Health & Environmental Research Online (HERO)


Print Feedback Export to File
1774861 
Journal Article 
Oxidation of sulfides to sulfones with hydrogen peroxide in the presence of acetic acid and Amberlyst 15 
Tumula, VRao; Bondwal, S; Bisht, P; Pendem, C; Kumar, J 
2012 
1 
Reaction Kinetics, Mechanisms and Catalysis
ISSN: 1878-5190 
107 
2 
449-466 
WOS:000310901200017 
The oxidation of thioanisole to its sulfone with hydrogen
peroxide (H2O2) in the presence of acetic acid and Amberlyst 15 was investigated and found to be
a simple and effective method. Oxidation experiments in the absence of acetic acid or Amberlyst
15 confirmed the essentiality of these components for the complete oxidation of thioanisole to
its sulfone with H2O2. In the two-step oxidation process of sulfide, in the oxidation of sulfide
to sulfoxide, H2O2 plays a major role, whereas in the oxidation of sulfoxide to sulfone,
peracetic acid formed with H2O2 in the presence of acetic acid and Amberlyst 15 plays a major
role. Sulfone formation increased with an increase in H2O2, temperature and Amberlyst 15 and
decreased with acetic acid. However, with a very low amount of acetic acid, sulfone formation
decreased due to water in H2O2 and released in the reaction. Reutilization of Amberlyst 15 for
six cycles resulted in a 6.8 % decrease in sulfone yield and 3.4 % decrease in oxygenation.
Dialkyl, dibenzyl, diphenyl, alkylaryl, arylbenzyl, alkylbenzyl sulfides are completely oxidized
with this oxidation system to their corresponding sulfones. The reactivity of sulfides is in the
order dialkyl > dibenzyl > diphenyl sulfides, which is in line with their order of
nucleophilicity. 
Sulfide oxidation; Peracetic acid; Hydrogen peroxide; Amberlyst 15; Sulfone; Thioanisole