Sulfolene, or butadiene sulfone is a cyclic organic

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 chemical

Chemical compound

A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...

 with a sulfone

Sulfone

A sulfone is a chemical compound containing a sulfonyl functional group attached to two carbon atoms. The central hexavalent sulfur atom is double bonded to each of two oxygen atoms and has a single bond to each of two carbon atoms, usually in two separate hydrocarbon substituents.-IUPAC name and...

 functional group

Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...

. It is the product of a (4+1) cycloaddition

Cycloaddition

A cycloaddition is a pericyclic chemical reaction, in which "two or more unsaturated molecules combine with the formation of a cyclic adduct in which there is a net reduction of the bond multiplicity." The resulting reaction is a cyclization reaction.Cycloadditions are usually described by the...

 between butadiene and sulfur dioxide

Sulfur dioxide

Sulfur dioxide is the chemical compound with the formula . It is released by volcanoes and in various industrial processes. Since coal and petroleum often contain sulfur compounds, their combustion generates sulfur dioxide unless the sulfur compounds are removed before burning the fuel...

.

Catalytic hydrogenation yields sulfolane

Sulfolane

Sulfolane is a clear, colorless liquid commonly used in the chemical industry as an extractive distillation solvent or reaction solvent. Sulfolane was originally developed by the Shell Oil Company in the 1960s as a solvent to purify butadiene...

, a solvent used in the petrochemical industry for the extraction of aromatics from hydrocarbon

Hydrocarbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls....

 streams. In the laboratory it is used as a solid source of butadiene, into which it decomposes by a reverse cycloaddition. However, the sulfur dioxide that is generated as a side product may cause side reactions with acid-sensitive substrates.

In electrochemical fluorination

Electrochemical fluorination

Electrochemical fluorination , or electrofluorination, is a foundational organofluorine chemistry method for the preparation of fluorocarbon-based organofluorine compounds. The general approach represents an application of electrosynthesis...

, butadiene sulfone can increase the yield of perfluorooctanesulfonyl fluoride

Perfluorooctanesulfonyl fluoride

Perfluorooctanesulfonyl fluoride is a synthetic perfluorinated compound with a sulfonyl fluoride functional group. It is used to make perfluorooctanesulfonic acid and PFOS-based compounds...

 by about 70%. It is "highly soluble in anhydrous HF and increases the conductivity of the electrolyte solution." In this application, it undergoes a ring opening and is fluorinated to form perfluorobutanesulfonyl fluoride

Sulfonyl halide

Sulfonyl halide groups occur when a sulfonyl functional group is singly bonded to a halogen atom. They have the general formula R-SO2-X where X is a halogen.-Sulfonyl fluorides:...

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