DE130629C - - Google Patents
Info
- Publication number
- DE130629C DE130629C DENDAT130629D DE130629DA DE130629C DE 130629 C DE130629 C DE 130629C DE NDAT130629 D DENDAT130629 D DE NDAT130629D DE 130629D A DE130629D A DE 130629DA DE 130629 C DE130629 C DE 130629C
- Authority
- DE
- Germany
- Prior art keywords
- indigo
- indole
- air
- ber
- bisulfite
- 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.)
- Active
Links
- SIKJAQJRHWYJAI-UHFFFAOYSA-N indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 20
- 229940097275 Indigo Drugs 0.000 claims description 15
- 235000000177 Indigofera tinctoria Nutrition 0.000 claims description 15
- CYKLSPVFSGLEEA-UHFFFAOYSA-N S(O)(O)=O.N1C=CC2=CC=CC=C12 Chemical compound S(O)(O)=O.N1C=CC2=CC=CC=C12 CYKLSPVFSGLEEA-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 240000007871 Indigofera tinctoria Species 0.000 claims 1
- 150000002926 oxygen Chemical class 0.000 claims 1
- 241001062009 Indigofera Species 0.000 description 14
- GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- KRVSOGSZCMJSLX-UHFFFAOYSA-L Chromic acid Chemical compound O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
- VZJVWSHVAAUDKD-UHFFFAOYSA-N Potassium permanganate Chemical compound [K+].[O-][Mn](=O)(=O)=O VZJVWSHVAAUDKD-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZJRXSAYFZMGQFP-UHFFFAOYSA-N Barium peroxide Chemical compound [Ba+2].[O-][O-] ZJRXSAYFZMGQFP-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 241000219873 Vicia Species 0.000 description 1
- 230000003213 activating Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229940001607 sodium bisulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Die Darstellung von Indigo aus seiner Grundsubstanz, dem Indol, gelang Nencki 1875 (Ber. 8, 727) durch Einwirkung von Ozon. Bei dieser Reaction tritt eine fast gänzliche .Verharzung des Indols ein, und erst wenn man das gebildete Harz mit Alkohol löst kommt die geringe Menge Indigo, welche entstanden ist, zum Vorschein.Nencki succeeded in producing indigo from its basic substance, indole, in 1875 (Ber. 8, 727) through the action of ozone. In this reaction there is an almost complete one Resinification of the indole, and only when the resin formed is dissolved with alcohol the small amount of indigo that has formed is revealed.
Engler und Janecke (Ber. 9, 1414) wiederholten 1876 den Versuch Nencki's, konnten aber ebenso wie dieser Gelehrte nur sehr wenig Indigo aus Indol darstellen Sie liefsen ferner, mit der Absicht zum Indigo zu gelangen, noch andere Oxydationsmittel auf Indol einwirken; so versuchten sie Wasserstoffsuperoxyd , Baryumsuperoxyd und Schwefelsäure, Chromsäure, Salpetersäure, Kaliumpermanganat, aber keines dieser Oxydationsmittel lieferte Indigo.Engler and Janecke (Ber. 9, 1414) repeated Nencki's attempt in 1876, but, like this scholar, could only very much represent a little indigo from indole You also ran with the intention of getting to indigo, other oxidizing agents act on indole; so they tried hydrogen peroxide , Barium superoxide and sulfuric acid, chromic acid, nitric acid, potassium permanganate, but none of these oxidizing agents gave indigo.
Auch Ladenburg (Ber. 10, 1131) versuchte 1877 Indol in Indigo überzuführen, und zwar durch Oxydation mit Eisenchlorid, doch erhielt er dabei nur einen grünen Körper, den er nicht näher untersuchte; er hoffte damals, durch eine Modification seines Verfahrens doch noch zum Indigo zu gelangen, hat aber seitdem nichts weiter mitgetheilt.Ladenburg (Ber. 10, 1131) also tried 1877 to convert indole into indigo by oxidation with ferric chloride, but in doing so he only got a green body, which he did not examine further; he at the time hoped to get to indigo by modifying his process, but has not communicated anything since then.
Die Erfinderin kann die Angaben von Engler und Janecke sowie von Ladenburg bestätigen und hat ferner constatirt, dafs auch Persulfat aus Indol keinen Indigo zu bilden vermag.The inventor can confirm the information provided by Engler and Janecke and von Ladenburg and has further stated that persulphate cannot form indigo from indole either able.
