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Ethylene oxide

Ethylene oxide
Ethylene oxide.svg
Ethylene-oxide-from-xtal-3D-balls.png
Names
IUPAC name
oxirane
Other names
epoxyethane, ethylene oxide, dimethylene oxide, oxacyclopropane, 1,2-Epoxy ethane
Identifiers
75-21-8 YesY
3D model (Jmol) Interactive image
Abbreviations EO, EtO
ChEBI CHEBI:27561 YesY
ChemSpider 6114 YesY
ECHA InfoCard 100.000.773
EC Number 200-849-9
KEGG D03474 YesY
MeSH Ethylene+Oxide
PubChem 6354
RTECS number KX2450000
UNII JJH7GNN18P YesY
Properties
C2H4O
Molar mass 44.05 g mol−1
Appearance colorless gas
Odor ether-like
Density 0.882 g/mL, 7.360 lbs/gallon
Melting point −111.3 °C (−168.3 °F; 161.8 K)
Boiling point 10.7 °C (51.3 °F; 283.8 K)
miscible
Vapor pressure 1.46 atm (20°C)
-30.7·10−6 cm3/mol
Thermochemistry
243 J mol−1 K−1
−52.6 kJ mol−1
Hazards
Main hazards carcinogen
extremely flammable
Safety data sheet ICSC 0155
Extremely Flammable F+ Toxic T
Carc. Cat. 1
R-phrases R45, R46, R12, R23, R36/37/38
S-phrases S53, S45
NFPA 704
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g., propane Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g., fluorine Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −20 °C (−4 °F; 253 K)
429 °C (804 °F; 702 K)
Explosive limits 3 to 100%
Lethal dose or concentration (LD, LC):
836 ppm (mouse, 4 hr)
4000 ppm (rat, 4 hr)
800 ppm (rat, 4 hr)
819 ppm (guinea pig, 4 hr)
1460 ppm (rat, 4 hr)
835 ppm (mouse, 4 hr)
960 ppm (dog, 4 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 1 ppm 5 ppm [15-minute Excursion]
REL (Recommended)
Ca TWA <0.1 ppm (0.18 mg/m3) C 5 ppm (9 mg/m3) [10-min/day]
IDLH (Immediate danger)
Ca [800 ppm]
Related compounds
Related heterocycles
Aziridine,
Thiirane,
Borirane
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

Ethylene oxide, properly called oxirane by IUPAC, is the organic compound with the formula C
2
H
4
O
. It is a cyclic ether. (A cyclic ether consists of an alkane with an oxygen atom bonded to two carbon atoms of the alkane, forming a ring.) Ethylene oxide is a colorless flammable gas at room temperature, with a faintly sweet odor; it is the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Because of its special molecular structure, ethylene oxide easily participates in addition reactions; e.g., opening its ring and thus easily polymerizing. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol.

Although it is a vital raw material with diverse applications, including the manufacture of products like polysorbate 20 and polyethylene glycol (PEG) that are often more effective and less toxic than alternative materials, ethylene oxide itself is a very hazardous substance. At room temperature it is a flammable, carcinogenic, mutagenic, irritating, and anaesthetic gas, with a misleadingly pleasant aroma.

The chemical reactivity that is responsible for many of ethylene oxide's hazards has also made it a key industrial chemical. Although too dangerous for direct household use and generally unfamiliar to consumers, ethylene oxide is used industrially for making many consumer products as well as non-consumer chemicals and intermediates. Ethylene oxide is important or critical to the production of detergents, thickeners, solvents, plastics, and various organic chemicals such as ethylene glycol, ethanolamines, simple and complex glycols, polyglycol ethers and other compounds. As a poison gas that leaves no residue on items it contacts, pure ethylene oxide is a disinfectant that is widely used in hospitals and the medical equipment industry to replace steam in the sterilization of heat-sensitive tools and equipment, such as disposable plastic syringes.


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Wikipedia

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