Ethylene oxide
Ethylene oxide, called oxirane by IUPAC, is an organic compound with the chemical formula C2H4O.[5] It is the simplest epoxide.
| Ethylene oxide | |
|---|---|
 |
 |
Oxirane | |
Epoxyethane Oxacyclopropane | |
| Other names | Ethylene oxide Dimethylene oxide 1,2-Epoxyethane [3]-crown-1 Epoxide |
| Identifiers | |
| Abbreviations | EO, EtO |
| CAS number | |
| PubChem | |
| EC number | 200-849-9 |
| KEGG | D03474 |
| MeSH | |
| ChEBI | CHEBI:27561 |
| RTECS number | KX2450000 |
| SMILES | C1CO1 |
| Properties | |
| Molecular formula | C2H4O |
| Molar mass | 44.052 g·mol−1[1] |
| Appearance | Colorless gas |
| Odor | Ether-like |
| Density | 0.8821 g·cm−3[1] |
| Melting point |
−112.46 °C, 161 K, -170 °F |
| Boiling point | |
| Solubility in water | Miscible |
| Vapor pressure | 1.46 atm (20 °C)[2] |
| −30.5·10−6 cm3/mol[3] | |
| Refractive index (nD) | 1.3597 (589 nm)[1] |
| Dipole moment | 1.94 D |
| Thermochemistry | |
| Std enthalpy of formation ΔfH |
−52.6 kJ·mol−1[4] |
| Standard molar entropy S |
242.5 J·mol−1·K−1[4] |
| Specific heat capacity, C | 47.9 J·mol−1·K−1[4] |
| Hazards | |
| EU classification |  F+  TCarc. Cat. 1 |
| Main hazards | Carcinogen Extremely flammable |
| NFPA 704 |
4
3
3
|
| R-phrases | Template:R45, Template:R46, R12, R23, R36/37/38 |
| S-phrases | S53, S45 |
| Explosive limits | 3 to 100% |
| U.S. Permissible exposure limit (PEL) |
TWA 1 ppm 5 ppm [15-minute excursion][2] |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
Ethylene Oxide Media
Ethylene oxide structure.
A small sample (about 1.5ml) of condensed ethylene oxide in a test tube
Ethylene oxide reactions
2-ACETYLBUTYROLACTONE SYNTHESIS
Friedel-Crafts reaction with ethylene oxide
Tetraoxathia-2-cycloundecanone
Dioxane synthesis
1,4-dioxane synthesis
mechanism synthesis thiiranes of ethylene oxide under the influence of thiocyanate ion
Ethylene carbonate synthesis
References
- ↑ 1.0 1.1 1.2 Haynes, p. 3.430
- ↑ 2.0 2.1 NIOSH Pocket Guide to Chemical Hazards. "#0275". National Institute for Occupational Safety and Health (NIOSH).
- ↑ Haynes, p. 3.576
- ↑ 4.0 4.1 4.2 Haynes, p. 5.22
- ↑ Rebsdat, Siegfried and Mayer, Dieter (2005) "Ethylene Oxide" in Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH, Weinheim. .