Di-tert-butyl ether

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Di-tert-butyl ether
Names
IUPAC name
2-Methyl-2-[(2-methylpropan-2-yl)oxy]propane
Other names
Methylisopropyl ether
t-Bu2O
t-Butyl ether
Properties
C8H18O
(C4H9)2O
Molar mass 130.23 g/mol
Appearance Colorless liquid
Odor Camphor-like
Density 0.7642 g/cm3
Melting point −61 °C (−78 °F; 212 K)
Boiling point 107.2 °C (225.0 °F; 380.3 K)
Vapor pressure 3730 Pa (at 22 °C)
Thermochemistry
-399.6 kJ·mol−1
Hazards
Safety data sheet Georganics
Related compounds
Related compounds
Diisopropyl ether
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Di-tert-butyl ether (also known as methylisopropyl ether), sometimes written as t-Bu2O, is tertiary ether, sometimes used as a solvent, albeit expensive.

Properties

Chemical

Di-tert-butyl ether will burn when ignited in air.

Physical

t-Bu2O is a colorless liquid, with a penetrating camphor-like odor. I has a density of 0.7642 g/cm3 at 20 °C.

Availability

Di-tert-butyl ether is sold by various chemical suppliers and can be purchased online.

Preparation

Di-tert-butyl ether can be prepared by reacting a tert-butyl halide, such as tert-butyl chloride, with very dry silver carbonate, by continuous stirring in diethyl ether at room temperature, for 24 hours.[1] Pentane can also be used as a solvent.[2] Byproducts of this reaction include tert-butanol, isobutylene, carbon dioxide, and silver chloride.

The Williamson route does not work for this compound, and will yield isobutylene and tert-butanol instead.

Projects

Handling

Safety

Di-tert-butyl ether is flammable and irritant. Handle with care.

Storage

In closed bottles, away from light and strong acids. Since it resists auto-oxidation, t-Bu2O does not form peroxides upon storage.

Disposal

Di-tert-butyl ether can be destroyed by burning it outside.

References

  1. Erickson; Ashton; Journal of the American Chemical Society; vol. 63; (1941); p. 1769
  2. Masada,H.; Sakajiri,T.; Bulletin of the Chemical Society of Japan; vol. 51; (1978); p. 866 - 868
  3. International Journal of Chemical Kinetics; vol. 28; nb. 4; (1996); p. 299 - 306

Relevant Sciencemadness threads