CH216317A - 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
- CH216317A CH216317A CH216317DA CH216317A CH 216317 A CH216317 A CH 216317A CH 216317D A CH216317D A CH 216317DA CH 216317 A CH216317 A CH 216317A
- Authority
- CH
- Switzerland
- Prior art keywords
- condensation product
- production
- parts
- nitrogen
- condensing agent
- 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
- 239000000975 dye Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 240000007817 Olea europaea Species 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid group Chemical group C(C=1C(C(=O)O)=CC=CC1)(=O)O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YZVWKHVRBDQPMQ-UHFFFAOYSA-N 1-aminopyrene Chemical compound C1=C2C(N)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 YZVWKHVRBDQPMQ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 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
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 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
- 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)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines stickstoffhaltigen Kondensationsproduktes. Es wurde gefunden, dass ein stickstoff haltiges Kondensationsprodukt erhalten wer den kann, wenn man auf das Produkt der Formel
EMI0001.0003
kondensierende Mittel und hierauf Phthal- säureanhydrid bis zum Eintritt eines Phthal- oylrestes einwirken lässt.
Das erhaltene Kondensationsprodukt bildet ein schwarzes Pulver, das sich in konzentrier ter Schwefelsäure mit grüner Farbe löst und einen Zersetzungspunkt von 360-370<B>0</B> be- sitzt. Es färbt Baumwolle aus rotbrauner Küpe in kräftigen, sehr echten Olivetönen.
Als kondensierende Mittel, die auf die Umsetzungsprodukte einwirken gelassen wer den, können beispielsweise saure kondensie rende Mittel, wie z. B. Halogenide 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 Ha logenide von garbonsäuren, wie z. B. Acetyl- chlorid oder Benzoylchlorid, besonders gut. <I>Beispiel:</I> 33,6 Teile 1-Chloranthrachinon-2-karbon- säure, 52 Teile 3-Aminopyren, 26 Teile ent wässertes Natriumacetat und 4,2 Teile Kup feracetat werden mit 700 Teilen Amylalkohol während 13;
4 Stunden unter Rückfluss zum Sieden erhitzt. Hierauf wird heiss von anor ganischen Bestandteilen und Verunreinigungen filtriert und das Filtrat erkalten gelassen. Dabei scheidet sich ein Umsetzungsprodukt als dunkles, kristallines Pulver ab, das nach dem Abfiltrieren,
Auswaschen und Trocknen mit 240 Teilen Nitrobenzol und 33 Teilen Acetylchlorid Stunden zum Sieden erhitzt wird. Nach dem Erkalten auf<B>901</B> wird ab- genutscht, mit Benzol und Alkohol ausge waschen und getrocknet.
In eine Schmelze von 500 Teilen Alumi- niumchlorid, 100 Teilen Chlorkalium und 70 Teilen Kochsalz wird unter Rühren innert 'f2 Stunde bei 11-115' eine Mischung aus 45 Teilen Phthalsäureanhydrid und 22,5 Teilen des im 1. Absatz erhaltenen Farbstoffes ein getragen. Hierauf wird die Temperatur auf 125-1301' erhöht und während S Stunden diese Temperatur gehalten.
Nach dem Er kalten wird die Reaktionsmasse zerkleinert, in verdünnte Salzsäure eingetragen, aufge kocht, filtriert und ausgewaschen. Der rohe Farbstoff wird durch Behandeln mit heisser, verdünnter Sodalösung und nachherigem Aus kochen mit Alkohol gereinigt.
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
EMI0001.0003
condensing agents and then phthalic anhydride can act until a phthaloylrest occurs.
The condensation product obtained forms a black powder which dissolves in concentrated sulfuric acid with a green color and has a decomposition point of 360-370 <B> 0 </B>. It dyes cotton from a red-brown vat in strong, very real olive tones.
As a condensing agent that is allowed to act on the reaction products who can, for example, acidic condensing agents such. B. halides 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.
As a condensing agent, the Ha logenides of garboxylic acids such. B. acetyl chloride or benzoyl chloride, particularly good. <I> Example: </I> 33.6 parts of 1-chloroanthraquinone-2-carbonic acid, 52 parts of 3-aminopyrene, 26 parts of dehydrated sodium acetate and 4.2 parts of copper acetate are mixed with 700 parts of amyl alcohol for 13;
Heated to boiling under reflux for 4 hours. Then hot inorganic components and impurities are filtered and the filtrate is allowed to cool. A reaction product separates out as a dark, crystalline powder, which after filtering off,
Washing and drying with 240 parts of nitrobenzene and 33 parts of acetyl chloride is heated to the boil for hours. After cooling to <B> 901 </B> it is suction filtered, washed out with benzene and alcohol and dried.
A mixture of 45 parts of phthalic anhydride and 22.5 parts of the dye obtained in the first paragraph is introduced into a melt of 500 parts of aluminum chloride, 100 parts of potassium chloride and 70 parts of sodium chloride, with stirring, within 2 hours at 11-115. The temperature is then increased to 125-1301 'and this temperature is maintained for 5 hours.
After he cold, the reaction mass is crushed, added to dilute hydrochloric acid, boiled up, filtered and washed. The raw dye is cleaned by treating it with hot, dilute soda solution and then boiling it with alcohol.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH197585T | 1936-10-24 | ||
| CH216317T | 1936-10-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH216317A true CH216317A (en) | 1941-08-15 |
Family
ID=25723018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH216317D CH216317A (en) | 1936-10-24 | 1936-10-24 | Process for the production of a nitrogen-containing condensation product. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH216317A (en) |
-
1936
- 1936-10-24 CH CH216317D patent/CH216317A/en unknown
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