Add time:08/30/2019         Source:sciencedirect.com

The kinetics for synthesizing Benzyl salicylate (cas 118-58-1) (C6H4(OH)COOCH2C6H5, denoted as Ph(OH)COOR) from the carboxylation of benzyl bromide (C6H5CH2Br, RBr) via solid–liquid phase-transfer catalysis (SLPTC) was investigated. The key component to conduct the substitution reaction is the catalytic intermediate generated from solid sodium salicylate (C6H4(OH)COONa, denoted as Ph(OH)COONa) reacted with tetraalkylammonium salt. The concentration of catalytic intermediate remained nearly constant after the induction period and increased with the increase of the amount of catalyst employed. The reaction between catalytic intermediate and organic reactant is identified as the controlling step. Factors affecting the formation of the catalytic intermediate include the relative amounts of catalyst, solid reactant, organic reactant, and extra addition of inorganic salts. Different phase-transfer catalysts were employed to compare their catalytic efficiency: tetra-n-butylammonium bromide (Bu4NBr, TBAB or QBr in general) > tetra-n-butylammonium iodide (TBAI) > tetra-n-butylphosphonium bromide (TBPB) > aliquat 336 > tetra-n-butylammonium hydrogen sulfate (TBAHS) > polyethylene glycol (PEG) 1500. The product yield above 98% was achieved within 1 h at 70 °C by using tetra-n-butylammonium bromide as the catalyst. A kinetic model was developed for the solid–liquid reaction. The overall reaction can be described by pseudo-first-order kinetics with the apparent activation energy in chlorobenzene to be 62.52 kJ mol−1.

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