Diisopropyl ether

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Diisopropyl ether
Names
IUPAC name
2-[(Propan-2-yl)oxy]propane
Other names
2-Isopropoxypropane
Diisopropyl oxide
Isopropyl ether
Properties
C6H14O
Molar mass 102.18 g/mol
Appearance Colorless liquid
Odor Ether-like
Density 0.725 g/cm3
Melting point −60 °C (−76 °F; 213 K)
Boiling point 68.5 °C (155.3 °F; 341.6 K)
0.2 g/100 ml at 20 °C
Solubility Miscible with glacial acetic acid, acetone, chloroform, diethyl ether, ethanol, hexane, THF, toluene
Immiscible with dimethylformamide
Vapor pressure 119 mmHg (20 °C)
Hazards
Safety data sheet Sigma-Aldrich
Flash point −28 °C (−18 °F; 245 K)
Lethal dose or concentration (LD, LC):
8,470 mg/kg (rat, oral)
38,138 ppm (rat)
30,840 ppm (rabbit)
28,486 ppm (rabbit)
Related compounds
Related compounds
Dipropyl ether
Dibutyl ether
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Diisopropyl ether is an organic compound, secondary ether, used as a solvent in labs for certain reactions. It is not as widely used as other ethers, like diethyl ether, as it's more prone to forming explosive peroxides that can explode without concentration.

Properties

Chemical

Diisopropyl ether is highly flammable and will burn in air if ignited.

Physical

Diisopropyl ether is a colorless liquid, with a sharp sweet smell, poorly soluble in water, but miscible with many organic solvents. It boils at 68.5 °C and freezes at −60 °C.

Availability

Diisopropyl ether is difficult to acquire from chemical suppliers, due to its hazards.

Preparation

Can be prepared via acid ether synthesis of isopropanol.

Projects

  • Solvent for organic reactions

Handling

Safety

Diisopropyl ether can form explosive peroxides upon contact with air for long periods. This reaction proceeds more easily than for ethyl ether, due to the secondary carbon next to the oxygen atom. The stored solvent should therefore be tested every 3 months, compared to every 12 months for diethyl ether. Unlike in the case of other ethers, if the peroxide amount is high enough, diisopropyl ether may explode without concentration. Because of this phenomenon, old diisopropyl ether bottles are very dangerous.

Storage

Diisopropyl ether should be stored in glass bottles, in a dry cold place, away from any heat source. As it tends to form peroxides much easier that the other ethers, BHT, para-benzylamimophenol or a copper wire should be added, to limit the formation of peroxides.

A much better way to store DIPE is to keep it in a glass joint flask, like a round bottom flask or (for better stability) a flat bottom flask, where all the oxygen has been removed and replaced with an inert gas, like argon. Pieces of sodium metal should be added to remove any traces of oxygen. The flask should be sealed with a well greased stopcock, held in place with a clamp. Keep the ether flask in a safe place.

Disposal

Diisopropyl ether can be safely burned, although samples containing peroxides should be neutralized first with a reducing agent, like sulfites.

References

Relevant Sciencemadness threads