METHOD FOR THE PRODUCTION OF PERYLEN-3,4:9,10-TETRACARBOXYLIC ACID DIIMIDES AND PERYLEN-3,4:9,10-TETRACARBOXYLIC ACID DIANHYDRIDE AND NAPHTALENE-1,8-DICARBOXYLIMIDES

摘要

Production of perylen-3,4:9,10-tetracarboxylic acid diimides of general formula (I), where R = C1-C30 alkyl, the carbon chain of which may be interrupted by one or several -O- groups and/or is substituted with C5-C8 cycloalkyl, which can be mono- or multiply-substituted by C1-C6 alkyl, phenyl or phenyl-C1-C6 alkyl, which can each be mono- or multiply-substituted with C1-C18 alkyl and/or C1-C6 alkoxy, and mono- or multiply-substituted by -OCOR1, -N(R1)2, -SO2NH2, -SO2N(R1)2, -CON(R1)2 and/or -COOR1; C5-C8 cycloalkyl, the carbon skeleton of which may be interrupted by one or more -O-, -S- and/or -NR2- groups and/or mono- or multiply-substituted with C1-C6 alkyl; phenyl, phenyl-C1-C6 alkyl, naphthyl or heteroaryl, which may be mono- or multiply-substituted with C1-C18 alkyl, C1-C6 alkoxy, phenylazo, naphthylazo, pyridylazo, pyrimidylazo, cyano, -N(R1)2, -CON(R1)2 and/ or -COOR1; R1 = C1-C6 alkyl, C5-C8 cycloalkyl, phenyl or phenyl-C1-C6 alkyl; R2 = C1-C6 alkyl, phenyl or phenyl-C1-C6 alkyl, by dimerisation of a naphthalene-1,8-dicarboximide of formula (II), whereby the dimerisation is carried out in a reaction medium essentially comprising a non-polar aprotic organic solvent and a base comprising an alkali metal and the leuco form of the perylen-3,4:9,10-tetracarboxylic acid diimide precipitating as the alkali metal salt then reoxidised in the presence of a polar solvent. The invention also relates to the production of perylen-3,4:9,10-tetracarboxylic acid anhydride and naphthalene-1,8-dicarboximides.