1,4-Dioxane

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1,4-Dioxane
Names
IUPAC names
1,4-Dioxane
1,4-Dioxacyclohexane
Other names
[1,4]Dioxane
[6]-crown-2
p-Dioxane
Diethylene dioxide
Diethylene ether
Dioxan
Properties
C4H8O2
Molar mass 88.11 g/mol
Appearance Colorless liquid
Odor Ether-like
Density 1.033 g/mL
Melting point 11.8 °C (53.2 °F; 284.9 K)
Boiling point 101.1 °C (214.0 °F; 374.2 K)
Miscible
Solubility Miscible with most organic solvents
Vapor pressure 29 mmHg (20 °C)
Thermochemistry
196.6 J·K−1·mol−1
-354 kJ/mol
Hazards
Safety data sheet Sigma-Aldrich
Flash point 12 °C (54 °F; 285 K)
Lethal dose or concentration (LD, LC):
5.7 g/kg (mouse, oral)
5.2 g/kg (rat, oral)
3.9 g/kg (guinea pig, oral)
7.6 g/kg (rabbit, dermal)
10,109 ppm (mouse, 2 hr)
12,568 ppm (rat, 2 hr)
Related compounds
Related compounds
Ethylene oxide
Tetrahydrofuran
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

1,4-Dioxane, also known as diethylene ether, diethylene dioxide or simply dioxane, as the 1,2 and 1,3 isomers are rarely encountered, is a heterocyclic organic compound, a cyclic ether.

Properties

Chemical

Dioxane can be reacted with dry chlorine gas to yield trans-2,3-dichloro-1,4-dioxane.

Physical

Dioxane is a colorless liquid, with a faint sweet odor similar to that of diethyl ether. It is miscible with many solvents and is hygroscopic. Dioxane boils at 101.1 °C and freezes at 11.8 °C.

Availability

Dioxan can be bought from eBay.

Preparation

Dioxane is produced by the acid-catalysed dehydration of ethylene glycol, using conc. sulfuric acid as catalyst. The reaction takes place under reflux. Commercial anti-freeze can be safely used as EG source, regardless of impurities and additives, though concentrated anti-freeze gives a better yield than the diluted version.

Frogfot wrote a synthesis of dioxane.

Projects

  • Stabilize trichloroethane
  • Medium for organic reactions
  • Purification of metallic sodium from sodium-magnesium oxide aggregate

Handling

Safety

Dioxane is considered carcinogenic. It is also very flammable.

Dioxane is sometimes confused with dioxin.

Storage

Dioxane should be stored in closed bottles, with a reducing agent to prevent the formation of peroxides. Dioxane is safe to keep without anti-oxidants for maximum one year, after which the levels of peroxides become too dangerous to handle.

Disposal

Dioxane can be safely burned, if there are no peroxides. If the dioxane tests positive for peroxides, neutralize peroxides first. Reducing agents, like as ferrous sulfate, sodium bisulfite or metabisulfite added in excess can be used to neutralize the peroxides. After incineration, the ether should be tested again for peroxides and if none are present, it can be safely burned. If it's an old bottle, which has peroxides on the cap, do not open the bottle, instead take it to a remote of special area and safely detonate it. The latter may or require professional help.

References

Relevant Sciencemadness threads