CH107338A - Process for the preparation of perylenetetracarboxylic acid monoimide. - Google Patents
Process for the preparation of perylenetetracarboxylic acid monoimide.Info
- Publication number
- CH107338A CH107338A CH107338DA CH107338A CH 107338 A CH107338 A CH 107338A CH 107338D A CH107338D A CH 107338DA CH 107338 A CH107338 A CH 107338A
- Authority
- CH
- Switzerland
- Prior art keywords
- perylenetetracarboxylic acid
- preparation
- monoimide
- red
- acid
- Prior art date
Links
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 title 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
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/33—Polycyclic acids
- C07C63/337—Polycyclic acids with carboxyl groups bound to condensed ring systems
- C07C63/42—Polycyclic acids with carboxyl groups bound to condensed ring systems containing three or more condensed rings
- C07C63/48—Polycyclic acids with carboxyl groups bound to condensed ring systems containing three or more condensed rings containing three or more carboxyl groups all bound to carbon atoms of the condensed ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Zusatzpatent zum Hauptpatent Nr. 103431. Verfahren zur Darstellung von Perylentetracarbonsäuremonoimid. Im Hauptpatent ist die Darstellung von Perylentetracarbonsäure durch Einwirkung starker Sieliwefelsäuren bei höherer Tempe ratur auf P#orylentetracarbonsäurediimid be schrieben, auf einen Farbstoff, dessen Her stellung in der deutschen Patentselirift Nr. <B>276357</B> angegeben ist.
Es ist nun gefunden worden, dass es gelingt, die Spaltung stufenweise durelizu- führen und das Monoimid der Perylentetra- carbonsäurp- zu erhalten, wenn man die Ein wirkung der Schwefels#,uren unter gernässig- ter-en Bedingungen, das heisst bei Tempera turen von<B>180</B> bis<B>190 ' C</B> vor sich gehen lässt.
<I>Beispiel:</I> <B>10</B> Teile des Farbstoff es, der durch Ver schmelzen von Naphtlialin-1.8-diearbon- säureimid mit Ätzkali erhältlich ist (Perylen- tetra,carbonsäurediimid) <B>.</B> werden mit<B>150</B> Gewielitsteilen Schwefelsäure von<B>6,6 '</B> B6 während einer Stunde auf ungefähr<B>180 '</B> unter Rühren erhitzt. Nachdem die Masse sich abgekühlt hat, wird sie abgesaugt. Die zurückbleibenden bräunliehen Kristalle wer den mit ungefähr<B>25</B> Gewielitsteilen Schwe- felsäure von<B>60'</B> B6 und dann mit Wasser gewaschen.
Auf dieseWeise erhält man das Monoimid der Perylentetracarbonsäure mit etwas Perylentetr-aearbonsäureanllydrid ver mischt. Da das Natriumsalz der Perylen- tetracarbonsäure leichter löslich ist als das des Monoimids der Perylentetracarbonsäure, können die beiden Körper in Form ihrer Na- triumsalze getrennt werden.
Das Perylentetracarbonsäuremonoimid wird aus seinem Natriumsalz durch Säuren ausgefällt. Es stellt, trocken ein rotbraunes Pulver dar, das in sehr verdünnten Alkali- lösungen mit intensiver roter Farbe löslich ist. Aus seinen alkaliselien Lösungen wird es vermittelst Säuren oder Salzen gefällt. In konzentrierter Schwefelsäure löst es sieh mit blaustichtig roter Farbe und starker seltarlacUroter Fluoreszenz.
Additional patent to main patent No. 103431. Process for the preparation of perylenetetracarboxylic acid monoimide. The main patent describes the preparation of perylenetetracarboxylic acid by the action of strong sulphuric acids at higher temperatures on P # orylenetetracarboxylic diimide, on a dye, the production of which is given in German patent publication no. 276357 </B>.
It has now been found that it is possible to carry out the cleavage step by step and to obtain the monoimide of the perylenetetracarboxylic acid if the action of the sulfuric acids is allowed to take place under more moderate conditions, that is to say at temperatures from <B> 180 </B> to <B> 190 'C </B>.
<I> Example: </I> <B> 10 </B> parts of the dye es, which can be obtained by fusing naphthlialin-1,8-diarboxylic acid imide with caustic potash (perylenetetra, carboxylic acid diimide) <B>. < / B> are heated with <B> 150 </B> parts by weight of sulfuric acid of <B> 6.6 '</B> B6 to about <B> 180' </B> for one hour while stirring. After the mass has cooled, it is sucked off. The brownish crystals that remain are washed with about <B> 25 </B> parts by weight sulfuric acid of <B> 60 '</B> B6 and then with water.
In this way, the monoimide of perylenetetracarboxylic acid is obtained mixed with a little perylenetetrarboxylic acid anhydride. Since the sodium salt of perylenetetracarboxylic acid is more soluble than that of the monoimide of perylenetetracarboxylic acid, the two bodies can be separated in the form of their sodium salts.
The perylenetetracarboxylic acid monoimide is precipitated from its sodium salt by acids. When dry it is a red-brown powder that is soluble in very dilute alkali solutions with an intense red color. It is precipitated from its alkaline solutions by means of acids or salts. It dissolves in concentrated sulfuric acid with a bluish red color and strong seltarac-red fluorescence.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH103431T | 1923-09-05 | ||
| CH107338T | 1923-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH107338A true CH107338A (en) | 1924-10-16 |
Family
ID=25706467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH107338D CH107338A (en) | 1923-09-05 | 1923-09-05 | Process for the preparation of perylenetetracarboxylic acid monoimide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH107338A (en) |
-
1923
- 1923-09-05 CH CH107338D patent/CH107338A/en unknown
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