CH290507A - Process for the production of a vat dye. - Google Patents
Process for the production of a vat dye.Info
- Publication number
- CH290507A CH290507A CH290507DA CH290507A CH 290507 A CH290507 A CH 290507A CH 290507D A CH290507D A CH 290507DA CH 290507 A CH290507 A CH 290507A
- Authority
- CH
- Switzerland
- Prior art keywords
- methylsulfon
- amino
- parts
- red
- production
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000984 vat dye Substances 0.000 title description 3
- GQWWDPHZIFNCTM-UHFFFAOYSA-N N-(4-amino-6,7-dichloro-9,10-dioxoanthracen-1-yl)benzamide Chemical compound NC1=CC=C(NC(=O)C2=CC=CC=C2)C2=C1C(=O)C1=CC(Cl)=C(Cl)C=C1C2=O GQWWDPHZIFNCTM-UHFFFAOYSA-N 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- -1 methylsulfon-benzoic acid halide Chemical class 0.000 claims 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- JTFGSWMBEWIWTK-UHFFFAOYSA-N 1-amino-6,7-dichloro-4-nitroanthracene-9,10-dione Chemical class NC1=CC=C(C2=C1C(=O)C1=CC(Cl)=C(Cl)C=C1C2=O)[N+]([O-])=O JTFGSWMBEWIWTK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- PLUFITIFLBGFPN-UHFFFAOYSA-N 1,2-dichloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(Cl)=CC=C3C(=O)C2=C1 PLUFITIFLBGFPN-UHFFFAOYSA-N 0.000 description 1
- YFEHGCGWUWOAFA-UHFFFAOYSA-N 1-amino-6,7-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC(Cl)=C(Cl)C=C2C(=O)C2=C1C=CC=C2N YFEHGCGWUWOAFA-UHFFFAOYSA-N 0.000 description 1
- KPYPNTLKDIYIKB-UHFFFAOYSA-N 2,3-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(Cl)C(Cl)=C2 KPYPNTLKDIYIKB-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Küpenfarbstoffes. Es wurde gefunden, dass man zu einem wertvollen Küpenfarbstoff gelangt, wenn man 1-Benzoylamino-4-amino-6,7 - dichloranthrachi- non mit einem den 3-Methylsidfon-benzoylrest abgebenden Mittel behandelt.
Der neue Farbstoff löst sich in konzen trierter Schwefelsäure mit rotvioletter Farbe und färbt Baumwolle aus olivgrüner Küpe in reinen, blauroten Tönen von vorzüglicher Liehtechtheit.
Das beim vorliegenden Verfahren als Aus gangsstoff dienende 1-Benzoylamino-4-amino- 6,7-dichloranthrachinon kann durch Mono- nitrierung von 2,3-Dichloranthrachinon und nachfolgende Reduktion des 1-Nitro-6,7-di- ehloranthrachinons, Nitrierung der Oxamin- säure des 1-Amino-6,7-dichloranthrachinons, Benzoylierung des 1-Amino-4-nitro-6,
7-dichlor- anthrachinons und Reduktion der Amino- gruppe hergestellt werden.
Als den 3-Methylsi-lfon-benzoylrest der Formel
EMI0001.0033
abgebendes Mittel kann zweckmässig ein reak tionsfähiges, funktionelles Derivat der 3-Me- thylsulfon-benzoesäure, beispielsweise ein Säurehalogenid und insbesondere das Säure chlorid, verwendet werden.
Die Umsetzung kann mit Vorteil in indifferenten, hochsieden- den Lösungsmitteln, wie Mono-, Di- oder Tri- chlorbenzol, Nitrobenzol oder Naphthalin, ge- wünschtenfalls in Anwesenheit säurebinden- der katalytisch wirksamer Mittel, wie tertiärer Basen (Pyridin oder Dimethyl- anilin), bei erhöhter Temperatur,
beispiels- weise zwischen 100 und dem Siedepunkt des verwendeten Lösungsmittels, durchgeführt werden. - .
<I>Beispiel: -</I> 20 Teile 3-Methylsulfon-benzoesäure wer den in 300 Teilen trockenem Nitrobenzol suspendiert und nach Zufügen von 15 Teilen Thionylchlorid und 0,1 Teil Pyridin andert halb Stunden bei 110 bis 115 verrührt. Hier auf fügt man 31 Teile 1-Benzoylamino-4- amino - 6,7 - dichlor - anthrachinon hinzu und rührt noch weitere zwei Stunden bei 125 bis 130 .
Der beim Erkalten in dunkelroten Kri- ställchen ausfallende Farbstoff wird abge saugt, mit Nitrobenzol und kochendem Alko hol gewaschen und getrocknet.
Das 1-Benzoylamino-4 - amino - 6,7 - dichlor- anthrachinon kann wie folgt hergestellt wer den: <B>29,8</B> Teile der in bekannter Weise herge stellten Oxaminsäure von 1-Amino-6,7-dichlor- anthrachinon (dieses lässt sich nach den An gaben des Hauptpatentes herstellen) werden in 300 Teilen konzentrierter Schwefelsäure bei 5 bis 10 gelöst.
Zu dieser Lösung lässt man bei der, gleichen Temperatur unter Rühren langsam 13 Teile Salpetersäure (65o/oig) in 25 \feilen konzentrierter Schwefelsäure ztl- tropfen. Nachdem noch drei Stunden bei 0 bis 5 verrührt wurde, wird in 1500 Teile kaltes Wasser ausgetragen, abgesaugt und neutral gewaschen.
