Journal of Molecular Catalysis A-Chemical, Vol.209, No.1-2, 69-73, 2004
One stage preparation of Schiff's bases from nitroarenes, aldehydes and carbon monoxide at presence of water
Results from one stage condensation reaction of nitroarenes (nitrobenzene, o-nitrotoluene, p-nitrotoluene, 4-chloro-1-nitrobenzene, 4-metboxy-1-nitrobenzene) or nitrosobenzene and carbonyl compounds (benzophenone, benzaldehyde, acetaldehyde) with carbon monoxide at the presence of water are presented. Schiff's bases are formed by this reaction. High conversion of nitro- and nitroso-arenes and selectivity to Schiff's bases up to 90% was observed with the sulphur based catalytic system (COS, or H2S, + Et3N + NH4VO3) at pressure 12 MPa of CO (measured at 25degreesC) and the temperature range from 90 to 165degreesC. A comparable reaction rate and conversion of nitro- and nitroso-arenes up to 99.8% was also reached (after 4 h, at 160degreesC) with benzaldehyde using Pd/(PdCl2 + FeCl3 + Et3N) system as a catalyst. Selectivity to the corresponding Schiff's bases was 79-82%. Aromatic nitrocarbonyl compounds, which possess poly-Schiff's bases, are formed at the temperature of 150 +/- 2degreesC, pressure of CO 12 MPa at 25degreesC and using sulphur base catalytic system. Sulphur based catalytic system was found to be very effective. Its low price and non-sensitivity to the common catalytic poisons makes it more advantageous than the other catalytic systems. (C) 2003 Elsevier B.V. All rights reserved.
Keywords:nitroarenes;nitrosoarenes;carbon monoxide;water;aldehydes;ketones;carbonylation condensation;sulphur based catalytic system;Schiff's bases;poly-Schiff's bases