Terrylene and quaterrylene derivatives
AssigneeBASF SE
InventorsNeil Gregory Pschirer, Jianqiang Qu, Martin Koenemann
Life of this patent
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Abstract
A process for preparing a rylenetetracarboxylic dianhydride, or a salt thereof having application formula Ib by subjecting a rylenetetracarboximide of application formula II to a hydrolysis under alkaline conditions in the presence of a polar organic solvent and removing the rylenetetracarboxylic dianhydride Ib from any rylenetetracarboxylic monoimide monoanhydride of application formula Ia which is formed to form the rylenetetracarboxylic dianhydride, or the salt thereof having formula Ib; or hydrolyzing the rylenetetracarboximide of application formula II under conditions that form the compound of application formula Ib and substantially no rylenetetracarboxylic monoimide monoanhydride of application formula Ia.
Claims12
A process for preparing a rylenetetracarboxylic dianhydride, or a salt thereof having formula Ib
- wherein
- R is phenoxy, phenylthio, pyridyloxy, pyrimidyloxy, pyridylthio or pyrimidyl-thio, each of which may optionally be mono- or polysubstituted by C1-C12-alkyl, C1-C12-alkoxy and/or aryl;
- m is 1 or 2;
- n is 4 when m=1;
- 4 or 6 when m=2,
- the process comprising
- a) subjecting a rylenetetracarboximide of general formula II
- wherein R, m and n are as defined above and R′ is hydrogen or a C1-C30-alkyl whose carbon chain may, optionally, be interrupted by one or more —O— and/or —CO— moieties and which may, optionally, be mono- or polysubstituted by:
- C1-C6-alkoxy, cyano and/or aryl which may, optionally, be mono- or polysubstituted by C1-C18-alkyl or C1-C6-alkoxy;
- or phenyl, or naphthyl, or pyridyl, or pyrimidyl, each of which may be, optionally, mono or polysubstituted by:
- C1-C18-alkyl, C1-C6-alkoxy, halogen, cyano, nitro, —CONR2R3, —SO2NR2R3, or phenyl or naphthylazo, each of which may be, optionally, mono- or polysubstituted by C1-C10-alkyl, C1-C6-alkoxy and/or cyano;
- or C5-C8-cycloalkyl which, optionally, may be mono- or polysubstituted by C1-C6-alkyl, where R2 and R3 are each independently hydrogen;
- C1-C18-alkyl whose carbon chain may be interrupted by one or more —O—, —S—, —CO—, —SO— and/or —SO2— moieties and which may be mono- or polysubstituted by C1-C12-alkoxy, C1-C6-alkylthio, hydroxyl, mercapto, halogen, cyano, nitro and/or —COOR1;
- aryl or hetaryl to each of which may be fused further saturated or unsaturated 5- to 7-membered rings whose carbon skeleton may be interrupted by one or more —O—, —S—, —CO— and/or —SO2— moieties, where the entire ring system may be mono- or polysubstituted by C1-C12-alkyl and/or the above radicals specified as substituents for alkyl;
- and R1 is hydrogen or C1-C18-alkyl, where the R1 radicals may be the same or different when they occur more than once;
- to a hydrolysis under alkaline conditions in the presence of a polar organic solvent and removing the rylenetetracarboxylic dianhydride Ib from any rylenetetracarboxylic monoimide monoanhydride of formula Ia which is formed
- where R′, R, n and m have the same meanings as above,
- to form the rylenetetracarboxylic dianhydride, or the salt thereof having formula Ib or
- b) hydrolyzing the rylenetetracarboximide of general formula II under conditions that form the compound of formula Ib and substantially no rylenetetracarboxylic monoimide monoanhydride of the formula Ia.
Dependencies are inferred from the claim text.