DE46869C - Process for the preparation of m-oxydiphenylamine BEzw. m-oxyphenyltolylamine - Google Patents
Process for the preparation of m-oxydiphenylamine BEzw. m-oxyphenyltolylamineInfo
- Publication number
- DE46869C DE46869C DENDAT46869D DE46869DA DE46869C DE 46869 C DE46869 C DE 46869C DE NDAT46869 D DENDAT46869 D DE NDAT46869D DE 46869D A DE46869D A DE 46869DA DE 46869 C DE46869 C DE 46869C
- Authority
- DE
- Germany
- Prior art keywords
- oxydiphenylamine
- preparation
- amidophenol
- bezw
- oxyphenyltolylamine
- 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 - Lifetime
Links
- 238000002360 preparation method Methods 0.000 title claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000004992 toluidines Chemical class 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Das m-Oxydiphenylamin und seine Homologen sind bis jetzt durch Condensation von Resorcin mit Anilin oder Toluidin bei Gegenwart von Chlorzink oder Chlorcalcium erhalten worden. Neue Untersuchungen haben ergeben, dafs sich die betreffenden Oxydiphenylaminverbindungen durch Condensation des m-Amidophenols mit den entsprechenden primären Aminen erhalten lassen. Es ist hierbei nicht erforderlich, die oben erwähnten Condensationsmittel anzuwenden, sondern es genügt, das Chlorhydrat des m-Amidophenols mit Anilin, Toluidin, Xylidin etc. oder die Chlorhydrate der letzteren Basen mit m- Amidophenol zu erhitzen.The m-oxydiphenylamine and its homologues are up to now by condensation of Resorcinol obtained with aniline or toluidine in the presence of zinc chloride or calcium chloride been. New investigations have shown that the oxydiphenylamine compounds in question can be obtained by condensation of the m-amidophenol with the corresponding primary amines. It is not necessary here to use the condensation agents mentioned above apply, but it is sufficient to combine the hydrochloride of m-amidophenol with aniline, Toluidine, xylidine etc. or the chlorohydrates of the latter bases with m-amidophenol heat.
Darstellung von m-Oxydiphenylamin.Preparation of m-oxydiphenylamine.
Es werden z. B.:There are z. B .:
10 kg salzsaures m-Amidophenol mit 6,5 bis 10 kg Anilin oder 10 kg m-Amidophenol mit 12 kg salzsaurem Anilin während· 8 Stunden im Autoclaven auf 210 bis 21 5 ° erhitzt.10 kg hydrochloric acid m-amidophenol with 6.5 to 10 kg aniline or 10 kg m-amidophenol with 12 kg of hydrochloric aniline for 8 hours heated in the autoclave to 210 to 21 5 °.
Das Reactionsproduct wird mit Wasser ausgelaugt, mit Natronlauge übersättigt und zur Entfernung von etwa noch vorhandenem Anilin mit Wasserdampf abgetrieben.The reaction product is leached with water, supersaturated with sodium hydroxide solution and used Removal of any aniline still present, stripped off with steam.
Aus der zurückbleibenden alkalischen Lösung des m-Oxydiphenylamins fällt dieses durch Ansäuern mit Essigsäure in Form einer rothbraunen Masse aus. Man extrahirt mit Salzsäure und fällt mit Natriumacetat. Zur Reinigung wird das so erhaltene m-Oxydiphenylamin in bekannter Weise mit überhitztem Wasserdampf destillirt und umkrystallisirt.From the remaining alkaline solution of the m-oxydiphenylamine this falls through acidification with acetic acid in the form of a red-brown mass. Extract with hydrochloric acid and falls with sodium acetate. For purification, the m-oxydiphenylamine obtained in this way is used in a known manner Way distilled with superheated steam and recrystallized.
Darstellungvonm-Oxyphenyl-p-Tolylamin. Preparation of m-oxyphenyl-p-tolylamine.
Dasselbe entsteht durch 8 stündiges Erhitzen von 10 kg salzsaurem m-Amidophenol mit 7,5 bis 10 kg p-Toluidin auf ca. 210 bis 2200.The same is formed by 8 hours of heating of 10 kg m-hydrochloric acid amidophenol with 7.5 to 10 kg of p-toluidine at about 210 to 220 0th
Die Reinigung geschieht wie beim m-Oxydiphenylamin. The cleaning is carried out as with m-oxydiphenylamine.
Darstellung von. m-Oxyphenyl-o-Toly 1-Display of. m-Oxyphenyl-o-Toly 1-
amin.amine.
Dieser Körper bildet sich in analoger Weise durch 8 stündiges Erhitzen von 10 kg salzsaurem m-Amidophenol mit 7,5 bis 10 kg o-Toluidin im Autoclaven auf 210 bis 2200.This body is formed in an analogous manner by 8 hours of heating of 10 kg m-hydrochloric acid amidophenol with 7.5 to 10 kg of o-toluidine in an autoclave at 210 to 220 0th
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE46869C true DE46869C (en) |
Family
ID=321946
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT46869D Expired - Lifetime DE46869C (en) | Process for the preparation of m-oxydiphenylamine BEzw. m-oxyphenyltolylamine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE46869C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0065720A1 (en) * | 1981-05-22 | 1982-12-01 | CASSELLA Aktiengesellschaft | Process for preparing hydroxyphenyl amine derivatives |
| US5560230A (en) * | 1993-09-13 | 1996-10-01 | Goldstar Co., Ltd. | Chaos washing machine and a method of washing thereof |
-
0
- DE DENDAT46869D patent/DE46869C/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0065720A1 (en) * | 1981-05-22 | 1982-12-01 | CASSELLA Aktiengesellschaft | Process for preparing hydroxyphenyl amine derivatives |
| US5560230A (en) * | 1993-09-13 | 1996-10-01 | Goldstar Co., Ltd. | Chaos washing machine and a method of washing thereof |
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