Preparation of perylene-3,4-dicarboxylic acid anhydrides

US6093834A · kind A · utility

Assignee

• Ciba Specialty Chemicals Corporation · US

Inventor

• Leonhard Feiler · Givisiez, CH

Key dates

• Filing date: Jan 26, 1999
• Grant date: Jul 25, 2000
• Expiry date: Jan 26, 2019

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D311/78
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Preparation of perylene-3,4-dicarboxylic acid anhydrides of the general formula I ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 can each be independently of one another hydrogen, halogen, C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.4 cycloalkyl, C.sub.1 -C.sub.20 alkoxy, phenyl, phenyloxy or phenylthio, where phenyl can in each case be mono- or polysubstituted by halogen, C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.14 cycloalkyl and/or C.sub.1 -C.sub.20 alkoxy; --NR.sup.5.sub.2 or --OR.sup.5, wherein R.sup.5 is hydrogen or C.sub.1 -C.sub.20 alkyl, or one of the pairs R.sup.1 /R.sup.2 and R.sup.3 /R.sup.4 each in 6,7- or 1,12-position is a bridge having the bridge atoms or bridge atom groups --O--, --S--, S.dbd.O, SO.sub.2 or --NR.sup.6, wherein R.sup.6 is hydrogen, C.sub.1 -C.sub.20 alkyl or C.sub.3 -C.sub.14 cycloalkyl, by treating a perylene-3,4-dicarboximide of formula II ##STR2## (a) in a first step with a base and, (b) in a second step, reacting the resultant anion with an alkylation agent R.sup.7 --X, X being halogen and R.sup.7 being unsubstituted or phenyl-substituted C.sub.1 -C.sub.20 alkyl, to the corresponding carboximide and, PA1 (c) in a third step, treating the alkyl…