CH137635A - Process for the preparation of a condensation product from cyclohexanone. - Google Patents
Process for the preparation of a condensation product from cyclohexanone.Info
- Publication number
- CH137635A CH137635A CH137635DA CH137635A CH 137635 A CH137635 A CH 137635A CH 137635D A CH137635D A CH 137635DA CH 137635 A CH137635 A CH 137635A
- Authority
- CH
- Switzerland
- Prior art keywords
- condensation product
- cyclohexanone
- preparation
- around
- dyes
- Prior art date
Links
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims description 8
- 239000007859 condensation product Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eifies Kondensationsproduktes aus Cykloheganon. Im Hauptpatent ist ein Verfahren zur Darstellung von Kondensationsprodukten durch Erhitzen von primären, sekundären oder tertiären aromatischen Basen mit freier p-Stellung zur Aminogruppe mit hydroaro inatischen Ringketonen in Gegenwart von sauren Kondensationsmitteln beschrieben.
Vorliegendes Patent bezieht sich nun auf ein Verfahren zur Darstellung eines neuen Kondensationsproduktes der wahrscheinlichen Formel
EMI0001.0007
dadurch gekennzeichnet, dass man Anilin mit Cyklohexanon in Gegenwart eines sauren Kondensationsmittels auf höhere Temperatur erhitzt und aus dem erhaltenen Reaktions produkt die dreikernige Verbindung isoliert.
Das neue Kondensationsprodukt kristalli siert aus Benzin in langen, strahligen Nadeln vom Schmelzpunkt 111 (Erweichen bei 105') und siedet unter einem Druck von 12 mm bei etwa 275-2761. Es ist leicht löslich in Mineralsäuren, leicht diazotierbar und kuppelt zu Azofarbstoffen. Es soll als Zwischen produkt zur Herstellung von Farbstoffen dienen.
<I>Beispiel</I> Man erhitzt eine Lösung von 30 Teilen Cyklohexanon und 100 Teilen Anilin in<B>350</B> Teilen Salzsäure (d=1,06) in einem Auto klaven einige Stunden auf 140-150 (vergl. Beispiel 1 des Hauptpatentes), bläst das überschüssige Anilin aus der alkalisch ge stellten Reäktionsmasse mit Dampf ab und behandelt das zurückbleibende, helle, in der Kälte erstarrende Ö1 nach Filtrieren und Trocknen mit organischen Lösungsmitteln, zum Beispiel mit Äther, aus denen das reine dreikernige Produkt auskristallisiert.
Process for the preparation of a condensation product from Cycloheganon. The main patent describes a process for the preparation of condensation products by heating primary, secondary or tertiary aromatic bases with a free p-position to the amino group with hydroaro inatic ring ketones in the presence of acidic condensing agents.
This patent now relates to a method for preparing a new condensation product of the probable formula
EMI0001.0007
characterized in that aniline is heated with cyclohexanone in the presence of an acidic condensing agent to a higher temperature and the trinuclear compound is isolated from the reaction product obtained.
The new condensation product crystallizes from gasoline in long, pointed needles with a melting point of 111 (softening at 105 ') and boiling under a pressure of 12 mm at about 275-2761. It is easily soluble in mineral acids, easily diazotized and couples to form azo dyes. It is intended to serve as an intermediate product in the manufacture of dyes.
<I> Example </I> A solution of 30 parts of cyclohexanone and 100 parts of aniline in 350 parts of hydrochloric acid (d = 1.06) is heated to 140-150 (cf. Example 1 of the main patent), blows the excess aniline out of the alkaline reaction mass with steam and treats the remaining, light, in the cold solidifying oil after filtering and drying with organic solvents, for example with ether, from which the pure trinuclear Product crystallized out.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE137635X | 1927-09-22 | ||
| CH133476T | 1928-02-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH137635A true CH137635A (en) | 1930-01-15 |
Family
ID=25712084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH137635D CH137635A (en) | 1927-09-22 | 1928-02-08 | Process for the preparation of a condensation product from cyclohexanone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH137635A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3670024A (en) * | 1969-06-24 | 1972-06-13 | Bayer Ag | Process for the production of 4,4{40 -diaminodiaryl alkanes |
-
1928
- 1928-02-08 CH CH137635D patent/CH137635A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3670024A (en) * | 1969-06-24 | 1972-06-13 | Bayer Ag | Process for the production of 4,4{40 -diaminodiaryl alkanes |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH137635A (en) | Process for the preparation of a condensation product from cyclohexanone. | |
| CH138197A (en) | Process for the preparation of a condensation product from methyl cyclohexanone. | |
| CH138194A (en) | Process for the preparation of a condensation product from cyclohexanone. | |
| CH136921A (en) | Process for the preparation of a basic azo dye. | |
| CH138193A (en) | Process for the preparation of a condensation product from cyclohexanone. | |
| CH172360A (en) | Process for the preparation of an arylamide. | |
| DE545399C (en) | Process for the preparation of 2- [4'-oxybenzoyl] benzoic acid and its salts | |
| CH200904A (en) | Process for the preparation of a nitrogen-containing aromatic aldehyde. | |
| CH138192A (en) | Process for the preparation of a condensation product from cyclohexanone. | |
| CH126194A (en) | Process for the preparation of a benzobenzanthronecarboxylic acid. | |
| CH138195A (en) | Process for the preparation of a condensation product from cyclohexanone. | |
| CH139803A (en) | Process for the preparation of a condensation product from cyclohexanone. | |
| CH136559A (en) | Process for the production of a condensation product. | |
| CH143608A (en) | Process for the preparation of an acidic wool dye. | |
| CH157829A (en) | Process for the preparation of 5-methoxy-6-ethoxy-8-aminoquinoline. | |
| CH141764A (en) | Process for the preparation of a condensation product from cyclohexanone. | |
| CH139639A (en) | Process for the preparation of a condensation product from cyclohexanone. | |
| CH165824A (en) | Process for the preparation of an oxycarbazole carboxylic acid aryl amide. | |
| CH143704A (en) | Process for the preparation of a carbazole derivative. | |
| CH175232A (en) | Process for the preparation of an arylamide. | |
| CH143279A (en) | Process for the preparation of a 6-arylamino-2-naphthol-3-carboxylic acid. | |
| CH200910A (en) | Process for the preparation of a nitrogen-containing aromatic aldehyde. | |
| CH232026A (en) | Process for the production of a condensation product. | |
| CH165053A (en) | Process for the production of a new vat dye. | |
| CH205790A (en) | Process for the preparation of a highly substantive 2,3-oxynaphthoic acid arylide. |