CH147687A - Process for the preparation of an aminodiphenylamine derivative. - Google Patents
Process for the preparation of an aminodiphenylamine derivative.Info
- Publication number
- CH147687A CH147687A CH147687DA CH147687A CH 147687 A CH147687 A CH 147687A CH 147687D A CH147687D A CH 147687DA CH 147687 A CH147687 A CH 147687A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminodiphenylamine
- derivative
- preparation
- base
- parts
- Prior art date
Links
- YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical class C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- RBKIPVPBQBMGNJ-UHFFFAOYSA-N 1-methoxy-2-nitrosobenzene Chemical compound COC1=CC=CC=C1N=O RBKIPVPBQBMGNJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical compound O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- -1 aminomethoxy Chemical group 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Aminodiphenylaminderivates. Vorliegendes Patent bezieht sich auf -ein Verfahren zur Herstellung eines Aminodi- phenylaminderivates, dadurch gekennzeichnet, dass man Nitrosobenzol mit o-Nitrosoanisol kondensiert und das Kondensationsprodukt mit einem Reduktionsmittel behandelt.
Die bisher nicht bekannte Base schmilzt naeh dem Reinigen über das Chlorhydrat und. Umkristallisieren aus Benzol bei 87 . Sie soll als Zwischenprodukt zur Herstellung von Farbstoffen verwendet werden.
Da die Base mit dem nach den Berichten der deutschen chemischen Gesellschaft, Bd. 42, Seite 1083, erhaltenen Aminomethogydiphenyl- amin nicht identisch ist, bleibt für dieselbe nur die Konstitution eines 4-Amino-3-meth- ogydiphenylamins übrig. <I>Beispiel:</I> Eine Lösung von 53,5 Teilen Nitroso- benzol und 68,5 Teilen o-Nitrosoanisol in 300 Teilen Eisessig wird in 21s Stunden in 1500 Teile Schwefelsäure von 66 Be bei 0-5 eintropfen gelassen.
Durch Eingiessen der Lösung in Kochsalzlösung wird das er haltene Kondensationsprodukt ausgefällt. Es schmilzt bei 1531. Es wird noch feucht in 3000 Teilen Wasser und 65 Teilen Ätz natronlauge von 38 Be gelöst und bei 60 mit einer Lösung von<B>175</B> Teilen gesehmol- zenem Schwefelnatrium in Wasser versetzt und eine halbe Stunde auf 80 erwärmt, wobei unter Hellfärbung der Lauge die Base als helles<B>Öl</B> ausfällt, das beim Abkühlen erstarrt und dann abgesaugt und ausge waschen wird.
Process for the preparation of an aminodiphenylamine derivative. The present patent relates to a process for the preparation of an aminodiphenylamine derivative, characterized in that nitrosobenzene is condensed with o-nitrosoanisole and the condensation product is treated with a reducing agent.
The previously unknown base melts after cleaning over the chlorohydrate and. Recrystallize from benzene at 87. It is intended to be used as an intermediate in the manufacture of dyes.
Since the base is not identical to the aminomethogydiphenylamine obtained according to the reports of the German Chemical Society, vol. 42, page 1083, only the constitution of a 4-amino-3-methogydiphenylamine remains for the same. <I> Example: </I> A solution of 53.5 parts of nitrosobenzene and 68.5 parts of o-nitrosoanisole in 300 parts of glacial acetic acid is allowed to drip into 1500 parts of sulfuric acid of 66 Be at 0-5 in 21s hours.
The condensation product obtained is precipitated by pouring the solution into saline solution. It melts at 1531. While still moist, it is dissolved in 3000 parts of water and 65 parts of caustic soda solution of 38 Be and, at 60, a solution of 175 parts of salted sulfuric sodium in water is added and it is increased for half an hour 80 heated, whereby the base precipitates as a light <B> oil </B> with a light coloration of the lye, which solidifies on cooling and is then suctioned off and washed out.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE147687X | 1929-02-15 | ||
| CH145992T | 1929-09-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH147687A true CH147687A (en) | 1931-06-15 |
Family
ID=25714778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH147687D CH147687A (en) | 1929-02-15 | 1929-09-20 | Process for the preparation of an aminodiphenylamine derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH147687A (en) |
-
1929
- 1929-09-20 CH CH147687D patent/CH147687A/en unknown
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