in
chemistry, sulfoxidation refers to two distinct reactions.
In one meaning, sulfoxidation refers to the reaction of
alkane
In organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms tha ...
s with a mixture of
sulfur dioxide
Sulfur dioxide ( IUPAC-recommended spelling) or sulphur dioxide (traditional Commonwealth English) is the chemical compound with the formula . It is a toxic gas responsible for the odor of burnt matches. It is released naturally by volcanic ...
and
oxygen
Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as we ...
. This reaction is employed industrially to produce
alkyl sulfonic acids, which are used as
surfactant
Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, fo ...
s. The reaction requires
UV-radiation.
:
RH + SO2 + 1/2 O2 -> RSO3H
The reaction favors secondary positions in accord with its
free-radical mechanism. Mixtures are produced. Semiconductor-sensitized variants have been reported.
Sulfoxidation can also refer to the
oxygenation of a
thioether to a
sulfoxide.
:
R2S + O -> R2SO
A typical source of "O" is
hydrogen peroxide
Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3% ...
.
[{{cite journal , doi=10.1016/j.ccr.2013.05.010, title=Metal-Catalyzed Asymmetric Sulfoxidation, Epoxidation and Hydroxylation by Hydrogen Peroxide , year=2013 , last1=Srour , first1=Hassan , last2=Le Maux , first2=Paul , last3=Chevance , first3=Soizic , last4=Simonneaux , first4=Gérard , journal=Coordination Chemistry Reviews , volume=257 , issue=21–22 , pages=3030–3050 , url=https://hal.archives-ouvertes.fr/hal-00865625/file/CCR_2_Simonneaux-accepted.pdf ]
References
Sulfoxides