CH190038A - Process for the production of an anthraquinone derivative. - Google Patents
Process for the production of an anthraquinone derivative.Info
- Publication number
- CH190038A CH190038A CH190038DA CH190038A CH 190038 A CH190038 A CH 190038A CH 190038D A CH190038D A CH 190038DA CH 190038 A CH190038 A CH 190038A
- Authority
- CH
- Switzerland
- Prior art keywords
- carried out
- production
- weight
- parts
- anthraquinone derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- 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 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910000831 Steel Inorganic materials 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000001879 copper Chemical class 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- -1 hydrogen halides Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000010959 steel Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Anthrachinonderipätes. Gegenstand vorliegender Erfindung ist ein Verfahren zur Herstellung eines Anthra- chinonderivates durch Einwirkung von Ha logenwasserstoff abspaltenden Mitteln auf Dibrom - 1 . 2'- naphthylaminoanthrachinon. Als Halogenwasserstoff abspaltende Mittel seien Alkalihydroxyd, Kaliumcarbonat und Kalinma.cetat genannt.
Die Reaktion wird zweckmässig in einem Lösungsmittel wie Benzylalkohol oder Nitrobenzol oder in ali- phatischen Alkoholen wie z. B. Amylalkohol, Heptylalkohol, Dodecylalkohol, Äthylen glykol oder Butylenglykol, vorteilhaft in Gegenwart von Kupfer oder einem Kupfer salz durchgeführt.
Das erhältliche Umsetzungsprodukt ist hellbraun gefärbt und löst sich in konzen trierter Schwefelsäure mit stahlblauer Farbe. Es soll als Nüpenfarbstoff und .als Zwi schenprodukt für die Herstellung anderer Verbindungen (z. B. Sulfierungsprodukte oder saure Schwefelsäureester der Leukover- bindungen) angewandt werden.
<I>Beispiel</I> r: 20 Gewichtsteile Dibrom-1 .2'-naphthyl- aminoanthraehinon (erhalten durch Bromie- ren von 1.
2'-Naphthylaminoanthrachinon in Nitrobenzol mit 2 Molen Brom) und 10- Ge wichtsteile galiumacetat lässt man in 300 Gewichtsteilen Athylenglykol so lange sie -den, bis die Farbstoffbildung beendet ist, wozu je nach dem -#Terteilungsb ad des Aus gangsmaterials etwa 2=4 :
Stunden benötigt werden. Nach dem Erkalten wird abgesaugt und mit Glykol, Alkohol und Wasser .ge waschen. Man erhält in sehr :guter Ausbeute ein Rohprodukt, dem erforderlichenfalls durch Lösungsmittel, wie kaltes Pyridin noch geringe Mengen von Nebenprodukten ent zogen werden können.
Dem entstandenen Produkt kommt sehr wahrscheinlich die For- mel eines im Naphtha.linkern mono-bromier- ten 3. 4-Benzo- 7 . 8-phthaloylcarbazols zu.
<I>Beispiel 2:</I> 10 Gewichtsteile des Ausboangsmaterials gemäss Beispiel 1, 4,3 Gewichtsteile Kalium- acetat und 200 Gewichtsteile Amylalkohol werden in einem Druckgefäss unter Rühren einige Stunden auf etwa 280 bis 2-50' C er hitzt, bis das Ausgangsmaterial verbraucht ist.
Die Aufarbeitung geschieht wie in Bei spiel 1 angegeben: man erhält gegebenenfalls nach dem Entfernen geringer Verunreini gungen mittels Pyridin, das Produkt ,gemäss Beispiel 1 in reiner Form.
<I>Beispiel 3:</I> Eine Mischung von 5 Gewichtsteilen Di- brom-1 . 2'-na-phthyla.minoanthrachinon in 50 Gewichtsteilen siedendem Benzylalkohol wird mit 1,5 Gewichtsteilen Kaliumacetat versetzt. Das Ausgangsmaterial .ist schon nach 1/2- bis 3/4stündigem Kochen nicht mehr nachweis bar. Nach .dem Erkalten wird das in guter Ausbeute auskristallisierernde Carbazol in üblicher Weise isoliert.
Process for the production of an anthraquinone chip. The present invention relates to a process for the preparation of an anthrachinone derivative by the action of agents which split off hydrogen halide on dibromine-1. 2'-naphthylaminoanthraquinone. Alkali hydroxide, potassium carbonate and Kalinma.cetat may be mentioned as agents which split off hydrogen halide.
The reaction is conveniently carried out in a solvent such as benzyl alcohol or nitrobenzene or in aliphatic alcohols such as. B. amyl alcohol, heptyl alcohol, dodecyl alcohol, ethylene glycol or butylene glycol, advantageously carried out in the presence of copper or a copper salt.
The available reaction product is light brown in color and dissolves in concentrated sulfuric acid with a steel blue color. It should be used as a pomaceous 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 </I> r: 20 parts by weight of dibromo-1,2'-naphthylaminoanthraehinone (obtained by brominating 1.
2'-Naphthylaminoanthraquinone in nitrobenzene with 2 moles of bromine) and 10 parts by weight of galium acetate are left in 300 parts by weight of ethylene glycol until the dye formation has ended, including about 2 = 4 depending on the - # Tteilungsb ad of the starting material :
Hours are needed. After cooling, it is vacuumed and washed with glycol, alcohol and water. A crude product is obtained in very good yield from which, if necessary, small amounts of by-products can be withdrawn by solvents such as cold pyridine.
The resulting product is very likely to have the formula of a 3,4-benzo-7 monobrominated in the naphtha linker. 8-phthaloylcarbazole too.
<I> Example 2: </I> 10 parts by weight of the output material according to Example 1, 4.3 parts by weight of potassium acetate and 200 parts by weight of amyl alcohol are heated in a pressure vessel with stirring for a few hours to about 280 to 2-50 ° C until the starting material has been used up.
The work-up is carried out as indicated in Example 1: the product according to Example 1 is obtained in pure form, if appropriate after removing minor impurities by means of pyridine.
<I> Example 3: </I> A mixture of 5 parts by weight of dibrom-1. 2'-na-phthyla.minoanthraquinone in 50 parts by weight of boiling benzyl alcohol is mixed with 1.5 parts by weight of potassium acetate. The starting material is no longer detectable after 1 / 2- to 3/4-hour boiling. After cooling, the carbazole which crystallizes out in good yield is isolated in the customary manner.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE190038X | 1934-08-01 | ||
| CH186555T | 1935-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH190038A true CH190038A (en) | 1937-03-31 |
Family
ID=25721384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH190038D CH190038A (en) | 1934-08-01 | 1935-07-31 | Process for the production of an anthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH190038A (en) |
-
1935
- 1935-07-31 CH CH190038D patent/CH190038A/en unknown
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