CH154992A - Process for the preparation of a diacylated diamine. - Google Patents
Process for the preparation of a diacylated diamine.Info
- Publication number
- CH154992A CH154992A CH154992DA CH154992A CH 154992 A CH154992 A CH 154992A CH 154992D A CH154992D A CH 154992DA CH 154992 A CH154992 A CH 154992A
- Authority
- CH
- Switzerland
- Prior art keywords
- diamine
- diacylated
- preparation
- benzidine
- parts
- Prior art date
Links
- 150000004985 diamines Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 3
- DLGBEGBHXSAQOC-UHFFFAOYSA-N 2-hydroxy-5-methylbenzoic acid Chemical compound CC1=CC=C(O)C(C(O)=O)=C1 DLGBEGBHXSAQOC-UHFFFAOYSA-N 0.000 claims description 2
- 239000003518 caustics Substances 0.000 claims description 2
- 150000008049 diazo compounds Chemical class 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines diaeylierten Diamins. Es wurde gefunden, dass man ein wert volles diacyliertes Diamin erhält, wenn man 2 Mol p-Kresothrsäure mit 1 Mol Benzidin kondensiert.
Das neue Produkt bildet ein grauweisses Pulver, das aus Pyridin umkristallisiert einen Zersetzungspunkt von 333 hat. Es löst sich in verdünnten Ätzalkalien leicht auf und zieht aus solchen Lösungen auf tierischer oder pflanzlicher Faser. Auf diesen Substraten vereinigt es sich mit Diazoverbindungen un ter Bildung echter Färbungen.
<I>Beispiel:</I> 76 Teile p-Kresotinsäure und 46 Teile Benzidin werden in 550 Teilen Toluol ein getragen. Bei zirka 90 lässt man innert zirka 1/z Stunde 34 Teile Phosphortrichlorid zu tropfen. Hierauf bringt man die Temperatur langsam auf<B>1100</B> und hält einige Stunden diese Temperatur inne. Dann wird das Re aktionsgemisch mit einem Überschuss an Soda versetzt und das Toluol mit Wasserdampf abgeblasen. Der Rückstand wird filtriert, mit Wasser nachgewaschen und durch Lösen in verdünnter Natronlauge, Filtrieren und Aus fällen mit Säuren gereinigt.
Statt in Toluol kann man in basischen Lösungsmitteln, wie zum Beispiel Diäthyl- anilin, arbeiten. In diesem Falle wird zweck mässig das rohe Kondensationsprodukt durch Eintragen der Reaktionsmasse in verdünnte Säuren gewonnen.
Process for the preparation of a diaylated diamine. It has been found that a valuable diacylated diamine is obtained if 2 moles of p-cresothric acid are condensed with 1 mole of benzidine.
The new product forms a gray-white powder which, when recrystallized from pyridine, has a decomposition point of 333. It dissolves easily in dilute caustic alkalis and from such solutions it draws on animal or vegetable fibers. On these substrates it combines with diazo compounds to form true colors.
<I> Example: </I> 76 parts of p-cresotinic acid and 46 parts of benzidine are introduced into 550 parts of toluene. At about 90, 34 parts of phosphorus trichloride are allowed to drip in about 1 / z hour. The temperature is then slowly brought to <B> 1100 </B> and held at this temperature for a few hours. Then the reaction mixture is mixed with an excess of soda and the toluene is blown off with steam. The residue is filtered, washed with water and purified by dissolving in dilute sodium hydroxide solution, filtering and precipitating with acids.
Instead of toluene, you can work in basic solvents such as diethyl aniline. In this case, the crude condensation product is advantageously obtained by introducing the reaction mass into dilute acids.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH152875T | 1930-09-27 | ||
| CH154992T | 1930-09-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH154992A true CH154992A (en) | 1932-05-31 |
Family
ID=25716041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH154992D CH154992A (en) | 1930-09-27 | 1930-09-27 | Process for the preparation of a diacylated diamine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH154992A (en) |
-
1930
- 1930-09-27 CH CH154992D patent/CH154992A/en unknown
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