Diisopropyl ether
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| UN number | 1159 |
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| Appearance | Colorless liquid |
| Odor | Sharp, sweet, ether-like[1] |
| Density | 0.725 g/ml |
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| Vapor pressure | 119 mmHg (20°C)[1] |
| Template:Longitem | −79.4·10−6 cm3/mol |
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Diisopropyl ether is a secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is also used as an oxygenate gasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propylene.[2] Diisopropyl ether is sometimes represented by the abbreviation DIPE.
Use as a solvent
Whereas at 20 °C, diethyl ether will dissolve 1% by weight water, diisopropyl ether dissolves 0.88%. Diisopropyl ether is used as a specialized solvent to remove or extract polar organic compounds from aqueous solutions, e.g. phenols, ethanol, acetic acid.
In the laboratory, diisopropyl ether is useful for recrystallizations because it has a wide liquid range.[3][4] Diisopropyl ether is used for converting bromoboranes, which are thermally labile, into isopropoxy derivatives.[5]
Safety
Diisopropyl ether forms explosive organic peroxides similar to TATP upon standing in air. This reaction proceeds more easily than for diethyl ether due to the increased lability of the C-H bond adjacent to oxygen. Many explosions have been known to occur during handling of old diisopropyl ether bottles.[6] Some laboratory procedures recommend use of freshly opened bottles.[3] Antioxidants such as butylated hydroxytoluene can be used to prevent this process. The stored solvent is generally tested for the presence of peroxides. It is recommended to test once every 3 months for diisopropyl ether compared to once every 12 months for diethyl ether.[7] Peroxides may be removed by stirring the ether with an aqueous solution of iron(II) sulfate (green vitriol) or sodium metabisulfite.[8][9] For safety reasons, methyl tert-butyl ether is often used as an alternative solvent.
See also
- Dimethyl ether
- Diethyl ether
- Dipropyl ether
- Di-tert-butyl ether
- Methyl tert-butyl ether
- List of gasoline additives
References
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