Ethenone

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Ethenone
Structural formula
Space-filling model
Identifiers
CAS number 463-51-4 YesY
PubChem 10038
ChemSpider 9643 YesY
EC number 207-336-9
ChEBI CHEBI:48003 YesY
RTECS number OA7700000
Beilstein Reference 1098282
Jmol-3D images Image 1
Properties
Molecular formula C2H2O
Molar mass 42.037 g/mol
Appearance Colourless gas
Odor penetrating
Density 1.93 g/cm3
Melting point −150.5 °C (−238.9 °F; 122.6 K)
Boiling point −56.1 °C (−69.0 °F; 217.1 K)
Solubility in water decomposes
Solubility soluble in acetone
ethanol
ethyl ether
aromatic solvents
halocarbons
Refractive index (nD) 1.4355
Thermochemistry
Specific
heat capacity
C
51.75 J/K mol
Std enthalpy of
formation
ΔfHo298
-87.24 kJ/mol
Hazards
MSDS External MSDS
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −107 °C (−161 °F; 166 K)
Explosive limits 5.5-18%
LD50 1300 mg/kg (oral, rat)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Ethenone is the formal name for ketene, an organic compound with formula C2H2O or H2C=C=O. It is the simplest member of the ketene class. It is a tautomer of ethynol.

Properties[edit]

Ethenone is a colourless gas at STP and has a sharp irritating odour. It is soluble in acetone, ethanol, ethyl ether, aromatic solvents and halocarbons.

Preparation[edit]

Ethenone can be prepared in the laboratory by pyrolysis of acetone vapor.[1]

Reactions[edit]

Ethenone is very reactive, tending to react with nucleophiles to form an acetyl group. For example, it reacts with acetic acid to form acetic anhydride. It also reacts with water to form acetic acid.[2]

Ethenone will also react with itself via 2+2 photocycloaddition to form cyclic dimers known as diketenes. For this reason, it should not be stored for long periods.[3]

Hazards[edit]

Exposure to concentrated levels causes humans to experience irritation of body parts such as the eye, nose, throat and lungs. Extended toxicity testing on mice, rats, guinea pigs and rabbits showed that ten minute exposures to concentrations of freshly generated ethenone as low as 0.2 mg/liter (116 ppm) may produce a high percentage of deaths in small animals. These findings put ethenone in the same order of toxicity as phosgene (0.2–20 mg/liter) and hydrogen cyanide (0.2-0.5 mg/liter). Death is from pulmonary edema and is entirely similar to, but much more rapid than is the case with phosgene poisoning.[4]

Occupational exposure limits are set at 0.5 ppm (0.9 mg/m3) over an eight-hour time-weighted average.[5] An IDLH limit is set at 5 ppm, as this is the lowest concentration productive of a clinically relevant physiologic response in humans.[6]

References[edit]

  1. ^ C. D. Hurd (1941), "Ketene", Org. Synth. ; Coll. Vol. 1: 330 .
  2. ^ ChemSpider http://www.chemspider.com/Chemical-Structure.9643.html
  3. ^ Christoph Taeschler :Ketenes, Ketene Dimers, and Related Substances, Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons, New York, 2010
  4. ^ H. A. Wooster, C. C. Lushbaugh, C. E. Redeman (1946). "The Inhalation Toxicity of Ketene and of Ketene Dimer". J. Am. Chem. Soc. 68 (12): 2743. doi:10.1021/ja01216a526. 
  5. ^ Centers for Disease Control and Prevention (4 April 2013). "Ketene". NIOSH Pocket Guide to Chemical Hazards. Retrieved 13 November 2013. 
  6. ^ Centers for Disease Control and Prevention (May 1994). "Ketene". Documentation for Immediately Dangerous To Life or Health Concentrations (IDLHs). Retrieved 13 November 2013.