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Names | |||
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IUPAC names
1,4-Dioxane
1,4-Dioxacyclohexane |
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Other names
[1,4]Dioxane
p-Dioxane [6]-crown-2 Diethylene dioxide Diethylene ether Dioxan |
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Identifiers | |||
123-91-1 | |||
3D model (Jmol) | Interactive image | ||
ChEBI | CHEBI:47032 | ||
ChEMBL | ChEMBL453716 | ||
ChemSpider | 29015 | ||
DrugBank | DB03316 | ||
ECHA InfoCard | 100.004.239 | ||
EC Number | 204-661-8 | ||
KEGG | C14440 | ||
UNII | J8A3S10O7S | ||
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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 | |||
Std molar
entropy (S |
196.6 J·K−1·mol−1 | ||
Std enthalpy of
formation (ΔfH |
-354 kJ/mol | ||
Std enthalpy of
combustion (ΔcH |
-2363 kJ/mol | ||
Hazards | |||
Main hazards | Carcinogen | ||
EU classification (DSD)
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Flammable (F) Carc. Cat. 3 Irritant (Xn) |
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R-phrases |
R11, R19, R36/37, R40, R66 |
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S-phrases |
(S2), S9, S16, S36/37, S46 |
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NFPA 704 | |||
Flash point | 12 °C (54 °F; 285 K) | ||
Explosive limits | 2.0%-22% | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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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) |
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LC50 (median concentration)
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10,109 ppm (mouse, 2 hr) 12,568 ppm (rat, 2 hr) |
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LCLo (lowest published)
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1000-3000 ppm (guinea pig, 3 hr) 12022 ppm (cat, 7 hr) 2085 ppm (mouse, 8 hr) |
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US health exposure limits (NIOSH): | |||
PEL (Permissible)
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TWA 100 ppm (360 mg/m3) [skin] | ||
REL (Recommended)
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Ca C 1 ppm (3.6 mg/m,3) [30-minute] | ||
IDLH (Immediate danger)
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Ca [500 ppm] | ||
Related compounds | |||
Related compounds
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Oxane Trioxane Tetroxane Pentoxane |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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what is ?) | (|||
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.