DE137782C - - Google Patents
Info
- Publication number
- DE137782C DE137782C DENDAT137782D DE137782DA DE137782C DE 137782 C DE137782 C DE 137782C DE NDAT137782 D DENDAT137782 D DE NDAT137782D DE 137782D A DE137782D A DE 137782DA DE 137782 C DE137782 C DE 137782C
- Authority
- DE
- Germany
- Prior art keywords
- yellow
- green
- sulfuric acid
- soluble
- nitric acid
- 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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 229960000583 Acetic Acid Drugs 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000001046 green dye Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FLEURRNKVDUGOR-UHFFFAOYSA-N 1-chloro-4-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2[N+](=O)[O-] FLEURRNKVDUGOR-UHFFFAOYSA-N 0.000 description 1
- WYRGXSUARSLNDY-UHFFFAOYSA-N 2-chloro-1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(Cl)=C2[N+](=O)[O-] WYRGXSUARSLNDY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000000802 nitrating Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000630 rising Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Es wurde gefunden, dafs durch Nilriren von a-Halogenanthrachinonen, wie man sie z. B. nach dem Verfahren des Patentes 131538 erhalten kann, in sehr glatter Weise Paranitrohalogenanthrachinone entstehen, welche Ausgangsmaterialien zu werthvollen grünen Farbstoffen sind.It has been found that by nitrating α-haloanthraquinones, as they are used, for. B. obtained by the method of patent 131538 can arise in a very smooth way Paranitrohalogenanthraquinones, which starting materials are valuable green dyes.
Es ist dieses Verfahren von hohem technischen Werth, da sich hauptsächlich die sehr wichtigen Paraverbindungen bilden, während die zur Darstellung der oben erwähnten Farbstoffe nicht geeigneten Isomeren, deren Bildung unter den gegebenen Bedingungen gerade so wahrscheinlich war, nur in geringerer Menge entstehen.This process is of great technical value, since it is mainly the very important Para connections form, while those for the representation of the above mentioned dyes not suitable isomers, their formation under the given conditions just like that was likely to arise only in smaller quantities.
Das vorliegende Verfahren besteht im Allgemeinen darin, dafs man die Halogenanthrachinone, in Lösungs- oder Suspensionsmitteln vertheilt, mit Salpetersäure behandelt.The present process generally consists in using the haloanthraquinones, distributed in solvents or suspending agents, treated with nitric acid.
Das Verfahren wird durch folgende Beispiele erläutert:The procedure is illustrated by the following examples:
25 kg a-Monoebloranthrachinon werden in 250 kg Schwefelsäure von 66° B. gelöst und mit 8 kg Salpetersäure von 42° B. versetzt, wobei darauf zu achten ist, dafs die Temperatur io° nicht übersteigt. Man läfst die Schmelze bei dieser Temperatur ca. 5 Stunden stehen, dabei scheidet sich das Chlornitroanthrachinon in gelben Nadeln ab. Dieselben werden abgesaugt, ausgewaschen und getrocknet. Durch Umkrystallisiren aus Eisessig erhält man das 1 · 4-Chlornitroanthrachinon in schönen gelben glänzenden Nadeln. Dieselben sind schwer löslich in Alkohol, leicht löslich in Nitrobenzol, schwer löslich in concentrirter Schwefelsäure.25 kg of a-monoebloranthraquinone are used in 250 kg of sulfuric acid of 66 ° B. dissolved and mixed with 8 kg of nitric acid of 42 ° B., Care must be taken that the temperature does not exceed 10 °. You run the Stand the melt at this temperature for about 5 hours, during which the chloronitroanthraquinone separates in yellow needles. The same are suctioned off, washed out and dried. Obtained by recrystallization from glacial acetic acid the 1 · 4-chloronitroanthraquinone in beautiful yellow shiny needles. The same are sparingly soluble in alcohol, easily soluble in nitrobenzene, sparingly soluble in concentrated form Sulfuric acid.
20 kg ι · 5-Dichloranthrachinon werden in 200 kg Schwefelsäure von 66° B. gelöst und bei ο bis 50 mit 10 kg Salpetersäure von 42° B. versetzt. Man läfst dann die Temperatur bis io° steigen, wobei sich ziemlich schnell das 1.5.4. 8-Dichlordinitroanthrachinon krystalünisch abscheidet. Nach einigen Stunden ist die Reaction beendet. Die ausgeschiedenen Krystalle werden abgesaugt, ausgewaschen und getrocknet. Durch Umkrystallisiren aus Nitrobenzol lassen sie sich rein erhalten in Form von gelben Nadeln, welche in Alkohol und Eisessig schwer löslich sind.20 kg · ι 5-dichloroanthraquinone are dissolved in 200 kg of sulfuric acid of 66 ° for example, and added at 0 to 5 ο with 10 kg of nitric acid of 42 ° for example. The temperature is then allowed to rise to 10 °, whereby the 1.5.4. 8-Dichlordinitroanthraquinone separates crystalline. The reaction is over after a few hours. The separated crystals are sucked off, washed out and dried. By recrystallizing them from nitrobenzene, they can be obtained in pure form in the form of yellow needles, which are sparingly soluble in alcohol and glacial acetic acid.
