US384480A - Signor to the faebweeke - Google Patents
Signor to the faebweeke Download PDFInfo
- Publication number
- US384480A US384480A US384480DA US384480A US 384480 A US384480 A US 384480A US 384480D A US384480D A US 384480DA US 384480 A US384480 A US 384480A
- Authority
- US
- United States
- Prior art keywords
- dimethylaniline
- signor
- faebweeke
- blue
- hydrochlorate
- 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
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- KMUONIBRACKNSN-UHFFFAOYSA-N Potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 8
- 239000007800 oxidant agent Substances 0.000 description 8
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 6
- 229940042115 Methylene blue Drugs 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229960000907 methylthioninium chloride Drugs 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229940069002 Potassium Dichromate Drugs 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- LGDPTPLJZGPOJL-UHFFFAOYSA-N N,N-dimethyl-2-nitrosoaniline Chemical compound CN(C)C1=CC=CC=C1N=O LGDPTPLJZGPOJL-UHFFFAOYSA-N 0.000 description 2
- ZXYNGLRGFYLTQZ-UHFFFAOYSA-M [Zn]Cl Chemical compound [Zn]Cl ZXYNGLRGFYLTQZ-UHFFFAOYSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atoms Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000001376 precipitating Effects 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
Definitions
- My invention relates to an improved process for producing the coloring-matter known as methylene-blue, in which a mixture of paramido-dimcthylaniline, C 11,: gggg fi hydrochlorate of dimethylaniline, and hyposulphite of sodium in aqueous solution, is subjected to the action of an oxidizing agent,
- Analogous coloringmatters are obtained when in this process the paramido'dimethylaniline is replaced by paramido-dimethylaniliue and the dimethylaniline by some other aromatic monamineas, for example, aniline, ortho-toluidine, and their mono and di alkyl derivatives.
Description
NITE TA'IES ATENT EDUARD ULLRIOH, OF HGOHST-ON-THE-MAIN, PRUSSIA, GERLWIAN Y, AS- SIGNOR TO THE FARBVVERKE, VORMALS MEIS'IER, LUCIUS & BRUNIN G,
OF SAME PLACE.
PRODUCTION OF BLUE COLORING-MATTER.
SPECIFICATION forming part of Letters Patent No. 384,480, dated June 12, 1888.
Application filed December 14, 1887. Serial No. 257,877.
(No specimens.) Patented in Germany December 25, 1885, No. 33,573,-
in France December 27, 1885, No. 173,137, and in England January 1, 1886, No. 43.
To aZZ whom it may concern.-
Be it known that I, EDUARD ULLRIOH, doctor of philosophy, a citizen of the Empire of Germany, residing at Hdchst-on-the-Main,
Prussia, in the Empire of Germany, have invented certain new and useful Improvements in Processes for Producing Blue Coloring-Matter; and I do hereby declare the following to be a full, clear, and exact description of the invention, such as will enable others skilled in the art to which it appertains to make and use the same.
My invention relates to an improved process for producing the coloring-matter known as methylene-blue, in which a mixture of paramido-dimcthylaniline, C 11,: gggg fi hydrochlorate of dimethylaniline, and hyposulphite of sodium in aqueous solution, is subjected to the action of an oxidizing agent,
(that apparently most suitable being potassium dichromate.)
In carrying out my invention I producefirst, in a manner well known, the amido-dimethyl- 2 5 aniline by reducing hydrochlorate of nitrosodimethylaniline by the action of zinc and hydrochloric acid. Of the zinc I employ the quantity necessary to use up all of the hydrochloric acid employed, so that there will not 0 remain any free hydrochloric acid. To this solution of amido-dimethylaniline, (one molecule,) containing chlor-zinc, I add hyposulphite of sodium (somewhat more than one molecule) and hydrochlorate of dimethylaniline, (one molecule) and oxidize by the addition of potassium dichromate, finishing up the operation by heating. For one molecule of amido-dimcthylaniline there will be required of the oxidizing agent the quantity corresponding to three atoms of oxygen. The dimethylaniline does not partake in the first stage of the reaction. It enters into action only when aboutone-third of the quantity of the oxidiz ing agent necessary has been added. Out of the product resulting from the reaction the methylene-blue is obtained by boiling, filtering, and precipitating from the solution by means of common salt. Analogous coloringmatters are obtained when in this process the paramido'dimethylaniline is replaced by paramido-dimethylaniliue and the dimethylaniline by some other aromatic monamineas, for example, aniline, ortho-toluidine, and their mono and di alkyl derivatives.
What I claim as new, and desire to secure by Letters Patent, is-
The production of methylene-blue by subjecting paramidodimethylaniline, hydrochlorate of dimethylaniline, and hyposulphite of sodium to the action of an oxidizing agent, as bichromate, with heat, substantially as set forth.
In testimony whereof I affix my signature in presence of two witnesses.
. EDUARD ULLRICH. l/Vitnesses:
JOSEPH REVERDY, HEINRICH HAHN.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US384480A true US384480A (en) | 1888-06-12 |
Family
ID=2453468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US384480D Expired - Lifetime US384480A (en) | Signor to the faebweeke |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US384480A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030148976A1 (en) * | 2001-08-17 | 2003-08-07 | Krieg Arthur M. | Combination motif immune stimulatory oligonucleotides with improved activity |
-
0
- US US384480D patent/US384480A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030148976A1 (en) * | 2001-08-17 | 2003-08-07 | Krieg Arthur M. | Combination motif immune stimulatory oligonucleotides with improved activity |
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