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Methacrolein

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(Redirected from Methacrylaldehyde) Chemical compound This article is about α-methacrolein. For β-methacrolein, see crotonaldehyde.
Methacrolein
Skeletal formula of methacrolein
Skeletal formula of methacrolein
Ball-and-stick model of methacrolein
Ball-and-stick model of methacrolein
Names
Preferred IUPAC name 2-Methylprop-2-enal
Other names Methacrolein
Methacrylaldehyde
Isobutenal
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.046 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H6O/c1-4(2)3-5/h3H,1H2,2H3Key: STNJBCKSHOAVAJ-UHFFFAOYSA-N
  • InChI=1/C4H6O/c1-4(2)3-5/h3H,1H2,2H3Key: STNJBCKSHOAVAJ-UHFFFAOYAU
SMILES
  • O=CC(=C)C
Properties
Chemical formula C4H6O
Molar mass 70.09 g/mol
Density 0.847 g/cm
Melting point −81 °C (−114 °F; 192 K)
Boiling point 69 °C (156 °F; 342 K)
Related compounds
Related alkenals Citral

Citronellal
trans-2-Methyl-but-2-enal

Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Methacrolein, or methacrylaldehyde, is an unsaturated aldehyde. It is a clear, colorless, flammable liquid.

Methacrolein is one of two major products resulting from the reaction of isoprene with OH in the atmosphere, the other product being methyl vinyl ketone (MVK, also known as butenone). These compounds are important components of the atmospheric oxidation chemistry of biogenic chemicals, which can result in the formation of ozone and/or particulates. Methacrylaldehyde is also present in cigarette smoke. It can be found in the essential oil of the plant Big Sagebrush (Artemisia tridentata) which contains 5% methacrolein.

Industrially, the primary use of methacrolein is in the manufacture of polymers and synthetic resins.

Exposure to methacrolein is highly irritating to the eyes, nose, throat and lungs.

See also

References

  1. Montzka, S. A.; Trainer, M.; Goldan, P. D.; Kuster, W. C.; Fehsenfeld, F. C. (1993). "Isoprene and its oxidation products, methyl vinyl ketone and methacrolein, in the rural troposphere". Journal of Geophysical Research: Atmospheres. 98 (D1): 1101–1111. Bibcode:1993JGR....98.1101M. doi:10.1029/92JD02382.
  2. Roy J. Shephard (1982). The risks of passive smoking. ISBN 978-0-7099-2334-3. Retrieved 2009-05-06.
  3. Shakhnoza, Azimova S.; et al. (2012). Lipids, Lipophilic Components and Essential Oils from Plant Sources. Springer. p. 844. ISBN 978-0-85729-323-7.

External links

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