DE225227C - - Google Patents
Info
- Publication number
- DE225227C DE225227C DE1908225227D DE225227DA DE225227C DE 225227 C DE225227 C DE 225227C DE 1908225227 D DE1908225227 D DE 1908225227D DE 225227D A DE225227D A DE 225227DA DE 225227 C DE225227 C DE 225227C
- Authority
- DE
- Germany
- Prior art keywords
- indigo
- bromine
- chlorosulfonic acid
- solvent
- brominating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229940097275 Indigo Drugs 0.000 claims description 11
- 241001062009 Indigofera Species 0.000 claims description 11
- 235000000177 Indigofera tinctoria Nutrition 0.000 claims description 11
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YCBBRNFFVPXEGQ-BUHFOSPRSA-N (2E)-5-bromo-2-(5-bromo-3-oxo-1H-indol-2-ylidene)-1H-indol-3-one Chemical class N/1C2=CC=C(Br)C=C2C(=O)C\1=C1/NC2=CC=C(Br)C=C2C1=O YCBBRNFFVPXEGQ-BUHFOSPRSA-N 0.000 description 1
- 241000854350 Enicospilus group Species 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 230000000694 effects Effects 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
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B7/00—Indigoid dyes
- C09B7/02—Bis-indole indigos
- C09B7/04—Halogenation thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JV! 225227 - KLASSE 22 e. GRUPPE - JV! 225227 - CLASS 22 e. GROUP
Verfahren zum Bromieren von Indigo. Patentiert im Deutschen Reiche vom 2. August 1908 ab.Process for brominating indigo. Patented in the German Empire on August 2, 1908.
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 Chlorsulfonsäure einwirken läßt. Die Reaktion geht unter Verwendung des genannten Lösungsmittels 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 sulfierenden Wirkung der Chlorsulfonsäure überraschend ist.The present process relates to the bromination of indigo and consists in that the halogen on the indigo in a solution or suspension of chlorosulfonic acid can act. The reaction proceeds more rapidly when the solvent mentioned is used than when others are used Solvent or diluent, which is probably primarily due to the good solubility of both of bromine as well as indigo and the brominated products in chlorosulfonic acid is. If one avoids excessive heating in the process, it hardly occurs or no sulphonation of the indigo at all, what in view of the otherwise so vigorously sulphurous Effect of chlorosulfonic acid is surprising.
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 nitriert, gewaschen, gepreßt und getrocknet.15 kg of bromine are dissolved in 50 kg of chlorosulfonic acid stirred in and then with continued thorough stirring while avoiding heating - what is achieved by external cooling - 5 kg of finely powdered indigo in small pieces Portions entered. The mixture is left to stir for a while and then the deeply colored, pure blue solution is poured onto ice. Of the deposited dye is nitrated, washed, pressed and dried.
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 etwa das oben angegebene Verhältnis erreicht ist. Selbstverständlich kann man auch an Stelle von Indigo unter entsprechender Verringerung der Brommenge von niedriger substituiertem Bromindigo ausgehen.One can also proceed in such a way that one does not see the whole set of the individual Use substances from the start, but alternate the chlorosulphonic acid with a little bromine and indigo added until about the above ratio is reached. Of course it can also be used instead of indigo with a corresponding reduction in the amount of bromine start from lower substituted bromoindigo.
Durch geringfügige Modifikationen des Verfahrens, namentlich bezüglich der Menge des angewandten Broms, kann man in ebenso glatter Weise die niedriger bromierten Indigoderivate erhalten.By making minor modifications to the process, particularly with regard to the quantity of the bromine used, the lower brominated indigo derivatives can be found just as easily obtain.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT54259D AT54259B (en) | 1908-08-01 | 1909-03-29 | Process for brominating indigo. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE225227C true DE225227C (en) |
Family
ID=485892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1908225227D Expired - Lifetime DE225227C (en) | 1908-08-01 | 1908-08-01 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE225227C (en) |
-
1908
- 1908-08-01 DE DE1908225227D patent/DE225227C/de not_active Expired - Lifetime
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