CH190039A - Process for the production of an anthraquinone derivative. - Google Patents
Process for the production of an anthraquinone derivative.Info
- Publication number
- CH190039A CH190039A CH190039DA CH190039A CH 190039 A CH190039 A CH 190039A CH 190039D A CH190039D A CH 190039DA CH 190039 A CH190039 A CH 190039A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- carried out
- anthraquinone derivative
- weight
- parts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 title description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 150000001879 copper Chemical class 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Anthrachinonderivates. Gegenstand vorliegender Erfindung ist ein Verfahren zur Herstellung eines Anthra- chinonderivates durch Einwirkung von Halo genwasserstoff abspaltenden Mitteln auf 1 . 2'- Naphthylamino -1'- bromanthrachinon. Als Halogenwasserstoff abspaltendes Mittel sei Kaliumcarbonat oder Alkalihydroxyd ge nannt.
Die Reaktion wird zweckmässig in einem Lösungsmittel wie Nitrobenzol, Kresol, Benzylalkohol oder einem aliphatischen Alkohol wie N-Butylalkohol oder Amyl- alkohol oder Glykol durchgeführt. Die Ab spaltung von Halogenwasserstoff kann durch Zusatz kleiner Mengen Kupfer oder eines Kupfersalzes beschleunigt werden.
Das erhältliche Umsetzungsprodukt ist orange gefärbt und löst sich in konzentrierter Schwefelsäure mit zunächst grünlich blauer, dann rein blauer Farbe. Es soll als Küpen- farbstoff und als Zwischenprodukt zur Her stellung anderer Verbindungen (z. B. Sulfie- rungsprodukte oder saure Schwefelsäureester der Leukoverbindungen) angewandt werden.
<I>Beispiel 1:</I> 50 Gewichtsteile 1 . 2'-Naphthylamino-1'- bromanthrachinon (erhalten durch Einwir kung von 1 Mol Brom auf eine Suspension von 1 . 2' - Naphthylaminoanthrachinon in Nitrobenzol) werden in 750 Gewichtsteilen Äthylenglykol mit 18 Gewichtsteilen Kalium acetat so lange zum. ,Sieden erhitzt, bis kein Ausgangsmaterial mehr nachzuweisen ist.
Die erkaltete Schmelze wird abgesaugt, der Rückstand mit Glykol, Pyridin und zuletzt mit Wasser gewaschen. Das erhaltene Pro dukt ist das 3.4-Benzo-7.8-phthaloylcar- bazol.
<I>Beispiel 2:</I> Eine Mischung von 50 Gewichtsteilendes Ausgangskörpers gemäss Beispiel 1, 600 Ge wichtsteilen einer technischen Mischung ver schiedener hoch siedender Alkohole mit Dode- cylalkohol als Hauptvertreter und 9 Ge wichtsteilen Pottasche lässt man etwa 1.5 bis 30 Minuten unter Rühren sieden. Beim Er kalten scheidet sich das entstandene Carba- zol gut kristallisiert aus. Es wird abgesaugt, mit Pyridin, Alkohol und Wasser gewaschen; es ist mit dem Reaktionsprodukt gemäss Bei spiel 1 identisch.
Process for the production of an anthraquinone derivative. The present invention relates to a process for the production of an anthrachinone derivative by the action of agents which split off halogenated hydrogen on 1. 2'-naphthylamino -1'-bromoanthraquinone. Potassium carbonate or alkali metal hydroxide may be mentioned as an agent which splits off hydrogen halide.
The reaction is conveniently carried out in a solvent such as nitrobenzene, cresol, benzyl alcohol or an aliphatic alcohol such as n-butyl alcohol or amyl alcohol or glycol. The elimination of hydrogen halide can be accelerated by adding small amounts of copper or a copper salt.
The available reaction product is orange in color and dissolves in concentrated sulfuric acid with an initially greenish blue, then purely blue color. It should be used as a vat dye and as an intermediate product for the production of other compounds (e.g. sulphonation products or acidic sulfuric acid esters of leuco compounds).
<I> Example 1: </I> 50 parts by weight 1. 2'-Naphthylamino-1'-bromoanthraquinone (obtained by action of 1 mol of bromine on a suspension of 1. 2 '- Naphthylaminoanthraquinone in nitrobenzene) are in 750 parts by weight of ethylene glycol with 18 parts by weight of potassium acetate as long as. , Heated to boiling until no more starting material can be detected.
The cooled melt is filtered off with suction, the residue is washed with glycol, pyridine and finally with water. The product obtained is 3.4-benzo-7.8-phthaloylcar- bazole.
<I> Example 2: </I> A mixture of 50 parts by weight of the starting material according to Example 1, 600 parts by weight of a technical mixture of various high-boiling alcohols with dodecyl alcohol as the main representative and 9 parts by weight of potash is left in for about 1.5 to 30 minutes Stir simmer. When it is cold, the resulting carbazole separates out well crystallized. It is filtered off with suction, washed with pyridine, alcohol and water; it is identical to the reaction product according to Example 1.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE190039X | 1934-08-01 | ||
| CH186555T | 1935-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH190039A true CH190039A (en) | 1937-03-31 |
Family
ID=25721385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH190039D CH190039A (en) | 1934-08-01 | 1935-07-31 | Process for the production of an anthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH190039A (en) |
-
1935
- 1935-07-31 CH CH190039D patent/CH190039A/en unknown
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