CH200067A - Process for the preparation of a compound of the 4,5,9,10-dibenzo-3,8-pyrenequinone series. - Google Patents
Process for the preparation of a compound of the 4,5,9,10-dibenzo-3,8-pyrenequinone series.Info
- Publication number
- CH200067A CH200067A CH200067DA CH200067A CH 200067 A CH200067 A CH 200067A CH 200067D A CH200067D A CH 200067DA CH 200067 A CH200067 A CH 200067A
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- pyrenequinone
- dibenzo
- series
- sulfuric acid
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
- DGQLVPJVXFOQEV-JNVSTXMASA-N carminic acid Chemical compound OC1=C2C(=O)C=3C(C)=C(C(O)=O)C(O)=CC=3C(=O)C2=C(O)C(O)=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DGQLVPJVXFOQEV-JNVSTXMASA-N 0.000 claims description 6
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 244000061775 Olea africana Species 0.000 claims 1
- 235000002852 Olea africana Nutrition 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002697 manganese compounds Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 239000012063 pure reaction product Substances 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- WQEVDHBJGNOKKO-UHFFFAOYSA-K vanadic acid Chemical compound O[V](O)(O)=O WQEVDHBJGNOKKO-UHFFFAOYSA-K 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer Verbindung der 4,ö,9,10-Dibenzo-3,8-pyrenchinonreihe. Es wurde gefunden, dass man bei der Oxy- dation von Bz2. Bz2' - Dibenzanthronchinon mit Nitrosylschwefelsäure in Gegenwart von Schwefelsäure 5',6'-Phthaloyl-2-oxy-4,5,9,10- dibenzopyren-3,8-chinon erhält, das die fol gende Formel besitzt:
EMI0001.0011
Die neue Verbindung ist ein gelbrotes Mehl, das sich in konzentrierter Schwefel- säure mit karminroter Farbe löst und eine karminrote bis violette güpe liefert. Seine Alkalisalze färben Baumwolle in braunviolet ten Tönen.
Die Oxydation wird durch Zusatz gerin ger Mengen katalytisch wirkender Stoffe wie Vanadinsäure, Selen-, Quecksilber- oder Man ganverbindung begünstigt.
<I>Beispiel:</I> Eine Lösung von 10 Teilen Bz2. Bz2'- Dibenzanthronchinon, 0,2 Teilen Ammoriium- vanadat und 60 Teilen Nitrosylschwefelsäure mit einem Gehalt von 16,5 % salpetriger Säure in 200 Teilen 82%iger Schwefelsäure wird so lange bei 120' C gerührt,
bis die Entwicklung nitroser Gase aufgehört hat und kein Dibenzanthronehinon mehr nachweisbar ist. Man kühlt die Mischung dann auf etwa 100 C ab, lässt 27 Teile Wasser zulaufen, saugt nach dem Abkühlen auf etwa 70 C ,die ausgeschiedenen braunvioletten Nadeln ab und wäscht sie zunächst mit etwa 80 % iger Schwefelsäure und dann mit Wasser, wobei sie eine leuchtend orange Farbe annehmen.
Das so in guter Ausbeute erhaltene 5', 6'- Phthaloyl - 2 -oxy -4,5,9,10- dibenzopyren- 3,8 - chinon ist in den meisten organischen Flüs sigkeiten schwer löslich, leicht löslich in konzentrierter Schwefelsäure mit karminroter Farbe. Es liefert aus einer karminroten güpe auf Baumwolle braunviolette Färbungen, die bei der Hydrolyse in ein kräftiges Orange übergehen.
Aus den schwefelsauren Mutter laugen lassen sich noch weitere Mengen eines weniger reinen Umsetzungsproduktes ab scheiden.
Process for the preparation of a compound of the 4, δ, 9,10-dibenzo-3,8-pyrenequinone series. It was found that the oxidation of Bz2. Bz2 '- dibenzanthronequinone with nitrosylsulfuric acid in the presence of sulfuric acid 5', 6'-phthaloyl-2-oxy-4,5,9,10-dibenzopyrene-3,8-quinone, which has the following formula:
EMI0001.0011
The new compound is a yellow-red flour that dissolves in concentrated sulfuric acid with a carmine-red color and gives it a carmine-red to purple color. Its alkali salts dye cotton in brown-violet tones.
The oxidation is promoted by the addition of small amounts of catalytically active substances such as vanadic acid, selenium, mercury or manganese compounds.
<I> Example: </I> A solution of 10 parts Bz2. Bz2'-dibenzanthronequinone, 0.2 parts of ammonium vanadate and 60 parts of nitrosylsulfuric acid with a content of 16.5% nitrous acid in 200 parts of 82% sulfuric acid is stirred at 120 ° C.
until the development of nitrous gases has ceased and no more dibenzanthronehinone can be detected. The mixture is then cooled to about 100 ° C., 27 parts of water are run in, and after cooling to about 70 ° C., the brown-violet needles that have separated out are suctioned off and washed first with about 80% sulfuric acid and then with water, making them glow take on orange color.
The 5 ', 6'-phthaloyl-2-oxy -4,5,9,10-dibenzopyrene-3,8-quinone obtained in this way in good yield is sparingly soluble in most organic liquids, easily soluble in concentrated sulfuric acid with carmine-red Colour. From a carmine-red güpe on cotton, it produces brown-violet colorations that turn into a strong orange on hydrolysis.
Further quantities of a less pure reaction product can be separated from the sulfuric acid mother liquors.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200067X | 1936-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH200067A true CH200067A (en) | 1938-09-30 |
Family
ID=5759216
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH200067D CH200067A (en) | 1936-09-30 | 1937-07-17 | Process for the preparation of a compound of the 4,5,9,10-dibenzo-3,8-pyrenequinone series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH200067A (en) |
-
1937
- 1937-07-17 CH CH200067D patent/CH200067A/en unknown
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