CH303276A - Process for the production of an intermediate product. - Google Patents
Process for the production of an intermediate product.Info
- Publication number
- CH303276A CH303276A CH303276DA CH303276A CH 303276 A CH303276 A CH 303276A CH 303276D A CH303276D A CH 303276DA CH 303276 A CH303276 A CH 303276A
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- production
- intermediate product
- formaldehyde
- nitrobenzene
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/51—Phenylenediamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Zwischenproduktes. Es wurde gefunden, dass man zu einem ":ertvollen Zwischenprodukt gelangt, wenn man 2,6-Dimethyl-l-nitrobenzol mit Formalde hyd oder formaldehydabgebenden Mitteln kon densiert und die so erhältliche Dinitrover- bindung zum Diamin reduziert.
Die neue Verbindung entspricht der For m e1
EMI0001.0009
und besitzt einen Schmelzpunkt von 147 bis 148 (unkorr.) und soll als Zwischenprodukt. zur Verstellung von Azofarbstoffen Verwen dung finden.
Die Kondensation des 2,6-Dimethyl-l- nitrobenzols mit Formaldehyd oder formalde- hydabgebenden Mitteln erfolgt in Gegenwart eines wasserabspaltenden Mittels, vorzugsweise in konzentrierter Schwefelsäure. Hierbei wer den unter Austritt von einem Molekül Wasser zwei Moleküle der Nitroverbindung mit. einem olekül Formaldehyd vereinigt. Man kann <B>1</B> hierbei auch eine Schwefelsäure verwenden, die freies Schwefeltrioxyd enthält, wenn man die Umsetzung unter solchen Bedingun gen ausführt, dass keine Sulfonierung statt findet.
Diese Umsetzung gelingt mit, sehr guter Ausbeute.
Die Reduktion der Dinitroverbindung zum Diamin kann nach an sich bekannten Me- thoden, beispielsweise mittels Eisenpulver und Salzsäure, erfolgen.
Beispiel: 500 Teile 100 .% ige Schwefelsäure werden auf 0 gekühlt und 302 Teile 2,6-Dimethyl-l- nitrobenzol unter gutem Rühren so zugegeben, da.ss die Temperatur nicht über + 3 steigt. Darauf werden 15 Teile Paraformaldehyd während 30 bis 40 Minuten so zugegeben, dass die Temperatur nicht über + 5 steigt. Dann wird eine Stunde bei 0 gerührt und darauf 14,1 Teile Paraformaldehyd bei gleichbleiben der Temperatur zugegeben.
Es wird 20 Stun den hei 5 bis 8 gerührt, auf 1200 Teile Eis gegossen und gewünsehtenfalls ein allfälliger geringer Überschuss an 2,6-Dimethyl-l-nitro- benzol durch Wasserdampfdestillation ent fernt. Der Rückstand wird scharf abgesaugt, in 500 Teilen Wasser von 55 angerührt, mit Natriumcarbonat (etwa 1,3 Teile) bleibend alkalisch gestellt, 15 Minuten bei 55 gerührt, bis ziun Erkalten weitergerührt, filtriert und der Rückstand mit kaltem Wasser neutral ge waschen.
Es werden über 300 Teile 3,3'- Dinitro - 2,4,2',4- - tetr amethyl - diphenylmethan vom Schmelzpunkt 153 bis 155 (unkorr.) er halten. Mehrmaliges Umkristallisieren aus Äthylalkohol ergibt ein analysenreines Pro dukt vom Schmelzpunkt 159 bis 160 (unkorr.).
500 Teile Eisenpulver, 645 Teile n-Butyl- a.lkohol und 93 Teile 30%ige Salzsäure wer den 30 Minuten unter gutem Rühren gekocht, auf 60 gekühlt und 62,8 Teile von dem ge mäss obigen Angaben erhaltenen rohen 3,3'- Dinitrö - 2,4,2',4' - t etr amethyl - diphenylmethan auf einmal zugegeben, wieder 30 Minuten ge kocht und auf 60 gekühlt und nochmals 62,8 Teile 3,3 - Dinitro - 2,4,2',4'-tetramethyl-di- phenylmethan auf einmal zugegeben.
Dann wird unter anteilweisem Zusatz von Eisen pulver und 30 % iger Salzsäure so lange weiter gekocht, bis die Reduktion des Nitrokörpers vollständig ist. Hierauf wird auf 80 gekühlt und Natriumcarbonat (etwa 140 Teile) bis zur schwach alkalischen Reaktion zugegeben und bei 80 filtriert. Der Rückstand wird zweimal mit je 1000 Raumteilen heissem Äthylalkohol extrahiert und filtriert. Die vereinigten Fil trate werden im Vakuum verdampft, der Rückstand in 1000 Teilen Wasser und 350 Tei len 30 % iger Salzsäure gelöst, mit 5 Teilen Aktivkohle 30 Minuten gekocht und heiss fil triert.
