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7656344 
Journal Article 
Novelties of cyanide displacement reaction in ibuprofen amide process by phase transfer catalysis: Solid-liquid versus solid-liquid (omega)-liquid systems 
Yadav, GD; Ceasar, JLeo; , 
2006 
Yes 
Journal of Molecular Catalysis A: Chemical
ISSN: 1381-1169 
ELSEVIER SCIENCE BV 
AMSTERDAM 
202-209 
WOS:000242327500033 
This work deals with the phase transfer catalysed cyanide displacement reaction on 1-(4-isobutyl phenyl) ethyl chloride to synthesize 2-(4-isobutyl phenyl) propionitrile, which is an intermediate for the synthesis of ibuprofen analogs, belonging to a class of NSAID (nonsteroidal anti-inflammatory drugs). The reaction was studied using solid-liquid phase transfer catalysis (S-L PTC) with trace quantities of water, forming the so-called omega phase at 90 degrees C. The rates of reaction and selectivity to the product are enhanced in the S-L(org.)-L (omega) PTC in comparison with S-L PTC, which in turn is superior to L-L PTC; the latter suffers from the disadvantage of side reactions in the aqueous phase. In the current work, the effects of various parameters such as catalyst structure, catalyst loading, substrate loading and temperature were studied on the conversion and rates of reaction of 1-(4-isobutyl phenyl) ethyl chloride with solid sodium cyanide under S-L and S-L(w)-L PTC at 90 degrees C with toluene as the organic solvent. Tetrabutylammonium bromide (TBAB) was found to be the best catalyst. The role of omega liquid phase in intensification of the S-L PTC was theoretically and experimentally investigated. The kinetic constants have been determined and the apparent activation energy is found as 4.2kcal/mol, which suggests that the reaction is quite fast, which is likely to bring in mass transfer effects. (c) 2006 Elsevier B.V. All rights reserved.