DE959550C - Process for the preparation of pyridine carboxylic acid esters - Google Patents
Process for the preparation of pyridine carboxylic acid estersInfo
- Publication number
- DE959550C DE959550C DEB21499A DEB0021499A DE959550C DE 959550 C DE959550 C DE 959550C DE B21499 A DEB21499 A DE B21499A DE B0021499 A DEB0021499 A DE B0021499A DE 959550 C DE959550 C DE 959550C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- carboxylic acid
- pyridine carboxylic
- acid esters
- addition
- 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.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
AUSGEGEBEN AM 7. MÄRZ 1957ISSUED MARCH 7, 1957
B si4PP IVb /12 pB si4PP IVb / 12 p
Zusatz zum. Patent 942Addition to. Patent 942
Gegenstand des Patents 942 509 ist eän Viarfahren zur Herstellung von Estern der Nicotinsäure, hei 'dem man freie Nicotinsäure mit überschüssigem Mengen vorn ein- oder mehrwertigen, äthiergaruppenfneiiien Alkoholen ohne Zuislatz 'van. Kktalysatofneni und ohne Entfernung des entstehenden Waisisieins in Druckgefäßen auf 120 bis 2oo° erhitzt.The subject of patent 942 509 is a process for the production of esters of nicotinic acid, that is to say free nicotinic acid with excess amounts of mono- or polyvalent, ethereal group-free alcohols without additives . Kktalysatofneni and heated to 120 to 200 ° in pressure vessels without removing the resulting orphan.
Gemäß dem ersten. Zuisatzpatent 957 032 werden nach, der gleichen Methode auch die Ester von anderen Pyridi-naarbionisäuren hergestellt.According to the first. Additional patent 957 032 will be according to the same method, the esters of other pyridienarbionic acids are also produced.
Es wurde nun gefunden, daß man die' Herstellung von Pyridincarbonsäureestern besonders vorteilhaft in der Weise ausführen kann, daß man eine Lösung bzw. Aufschlämmung der Pyridincarbonsäure in einer überschüssigen Menge eines ein- oder mehrwertigen äthergruppenfreien Alkohols ohne Zusatz von Katalysatoren und ohne Entfernung des entstehenden Wassers kontinuierlich durch auf· etwa 150 bis 2ooc erhitzte Druckrohre pumpt. Dabei benötigt man erheblich weniger Alkohol als beim diskontinuierlichen Verfahren; überdies wird die Reaktionszeit wesentlich verkürzt und die Ausbeute verbessert.It has now been found that the 'preparation of pyridine carboxylic acid esters can be carried out particularly advantageously by a solution or suspension of the pyridine carboxylic acid in an excess amount of a monohydric or polyhydric ether group-free alcohol without the addition of catalysts and without removing the water formed pumps continuously through pressure pipes heated to approx. 150 to 2oo c. Significantly less alcohol is required here than with the discontinuous process; In addition, the reaction time is significantly shortened and the yield is improved.
Der überschüssige Alkohol wild beim Entspannen des Reaktionsgemisches in der Hitze bereits größten-The excess alcohol wildly when the reaction mixture is relaxed in the heat is already greatest-
teils verdampft. Aus dem Rückstand gewinnt man den Ester in üblicher Weise.partly evaporated. The ester is obtained from the residue in the usual way.
Beispiel ιExample ι
Eine etwa ioo° warme Lösung von ioog Isonicotinsäure in 400 g n-Propanol wird derart durch ein 60 m langes, auf 2000 .geheiztes Rohrschlangensystem aus rostfreiem Stahl gepumpt, daß die Verweilzeit 6 bis 7 Stunden beträgt. Das Reaktionsgemisch wird direkt in eine auf 110 bis 1200 geheizte Kolonne entspannt, in der das überschüssige n-Propanol verdampft. Die nicht verdampften Anteile ergeben bei der fraktionierten Destillation bei vermindertem Druck in nahezu quantitativer Ausbeute den Isonicotinsäure-n-propylester vom Kp.2O 1280.An approximately ioo ° ioog warm solution of isonicotinic acid in 400 g n-propanol is pumped such through a 60 m long, 200 0 .geheiztes coil system consisting of stainless steel, that the residence time is 6 to 7 hours. The reaction mixture is laid directly into a 110 to 120 to 0 heated column in which the excess n-propanol is evaporated. The fractions that have not evaporated give the isonicotinic acid n-propyl ester with a boiling point of 20 128 0 in the fractional distillation at reduced pressure.
In entsprechender Weise kann man Ester der Nicotinsäure und anderer Pyridincarbonsäuren herätellen. Esters of nicotinic acid and other pyridinecarboxylic acids can be prepared in a corresponding manner.
Man pumpt durch das im Beispiel 1 beschriebene, auf 150 bis i6o° beheizte Rohrschlangensystem eine auf 'etwa ioo° vorgewärmte Mischung aus 100 g Nicotinsäure und 300 g Benzylalkohol, derart, daß as die Verweilzeit 7 bis 8 Stunden beträgt. Bei der fraktionierten Destillation des Reaktionsproduktes unter vermindertem Druck erhält man neben unverändertem Benzylalkohol den unter 2 mm Druck bei bis 169° übergehenden Nicotinsäurebenzylester in einer Ausbeute von etwa 650/0 der Theorie.One pumps through the pipe coil system, which is described in Example 1 and heated to 150 to 160 ° Mixture of 100 g preheated to about 100 ° Nicotinic acid and 300 g of benzyl alcohol, such that as the residence time is 7 to 8 hours. In the fractional distillation of the reaction product under reduced pressure, in addition to unchanged benzyl alcohol, the under 2 mm pressure is obtained Benzyl nicotinate transitioning to 169 ° in a yield of about 650/0 of theory.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB21499A DE959550C (en) | 1952-08-07 | 1952-08-07 | Process for the preparation of pyridine carboxylic acid esters |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB21499A DE959550C (en) | 1952-08-07 | 1952-08-07 | Process for the preparation of pyridine carboxylic acid esters |
Publications (1)
Publication Number | Publication Date |
---|---|
DE959550C true DE959550C (en) | 1957-03-07 |
Family
ID=6960659
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEB21499A Expired DE959550C (en) | 1952-08-07 | 1952-08-07 | Process for the preparation of pyridine carboxylic acid esters |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE959550C (en) |
-
1952
- 1952-08-07 DE DEB21499A patent/DE959550C/en not_active Expired
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