Ethyl Ether

Title: Ethyl Ether
CAS Registry Number: 60-29-7
CAS Name: 1,1¢-Oxybisethane
Additional Names: ethoxyethane; ether; diethyl ether; ethyl oxide; diethyl oxide; sulfuric ether; anesthetic ether
Molecular Formula: C4H10O
Molecular Weight: 74.12
Percent Composition: C 64.82%, H 13.60%, O 21.59%
Line Formula: C2H5OC2H5
Literature References: Produced on a large scale by dehydration of ethanol or by hydration of ethylene, both processes being carried out in the presence of sulfuric acid. Review of mfg processes: Himmler in Ullmanns Encyklopädie der technischen Chemie vol. 5 (1954) pp 777-782; D. E. Keeley in Kirk-Othmer Encyclopedia of Chemical Technology vol. 9 (Wiley-Interscience, New York, 3rd ed., 1980) pp 381-393.
Properties: Mobile, very volatile, highly flammable liq. Explosive! Vapor heavier than air. Characteristic, sweetish, pungent odor, more agreeable than chloroform. Burning taste. Tends to form explosive peroxides under the influence of air and light, esp when evaporation to dryness is attempted. Peroxides may be removed from ether by shaking with 5% aq ferrous sulfate soln. Addition of naphthols, polyphenols, aromatic amines, and aminophenols has been proposed for the stabilization of ethyl ether. d40 0.7364; d410 0.7249; d420 0.7134; d430 0.7019. Vapor density 2.55 (air = 1.0). mp -116.3° (stable crystals); mp -123.3° (metastable crystals). bp760 34.6°; bp400 17.9°; bp200 2.2°; bp100 -11.5°; bp10 -48.1°; bp1.0 -74.3°. Satd vapor press. at 0°: 184.9 mm; at 10°: 290.8 mm; at 20°: 439.8 mm; at 50°: 1276 mm; at 70°: 2304 mm. Critical temp 192.7°; crit press. 35.6 atm. Flash pt, closed cup: -49°F (-45°C). Air-ether mixtures containing more than 1.85 volume-% of ether vapor, are explosive hazards. Autoignition temp 180-190°. nD15 1.35555. Dielectric constant at 26.9° and 85.8 kilocycles = 4.197; good insulator. When shaken under absolutely dry conditions ether can generate enough static electricity to start a fire. Surface tension at 20°: 17.06 dynes/cm. Viscosity at 20°: 0.2448 cP. Heat of vaporization at 30°: 89.80 cal/g. Produces considerable coldness on quick evaporation. Heat of formation -907 cal/g; heat of combustion -8.807 kcal/g. Ether is slightly sol in water and water is slightly sol in ether. A satd water soln contains 8.43% (w/w) of ether at 15° and 6.05% (w/w) at 25°. Ether satd with water contains 1.2% H2O at 20°. Soly in water increased by HCl. Sol in concd hydrochloric acid. May explode when brought in contact with anhydr nitric acid. Miscible with lower aliphatic alcohols, benzene, chloroform, petr ether, other fat solvents, many oils. Azeotrope with water (1.3%), bp 34.2°.
Melting point: mp -116.3° (stable crystals); mp -123.3° (metastable crystals)
Boiling point: bp760 34.6°; bp400 17.9°; bp200 2.2°; bp100 -11.5°; bp10 -48.1°; bp1.0 -74.3°; bp 34.2°
Flash point: Flash pt, closed cup: -49°F (-45°C)
Index of refraction: nD15 1.35555
Density: d40 0.7364; d410 0.7249; d420 0.7134; d430 0.7019
CAUTION: Potential symptoms of overexposure are dizziness; drowsiness; headache, excitedness and narcosis; nausea, vomiting; irritation of eyes, upper respiratory system and skin. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 140.
Use: Solvent for waxes, fats, oils, perfumes, alkaloids, gums. Excellent solvent for nitrocellulose when mixed with alc. Important reagent in organic syntheses, esp in Grignard and Wurtz type reactions. Easily removable extractant of active principles (hormones, etc.) from plant and animal tissues. In the manuf of gun powder. As primer for gasoline engines.
Therap-Cat: Anesthetic (inhalation).
Therap-Cat-Vet: Anesthetic (inhalation). Has been used orally in colic, subcutaneously as a stimulant.
Keywords: Anesthetic (Inhalation).
Ethyl Formate Ethyl Iodide Ethyl Isobutyrate Ethyl Isothiocyanate Ethyl Isovalerate

Diethyl ether
Identifiers
CAS number 60-29-7 YesY
PubChem 3283
ChemSpider 3168 YesY
UNII 0F5N573A2Y YesY
KEGG D01772 YesY
ChEBI CHEBI:35702 YesY
ChEMBL CHEMBL16264 YesY
RTECS number KI5775000
ATC code N01AA01
Jmol-3D images Image 1
Properties
Molecular formula C4H10O
Molar mass 74.12 g mol−1
Appearance Colorless liquid
Density 0.7134 g/cm3, liquid
Melting point −116.3 °C, 156.9 K, −177.3 °F
Boiling point 34.6 °C, 307.8 K, 94.3 °F
Solubility in water 69 g/L (20 °C)
Refractive index (nD) 1.353 (20 °C)
Viscosity 0.224 cP (25 °C)
Structure
Dipole moment 1.15 D (gas)
Hazards
MSDS External MSDS
R-phrases R12 R19 R20/22 R66 R67
S-phrases S9 S16 S29 S33
Main hazards Extremely Flammable, harmful to skin
NFPA 704
NFPA 704.svg
4
2
1
Flash point −45 °C[1]
Autoignition temperature 160 °C[1]
Explosive limits 1.9-48.0% [2]
Related compounds
Related Ethers Dimethyl ether
Methoxypropane
Related compounds Diethyl sulfide
Butanols (isomer)
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Diethyl ether, also known as ethyl ether, sulfuric ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula (C
2
H
5
)
2
O
. It is a colorless, highly volatile flammable liquid. It is commonly used as a solvent and was once used as a general anesthetic. It has narcotic properties and has been known to cause temporary psychological addiction, sometimes referred to as etheromania.