mit Füllkörpern versehenes druck festes Rohr rieseln lässt und die entstehenden Gase durch ein auf einen bestimmten Druck eingestelltes Ventil entweichen lässt.
Die in folgendem Beispiel angegebenen Teile sind Gewichtsteile. <I>Beispiel:</I> 121 Teile 2=Methyl-5-äthylpyridin werden mit 1795 Teilen 20%i,-,er Salpetersäure im Druckgefäss erhitzt. Bei etwa 190 beginnt der Druck infolge der stattfindenden Um setzung über den durch den Dampfdruck der Ausgangsstoffe bedingten Druck zu steigen.
Nach weiterem langsamem Aufheizen auf 210 bis 215 steigen Druck und Temperatur von selbst noch an, bis bei etwa 235 die Reaktion wieder abklingt. Durch Eindampfen der erhaltenen Lösung und Umkristallisiere:n des Trockenrückstandes erhält man in sehr guter Ausbeute Nitotinsäure. Die Äthylgruppe ist also zur Carboxylgruppe oxydiert worden, während die Methylgruppe in der 2-Stellung bei der Oxydation abgespalten worden ist.
Process for the production of nicotinic acid. It has been found that 2-methyl-5-ethylpyridine can be converted into nicotinic acid in a very simple manner if this is treated with dilute nitric acid at elevated temperature under pressure.
It is advisable to use 5 to 40%, advantageously about 20%, acid. During the oxidation, the side lettuces are first broken down into carboxyl groups; on further heating, for example to 180 to 220, the carboxyl group in a position to the nitrogen atom is split off. By adding oxidation-accelerating cata- lysts, such as iron, manganese, copper or vanadium compounds, the reaction temperature can be reduced.
The process can be carried out batchwise; however, it is advantageous to work continuously by, for example, letting the reaction mixture trickle under pressure through a pressure-tight tube that is heated and provided with packing elements and letting the resulting gases escape through a valve set to a certain pressure.
The parts given in the following example are parts by weight. <I> Example: </I> 121 parts of 2 = methyl-5-ethylpyridine are heated in a pressure vessel with 1795 parts of 20% i, -, er nitric acid. At around 190, the pressure begins to rise above the pressure caused by the vapor pressure of the starting materials as a result of the conversion taking place.
After a further slow heating to 210 to 215, the pressure and temperature rise by themselves until the reaction subsides again at about 235. By evaporating the resulting solution and recrystallizing the dry residue, nitotinic acid is obtained in very good yield. The ethyl group has thus been oxidized to the carboxyl group, while the methyl group in the 2-position has been split off during the oxidation.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE234588X | 1941-12-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH234588A true CH234588A (en) | 1944-10-15 |
Family
ID=5892302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH234588D CH234588A (en) | 1941-12-31 | 1943-03-05 | Process for the production of nicotinic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH234588A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2702802A (en) * | 1951-12-27 | 1955-02-22 | Robert S Aries | Process of making isocinchomeronic acid and decarboxylation of same to niacin |
| US2708196A (en) * | 1951-12-27 | 1955-05-10 | Aries | Cyclic process for the preparation of isocinchomeronic acid and niacin and recovery of niacin |
-
1943
- 1943-03-05 CH CH234588D patent/CH234588A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2702802A (en) * | 1951-12-27 | 1955-02-22 | Robert S Aries | Process of making isocinchomeronic acid and decarboxylation of same to niacin |
| US2708196A (en) * | 1951-12-27 | 1955-05-10 | Aries | Cyclic process for the preparation of isocinchomeronic acid and niacin and recovery of niacin |
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