Premium
Phase‐transfer catalysis of the reaction of α‐bromo‐ p ‐xylene with iron carbonyls
Author(s) -
Wu HoShing,
Tan WenHan
Publication year - 1996
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/(sici)1097-4660(199612)67:4<381::aid-jctb587>3.0.co;2-p
Subject(s) - catalysis , chemistry , selectivity , xylene , yield (engineering) , solvent , ketone , carbonylation , phase (matter) , inorganic chemistry , organic chemistry , toluene , carbon monoxide , materials science , metallurgy
The carbonylation of α‐Bromo‐ p ‐xylene (BrCH 2 C 6 H 4 CH 3 , BX) with iron pentacarbonyl (Fe(CO) 5 ) by phase‐transfer catalysis was studied in an organic solvent/alkaline solution. The reaction mechanism was corrected and clarified. The concentrations of base, reactant and catalyst, volume ratio, the kind of catalysts, organometals and solvents were evaluated to find the optimum condition in this reaction. The technique of phase‐transfer catalysis has a dramatic accelerating effect on the reaction. In examining eight kinds of phase‐transfer catalysts, tetra‐ n ‐butylammonium cation and tetra‐ n ‐butylphosphonium cation were found to be the best for increasing the yield of bis( p ‐methylbenzyl) ketone (( p ‐CH 3 C 6 H 4 CH 2 ) 2 CO, BMBK). The amount of phase‐transfer catalyst, the concentration of NaOH, the molar ratio of BX to Fe(CO) 5 and the volume ratio of aqueous to organic phase affected the product selectivity.