20 kg ι · 5-Dibromanthrachinon werden in 200 kg Schwefelsäure von 66° B. gelöst und bei ο bis 50 mit 8 kg Salpetersäure von 42° B. versetzt. Man läfst dann ohne Kühlung stehen, wobei die Temperatur bis 25° steigt. Das 1.5.4. 8-Dibromdinitroanthrachinon beginnt sich bei ca. 150 krystalünisch abzuscheiden. Nach 2 bis 3 Stunden ist die Reaction beendet. Die ausgeschiedenen Krystalle werden abgesaugt, ausgewaschen und getrocknet. Durch Umkrystallisiren aus Nitrobenzol lassen sie sich rein erhalten in Form von gelben Nadeln, welche in Alkohol und Eisessig schwer löslich sind.20 kg · ι 5-dibromoanthraquinone dissolved in 200 kg of sulfuric acid of 66 ° for example, and added at 0 to 5 ο with 8 kg of nitric acid of 42 ° for example. It is then left to stand without cooling, the temperature rising to 25 °. The 1.5.4. 8-Dibromdinitroanthrachinon begins krystalünisch deposit at about 15 0th The reaction has ended after 2 to 3 hours. The separated crystals are sucked off, washed out and dried. By recrystallizing them from nitrobenzene, they can be obtained in pure form in the form of yellow needles, which are sparingly soluble in alcohol and glacial acetic acid.
Ganz analog verläuft die Nitrirung des 1 · 8-Dichloranthrachinons, sowie der anderen z. B.The nitration of 1 · 8-dichloroanthraquinone proceeds quite analogously, as well as the other z. B.
nach dem Verfahren des Patentes 131538 erhältlichen a-Halogenanthrachinone. Man erhält so Paranitrohalogenanthrachinone, welche sämmtlich die charakteristische, technisch äufserst werthvolle Eigenschaft besitzen, beimobtainable by the method of patent 131538 α-haloanthraquinones. This gives paranitrohalogenanthraquinones, which all possess the characteristic, technically extremely valuable property, at
Erhitzen mit primären aromatischen Aminen grüne Farbstoffe zu liefern.Heating with primary aromatic amines to provide green dyes.
Die Eigenschaften der so erhältlichen Produkte sind in folgender Tabelle zusammengestellt: The properties of the products available in this way are summarized in the following table:
EisessigSolution
Glacial acetic acid
Pyriding in:
Pyridine
Schwefelsäuremore concentrated
sulfuric acid
mit p-Toluidinwill when cooking
with p-toluidine
chinonι: 4-chloronitroanthra-
chinone
gelber Farbepoorly soluble with
yellow color
chinonι: 4-bromonitroanthra-
chinone
gelber Farbepoorly soluble with
yellow color
anthrachinonι: 5-dichloro-4: 8-dinitro-
anthraquinone
gelber Farbepoorly soluble with
yellow color
anthrachinonι: 8-dichloro-4: 5-dinitro-
anthraquinone
gelber Farbepoorly soluble with
yellow color
anthrachinonι: 5-dibromo-4: 8-dinitro-
anthraquinone
gelber Farbepoorly soluble with
yellow color
Claims (1)
Verfahren zur Darstellung von p-Nitrochlor- oder p-Nitrobromanthrachinonen, darin bestehend, dafs man in α-Stellung chlorirte bezw. bromirte Anthrachinone mit Salpetersäure behandelt. Patent claim:
Process for the preparation of p-nitrochloro- or p-nitrobromoanthraquinones, consisting in that one chlorinated resp. brominated anthraquinones treated with nitric acid.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE137782C true DE137782C (en) |
Family
ID=405637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT137782D Active DE137782C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE137782C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5306166A (en) * | 1992-12-14 | 1994-04-26 | Wyse Technology, Inc. | Chip storage insertion guide |
| US6554628B2 (en) * | 1999-08-05 | 2003-04-29 | General Electric Co. | Remote cable extractor |
-
0
- DE DENDAT137782D patent/DE137782C/de active Active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5306166A (en) * | 1992-12-14 | 1994-04-26 | Wyse Technology, Inc. | Chip storage insertion guide |
| US6554628B2 (en) * | 1999-08-05 | 2003-04-29 | General Electric Co. | Remote cable extractor |
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