US955410A - Tetrachlor-indigo and process of making same. - Google Patents
Tetrachlor-indigo and process of making same. Download PDFInfo
- Publication number
- US955410A US955410A US52856209A US1909528562A US955410A US 955410 A US955410 A US 955410A US 52856209 A US52856209 A US 52856209A US 1909528562 A US1909528562 A US 1909528562A US 955410 A US955410 A US 955410A
- Authority
- US
- United States
- Prior art keywords
- indigo
- tetrachlor
- making same
- parts
- blue
- 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 title description 8
- 238000000034 method Methods 0.000 title description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 241001062009 Indigofera Species 0.000 description 4
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 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 3
- 150000004702 methyl esters Chemical group 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003034 coal gas Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 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
Definitions
- Our invention relates to the production of 4.4.5.5-tetrachlor-indigo.
- Vi e have invented a process for its production by the saponi It can be converted into the corresponding fication and oxidation of an ester of 4.5- I indigo coloring matter by boiling tw.0 hunchlor-indoxyl carboxylic acid.
- a process for its production by the saponi It can be converted into the corresponding fication and oxidation of an ester of 4.5- I indigo coloring matter by boiling tw.0 hunchlor-indoxyl carboxylic acid.
- coal gas for thirty minutes, of coal gas through Then add twelve thousand f l parts of boiling water to the mixture and / ⁇ /NH ⁇ NH ⁇ lpass air through it, at a temperature'oit v I about one hundred degrees cen tigrade, until l l l the oxldatlon is complete. It desired, the I saponification can be carried out in the ab sence of coal gas.
- the said shades retain their greenish tint when viewed by artificial light, whereas the other tetrahalogcn indigoes hitherto describcdassume a reddish or violet-black tint under similar conditions.
- our 4i.4'-5.i-tetrachlor-indigo yields 4.5-dichlorisatin which can be recrystallized from glacial acetic acid and thus obtained in the form of red needles which melt at about 247 C.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Description
' No Drawing.
4.5-dichlor-indoxyl carboxylic UNITED STATES PATENT rare.
PAUL JULIUS, VIKTOR VILLIGER, AND PAUL NAVVIASKY, OF LUDWIGSHAFEN-ON-THE- RHINE, GERMANY, ASSIGNORS TO .BADISOHE ANILIN & SODA FABRIK, 0 LUDWIGS- HAFEN-ON-THE-RHINE, GERMANY, A CORPORATION.
rErRAcHLoR-rnnmo Ann rnocnss or MAKING saME.
955,410. Specification of Letters Patent.
Application filed November 17, 1909.
Patented Apr. 19, rare. Serial no. 528,562..
To all whom it mag concern;
Be it known that We, PAUL J ULIUs, Ph. 1)., VIKTOR VILLIGER, Ph. 1)., and PAUL Nawr'l ASKY, Ph. D.,' chemists, the first and third subjects of the Emperor of Austria-Hun-v gary and the second a citizen of the Swiss ltepublic are 1 a u w b hai'en-on-the-Rhine, Germany, have invented new and-useful Improvements in Tetrachlor-Indigo and Processes of Making Same, of which the following is a specification.
Our invention relates to the production of 4.4.5.5-tetrachlor-indigo. Vi e have invented a process for its production by the saponi It can be converted into the corresponding fication and oxidation of an ester of 4.5- I indigo coloring matter by boiling tw.0 hunchlor-indoxyl carboxylic acid. Thus, upon dred and-sixty parts of it with'six thousand. operating in this way upon the methyl ester parts of water of l.5-dichlorindoxyl carboxylic acid, we, parts of caustic potash, obtain the new product 4.45.5tetrachlorj While passing a current indigo of a constitution corresponding-to the the solution.
Introduce, While stirring, two hundred and ninety-two parts of the methyl ester of 3.4-dichlorphenyl-glycin --2 carboxylic acid into a solution of twenty-three parts of so dium in one thousand parts of methyl alcohol, and maintain the Whole at seventy der s centigrade for thirty minutes. Distil off the meth 1 alcohol, digest the residue with one thdu sa arts of water and two hundred parts of thir per cent. acetic acid, and filter off and wash and dry the 4.5- dichlor-indoxylcarboxylic acid ester, which is insoluble in water and is difiicultly soluble in most of the common organic solvents.
for thirty minutes, of coal gas through Then add twelve thousand f l parts of boiling water to the mixture and /\/NH\ NH\ lpass air through it, at a temperature'oit v I about one hundred degrees cen tigrade, until l l l the oxldatlon is complete. It desired, the I saponification can be carried out in the ab sence of coal gas.
