CH134830A - Process for the preparation of a dye intermediate of the benzanthrone series. - Google Patents
Process for the preparation of a dye intermediate of the benzanthrone series.Info
- Publication number
- CH134830A CH134830A CH134830DA CH134830A CH 134830 A CH134830 A CH 134830A CH 134830D A CH134830D A CH 134830DA CH 134830 A CH134830 A CH 134830A
- Authority
- CH
- Switzerland
- Prior art keywords
- bzl
- preparation
- sulfide
- melting point
- dye intermediate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical class C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 title description 2
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 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 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 229920001021 polysulfide Polymers 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical class [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-N sodium polysulfide Chemical compound [Na+].S HYHCSLBZRBJJCH-UHFFFAOYSA-N 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines Farbstoffzwischenproduktes der Benzanthronreihe. Gegenstand dieser Erfindung ist ein Ver fahren zur Darstellung eines Diphenoxy- Bzl.-Bzl'-benzanthronylsulfids
EMI0001.0005
welches dadurch gekennzeichnet ist, daB man Dibrom-Bzl-Bz.l'-benzanthronylsulfid vom Schmelzpunkt HO', welches man durch Um setzung von Brom-Bz-l-brombenzanthron vom Schmelzpunkt 255 bis 257 mit Natrium- sulfid erhalten kann, mit Phenol bei höherer Temperatur behandelt.
Das erhaltene Kon densationsprodukt kann als Zwischenprodukt für die Herstellung von Farbstoffen dienen. <I>Beispiel:</I> 50 Gewichtsteile DibrombenzaDthron.5-i- sulfid vom Schmelzpunkt<B>360',</B> welches man durch Umsetzung von Brom-Bz-l-brombenz- anthron vom Schmelzpunkt 255 bis 257 mit Natriumpolysulfid erhalten kann, werden mit 100 Gewichtsteilen Phenol, 15 Gewichtstei len entwässertem Kaliumkarbonat und 0,5 Gewichtsteilen Kupferpulver unter Rühren auf 160 bis 170 erhitzt, bis sich kein unver ändertes Ausgangsmaterial mehr nachweisen lässt.
Durch Auskochen mit verdünnter Na tronlauge wird das Umsetzungsprodukt vom Phenol befreit, abgesaugt und mit Wasser gewasehen. Es ist ein gelbbraunes Pulver und löst sich in konzentrierter Schwefelsäure mit grüner Farbe.
Process for the preparation of a dye intermediate of the benzanthrone series. This invention relates to a process for the preparation of a Diphenoxy- Bzl.-Bzl'-benzanthronyl sulfide
EMI0001.0005
which is characterized in that dibromo-Bzl-Bz.l'-benzanthronyl sulfide with a melting point of HO ', which can be obtained by reacting bromine-Bz-l-bromobenzanthrone with a melting point of 255 to 257 with sodium sulfide, with phenol treated at a higher temperature.
The condensation product obtained can serve as an intermediate for the production of dyes. <I> Example: </I> 50 parts by weight of DibrombenzaDthron.5-i-sulfide with a melting point of <B> 360 ', </B> which is obtained by reacting bromine-Bz-1-bromobenzanthrone with a melting point of 255 to 257 Sodium polysulfide can be obtained with 100 parts by weight of phenol, 15 parts by weight of dehydrated potassium carbonate and 0.5 parts by weight of copper powder heated to 160 to 170 with stirring until no unchanged starting material can be detected.
The reaction product is freed from the phenol by boiling with dilute sodium hydroxide solution, suction filtered and washed with water. It is a yellow-brown powder and dissolves in concentrated sulfuric acid with a green color.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE134830X | 1926-08-02 | ||
| CH130151T | 1927-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH134830A true CH134830A (en) | 1929-08-15 |
Family
ID=25711371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH134830D CH134830A (en) | 1926-08-02 | 1927-08-01 | Process for the preparation of a dye intermediate of the benzanthrone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH134830A (en) |
-
1927
- 1927-08-01 CH CH134830D patent/CH134830A/en unknown
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