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Dioxane

1,4-Dioxane
Chemical structure of dioxane
1,4-dioxane
Names
IUPAC names
1,4-Dioxane
1,4-Dioxacyclohexane
Other names
[1,4]Dioxane
p-Dioxane
[6]-crown-2
Diethylene dioxide
Diethylene ether
Dioxan
Identifiers
123-91-1 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:47032 YesY
ChEMBL ChEMBL453716 YesY
ChemSpider 29015 YesY
DrugBank DB03316 YesY
ECHA InfoCard 100.004.239
EC Number 204-661-8
KEGG C14440 YesY
UNII J8A3S10O7S YesY
Properties
C4H8O2
Molar mass 88.11 g·mol−1
Appearance Colorless liquid
Odor mild, 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
Vapor pressure 29 mmHg (20°C)
-52.16·10−6 cm3/mol
Thermochemistry
196.6 J·K−1·mol−1
-354 kJ/mol
-2363 kJ/mol
Hazards
Main hazards Carcinogen
Flammable (F)
Carc. Cat. 3
Irritant (Xn)
R-phrases R11, R19, R36/37,
R40, R66
S-phrases (S2), S9, S16,
S36/37, S46
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 12 °C (54 °F; 285 K)
Explosive limits 2.0%-22%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
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)
1000-3000 ppm (guinea pig, 3 hr)
12022 ppm (cat, 7 hr)
2085 ppm (mouse, 8 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 100 ppm (360 mg/m3) [skin]
REL (Recommended)
Ca C 1 ppm (3.6 mg/m,3) [30-minute]
IDLH (Immediate danger)
Ca [500 ppm]
Related compounds
Related compounds
Oxane
Trioxane
Tetroxane
Pentoxane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

1,4-Dioxane is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers (1,2- and 1,3-) are rarely encountered.

Dioxane is used as a solvent for a variety of practical applications as well as in the laboratory, and also as a stabilizer for the transport of chlorinated hydrocarbons in aluminum containers.

Dioxane is produced by the acid-catalysed dehydration of diethylene glycol, which in turn is obtained from the hydrolysis of ethylene oxide.

In 1985, the global production capacity for dioxane was between 11,000 and 14,000 tons. In 1990, the total U.S. production volume of dioxane was between 5,250 and 9,150 tons.

The dioxane molecule is centrosymmetric, meaning that it adopts a chair conformation, typical of relatives of cyclohexane. However, the molecule is conformationally flexible, and the boat conformation is easily adopted, e.g. in the chelation of metal cations.

In the 1980s, most of the dioxane produced was used as a stabilizer for 1,1,1-trichloroethane for storage and transport in aluminium containers. Normally aluminium is protected by a passivating oxide layer, but when these layers are disturbed, the metallic aluminium reacts with trichloroethane to give aluminium trichloride, which in turn catalyses the dehydrohalogenation of the remaining trichloroethane to vinylidene chloride and hydrogen chloride. Dioxane "poisons" this catalysis reaction by forming an adduct with aluminum trichloride.


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