Der Filterkuchen wird in 1000 Tei len Wasser suspendiert und nach Ziüügen von 30 Teilen Soda zwei Stunden bei 90 bis 95 verrührt, heiss abgesaugt, neutral gewa schen und getrocknet. Aus Anisol oder Nitro- benzol iunkristallisiert, erhält man 1-Amino-4- nitro-6,7-dichlor-anthrachinon in. roten Nädel- chen.
EMI0002.0019
Analyse:
<SEP> Ber. <SEP> Gef.
<tb> N <SEP> 8,3 <SEP> 0l0 <SEP> <B>8,20%</B>
<tb> Cl <SEP> 21,070/0 <SEP> 20,91% 135 Teile 1-Amino-4-nitro-6-,7-dichlor-anthra- chinon und 90 Teile Benzoylchlorid werden in 840 Teilen trockenem Nitrobenzol drei Stun den bei 135 bis 140 verrührt. Der Benzoyl- aminokörper fällt beim Erkalten in grün sticbiggelben Kriställchen aus.
Durch Reduk tion nach den üblichen Methoden erhält man 1-Benzoylamino-4-amino-6,7-dichlor-anthrachi- non als violettes Pulver, welches sich in kon zentrierter Schwefelsäure = _ mit rotvioletter Farbe löst.
Process for the production of a vat dye. It has been found that a valuable vat dye is obtained if 1-benzoylamino-4-amino-6,7-dichloroanthraquinone is treated with an agent which releases the 3-methylsidphone-benzoyl radical.
The new dye dissolves in concentrated sulfuric acid with a red-violet color and dyes cotton from an olive-green vat in pure, blue-red tones with excellent light fastness.
The starting material used in the present process 1-benzoylamino-4-amino-6,7-dichloroanthraquinone can ehloranthraquinone by mononitration of 2,3-dichloroanthraquinone and subsequent reduction of 1-nitro-6,7-di- ehloranthraquinone, nitration Oxamic acid of 1-amino-6,7-dichloroanthraquinone, benzoylation of 1-amino-4-nitro-6,
7-dichloro-anthraquinones and reduction of the amino group are produced.
As the 3-methylsilphon-benzoyl radical of the formula
EMI0001.0033
A reactive, functional derivative of 3-methylsulfonobenzoic acid, for example an acid halide and in particular the acid chloride, can expediently be used as a releasing agent.
The reaction can advantageously be carried out in inert, high-boiling solvents such as mono-, di- or trichlorobenzene, nitrobenzene or naphthalene, if desired in the presence of acid-binding, catalytically active agents such as tertiary bases (pyridine or dimethylaniline). , at elevated temperature,
for example between 100 and the boiling point of the solvent used. -.
<I> Example: - </I> 20 parts of 3-methylsulfon-benzoic acid are suspended in 300 parts of dry nitrobenzene and, after adding 15 parts of thionyl chloride and 0.1 part of pyridine, stirred at 110 to 115 for one and a half hours. Here 31 parts of 1-benzoylamino-4-amino-6,7-dichloro-anthraquinone are added and the mixture is stirred for a further two hours at 125 to 130.
The dye which precipitates out in dark red crystals on cooling is filtered off with suction, washed with nitrobenzene and boiling alcohol and dried.
The 1-benzoylamino-4-amino-6,7-dichloro-anthraquinone can be prepared as follows: <B> 29.8 </B> parts of the oxamic acid of 1-amino-6,7- produced in a known manner dichloro-anthraquinone (this can be produced according to the specifications of the main patent) are dissolved in 300 parts of concentrated sulfuric acid at 5 to 10.
13 parts of nitric acid (65%) in 25 parts of concentrated sulfuric acid are slowly added dropwise to this solution at the same temperature while stirring. After stirring for a further three hours at 0 to 5, cold water is poured into 1500 parts, filtered off with suction and washed neutral.
The filter cake is suspended in 1000 parts of water and, after adding 30 parts of soda, stirred for two hours at 90 to 95, suction filtered while hot, washed neutral and dried. Uncrystallized from anisole or nitrobenzene, 1-amino-4-nitro-6,7-dichloro-anthraquinone is obtained in red needles.
EMI0002.0019
Analysis:
<SEP> Ber. <SEP> found
<tb> N <SEP> 8.3 <SEP> 0l0 <SEP> <B> 8.20% </B>
<tb> Cl <SEP> 21.070 / 0 <SEP> 20.91% 135 parts of 1-amino-4-nitro-6-, 7-dichloro-anthraquinone and 90 parts of benzoyl chloride are in 840 parts of dry nitrobenzene for three hours stirred at 135 to 140. The benzoylamino body precipitates out in green, yellowish-yellow crystals on cooling.
By reduction according to the usual methods, 1-benzoylamino-4-amino-6,7-dichloro-anthraquinone is obtained as a violet powder, which dissolves in concentrated sulfuric acid = _ with a red-violet color.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH286501T | 1949-07-22 | ||
| CH290507T | 1949-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH290507A true CH290507A (en) | 1953-04-30 |
Family
ID=25732608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH290507D CH290507A (en) | 1949-07-22 | 1949-07-22 | Process for the production of a vat dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH290507A (en) |
-
1949
- 1949-07-22 CH CH290507D patent/CH290507A/en unknown
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