CH212430A - Process for the production of a cyclic carboxylic acid. - Google Patents
Process for the production of a cyclic carboxylic acid.Info
- Publication number
- CH212430A CH212430A CH212430DA CH212430A CH 212430 A CH212430 A CH 212430A CH 212430D A CH212430D A CH 212430DA CH 212430 A CH212430 A CH 212430A
- Authority
- CH
- Switzerland
- Prior art keywords
- carboxylic acid
- acid
- production
- cyclic carboxylic
- converted
- Prior art date
Links
- -1 cyclic carboxylic acid Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000975 dye Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 238000003756 stirring 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Verfahren zur Herstellung einer cyclischen Carbonsäure. Es wurde gefunden, dass man in einfacher Weise eine Tetracarbonsäure des Kupfer- phthalocyanins erhält, wenn man Kupfer- phthalocyanin in einer geschmolzenen Mischung von wasserfreiem Aluminium chlorid und Alkalihalogenid mit Phosgen umsetzt und das erhaltene Säurechlorid durch Einwirkenlassen von Wasser in die freie Carbonsäure überführt.
Die Kupferphthalocyanintetracarbonsäure wird so in Form lebhaft violett glänzender Kristalle erhalten, die sich in starker Schwe felsäure mit grüngelber Farbe lösen; beim Verdünnen der schwefelsauren Lösung mit Wasser fällt der Farbstoff in blauen Flocken aus. Die Lösung in Ammoniak oder verdünn ter Alkalilauge ist leuchtend blau, auf Zu satz von Natriumhydrosulfit wird sie violett blau.
Die Kupferphthalocyanintetracärbonsäure Emdet Verwendung als Farbstoff oder als Zwischenprodukt zur Herstellung von Farb stoffen.
<I>Beispiel:</I> 100 Gewichtsteile Kupferphthaloeyanin werden bei 120 C unter Rühren in eine ge schmolzene Mischung von 900 Gewichtsteilen wasserfreiem Aluminiumchlorid und 133 Ge wichtsteilen Natriumchlorid eingetragen. Dann wird die Schmelze unter Einleiten von Phosgen allmählich auf 155-160 C er hitzt und dies, so lange fortgesetzt, bis eine Probe der Masse in stark verdünntem wäss- rigem. Alkali ohne Rückstand löslich ist.
Dann lässt man etwas abkühlen und giesst das Umsetzungsgemisch auf Eis., saugt die ausgeschiedenen, violett glänzenden Kri stalle ab, wäscht sie mit verdünnter wässriger Salzsäure und dann mit Wasser aus und trocknet sie.
Die so erhaltene Kupferphthalocyanin- tetracarbonsäure löst sich in starker Schwe felsäure mit grüngelber und in verdünnten wässrigen Alkalien mit leuchtend blauer Farbe.
An Stelle von Natriumchlorid kann man auch andere Alkalihalogenide oder Gemische dieser verwenden.
Process for the production of a cyclic carboxylic acid. It has been found that a tetracarboxylic acid of copper phthalocyanine is obtained in a simple manner if copper phthalocyanine is reacted with phosgene in a molten mixture of anhydrous aluminum chloride and alkali metal halide and the acid chloride obtained is converted into the free carboxylic acid by exposure to water.
The copper phthalocyanine tetracarboxylic acid is obtained in the form of bright violet shining crystals, which dissolve in strong sulfuric acid with a greenish yellow color; when the sulfuric acid solution is diluted with water, the dye precipitates in blue flakes. The solution in ammonia or dilute alkali lye is bright blue; when sodium hydrosulfite is added, it turns violet blue.
The copper phthalocyanine tetracarboxylic acid Emdet is used as a dye or as an intermediate for the production of dyes.
<I> Example: </I> 100 parts by weight of copper phthaloeyanine are introduced into a molten mixture of 900 parts by weight of anhydrous aluminum chloride and 133 parts by weight of sodium chloride at 120 ° C. with stirring. Then the melt is gradually heated to 155-160 ° C. while passing in phosgene and this is continued until a sample of the mass is in highly diluted aqueous. Alkali is soluble without residue.
The mixture is then allowed to cool slightly and the reaction mixture is poured onto ice, the precipitated, shiny violet crystals are filtered off with suction, washed with dilute aqueous hydrochloric acid and then with water and dried.
The copper phthalocyanine tetracarboxylic acid thus obtained dissolves in strong sulfuric acid with a green-yellow color and in dilute aqueous alkalis with a bright blue color.
Other alkali halides or mixtures of these can also be used instead of sodium chloride.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE212430X | 1938-02-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH212430A true CH212430A (en) | 1940-11-30 |
Family
ID=5808050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH212430D CH212430A (en) | 1938-02-15 | 1939-02-14 | Process for the production of a cyclic carboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH212430A (en) |
-
1939
- 1939-02-14 CH CH212430D patent/CH212430A/en unknown
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