Vinyl alcohol

Vinyl alcohol
IUPAC name

Ethenol
Other names

Hydroxyethene
Hydroxyethylene
Identifiers
CAS number 557-75-5 Y
PubChem 11199
ChemSpider 10726 Y
ChEMBL CHEMBL76101 Y
Jmol-3D images Image 1
Properties
Molecular formula C2H4O
Molar mass 44.053 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Vinyl alcohol, also called ethenol (IUPAC name), is an alcohol. It is not to be confused with the drinking alcohol, ethanol. With the formula CH2CHOH, vinyl alcohol is an isomer of acetaldehyde and ethylene oxide. Under normal conditions, it converts (tautomerizes) to acetaldehyde:

Contents

Relationship to polyvinylalcohol

Because of the instability of vinyl alcohol, the thermoplastic polyvinyl alcohol (PVA or PVOH) is made indirectly by polymerization of vinyl acetate followed by hydrolysis of the ester bonds (Ac = acetyl, HOAc = acetic acid):

n CH2=CHOAc → (CH2-CHOAc)n
(CH2-CHOAc)n + n H2O → (CH2-CHOH)n + n HOAc

As a ligand

Several metal complexes are known that contain vinyl alcohol as a ligand. One example is Pt(acac)(η2-C2H3OH)Cl.[1]

Occurrence in interstellar medium

Vinyl alcohol was discovered in the molecular cloud Sagittarius B using the 12-meter radio telescope at the Kitt Peak National Observatory.[2] This vinyl alcohol being stable in the (dilute) interstellar medium shows that its tautomerization is not unimolecular.

See also

References

  1. ^ F. A. Cotton, J. N. Francis, B. A. Frenz, M. Tsutsui "Structure of a dihapto(vinyl alcohol) complex of platinum(II)" Journal of the American Chemical Society, 1973, volume 95, p. 2483-6. doi:10.1021/ja00789a011
  2. ^ "Scientists Toast the Discovery of Vinyl Alcohol in Interstellar Space". National Radio Astronomy Observatory. 2001-10-01. http://www.nrao.edu/pr/2001/vinylalco/. Retrieved 2006-12-20.