AT53786B - Process for the representation of tri- and tetrahalogenindigo. - Google Patents
Process for the representation of tri- and tetrahalogenindigo.Info
- Publication number
- AT53786B AT53786B AT53786DA AT53786B AT 53786 B AT53786 B AT 53786B AT 53786D A AT53786D A AT 53786DA AT 53786 B AT53786 B AT 53786B
- Authority
- AT
- Austria
- Prior art keywords
- tri
- indigo
- tetrahalogenindigo
- representation
- bromine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 229940097275 indigo Drugs 0.000 description 6
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ZLHGTHCCYUEAIK-UHFFFAOYSA-N 5,7-dibromo-2-(5,7-dibromo-3-hydroxy-1H-indol-2-yl)indol-3-one Chemical compound [O-]c1c([nH]c2c(Br)cc(Br)cc12)C1=[NH+]c2c(cc(Br)cc2Br)C1=O ZLHGTHCCYUEAIK-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Tri und Tetrahalogenindigo,
In der Stammpatentschrift Nr. 53532 und der Zusatzpatentschrift Nr. 53785 wurde beschrieben, dass man in glatter Weise Tri-und Tetrahalogenindigo dadurch erhalten kann, dass man Indigo, niedriger gebromten Indigo oder Mono-bzw. Dichlorindigo in konzentrierter Schwefelsäure bei mässiger Temperatur mit der entsprechenden, d. h. mindestens der doppelten der in das Indigomolekül einzuführenden Menge Brom behandelt.
Es wurde nun gefunden, dass man dasselbe Ziel auch bei Anwendung erheblich geringerer Mengen von Brom erreichen kann. Diese Tatsache ist so zu erklären, dass der bei der Bromierung entstehende und in der Schwefelsäure gelöste Bromwasserstoff im Laufe der Reaktion von der Schwefelsäure unter Bildung von schwefliger Säure oxydiert wird
EMI1.1
Arbeiten in geschlossenen Gefässen verhindert, die Reaktion auch schon fast mit der werte der theoretischen Menge Brom ausführen.
Beispiel :
100 Teile fein gepulverter Indigo werden in die 2nfache Alenge konzentrierter Schwefelsäure (66 Bé) eingetragen, wobei man durch gute Kühtnng Sorge trägt, dass eine Sulnerung
EMI1.2
zwei Stunden unter Kühlung einwirken und steigert dann die Temperatur langsam auf etwa 4Uo. Naehdem die. Masse bei dieser Temperatur noch etwa zwölf Stunden lang ge- gertthrt worden ist, giesst man in Wasser und nitriert den in fast theoretischer Ausbeute
EMI1.3
identisch ist.
Wendet man in dem Beispiel statt 200 Teile Brom nur 140 Teile Brom an, so erhilt man den Tribromindigo, der in Nuance und Eigenschaften dein Tetrabromindigo sehr nahe steht, von letzterem jedoch sich leicht dadurch unterscheiden lässt, dass seine Färbungen beim Betupfen mit Salpetersäure weiss werden, während die Färbungen des Tetrabrom- indigos sich durch dieses Reagens kaum ändern.
Das Verfahren zur Herstellung der gemischten Tri- und Tetrahalogenindigos gemäss dem ersten Zusatzpatente Nr. 53785 verläuft in ganz analoger Weise.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the representation of tri and tetrahalo indigo
In the parent patent specification No. 53532 and the additional patent specification No. 53785 it was described that tri- and tetrahalogenindigo can be obtained in a smooth manner by using indigo, lower bromine indigo or mono- or. Dichloroindigo in concentrated sulfuric acid at moderate temperature with the corresponding, d. H. treated at least twice the amount of bromine to be introduced into the indigo molecule.
It has now been found that the same goal can also be achieved using considerably smaller amounts of bromine. This fact can be explained by the fact that the hydrogen bromide formed during the bromination and dissolved in the sulfuric acid is oxidized in the course of the reaction by the sulfuric acid with the formation of sulphurous acid
EMI1.1
Working in closed vessels prevents the reaction from being carried out with almost the theoretical amount of bromine.
Example:
100 parts of finely powdered indigo are added to twice the amount of concentrated sulfuric acid (66 Bé), whereby good cooling is used to ensure that the water is dissolved
EMI1.2
act for two hours with cooling and then slowly increase the temperature to about 4Uo. Well the. After the mass has been fermented at this temperature for about twelve hours, it is poured into water and nitrated in an almost theoretical yield
EMI1.3
is identical.
If, in the example, only 140 parts of bromine are used instead of 200 parts of bromine, the result is tribromo indigo, which is very similar in shade and properties to tetrabromo indigo, but can easily be distinguished from the latter in that its coloration becomes white when dabbed with nitric acid , while the colors of the tetrabromo indigo hardly change by this reagent.
The process for the preparation of the mixed tri- and tetrahalogenindigos according to the first additional patent no. 53785 proceeds in a completely analogous manner.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE53786X | 1908-02-29 | ||
| AT53532D AT53532B (en) | 1907-10-04 | 1909-01-18 | Process for the representation of tri- and tetrabromo indigo. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT53786B true AT53786B (en) | 1912-06-10 |
Family
ID=25602101
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT53786D AT53786B (en) | 1908-02-29 | 1909-02-13 | Process for the representation of tri- and tetrahalogenindigo. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT53786B (en) |
-
1909
- 1909-02-13 AT AT53786D patent/AT53786B/en active
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