CH189794A - Process for the preparation of a condensation product from phloroglucinol and 1-amino-4-nitrobenzene. - Google Patents
Process for the preparation of a condensation product from phloroglucinol and 1-amino-4-nitrobenzene.Info
- Publication number
- CH189794A CH189794A CH189794DA CH189794A CH 189794 A CH189794 A CH 189794A CH 189794D A CH189794D A CH 189794DA CH 189794 A CH189794 A CH 189794A
- Authority
- CH
- Switzerland
- Prior art keywords
- nitrobenzene
- amino
- phloroglucinol
- preparation
- condensation product
- Prior art date
Links
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 title claims description 7
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 title claims description 7
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 title claims description 6
- 229960001553 phloroglucinol Drugs 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000007859 condensation product Substances 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 1
- RUOKPLVTMFHRJE-UHFFFAOYSA-N benzene-1,2,3-triamine Chemical compound NC1=CC=CC(N)=C1N RUOKPLVTMFHRJE-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Kondensationsproduktes aus Phloroglncin und 1-Amino-4-nitrobenzol. Gegenstand des vorliegenden Zusatzpa tentes ist ein Verfahren zur Darstellung eines Kondensationsproduktes aus Phloroglucin und und 1-Amino-4-nitrobenzol, bei dem noch zwei Hydroxylgruppen des Phlorogluoinkerns vorhanden sind, welches dadurch gekenn zeichnet ist, dass man Phloroglucin mit 1 t mino-4-nitrobenzol im Verhältnis 1 : 1 in Gegenwart von Wasser erhitzt.
Die so erhaltene neue Verbindung stellt ein wertvolles Zwischenprodukt für die Her stellung von Farbstoffen oder andern orga nischen Verbindungen dar. Beispiel: 162 Gewichtsteile Phloroglucin, kristall wasserhaltig, werden in 4000 Gewichtsteilen Wasser mit 201 Gewichtsteilen 1-Amino- 4-nitrobenzol und 80 Volumteilen Salzsäure (spei. Gew. 1,163) oder der äquivalenten Menge Schwefelsäure 20 Stunden unter Rüh ren am Rückflusskühler gekocht.
Die Reak- tionsmasse wird heiss abgesaugt und der Rück stand mehrmals mit verdünnter Sodalösung ausgekocht. Die vereinigten Filtrate scheiden nach dem Erkalten etwas unverbrauchtes 1-Amino-4-nitrobenzol aus. Aus dem alkali schen Filtrat fällt beim Ansäuern mit Essig säure das 1 . 3-Dioxy-5-(4'-nitrophenylamino)- benzol als rotes Pulver aus; es hat den Schmelzpunkt 205 C und löst sich in heissem Wasser und verdünnter Sodalösung.
Process for the preparation of a condensation product from Phloroglncin and 1-Amino-4-nitrobenzene. The subject of the present additional patent is a process for the preparation of a condensation product of phloroglucinol and 1-amino-4-nitrobenzene, in which two hydroxyl groups of the phlorogluoin nucleus are still present, which is characterized in that one phloroglucinol with 1 t mino-4- nitrobenzene in a ratio of 1: 1 heated in the presence of water.
The new compound obtained in this way is a valuable intermediate for the manufacture of dyes or other orga African compounds. Example: 162 parts by weight of phloroglucinol, containing crystal water, are mixed with 201 parts by weight of 1-amino-4-nitrobenzene and 80 parts by volume of hydrochloric acid in 4000 parts by weight of water (spei. Gew. 1.163) or the equivalent amount of sulfuric acid boiled for 20 hours with stirring on the reflux condenser.
The reaction mass is suctioned off while hot and the residue is boiled several times with dilute soda solution. The combined filtrates separate out some unused 1-amino-4-nitrobenzene after cooling. When acidifying with acetic acid, the 1 st precipitates from the alkaline filtrate. 3-Dioxy-5- (4'-nitrophenylamino) benzene as a red powder; it has a melting point of 205 C and dissolves in hot water and dilute soda solution.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE189794X | 1933-01-20 | ||
| CH184303T | 1934-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH189794A true CH189794A (en) | 1937-03-15 |
Family
ID=25720995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH189794D CH189794A (en) | 1933-01-20 | 1934-01-15 | Process for the preparation of a condensation product from phloroglucinol and 1-amino-4-nitrobenzene. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH189794A (en) |
-
1934
- 1934-01-15 CH CH189794D patent/CH189794A/en unknown
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