Es wurde dagegen gefunden, dafs sich Indol in Indigo überführen läfst, wenn man es der Einwirkung von »activirtem« Sauerstoff (vergl.On the other hand, it has been found that indole can be converted into indigo if one does so The effect of "activated" oxygen (cf.
z.B. Engler und Wild, Ber. 30, Seite 1669, Engler, Ber. 33, Seite 1097) unterwirft, wie solcher aus Luftsauerstoff durch geeignete activirende Substanzen, z. B. Natriumsulfit, Natriumbisulfit (Wicke, Zeitschrift für Chemie 1865, S. 86 und 305) u. s. w. entsteht (Jorissen, Zeitschrift für physikalischeChemie 23, Seite667). Die Erfindung wird durch folgende Beispiele erläutert:e.g. Engler and Wild, Ber. 30, page 1669, Engler, Ber. 33, page 1097) subjects how those from atmospheric oxygen by suitable activating substances, e.g. B. sodium sulfite, Sodium bisulfite (vetch, magazine for chemistry 1865, p. 86 and 305) and so on. The invention is illustrated by the following examples:
5 Th. Indol werden in 3000 Th. Wasser gelöst; dazu giebt man 10 Th. Natriumsulfit, gelöst in 50 Th. Wasser. Die Lösung nimmt beim Stehen an der Luft nach einiger Zeit, schneller beim Durchblasen von Luft eine grüne Fluorescenz an und scheidet dann, nachdem sie alkalisch gemacht ist, bei weiterem Stehen an der Luft oder beim Einleiten von Luft Indigo ab.5 Th. Indole are dissolved in 3000 Th. Water; add 10 th. sodium sulfite, dissolved in 50 parts of water. The solution decreases after some time when standing in the air, a green fluorescence faster when air is blown through and then separates after it is made alkaline if it is left to stand in the air or if it is introduced Exhaust Indigo.
5 Th. Indol werden in 3000 Th. Wasser gelöst; dazu giebt man 50 Th. Bisulfit 400. Die Lösung scheidet nach einigem Stehen an der Luft oder beim Durchblasen von Luft Indigo ab. Durch Zusatz von Lauge bis zu alkalischer Reaction und erneutes Lufteinblasen wird eine weitere Menge Indigo abgeschieden. 5 Th. Indole are dissolved in 3000 Th. Water; 50 Th. Bisulfite 40 0 are added to this . The solution separates indigo after standing in the air for some time or when air is blown through it. By adding lye up to an alkaline reaction and blowing in air again, a further amount of indigo is deposited.
Beispiel III.Example III.
10 Th. Indolbisulfit (bereitet nach Hesse, Ber. 32, 2615) werden mit 10 Th. Bisulfit 40° in 500 Th. Wasser suspendirt. Durch Ein-10 Th. Indole bisulfite (prepared according to Hesse, Ber. 32, 2615) with 10 Th. Bisulfite 40 ° suspended in 500 parts of water. Through a-
wirkung der Luft scheidet sich nach einiger Zeit der Indigo aus. Auch hier lä'fst sich nach Zusatz von Lauge bis zur alkalischen Reaction und erneutem Lufteinblasen e'ine weitere Menge Indigo gewinnen.effect of the air, the indigo separates out after a while. Here, too, it lapses Addition of lye until an alkaline reaction occurs and a further amount of air is blown in Win indigo.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE130629C true DE130629C (en) |
Family
ID=399016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT130629D Active DE130629C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE130629C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0330419A2 (en) * | 1988-02-23 | 1989-08-30 | MITSUI TOATSU CHEMICALS, Inc. | Process for the preparation of indigo compound |
| EP0335524A2 (en) * | 1988-03-17 | 1989-10-04 | MITSUI TOATSU CHEMICALS, Inc. | Process for the preparation of indigo compounds |
-
0
- DE DENDAT130629D patent/DE130629C/de active Active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0330419A2 (en) * | 1988-02-23 | 1989-08-30 | MITSUI TOATSU CHEMICALS, Inc. | Process for the preparation of indigo compound |
| EP0330419A3 (en) * | 1988-02-23 | 1990-12-12 | Mitsui Toatsu Chemicals Inc. | Process for the preparation of indigo compound |
| EP0335524A2 (en) * | 1988-03-17 | 1989-10-04 | MITSUI TOATSU CHEMICALS, Inc. | Process for the preparation of indigo compounds |
| EP0335524A3 (en) * | 1988-03-17 | 1990-12-12 | Mitsui Toatsu Chemicals, Incorporated | Process for the preparation of indigo compounds |
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