Bis-o-amino(thio)phenols and their preparartion

• Main Authors: KEITMANN, MICHAEL, SEZI, RECAI
• Format: Patent
• Language: English; French; German
• Published: 12.12.2001
• Edition: 7
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; APPARATUS SPECIALLY ADAPTED THEREFOR; CHEMISTRY; CINEMATOGRAPHY; ELECTROGRAPHY; HETEROCYCLIC COMPOUNDS; HOLOGRAPHY; MATERIALS THEREFOR; METALLURGY; ORGANIC CHEMISTRY; ORIGINALS THEREFOR; PHOTOGRAPHY; PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES,e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTORDEVICES; PHYSICS

New bis-o-amino-phenol and -thiophenol compounds are obtained by reacting two halogenated nitroaromatic compounds with an alkali hydroxide or hydrosulfide, or a diol or dithiol in presence of a base, or an alkali salt of such diols or dithiols, and then reducing the nitro groups. Bis-o-amino-phenols and -thiophenols of formula (I) are new: A -A = H, F, CH3, CF3, OCH3, OCF3, CH2CH3, CF2CF3, OCH2CH3 or OCF2CF3, where at least one of these groups is a fluorinated group; T = O or S; m = 0 or 1; z = a divalent aromatic residue in which ring CH groups are replaced by Q, i.e. o-, m- or p- phenylene with Q in all other ring positions, all possible combinations of naphthylene residues with Q in all other positions, and various divalent groups derived from the unit Ar-M-Ar, e.g. as follows (25 structures listed): An Independent claim is also included for a process for the production of (I), comprising (a) reaction of a nitro compound (II) and a nitro compound (III) in a solvent at -10 to 80 degrees C with (i) an alkali hydroxide or hydrosulfide or (ii) a diol or dithiol of formula HT-Z-TH in presence of a base or (iii) an alkali salt of such diol or dithiol, followed by (b) reduction of the dinitro compound to the diamino compound X = halogen