| Sulfolene[1] | |
|---|---|
|
2,5-Dihydrothiophene 1,1-dioxide |
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Other names
Butadiene sulfone |
|
| Identifiers | |
| CAS number | 77-79-2 |
| PubChem | 6498 |
| ChemSpider | 6253 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C4H6O2S |
| Molar mass | 118.15 g mol−1 |
| Melting point |
65-66 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Sulfolene, or butadiene sulfone is a cyclic organic chemical with a sulfone functional group. It is the product of a (4+1) cycloaddition between butadiene and sulfur dioxide.
Catalytic hydrogenation yields sulfolane, a solvent used in the petrochemical industry for the extraction of aromatics from hydrocarbon streams. In the laboratory it is used as a solid source of butadiene[2], into which it decomposes by a reverse cycloaddition.[3] However, the sulfur dioxide that is generated as a side product may cause side reactions with acid-sensitive substrates.
In electrochemical fluorination, butadiene sulfone can increase the yield of perfluorooctanesulfonyl fluoride by about 70%.[4] It is "highly soluble in anhydrous HF and increases the conductivity of the electrolyte solution."[4] In this application, it undergoes a ring opening and is fluorinated to form perfluorobutanesulfonyl fluoride.