Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-07-21
1998-09-15
Kight, John
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
106498, C07D22118, C07D40104, C07D40704, C07D40904
Patent
active
058080732
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP96/00167, filed Jan. 12, 1996.
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a novel process for preparing perylene-3,4-dicarbimides by reacting a perylene-3,4,9,10-tetracarboxylic acid, or the corresponding anhydrides, with a primary amine.
The invention also relates to a novel process for purifying perylene-3,4-dicarbimides obained by reaction of a perylene-3,4,9,10-tetracarboxylic acid or of the corresponding anhydrides with a primary amine.
The invention finally relates to novel perylene-3,4-dicarbimides of the general formula Ia ##STR1## where
R.sup.1' is C.sub.14 -C.sub.30 -alkyl whose carbon chain may be interrupted by one or more of --O--, --S--, --NR.sup.3 --, --CO-- and/or --SO.sub.2 -- and which may be monosubstituted or polysubstituted by carboxyl, sulfo, hydroxyl, cyano, C.sub.1 -C.sub.6 -alkoxy or a 5-, 6- or 7-membered heterocyclic radical which is attached via a nitrogen atom and which may contain further heteroatoms and may be aromatic, where
C.sub.5 -C.sub.8 -cycloalkyl whose carbon skeleton may be interrupted by one or more of --O--, --S-- and/or --NR.sup.3 --; phenyl which is monosubstituted or polysubstituted by C.sub.1 -C.sub.4 -alkyl or methoxy at least in the two ortho positions, by C.sub.5 -C.sub.18 -alkyl, C.sub.2 -C.sub.6 -alkoxy, halogen, hydroxyl, cyano, carboxyl, --CONHR.sup.4, --NHCOR.sup.4 and/or aryl- or hetaryl-azo, which may each be substituted by C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.6 -alkoxy, halogen, hydroxyl, cyano or carboxyl, where each be substituted by C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, halogen, hydroxyl or cyano; mentioned for phenyl, in which case the C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.6 -alkoxy substituents may be in any desired position on the ring system;
R.sup.2 is in each instance independently of the other instances hydrogen; halogen; C.sub.1 -C.sub.18 -alkyl; aryloxy, arylthio, hetaryloxy or hetarylthio, which may each be substituted by C.sub.1 -C.sub.10 -alkyl, C.sub.1 -C.sub.6 -alkoxy, cyano or carboxyl.
2. Description of the Background
Perylene-3,4-dicarbimides of the formula ##STR2## (A: hydrogen or organic radical) are known to be suitable for use as intermediates for making pigment additives, fluorescent dyes and fluorescent pigments (unpublished DE-A-43 25 247; EP-A-596 292; Chimia 48, 503-505 (1994)).
As well as the unsubstituted perylene-3,4-dicarbimide (A=H), only a few N-alkyl- and N-phenyl-substituted perylene-3,4-dicarbimides (A=methyl, ethyl, n-propyl, n-butyl, isobutyl, n-pentyl, n-hexyl, n-octyl, n-dodecyl, phenyl, 4-tolyl, 4-anisyl, 2,5-di-tert-butylphenyl) are known so far and they are prepared by complicated, multistage processes starting from perylene-3,4,9,10-tetracarboxylic dianhydride ##STR3## via the corresponding perylene-3,4,9,10-tetracarbimide anhydrides ##STR4## in usually unsatisfactory yields and purities which necessitate costly methods of purification (extraction, column chromatography).
For instance, the unsubstituted and the N-alkyl-substituted perylene-3,4-dicarbimides are obtained by alkaline decarboxylation of the imide-anhydrides at temperatures .gtoreq.220.degree. C. under superatmospheric pressure (reaction times of 18 h) (DE-C-486 491; Bulletin of the Chemical Society of Japan 54, 1575-1576 (1981); EP-A 596 292). However, this process is only suitable for aliphatic imides which are stable to bases.
To prepare the N-phenyl-, -tolyl- and -anisyl-substituted (as well as N-methyl- and -ethyl-substituted) perylene-3,4-dicarbimides, the initially prepared unsubstituted perylene-3,4-dicarbimide is sulfonated with sulfuric acid, then converted with potassium hydroxide solution into the sulfonated anhydride, whch is then reacted with the corresponding primary amine to form the sulfonated N-substituted imide, which is finally desulfonated with sulfuric acid to the desired perylene-3,4-dicarbimide (Bulletin of the Chemical Society of Japan 52, 1723-1726 (1979), Shikizai Kyokaishi 49, 29-34 (1976) = Chemical Abstracts 85:
REFERENCES:
patent: 5405962 (1995-04-01), Muellen
patent: 5472494 (1995-12-01), Hetzenegger et al.
patent: 5650513 (1997-07-01), Langhals
Chemical Abstracts 85:20928, abstract of Nagao, Shikizai Kyokaishi (1976), vol. 49(1), pp. 29-34.
Chemical Abstracts 123:85915, abstract of Quante, Angew. Chem., Int. Ed. Engl. (1995), 34(12), pp. 1323-1325.
Chemical Abstracts 123:202037, abstract of DE 4338784, May 18, 1995.
Chima 48 (1994)503-505, Langhals.
Chemical Society of Japoan 52, 1723-1726 (1979), Nagao.
Bohm Arno
Helfer Willi
BASF - Aktiengesellschaft
Kight John
M. Mach D. Margaret
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