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Physical Data: mp -89.0 °C; bp 162.7 °C; d 1.743 g cm-3.
Solubility: sol nitrobenzene, diethyl ether, acetic acid, ethyl acetate; insol carbon disulfide, carbon tetrachloride, chloroform. It dissolves most organic compounds that are potential proton acceptors.
Handling, Storage, and Precautions: fluorosulfuric acid is highly toxic and corrosive and should always be handled in a fume hood with proper protection. It can be purified by distillation under anhydrous conditions using common glassware. When water is excluded, it may be handled and stored in glass containers, but containers should always be cooled before opening because HF gas pressure may have developed due to hydrolysis. For long-term laboratory storage, however, Teflon bottles are recommended.
Many hydrocarbons, especially terpenes, rearrange readily in fluorosulfuric acid, usually at low temperatures, with the intermediacy of carbocations.2-15 Compared to conventional acid systems, the use of HSO3F often alters the normal course of acid-catalyzed isomerization and rearrangement, since the carbocation intermediates formed during the reactions are stabilized in the superacid system. For example, treatment of 1,8-p-menthadiene (limonene) with HSO3F gave a- and b-phellandrenes (eq 1)14 which were not obtained by other weaker acid systems.
Temperature also plays an important role in determining the reaction pathway. Quenching of the reactions with bases or nucleophiles at specific temperatures can control the nature of the products.
Aromatics react with HSO3F in the presence of variable amounts of Antimony(V) Fluoride to give aromatic sulfonyl fluorides and diaryl sulfones (see Fluorosulfuric Acid-Antimony(V) Fluoride).
Fluorosulfuric Acid-Antimony(V) Fluoride; Hydrogen Fluoride; Hydrogen Fluoride-Antimony(V) Fluoride; Nafion-H.
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