CH216314A - Process for the production of a nitrogen-containing condensation product. - Google Patents
Process for the production of a nitrogen-containing condensation product.Info
- Publication number
- CH216314A CH216314A CH216314DA CH216314A CH 216314 A CH216314 A CH 216314A CH 216314D A CH216314D A CH 216314DA CH 216314 A CH216314 A CH 216314A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- condensation product
- production
- green
- nitrogen
- Prior art date
Links
- 239000007859 condensation product Substances 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 4
- 229920000742 Cotton Polymers 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- WIGAVRUYAYGVPK-UHFFFAOYSA-N 1-ethoxypyrene Chemical compound C1=C2C(OCC)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 WIGAVRUYAYGVPK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/34—Anthraquinone acridones or thioxanthrones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines stickstoffhaltigen Kondensationsproduktes. Es wurde gefunden, dass ein stickstoffhaltiges Kondensationsprodukt erhalten werden kann, wenn man auf das Produkt der Formel
EMI0001.0002
kondensierende Mittel einwirken lässt.
Das erhaltene Kondensationsprodukt, dem wahrscheinlich die Formel
EMI0001.0004
zukommt, stellt ein grünes Pulver dar. Es lässt sich aus a-Chlornaphtalin umkristallisieren, wobei ein grünes kristallines Pulver vom Schmelzpunkt 338-342'' erhalten wird. Die ses löst sich in konzentrierter Schwefelsäure mit leuchtend oranger Farbe und färbt Baum- wolle aus brauner Küpe in lebhaften, reinen gelbgrünen Tönen.
Als kondensierende -Mittel, die auf die Lmsetzungsprodukte einwirken gelassen wer den, können beispielsweise saure kondensie rende Mittel, wie z. B. Halogeliide organischer Säuren, Schwefelsäure oder Halogensulfon- säure verwendet werden.
Die Einwirkung dieser kondensierenden Mittel kann bei höhe ren Temperaturen in Anwesenheit von Lö- sungs- oder Verdünnungsmitteln erfolgen. Als kondensierende -Mittel eignen sich die Halo- genide von Karbonsäuren, wie z. B. Acet3-1- chlorid oder Benzoylchlorid, besonders gut.
<I>Beispiel:</I> 5,9 Teile 1-Chloranthracliinoli-2-carbon- säureäthylester, 4,6 Teile Amino-3-inethoxy- pyren, 4,2 Teile entwässertes Natriumacetat und 0,7 Teile Kupferacetat werden in 10-1 Teilen Amylalkoliol 3 Stunden im Sieden gehalten.
Nach dem Erkalten wird filtriert, ausgewaschen, hierauf der Rückstand mit 2 oiger Salzsäure ausgekocht, wieder filtriert, ausgewaschen und mit 3 0, oigem alkoholischem Kali durch 1 1/c stiindiges Sieden verseift. Dabei erhält man ein dunkel gefärbtes 'Um setzungsprodukt, das bei 22()' schmilzt und sich in konz. Schwefelsäure mit brauner Farbe löst.
Dieses Produkt wird mit 91 Teilen Nitro- benzol und 12 Teilen Acetylchlorid erhitzt, zuerst während '/;a Stunde bei 1l0-120 ", dann während 1 Stunde bei. 200-210 . Nach dem Abkühlen auf 90 wird filtriert, mit Ben zol und Alkohol ausgewaschen und getrocknet.
Das in diesem Beispiel verwendete :lniino- 3-metlioxypyl-en kann wie folgt hergestellt werden 23,2 Teile 3-1Iethoxypyren, hergestellt durch Methylieren von 3-Oxypyren, werden in 300 Teilen Eisessig suspendiert und bei 50-60 unter starkem Rühren 10 Teile 68 ";!o ige Salpetersäure in 3/i Stander. zutro- pfen gelassen. Nun wird die Temperatur auf <B>80-850</B> erhöht und 6 Stunden weiter bei dieser Temperatur gerührt.
Nach dem Abküh len auf 60o wird filtriert, ausgewaschen und das bei<B>160</B> schmelzende, gelbe Nitroprodukt durch Erhitzen mit alkoholischem Schwefel natrium reduziert. --Man lässt erkalten und verdünnt mit Wasser, wobei das Amino-3- inethoxypyren in öliger Form ausfällt, jedoch alsbald kristallinisch erstarrt. Durch L mkri- stallisieren aus Benzin wird das Amino-3- metlioxypyren in schwefelgelben Kristallen erhalten,
die bei 125 " schmelzen.
Process for the production of a nitrogen-containing condensation product. It has been found that a nitrogen-containing condensation product can be obtained by referring to the product of the formula
EMI0001.0002
allows condensing agents to act.
The condensation product obtained, which probably has the formula
EMI0001.0004
is a green powder. It can be recrystallized from α-chloronaphthalene to give a green crystalline powder with a melting point of 338-342 ". This dissolves in concentrated sulfuric acid with a bright orange color and dyes cotton from a brown vat in lively, pure yellow-green tones.
As a condensing agent that is allowed to act on the Lmsetzungprodukte who can, for example, acidic condensing agents such. B. Halogeliide of organic acids, sulfuric acid or halosulfonic acid can be used.
The action of these condensing agents can take place at higher temperatures in the presence of solvents or diluents. Suitable condensing agents are the halides of carboxylic acids, such as. B. Acet3-1- chloride or benzoyl chloride, particularly good.
<I> Example: </I> 5.9 parts of 1-chloroanthracliinoli-2-carboxylic acid ethyl ester, 4.6 parts of amino-3-inethoxypyrene, 4.2 parts of dehydrated sodium acetate and 0.7 parts of copper acetate are in 10 -1 parts of amyl alcohol kept boiling for 3 hours.
After cooling, it is filtered, washed, then the residue is boiled with 2% hydrochloric acid, filtered again, washed and saponified with 30% alcoholic potash by boiling for 1 1 / c for 1 hour. This gives a dark-colored 'To implementation product that melts at 22 ()' and is in conc. Sulfuric acid dissolves with a brown color.
This product is heated with 91 parts of nitrobenzene and 12 parts of acetyl chloride, first for 1 hour at 110-120 ", then for 1 hour at 200-210. After cooling to 90 it is filtered, with benzene and Alcohol washed out and dried.
The one used in this example: Inino-3-metlioxypylen-en can be prepared as follows 23.2 parts of 3-1-ethoxypyrene, prepared by methylating 3-oxypyrene, are suspended in 300 parts of glacial acetic acid and 10 parts at 50-60 with vigorous stirring 68% nitric acid in a 3 / i stander. Is added dropwise. The temperature is now increased to <B> 80-850 </B> and stirring is continued for 6 hours at this temperature.
After cooling to 60o, it is filtered, washed and the yellow nitro product, which melts at <B> 160 </B>, is reduced by heating with alcoholic sodium sulphide. - Allow to cool and dilute with water, whereby the amino-3-inethoxypyrene precipitates in an oily form, but soon solidifies in a crystalline manner. By crystallizing from gasoline, the amino-3-metlioxypyrene is obtained in sulfur-yellow crystals,
which melt at 125 ".
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH216314T | 1936-10-24 | ||
| CH197585T | 1936-10-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH216314A true CH216314A (en) | 1941-08-15 |
Family
ID=25723015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH216314D CH216314A (en) | 1936-10-24 | 1936-10-24 | Process for the production of a nitrogen-containing condensation product. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH216314A (en) |
-
1936
- 1936-10-24 CH CH216314D patent/CH216314A/en unknown
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