chemistry Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds made of atoms, molecules and ions ...

, sulfoxidation refers to two distinct reactions. In one meaning, sulfoxidation refers to the reaction of

alkane In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which ...

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 activ ...

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 wel ...

. 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, foaming ...

s. The reaction requires

UV-radiation Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nm (with a corresponding frequency around 30 PHz) to 400 nm (750 THz), shorter than that of visible light, but longer than X-rays. UV radiation i ...

. :RH + SO2 + 1/2 O2 -> RSO3H The reaction favors secondary positions in accord with its

free-radical In chemistry, a radical, also known as a free radical, is an atom, molecule, or ion that has at least one unpaired valence electron. With some exceptions, these unpaired electrons make radicals highly chemically reactive. Many radicals spon ...

mechanism. Mixtures are produced. Semiconductor-sensitized variants have been reported. Sulfoxidation can also refer to the oxygenation of a

thioether In organic chemistry, an organic sulfide (British English sulphide) or thioether is an organosulfur functional group with the connectivity as shown on right. Like many other sulfur-containing compounds, volatile sulfides have foul odors. A sul ...

to a

sulfoxide In organic chemistry, a sulfoxide, also called a sulphoxide, is an organosulfur compound containing a sulfinyl () functional group attached to two carbon atoms. It is a polar functional group. Sulfoxides are oxidized derivatives of sulfides. E ...

. :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