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 oxygenategasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propylene.[3] 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.[4][5] Diisopropyl ether is used for converting bromoboranes, which are thermally labile, into isopropoxy derivatives.[6]
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.[7] Some laboratory procedures recommend use of freshly opened bottles.[4]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.[8] Peroxides may be removed by stirring the ether with an aqueous solution of iron(II) sulfate (green vitriol) or sodium metabisulfite.[9][10] For safety reasons, methyl tert-butyl ether is often used as an alternative solvent.
^Shoji Hara, Akira Suzuk (1998). "Synthesis of 4-(2-Bromo-2-Propenyl)-4-Methyl-Y-Butyrolactone by the Reaction of Ethyl Levulinate with (2-Bromoallyl)Diisopropoxyborane Prepared by Haloboration of Allene". Organic Syntheses. 75: 129. doi:10.15227/orgsyn.075.0129.
^Chai, Christina Li Lin; Armarego, W. L. F. (2003). Purification of laboratory chemicals. Oxford: Butterworth-Heinemann. p. 176. ISBN978-0-7506-7571-0.
^Hamstead, A. C. (1964). "Destroying Peroxides of Isopropyl Ether". Industrial and Engineering Chemistry. 56 (6): 37-42. doi:10.1021/ie50654a005.
