AT54259B - Process for brominating indigo. - Google Patents
Process for brominating indigo.Info
- Publication number
- AT54259B AT54259B AT54259DA AT54259B AT 54259 B AT54259 B AT 54259B AT 54259D A AT54259D A AT 54259DA AT 54259 B AT54259 B AT 54259B
- Authority
- AT
- Austria
- Prior art keywords
- indigo
- brominating
- bromine
- desc
- little
- Prior art date
Links
- 235000000177 Indigofera tinctoria Nutrition 0.000 title claims description 11
- 229940097275 indigo Drugs 0.000 title claims description 11
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LRBZENFZSJNJCR-UHFFFAOYSA-N 5-bromo-2-(5-bromo-3-hydroxy-1H-indol-2-yl)indol-3-one Chemical class [O-]c1c([nH]c2ccc(Br)cc12)C1=[NH+]c2ccc(Br)cc2C1=O LRBZENFZSJNJCR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Description
<Desc/Clms Page number 1>
Verfahren zum Bromieren von Indigo.
Vorliegendes Verfahren bezieht sich auf die Bromierung von Indigo und besteht darin, dass man das Halogen auf den Indigo in einer Lösung oder Suspension von Chlor-
EMI1.1
mittels rascher vor sich als bei Anwendung anderer Lösungs- oder Verdünnungsmittel, was wohl in erster Linie auf die gute Löslichkeit sowohl des Broms als auch des Indigos und der bromierten Produkte in Chlorsulfonsäure zurückzuführen ist. Vermeidet man bei dem Verfahren zu starke Erwärmung, so tritt kaum oder gar keine Sulfierung des Indigos ein, was angesichts der sonst so energisch sulnerenden Wirkung der Chlorsulfonsäure überraschend ist.
Beispiel :
15 kg Brom werden in 50 kg Chlorsulfonsäure eingerührt und sodann unter weiterem guten Rühren bei Vermeidung von Erwärmung-was durch Aussenkühlung erreicht wird- 5 kg fein gepulverter Indigo in kleinen Portionen eingetragen. Man lässt noch einige Zeit rühren und giesst sodann die tiefgefärbte rein blaue Lösung auf Eis. Der abgeschiedene Farbstoff wird filtriert, gewaschen, gepresst und getrocknet.
Man kann auch in der Weise verfahren, dass man nicht die ganze Menge der einzelnen Stoffe von vornherein anwendet, sondern die Chlorsulfonsäure abwechselnd mit etwas Brom und Indigo versetzt, bis das oben angegebene Verhältnis erreicht ist. Selbstverständlich kann man auch an Stelle von Indigo unter entsprechender Verringerung der Brommenge von niedriger substituiertem Bromindigo ausgehen.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for brominating indigo.
The present process relates to the bromination of indigo and consists in that the halogen on the indigo in a solution or suspension of chlorine
EMI1.1
faster than when using other solvents or diluents, which is primarily due to the good solubility of both bromine and indigo and the brominated products in chlorosulfonic acid. If excessive heating is avoided in the process, then little or no sulphonation of the indigo occurs, which is surprising in view of the otherwise energetic sulphurizing effect of chlorosulphonic acid.
Example:
15 kg of bromine are stirred into 50 kg of chlorosulphonic acid and then 5 kg of finely powdered indigo are added in small portions while continuing to stir thoroughly while avoiding heating - which is achieved by external cooling. The mixture is left to stir for a while and then the deeply colored, pure blue solution is poured onto ice. The deposited dye is filtered, washed, pressed and dried.
You can also proceed in such a way that you do not use the whole amount of the individual substances from the start, but alternately add a little bromine and indigo to the chlorosulfonic acid until the ratio given above is reached. Of course, instead of indigo, one can also start from lower substituted bromoindigo with a corresponding reduction in the amount of bromine.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1908225227D DE225227C (en) | 1908-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT54259B true AT54259B (en) | 1912-07-10 |
Family
ID=5860006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT54259D AT54259B (en) | 1908-08-01 | 1909-03-29 | Process for brominating indigo. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT54259B (en) |
-
1909
- 1909-03-29 AT AT54259D patent/AT54259B/en active
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