DE58955C - Process for the preparation of tetraalkyldiamidodioxydiphenylmethanes - Google Patents
Process for the preparation of tetraalkyldiamidodioxydiphenylmethanesInfo
- Publication number
- DE58955C DE58955C DENDAT58955D DE58955DA DE58955C DE 58955 C DE58955 C DE 58955C DE NDAT58955 D DENDAT58955 D DE NDAT58955D DE 58955D A DE58955D A DE 58955DA DE 58955 C DE58955 C DE 58955C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- solution
- tetraalkyldiamidodioxydiphenylmethanes
- formaldehyde
- amidophenol
- 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 3
- 238000000034 method Methods 0.000 title claims 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 8
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims 1
- 238000006011 modification reaction Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged Effects 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
- 239000000126 substance Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical class CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHES /k IMPERIAL / k
PATENTSCHRIFTPATENT LETTERING
KL'ASSE 22: Farbstoffe, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
Patentirt Im Deutschen Reiche vom 37. Juni 1889 ab. ;Patented in the German Empire on June 37, 1889. ;
Lafst man Formaldehyd auf substituirte Metaamidophenole zweckmafsig bei Gegenwart einer Mineralsäure einwirken, so entsteht ein Di-If formaldehyde is added to substituted metaamidophenols, it is expedient in the presence of a Mineral acid act, this creates a di-
,OH,OH
phenylmethanderivat unter Anwendung von Dimethyl-m-amidophenol nach folgender Gleichung: phenylmethane derivative using Dimethyl-m-amidophenol according to the following equation:
/N(CHJ2 / N (CHJ 2
+ CH2O = CH2 + CH 2 O = CH 2
N (CHJ2 N (CHJ 2
Die Darstellung geschieht in folgender Weise:It is displayed in the following way:
1. Eine Lösung von 28 kg Dimethyl-mamidophenol in 60 i Alkohol wird mit einer ca. 30 procentigen wässerigen Lösung von 3 kg Formaldehyd versetzt. Das Gemisch erwärmt sich von selbst, und nach längerem Stehen bei gewöhnlicher Temperatur scheidet sich das gebildete Condensationsproduct (Tetramethyldiamidodioxydiphenilmethan) krystallisirt aus.1. A solution of 28 kg of dimethyl mamidophenol in 60 I alcohol is with a approx. 30 percent aqueous solution of 3 kg formaldehyde is added. The mixture heats up by itself, and after prolonged standing at ordinary temperature, the condensation product formed separates out (tetramethyldiamidodioxydiphenilmethane) crystallizes out.
Man reinigt es durch Umkrystallisiren aus Spiritus und erhalt so glänzende Blättchen vom Schmelzpunkt 1800C. Der Körper besitzt basische und saure Eigenschaften; aus der Lösung in Salzsäure wird er durch Soda, aus der Lösung in Natronlauge durch Essigsäure ausgefällt. It is purified by recrystallization from alcohol and obtained as shiny flakes of melting point 180 0 C. The body has basic and acidic properties; from the solution in hydrochloric acid it is precipitated with soda, from the solution in sodium hydroxide solution with acetic acid.
2. Zu einer Lösung von 33 kg Diäthyl-mamidophenol in 70 1 Methylalkohol und 10 1 concentrirter Salzsäure wird eine ca. 30 procentige wässerige Lösung von 3 kg Formaldehyd hinzugefügt. Nach längerem Stehen bei gewöhnlicher Temperatur versetzt man die Flüssigkeit mit einer Lösung von 15 kg Natriumacetat in 30 1 Methylalkohol, filtrirt das ausgeschiedene Condensationsproduct ab und reinigt es durch Umkrystallisiren. Es schmilzt bei 1650C. und gleicht in seinem chemischen Verhalten dem unter 1. erwähnten Methyldefivat. Die erhaltenen Producte sind einer industriellen Anwendung behufs Darstellung von Azofarbstoffen etc. fähig.2. To a solution of 33 kg of diethyl mamidophenol in 70 liters of methyl alcohol and 10 liters of concentrated hydrochloric acid, an approximately 30 percent aqueous solution of 3 kg of formaldehyde is added. After standing for a long time at ordinary temperature, the liquid is mixed with a solution of 15 kg of sodium acetate in 30 l of methyl alcohol, the precipitated condensation product is filtered off, and it is purified by recrystallization. It melts at 165 ° C. and is similar in its chemical behavior to the methyl defivate mentioned under 1. The products obtained are capable of industrial application for the preparation of azo dyes, etc.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE58955C true DE58955C (en) |
Family
ID=333211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT58955D Expired - Lifetime DE58955C (en) | Process for the preparation of tetraalkyldiamidodioxydiphenylmethanes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE58955C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2818433A (en) * | 1955-09-19 | 1957-12-31 | Monsanto Chemicals | Process for making methylenedianilines |
| US2974168A (en) * | 1955-09-19 | 1961-03-07 | Monsanto Chemicals | Process for making methylenedianiline |
-
0
- DE DENDAT58955D patent/DE58955C/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2818433A (en) * | 1955-09-19 | 1957-12-31 | Monsanto Chemicals | Process for making methylenedianilines |
| US2974168A (en) * | 1955-09-19 | 1961-03-07 | Monsanto Chemicals | Process for making methylenedianiline |
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