Catalytic carbonylation for the synthesis of chemical intermediates
- 1 February 1998
- journal article
- Published by Springer Nature in Research on Chemical Intermediates
- Vol. 24 (2) , 197-211
- https://doi.org/10.1163/156856798x00771
Abstract
Chemistry related to three catalytic carbonylation reactions is discussed. Synthesis of diphenylurea from nitrobenzene, aniline, and CO gives isolated yields above 98% at 100–120 °C and 15–60 bar of CO in the presence of a palladium (II) complex, PPh3 and NEt4Cl. Experimental evidence was provided to prove a new reaction stoichiometry and involvement of a carbamoyl intermediate. In carbonylation of HCHO over ion exchange resin catalysts, reaction temperature, time, pressure, and solvent were important variables to obtain high yields of methyl glycolate. Carbonylation of isobutylphenylethanol at 120°C and 40 bar of CO in the presence of PdCl2−PPh3−HCl gives 98% yield of α-(4-isobutylphenyl) propionic acid (ibuprofen). Each catalyst component had a definite role that is indispensable for an efficient overall reaction.Keywords
This publication has 40 references indexed in Scilit:
- A palladium complex catalyst for the regioselective hydrocarboxylation of 4-methylstyreneJournal of Molecular Catalysis A: Chemical, 1997
- The regioselective hydrocarboalkoxylation of 4-methylstyrene catalyzed by palladium complexesJournal of Molecular Catalysis A: Chemical, 1995
- A highly active palladium complex catalyst in the synthesis of N,N?-diphenylurea from nitrobenzene, aniline and carbon monoxideCatalysis Letters, 1993
- Palladium-catalyzed synthesis of N,N'-diphenylurea from nitrobenzene, aniline, and carbon monoxideIndustrial & Engineering Chemistry Research, 1991
- On the Regioselectivity Control in the Palladium‐Catalyzed Hydro‐alkoxycarbonylation of α,β‐Unsaturated EstersHelvetica Chimica Acta, 1991
- Carbonylation of formaldehyde and its derivatives.Journal of The Japan Petroleum Institute, 1991
- Nickel-catalysed isomerization of methyl formate to acetic acidJournal of the Chemical Society, Chemical Communications, 1990
- Ruthenium carbonyl catalyzed reductive carbonylation of aromatic nitro compounds. A selective route to carbamatesThe Journal of Organic Chemistry, 1988
- Low-pressure, palladium-catalyzed N,N'-diarylurea synthesis from nitro compounds, amines, and carbon monoxideThe Journal of Organic Chemistry, 1975
- A new selenium–triethylamine catalysed synthesis of arylureas from carbon monoxide and aromatic aminesJournal of the Chemical Society, Chemical Communications, 1972