Tetrahydrofuran

CAS RN: 109-99-9

Reactivities / Incompatibilities

Reacts with lithium tetrahydroaluminate or borane to form explosive hydrogen gas. Violent reaction with metal halides (e.g., hafnium tetrachloride, titanium tetrachloride, zirconium tetrachloride). Vigorous reaction with bromine, calcium hydride + heat. Can react with oxidizing materials.
An attempt to remove peroxides /from tetrahydrofuran/ by shaking with solid ferrous sulfate before distillation did not prevent explosion of the distillation residue. Alkali treatment to destroy peroxides appears not to be safe.
Tetrahydrofuran had been dried over the aluminate and then stored over calcium hydride for 2 yr to prevent peroxide formation. Subsequent addition of more aluminate caused a strong exotherm and ignition of liberated hydrogen.
During synthesis of sodium tetrahydroaluminate from its elements in tetrahydrofuran, a violent explosion occurred when absorption of hydrogen had stopped. This was attributed to deposition of solid above the liquid level, overheating and reaction with solvent to give butoxyaluminohydrides. Vigorous stirring and avoiding overheating are essential.
Rapid addition of bromine to the dried solvent /tetrahydrofuran/ to make a 10% solution caused a vigorous reaction with gas evolution. ... Photocatalyzed bromination of the solvent may have been involved. ...
Addition of anhydrous chlorides (hafnium tetrachloride, titanium tetrachloride, and zirconium tetrachloride) directly to tetrahydrofuran caused a violent exothermic reaction.
2-Aminophenol was being oxidized in tetrahydrofuran solution at 65 deg C using a larger than normal proportion of potassium dioxide. When stirring was stopped after 6 hr, a violent explosion occurred. ... attributed to formation of tetrahydrofuranyl hydroperoxide by the excess dioxide.
A glass bottle containing a 1 m solution /which is stabilized with 5 mol% of sodium tetrahydroborate/ of the complex /borane-tetrahydrofuran/ in THF exploded after 2 wk in undisturbed lab storage out of direct sunlight at 15 deg C. ... Tetrahydroborate content may in fact have destabilized the borane-THF reagent, with generation of hydrogen pressure in the closed bottle.
A violent explosion during reflux of the solvent /tetrahydrofuran/ with calcium hydride was attributed to cleavage of the cyclic ether by overheated excess hydride.
Fire can occur when tetrahydrofuran is used as a solvent for lithium aluminum hydride. Peroxides of tetrahydrofuran or their reaction products probably caused a vigorous reaction with lithium aluminum hydride, and subsequent fire.
Using potassium hydroxide /or sodium hydroxide/ to dry impure tetrahydrofuran, which can contain peroxides, is hazardous. Serious explosions can occur.
Strong oxidizers, lithium-aluminum alloys [Note: Peroxides may accumulate upon prolonged storage in presence of air].
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