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Sulfolane is used as an industrial solvent utilized for the extraction of aromatic hydrocarbons from hydrocarbon mixtures and to purify natural gas. Further, it is used in refineries and the petrochemical industry.
Solvent for nitrations using Nitronium tetrafluoroborate, B20167.
Widely used as solvent in the nucleophilic displacement of chloroaromatics with F- (Halex fluorination). For example, chlorinated benzaldehydes were converted to their fluoro-analogues by heating with KF in tetramethylene sulfone at 220o: J. Fluorine Chem., 46, 529 (1990). Nitro groups have also been displaced by F- by heating in the presence of tetramethylammonium chloride and phthaloyl chloride as a nitrite trap: J. Org. Chem., 56, 6406 (1991). See, however, Tetrahydrothiophene 1-oxide, A17502 and Potassium fluoride, 14130.
Use of this solvent makes possible the reduction of alkyl bromides to alkanes by NaBH4: Tetrahedron Lett., 3495 (1969).
Can be doubly metallated at the ɑ-positions with strong bases such as NaNH2, LiNH2 or n-BuLi, and the resulting dianion reacted with one or two equivalents of benzophenone to give the mono- or bis-adduct respectively: J. Org. Chem., 35, 1834 (1970); J. Organomet. Chem., 59, 53 (1973). For alkylation of the monolithio-derivative, see: Synth. Commun., 18, 583 (1988).
Solvent for the Baylis-Hillman reaction, using 1,4-Diazabicyclo[2.2.2]octane, A14003, which enables short reaction times at room temperature: Tetrahedron Lett., 45, 1183 (2004).
Vergaelen, M.; Verbraeken, B.; Monnery, B. D.; Hoogenboom, R. Sulfolane as Common Rate Accelerating Solvent for the Cationic Ring-Opening Polymerization of 2-Oxazolines. ACS Macro Lett. 2015, 4 (8), 825-828.
Raghuram, N.; Suresh, R.; Ramesh, G.; Sowjanya, G.; Jyostna, T. S. Excess parameters for the binary mixtures of sulfolane with chloroethanes at different temperatures. J. Therm. Anal. Calorim. 2015, 119 (3), 2107-2117.
Hazard Statements: H302
Harmful if swallowed.
Precautionary Statements: P262-P308+P313-P330
Do not get in eyes, on skin, or on clothing. IF exposed or concerned: Get medical advice/attention. Rinse mouth.