Reaction Kinetics, Mechanisms and Catalysis
Volume/Issue:
Volume 107: Issue 2
Oxidation of sulfides to sulfones with hydrogen peroxide in the presence of acetic acid and Amberlyst 15
Authors:
Venkateshwar Rao Tumula Council of Scientific & Industrial Research, Indian Institute of Petroleum, Dehradun 248005, India

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Sapna Bondwal Council of Scientific & Industrial Research, Indian Institute of Petroleum, Dehradun 248005, India

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Priyanka Bisht Council of Scientific & Industrial Research, Indian Institute of Petroleum, Dehradun 248005, India

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Chandrashekar Pendem Council of Scientific & Industrial Research, Indian Institute of Petroleum, Dehradun 248005, India

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Jagdish Kumar Council of Scientific & Industrial Research, Indian Institute of Petroleum, Dehradun 248005, India

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Pages:
449–466
Online Publication Date:
26 Aug 2012
Publication Date:
01 Dec 2012
Article Category:
Research Article
DOI:
https://doi.org/10.1007/s11144-012-0491-8
Keywords:
Sulfide oxidation; Peracetic acid; Hydrogen peroxide; Amberlyst 15; Sulfone; Thioanisole
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Abstract

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.

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Cover Reaction Kinetics, Mechanisms and Catalysis
Reaction Kinetics, Mechanisms and Catalysis
Print ISSN:
1878-5190
Online ISSN:
1878-5204

Reaction Kinetics, Mechanisms and Catalysis
Language English
Size B5
Year of
Foundation		 1974
Volumes
per Year		 1
Issues
per Year		 6
Founder Akadémiai Kiadó
Founder's
Address		 H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
Publisher Akadémiai Kiadó
Springer Nature Switzerland AG
Publisher's
Address		 H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
CH-6330 Cham, Switzerland Gewerbestrasse 11.
Responsible
Publisher		 Chief Executive Officer, Akadémiai Kiadó
ISSN 1878-5190 (Print)
ISSN 1878-5204 (Online)

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