Das Filtrat wird mit 200 Teilen Na triumchlorid versetzt, kalt gerührt und die entstandene Suspension filtriert. Es wird auf diese Weise das Dichlorhydrat des 3,3'-Di- amino-2,4,2',4'-tetramethyl-diphenylmethan in guter Ausbeute (entsprechend über 90 Teilen freier Base) erhalten.
Process for the production of an intermediate product. It has been found that a "valuable intermediate" is obtained if 2,6-dimethyl-1-nitrobenzene is condensed with formaldehyde or formaldehyde-releasing agents and the thus obtainable dinitro compound is reduced to the diamine.
The new connection corresponds to the form e1
EMI0001.0009
and has a melting point of 147 to 148 (uncorr.) and is said to be an intermediate. find use to adjust azo dyes.
The condensation of 2,6-dimethyl-1-nitrobenzene with formaldehyde or formaldehyde-releasing agents takes place in the presence of a dehydrating agent, preferably in concentrated sulfuric acid. Here who the with the escape of one molecule of water with two molecules of the nitro compound. one molecule of formaldehyde combined. It is also possible to use a sulfuric acid which contains free sulfur trioxide if the reaction is carried out under such conditions that no sulfonation takes place.
This implementation succeeds with a very good yield.
The reduction of the dinitro compound to the diamine can be carried out according to methods known per se, for example using iron powder and hydrochloric acid.
Example: 500 parts of 100% strength sulfuric acid are cooled to 0 and 302 parts of 2,6-dimethyl-1-nitrobenzene are added with thorough stirring so that the temperature does not rise above +3. 15 parts of paraformaldehyde are then added over a period of 30 to 40 minutes in such a way that the temperature does not rise above + 5. The mixture is then stirred for one hour at 0 and 14.1 parts of paraformaldehyde are then added while the temperature remains the same.
It is stirred for 20 hours at a temperature of 5 to 8, poured onto 1200 parts of ice and, if desired, a small excess of 2,6-dimethyl-1-nitrobenzene is removed by steam distillation. The residue is suctioned off sharply, stirred in 500 parts of 55 water, made permanently alkaline with sodium carbonate (about 1.3 parts), stirred at 55 for 15 minutes, stirred until it cools down, filtered and the residue washed neutral with cold water.
There are over 300 parts of 3,3'-dinitro - 2,4,2 ', 4 - tetramethyl - diphenylmethane with a melting point of 153 to 155 (uncorrupted). Repeated recrystallization from ethyl alcohol results in an analytically pure product with a melting point of 159 to 160 (uncorr.).
500 parts of iron powder, 645 parts of n-butyl alcohol and 93 parts of 30% hydrochloric acid are boiled for 30 minutes with thorough stirring, cooled to 60 and 62.8 parts of the raw 3,3'- Dinitro-2,4,2 ', 4'-tetramethyl-diphenylmethane was added all at once, again boiled for 30 minutes and cooled to 60, and again 62.8 parts of 3,3-dinitro-2,4,2', 4 '-tetramethyl-diphenylmethane added all at once.
Then, with the partial addition of iron powder and 30% hydrochloric acid, further cooking until the reduction of the nitro body is complete. It is then cooled to 80 and sodium carbonate (about 140 parts) is added until the reaction is weakly alkaline and filtered at 80. The residue is extracted twice with 1000 parts by volume of hot ethyl alcohol and filtered. The combined Fil trates are evaporated in vacuo, the residue dissolved in 1000 parts of water and 350 parts of 30% hydrochloric acid, boiled with 5 parts of activated charcoal for 30 minutes and filtered hot.
The filtrate is mixed with 200 parts of sodium chloride, stirred while cold and the resulting suspension is filtered. In this way, the dichlorohydrate of 3,3'-di-amino-2,4,2 ', 4'-tetramethyl-diphenylmethane is obtained in good yield (corresponding to over 90 parts of free base).
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH303276T | 1951-10-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH303276A true CH303276A (en) | 1954-11-30 |
Family
ID=4491673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH303276D CH303276A (en) | 1951-10-02 | 1951-10-02 | Process for the production of an intermediate product. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH303276A (en) |
-
1951
- 1951-10-02 CH CH303276D patent/CH303276A/en unknown
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