Now what we claim is z- -l. The process of producing erastetrachlor-indigo by saponii'ying and oxidizing an ester of 4.5-dichlor indoxyl carboxylic acid substantially as described.
2. Asa new article of manufacture 4.4.5.5-tetrachlor indigo which when dry of a greenish blue powder, yielils a blue solution in cold concentrated sulfuric acid, and a blue solution in hot dimethyl anilin; it dyes co.l:on particularly greenish It consists, when dry, of a greenish blue powder which yields a blue solution in cold l concentrated sulfuric acid and a blue solul tion in hot dimethyl anilin. It differs from all known tetrachlor-indigoes in that it dyes cotton from a vat exceptionally greenish shades of blue which are fast against wash ing, light, and chlorin. Moreover, the said shades retain their greenish tint when viewed by artificial light, whereas the other tetrahalogcn indigoes hitherto describcdassume a reddish or violet-black tint under similar conditions. Upon being oxidized in aqueous suspension with nitric acid, our 4i.4'-5.i-tetrachlor-indigo yields 4.5-dichlorisatin which can be recrystallized from glacial acetic acid and thus obtained in the form of red needles which melt at about 247 C.
The following example will serve to illustrate further the nature of this invention and how it can be carried into practical effect, but our invention is not confined to this example. The parts are by Weight. In this example we first, for convenience, describe the production of the methyl ester of acid.
suspension by means of nitric acid gives rise to 4.5-dichlor-isatin, which aij-vdichlor-isatin can be recrystallized from glacial acetic acid and thus be obtained in the form of red needles whichmelt at about 247 C. v
In testimony whereofflwe have hereunto set our hands in the presence of two sul scribing Witnesses.
PAUL JULIUS. VIKTOR VILLIGER. PAUL NAWIASKY.
Witnesses:
J. ALEc. LLOYD, W. W. Sonmmr.
consists and five hundred and eleven shades of blue, ahd on oxidation in aqueous
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52856209A US955410A (en) | 1909-11-17 | 1909-11-17 | Tetrachlor-indigo and process of making same. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52856209A US955410A (en) | 1909-11-17 | 1909-11-17 | Tetrachlor-indigo and process of making same. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US955410A true US955410A (en) | 1910-04-19 |
Family
ID=3023814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US52856209A Expired - Lifetime US955410A (en) | 1909-11-17 | 1909-11-17 | Tetrachlor-indigo and process of making same. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US955410A (en) |
-
1909
- 1909-11-17 US US52856209A patent/US955410A/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US995936A (en) | Green anthracene dyes and process of making the same. | |
| US948241A (en) | Halogenated indigo and process of making. | |
| US502603A (en) | Rene bohn | |
| US1003268A (en) | Anthracene dye and process of making same. | |
| US1734442A (en) | Production of vat dyestuffs | |
| US1633997A (en) | Manufacture of vat dyestuffs | |
| US1704983A (en) | Dyestuff of the isodibenzanthrone series | |
| US820379A (en) | Anthracene dye and process of making same. | |
| US998772A (en) | Blue dyestuff and process of making same. | |
| US1063000A (en) | Anthracene dyes and making the same. | |
| US1004433A (en) | Dianthraquinonyl-dialdehydes and process of making them. | |
| US1054888A (en) | Blue-green vat coloring-matter. | |
| US644326A (en) | Process of making indigo products. | |
| US1018836A (en) | Orange-red vat dye. | |
| US2186389A (en) | Vat dyestuffs and their leuco esters | |
| US677239A (en) | Halogen-substituted indigo and process of making same. | |
| US957683A (en) | Dichlor-dibrom-indigo and process of making same. | |
| US922282A (en) | Anthracene dye and process of making same. | |
| US796393A (en) | Anthracene coloring-matter and process of producing the same. | |
| US809892A (en) | Violet dye and process of making same. | |
| US2141872A (en) | Compounds of the pyrazolanthrone series | |
| US1035023A (en) | Vat dyes and making the same. | |
| US937040A (en) | Tribromindigo and process of making same. | |
| US2706731A (en) | Anthraquinone vat dyestuffs | |
| US940586A (en) | Brown vat dye and process of making same. |