CH191742A - Process for the preparation of 1: 4-di-p-iso-amylaniline anthraquinone disulfonic acid. - Google Patents
Process for the preparation of 1: 4-di-p-iso-amylaniline anthraquinone disulfonic acid.Info
- Publication number
- CH191742A CH191742A CH191742DA CH191742A CH 191742 A CH191742 A CH 191742A CH 191742D A CH191742D A CH 191742DA CH 191742 A CH191742 A CH 191742A
- Authority
- CH
- Switzerland
- Prior art keywords
- iso
- amylaniline
- acid
- anthraquinone
- disulfonic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- PTKWYSNDTXDBIZ-UHFFFAOYSA-N 9,10-dioxoanthracene-1,2-disulfonic acid Chemical compound C1=CC=C2C(=O)C3=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C3C(=O)C2=C1 PTKWYSNDTXDBIZ-UHFFFAOYSA-N 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 5
- 238000006277 sulfonation reaction Methods 0.000 claims description 5
- JUXQDLFYTNOQRC-UHFFFAOYSA-N 4-(3-methylbutyl)aniline Chemical compound CC(C)CCC1=CC=C(N)C=C1 JUXQDLFYTNOQRC-UHFFFAOYSA-N 0.000 claims description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 4
- 239000004327 boric acid Substances 0.000 claims description 4
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 238000011282 treatment Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- FVXPBEUYCCZFJT-UHFFFAOYSA-N 9,10-dihydroxy-2,3-dihydroanthracene-1,4-dione Chemical compound C1=CC=C2C(O)=C(C(=O)CCC3=O)C3=C(O)C2=C1 FVXPBEUYCCZFJT-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 238000009963 fulling Methods 0.000 claims description 2
- 239000010446 mirabilite Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 claims description 2
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- BKNBVEKCHVXGPH-UHFFFAOYSA-N anthracene-1,4,9,10-tetrol Chemical compound C1=CC=C2C(O)=C3C(O)=CC=C(O)C3=C(O)C2=C1 BKNBVEKCHVXGPH-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 150000004056 anthraquinones Chemical class 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung der 1:4-Di-p-iso-amylanilinanthrachinondisulfosäure. Wir stellen die 1 : 4-Di-p-iso-amylan.ilin- anthrachinondisulfosäure durch Behandlung von p-Iso-amylanilin mit Leuko-Chinizarin, welches Chinizarin enthalten kann, und nach folgender Sulfonierung des erhaltenen 1 : 4- Di-p-amyla.nilinanthracbinon.s, her.
Die Behandlung mit p - Iso - amylanilin kann in Gegenwart von Kresolsäure und un ter Zufügung von Borsäure geschehen. Die Sulfonierung kann durch Auflösen des 1 : 4- Di-p-iso-amylanilina.nthrachinon3 in konzen trierter Schwefelsäure und Zufügen von Oleum ausgeführt werden.
Die 1 : 4-Di-p-iso-amyla.nilinan.thrachinon- disulfosäure ist neu. Sie ist grün und löst sich in Wasser zu einer bläulich-grünen Farbe. Sie färbt Wolle und andere tierische Fasern in neutralem oder sehwaehsaurem Bade, mit Vorzug in Gegenwart eines Hilfs- Färbemittels, wie Natrium-Cetylsulfat oder Glaubersalz, in hellen, stark grünen Tönen von besonderer Festigkeit gegen strenges Waschen, Walken und Licht.
<I>Beispiel:</I> 1'9 Teile lieuko-Chinizarin, 18 Teile p-Iso- amylanilin (analog wie bei :dem von Ilickin- bottom beschriebenen Verfahren, J. Chem. hoc, 1930,<B>1565,</B> hergestellt), 60 Teile Kre- solsäure und 6 Teile Borsäure werden mitein ander bei<B>100</B> C 48 Stunden lang umgerührt. 90 Teile Alkohol werden zugefügt, um die weiteren Behandlungen leichter auszuführen. Das Gemisch wird dann ,auf 40 C gekühlt und filtriert.
Der Rückstand wird mit kal tem Alkohol ;gewaschen, bis sich nichts wei teres mehr löst, und dann mit heissem Wasser gewaschen, um die Borsäure zu entfernen, und getrocknet.
Zur Sulfonierung werden 5 Teile der Verbindung bei 20' C in 50 Teilen einer l00 % igen Schwefelsäure gelöst und dann 20 Teile Oleum (21% S03) langsam zu- gegeben. Das Gemisch wird bei 215 bis 30 C während einer halben Stunde gerührt und dann zu<B>180</B> Teilen Eis gegossen. Nachdem dass Eis ,geschmolzen, wird das Gemisch fil triert und der Rückstand gut gepresst.
Er wird dann in heissem Wasser gelöst,,die Lö sung mit kaustischer Soda gehörig alkalisch gemacht und der Farbstoff ausgesalzen, ge- presst und getrocknet.
Process for the preparation of 1: 4-di-p-iso-amylaniline anthraquinone disulfonic acid. We make the 1: 4-di-p-iso-amylan.iline-anthraquinone disulfonic acid by treating p-iso-amylaniline with leuco-quinizarine, which may contain quinizarine, and after subsequent sulfonation of the 1: 4- di-p- amyla.nilinanthracbinon.s, her.
The treatment with p-iso-amylaniline can be carried out in the presence of cresolic acid and with the addition of boric acid. The sulfonation can be carried out by dissolving the 1: 4-di-p-iso-amylanilina.nthraquinone3 in concentrated sulfuric acid and adding oleum.
The 1: 4-di-p-iso-amyla.nilinan.thraquinone-disulfonic acid is new. It is green and dissolves in water to a bluish-green color. It dyes wool and other animal fibers in a neutral or slightly acidic bath, preferably in the presence of an auxiliary dye such as sodium cetyl sulfate or Glauber's salt, in light, strong green shades that are particularly resistant to severe washing, fulling and light.
<I> Example: </I> 1'9 parts of lieuko-quinizarine, 18 parts of p-iso-amylaniline (analogous to: the process described by Ilickin-bottom, J. Chem. Hoc, 1930, <B> 1565, </B>), 60 parts of creolic acid and 6 parts of boric acid are stirred together at <B> 100 </B> C for 48 hours. 90 parts of alcohol are added to make further treatments easier. The mixture is then cooled to 40 ° C. and filtered.
The residue is washed with cold alcohol until nothing else dissolves, then washed with hot water to remove the boric acid and dried.
For the sulfonation, 5 parts of the compound are dissolved in 50 parts of 100% strength sulfuric acid at 20 ° C. and then 20 parts of oleum (21% SO3) are slowly added. The mixture is stirred at 215 to 30 ° C. for half an hour and then poured into 180 parts of ice. After the ice has melted, the mixture is filtered and the residue is pressed well.
It is then dissolved in hot water, the solution is made properly alkaline with caustic soda and the dye is salted out, pressed and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB191742X | 1934-11-14 | ||
| CH185954T | 1935-11-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH191742A true CH191742A (en) | 1937-06-30 |
Family
ID=25721321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH191742D CH191742A (en) | 1934-11-14 | 1935-11-14 | Process for the preparation of 1: 4-di-p-iso-amylaniline anthraquinone disulfonic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH191742A (en) |
-
1935
- 1935-11-14 CH CH191742D patent/CH191742A/en unknown
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