CH183384A - Process for the production of an anthraquinone derivative. - Google Patents
Process for the production of an anthraquinone derivative.Info
- Publication number
- CH183384A CH183384A CH183384DA CH183384A CH 183384 A CH183384 A CH 183384A CH 183384D A CH183384D A CH 183384DA CH 183384 A CH183384 A CH 183384A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- anthraquinone derivative
- solution
- diaminochrysazine
- blue
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 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 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 claims description 4
- GUXSVLKPLFZZEV-UHFFFAOYSA-N benzene;benzoyl chloride Chemical compound C1=CC=CC=C1.ClC(=O)C1=CC=CC=C1 GUXSVLKPLFZZEV-UHFFFAOYSA-N 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- 239000011877 solvent mixture Substances 0.000 claims description 4
- 238000001228 spectrum Methods 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 241000974482 Aricia saepiolus Species 0.000 description 1
- -1 benzoyl chloride-trichlorobenzene Chemical compound 0.000 description 1
- QBPFLULOKWLNNW-UHFFFAOYSA-N chrysazin Chemical compound O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O QBPFLULOKWLNNW-UHFFFAOYSA-N 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation 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 Herstellung eines Antlirachinonderivates. Das Hauptpatent betrifft ein Verfahren zur Herstellung eines Anthrachinonderivates, bei dem Diaminochrysazin der Formel:
EMI0001.0005
mit einem methylierend wirkenden Mittel so lange behandelt wird, bis das Spektrum einer entnommenen und aufgearbeiteten Probe in einem Benzoylchlorid-Benzolgemisch (1:5) erkennen lässt, dass zwei der Lösung des Diaminochrysazins in dem gleichen Lösungs- mittelgemisch charakteristische Absorptions banden; deren Maxima bei 610 pss und 570 ,uss liegen, praktisch eben verschwunden sind.
Es wurde nun gefunden, dass man ein ähnlich wertvolles, neues Anthrachinonderivat erhalten kann, wenn man Diaminochrysazin mit einem oxäthylierend wirkenden Mittel so lange behandelt, bis das Spektrum einer entnommenen und aufgearbeiteten Probe in einem Benzoylchlorid-Benzolgemisch (1 :5) erkennen lässt, dass die zwei erwähnten, der Lösung des Diaminochrysazins in dem glei chen Lösungsmittelgemisch charakteristischen Absorptionsbanden praktisch eben verschwun-_ den sind.
Geeignete, oxäthylierend wirkende Mittel sind beispielsweise Äthylenoxyd und Äthylen- chlorhydrin.
Das erhaltene Anthrachinonderivat liefert auf Acetatseide klare, blaue Töne von guter Ausgiebigkeit, löst sich in organischen Lö sungsmitteln mit grünstichigblauer, in kon zentrierter Schwefelsäure mit gelber, in Na tronlauge beim Erwärmen mit grünstichig- blauer und in alkalischer Natriumhydrosulfit- lösung mit gelbroter Farbe und kann auch als Zwischenprodukt für die Herstellung von Farbstoffen Verwendung finden.
<I>Beispiel 1:</I> Man erhitzt 10 Teile Diaminochrysazin mit 50 Teilen Äthylenchlorhydrin und 3 Teilen Natriumacetat in einem geeigneten Gefäss so lange zum Sieden, bis eine entnommene und aufgearbeitete Probe sich in einem Ben- zoylchlorid-Trichlorbenzolgemisch (1:5) mit blauer Farbe löst und die Lösung in einem Benzoylchlorid-Benzolgemisch (1: 5) ein Spek trum zeigt, in dem die zwei erwähnten, der Lösung des Ausgangsmaterials in dem glei chen Lösungsmittelgemisch charakteristischen Absorptionsbanden fast oder eben völlig ver schwunden sind.
Das Reaktionsgemisch wird darauf in Wasser gegossen, der ausgefallene Farbstoff abgesaugt, gewaschen und zur Farb- stoffpaste verarbeitet. <I>Beispiel 2:</I> Ein Gemisch aus 20 Teilen Diamino- chrysazin, 400 Teilen o-Dichlorbenzol, 10 Teilen Äthylenoxyd und 0,5 Teilen Natrium acetat wird im Autoklaven so lange auf höhere Temperaturen, z. B. 120-150 C, erhitzt, bis eine entnommene und aufge arbeitete Probe die in Beispiel 1 angegebenen Eigenschaften besitzt.
Nach Entfernung des o-Dichlorbenzols durch Wasserdampfdestilla- tion wird in üblicher Weise aufgearbeitet.
Process for the preparation of an antlirachinone derivative. The main patent relates to a process for the production of an anthraquinone derivative, in which diaminochrysazine of the formula:
EMI0001.0005
is treated with a methylating agent until the spectrum of a sample taken and processed in a benzoyl chloride-benzene mixture (1: 5) shows that two of the diaminochrysazine solution in the same solvent mixture bound characteristic absorption; whose maxima are at 610 pss and 570 pss, have practically just disappeared.
It has now been found that a similarly valuable, new anthraquinone derivative can be obtained if diaminochrysazine is treated with an oxidizing agent until the spectrum of a sample taken and processed in a benzoyl chloride-benzene mixture (1: 5) shows that the two absorption bands mentioned, characteristic of the solution of diaminochrysazine in the same solvent mixture, have practically just disappeared.
Suitable agents with an oxidizing effect are, for example, ethylene oxide and ethylene chlorohydrin.
The anthraquinone derivative obtained provides clear, blue tones on acetate silk with good abundance, dissolves in organic solvents with greenish blue, in concentrated sulfuric acid with yellow, in sodium hydroxide solution when heated with greenish-blue and in alkaline sodium hydrosulfite solution with yellow-red color and can can also be used as an intermediate for the production of dyes.
<I> Example 1: </I> 10 parts of diaminochrysazine with 50 parts of ethylene chlorohydrin and 3 parts of sodium acetate are heated to the boil in a suitable vessel until a sample that has been taken and worked up is in a benzoyl chloride-trichlorobenzene mixture (1: 5 ) with blue color and the solution in a benzoyl chloride-benzene mixture (1: 5) shows a spectrum in which the two mentioned absorption bands characteristic of the solution of the starting material in the same solvent mixture have almost or completely disappeared.
The reaction mixture is then poured into water, the precipitated dye is filtered off with suction, washed and processed into a dye paste. <I> Example 2: </I> A mixture of 20 parts of diamino chrysazine, 400 parts of o-dichlorobenzene, 10 parts of ethylene oxide and 0.5 part of sodium acetate is kept in the autoclave at higher temperatures, e.g. B. 120-150 C, heated until a sample taken and worked up has the properties specified in Example 1. Die Temperatures sind in der Example 1 in der von Example 1.
After the o-dichlorobenzene has been removed by steam distillation, it is worked up in the customary manner.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE183384X | 1933-11-01 | ||
| CH178821T | 1934-10-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH183384A true CH183384A (en) | 1936-03-31 |
Family
ID=25720219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH183384D CH183384A (en) | 1933-11-01 | 1934-10-18 | Process for the production of an anthraquinone derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH183384A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3195973A (en) * | 1960-04-02 | 1965-07-20 | Hoechst Ag | N-methylolated diamino-dihydroxyanthraquinones, mixtures thereof and their production |
-
1934
- 1934-10-18 CH CH183384D patent/CH183384A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3195973A (en) * | 1960-04-02 | 1965-07-20 | Hoechst Ag | N-methylolated diamino-dihydroxyanthraquinones, mixtures thereof and their production |
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