CH189795A - Process for the preparation of 4-amino-6-methyl-3,4'dinitrodiphenylamine. - Google Patents
Process for the preparation of 4-amino-6-methyl-3,4'dinitrodiphenylamine.Info
- Publication number
- CH189795A CH189795A CH189795DA CH189795A CH 189795 A CH189795 A CH 189795A CH 189795D A CH189795D A CH 189795DA CH 189795 A CH189795 A CH 189795A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- dinitrodiphenylamine
- methyl
- sulfonic acid
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- 229960000583 acetic acid Drugs 0.000 claims description 4
- 239000012362 glacial acetic acid Substances 0.000 claims description 4
- PJRDJHIRYREDHP-UHFFFAOYSA-N 2-methyl-5-nitrobenzene-1,4-diamine Chemical compound CC1=CC(N)=C([N+]([O-])=O)C=C1N PJRDJHIRYREDHP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- GNTARUIZNIWBCN-UHFFFAOYSA-N 2-chloro-5-nitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1Cl GNTARUIZNIWBCN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 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
- 239000002253 acid Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von 4-Amino-6-methyl-3.4'-dinitrodiphenylamin. Gegenstand des vorliegenden Zusatzpa tentes ist ein Verfahren zur Darstellung von 4-Amino-6-methyl- 3. 4'- dinitrodiphenylamin, welches darin besteht, dass man 4-Nitro-l- chlorbenzol-2-sulfonsäure mit 1.4-Diamino- 3-nitro-6-methylbenzol kondensiert und die so erhaltene 4-Amino-6-methyl-3.4'-dinitro- diphenylamin-2'-sulfonsäure mit einem die Sul- fonsäuregruppe abspaltenden Mittel behandelt.
Die so erhaltene neue Verbindung stellt einen wichtigen Ausgangsstoff zur Herstel lung von Azofarbstoffen dar.
<I>Beispiel:</I> 300 Gewichtsteile 6-Methyl-3-nitro-1.4- diaminobenzol werden mit 680 Gewichtsteilen 4-nitt-o-l-chlorbenzol-2-sulfonsaurem Natrium (62-prozentig, berechnet auf Säure, Mol. Gew. 237,5), 150 Gewichtsteilen Calciumkarbonat und 2500 Gewichtsteilen Wasser 24 Stunden im Druckkessel auf 140<B>0</B> C erhitzt.
Der Kes- selinhalt wird sodann heiss filtriert und der Nutschenrückstand mit heissem Wasser ausge zogen; die vereinigten Filtrate werden mit 110 Gewichtsteilen Chlorcalcium versetzt und bis zur beginnenden Salzhautbildung eingedampft. Nach dem Erhalten wird das ausgeschiedene Calciumsalz der 4-Amino-6- methyl -3 . 4'- dinitrodiphenylamin - 2'- sulfon- säure abgesaugt, gepresst und getrocknet.
Zwecks Abspaltung der Sulfonsäuregruppe wird dasselbe in die 10fache Menge 78 % iger Schwefelsäure bei ungefähr 60 o C eingetragen und 15 Minuten auf<B>100'</B> C erhitzt. Hierauf wird die Reaktionsmasse in Eiswasser ein gerührt, die Fällung abgesaugt und mit Was ser ausgewaschen.
Um etwa noch vorhandene Sulfonsäure zu entfernen, wird das noch feuchte Produkt mit Wasser verrührt und mit wenig Ammoniak versetzt, kurz aufge kocht, nochmals abgesaugt, mit heissem Wasser nachgewaschen und getrocknet. Das erhaltene 4-Amino-6-methyl-3.4'- dinitrodiphenylamin lässt sich aus Dichlor- benzol oder Eisessig umkristallisieren. Das aus Eisessig umkristallisierte Produkt be sitzt nach dem Trocknen bei<B>110'</B> C den Schmelzpunkt 2210 C.
EMI0002.0006
Die <SEP> Analyse <SEP> ergab: <SEP> Gefunden: <SEP> N <SEP> 19,6 <SEP> %
<tb> Berechnet: <SEP> N <SEP> 19,45%
Process for the preparation of 4-amino-6-methyl-3,4'-dinitrodiphenylamine. The subject of the present additional patent is a process for the preparation of 4-amino-6-methyl- 3. 4'-dinitrodiphenylamine, which consists in that 4-nitro-1-chlorobenzene-2-sulfonic acid with 1,4-diamino-3- Nitro-6-methylbenzene condenses and the 4-amino-6-methyl-3,4'-dinitro-diphenylamine-2'-sulfonic acid thus obtained is treated with an agent which splits off the sulfonic acid group.
The new compound obtained in this way is an important starting material for the manufacture of azo dyes.
<I> Example: </I> 300 parts by weight of 6-methyl-3-nitro-1,4-diaminobenzene are mixed with 680 parts by weight of 4-nitt-ol-chlorobenzene-2-sulfonic acid sodium (62 percent, calculated on acid, mol. Wt 237.5), 150 parts by weight of calcium carbonate and 2500 parts by weight of water are heated to 140 ° C. in a pressure vessel for 24 hours.
The kettle contents are then filtered while hot and the residue on the suction filter is extracted with hot water; the combined filtrates are mixed with 110 parts by weight of calcium chloride and evaporated until the formation of a salt skin begins. After receiving, the precipitated calcium salt becomes the 4-amino-6-methyl -3. 4'-dinitrodiphenylamine - 2'-sulfonic acid sucked off, pressed and dried.
For the purpose of splitting off the sulfonic acid group, the same is added to 10 times the amount of 78% strength sulfuric acid at about 60 ° C. and heated to 100 ° C. for 15 minutes. The reaction mass is then stirred into ice water, the precipitate is filtered off with suction and washed out with water.
In order to remove any sulfonic acid that may still be present, the still moist product is stirred with water and mixed with a little ammonia, boiled briefly, suctioned off again, washed with hot water and dried. The 4-amino-6-methyl-3,4'-dinitrodiphenylamine obtained can be recrystallized from dichlorobenzene or glacial acetic acid. The product recrystallized from glacial acetic acid has a melting point of 2210 C after drying at <B> 110 '</B> C.
EMI0002.0006
The <SEP> analysis <SEP> resulted in: <SEP> Found: <SEP> N <SEP> 19.6 <SEP>%
<tb> Calculated: <SEP> N <SEP> 19.45%
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE189795X | 1934-06-02 | ||
| DE281134X | 1934-11-28 | ||
| CH184878T | 1935-05-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH189795A true CH189795A (en) | 1937-03-15 |
Family
ID=27177720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH189795D CH189795A (en) | 1934-06-02 | 1935-05-31 | Process for the preparation of 4-amino-6-methyl-3,4'dinitrodiphenylamine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH189795A (en) |
-
1935
- 1935-05-31 CH CH189795D patent/CH189795A/en unknown
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