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Methacrolein information


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
  • 78-85-3 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 6314 checkY
ECHA InfoCard 100.001.046 Edit this at Wikidata
PubChem CID
  • 6562
UNII
  • 9HRB24892H checkY
CompTox Dashboard (EPA)
  • DTXSID0052540 Edit this at Wikidata
InChI
  • InChI=1S/C4H6O/c1-4(2)3-5/h3H,1H2,2H3 checkY
    Key: STNJBCKSHOAVAJ-UHFFFAOYSA-N checkY
  • InChI=1/C4H6O/c1-4(2)3-5/h3H,1H2,2H3
    Key: STNJBCKSHOAVAJ-UHFFFAOYAU
SMILES
  • O=CC(=C)C
Properties
Chemical formula
C4H6O
Molar mass 70.09 g/mol
Density 0.847 g/cm3
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 [77 °F], 100 kPa).
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Infobox references

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).[1] 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.[2] It can be found in the essential oil of the plant Big Sagebrush (Artemisia tridentata) which contains 5% methacrolein.[3]

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.

  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.

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Methacrolein

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Methacrolein, or methacrylaldehyde, is an unsaturated aldehyde. It is a clear, colorless, flammable liquid. Methacrolein is one of two major products resulting...

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Methyl methacrylate

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with formaldehyde to produce methacrolein, The condensation is catalyzed by a secondary amine. Air oxidation of methacrolein to methacrylic acid completes...

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Methacrolein diacetate

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Methacrolein diacetate is a chemical compound with the molecular formula C8H12O4 and a molecular weight of 172.17848. It is a colorless liquid. It is listed...

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Crotonaldehyde

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LD50 of 174 mg/kg (rats, oral). Crotyl Crotonic acid Crotyl alcohol Methacrolein Merck Index, 11th Edition, 2599 NIOSH Pocket Guide to Chemical Hazards...

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Methacrylic acid

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tert-butanol. Isobutylene is oxidized sequentially to methacrolein and then methacrylic acid. Methacrolein for this purpose can also be obtained from formaldehyde...

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Isobutylene

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isooctane, a fuel additive. Isobutylene is also used in the production of methacrolein. Polymerization of isobutylene produces butyl rubber (polyisobutylene...

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Isobutyraldehyde

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isobutyraldehyde. Hydrogenation of the aldehyde gives isobutanol. Oxidation gives methacrolein or methacrylic acid. Condensation with formaldehyde gives hydroxypivaldehyde...

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Artemisia tridentata

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oil contains approximately 40% l-camphor; 20% pinene; 7% cineole; 5% methacrolein; and 12% a-terpinene, d-camphor, and sesqiterpenoids. Much discussion...

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Citronellal

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P262, P273, P280, P302+P352 Related compounds Related alkenals Citral Methacrolein trans-2-Methyl-2-butenal Except where otherwise noted, data are given...

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C4H6O

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Cyclobutanone Dihydrofurans 2,3-Dihydrofuran 2,5-Dihydrofuran Divinyl ether Methacrolein Methyl vinyl ketone This set index page lists chemical structure articles...

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Mechlorethamine Mercuric acetate Mercuric chloride Mercuric oxide Methacrolein diacetate Methacrylic anhydride Methacrylonitrile Methacryloyl chloride...

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Dietrich Arntz; Achim Fischer; Mathias Höpp; et al. (2012). "Acrolein and Methacrolein". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH...

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C8H12O4

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172.178 g/mol) may refer to: Diethyl maleate 1,6-Dioxecane-2,7-dione Methacrolein diacetate 1,4-Cyclohexanedicarboxylic acid This set index page lists...

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Citral

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91 °C (196 °F; 364 K) Related compounds Related alkenals Citronellal Methacrolein trans-2-Methyl-2-butenal Except where otherwise noted, data are given...

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Chiara Giorio

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Isoprene and Methacrolein Photooxidation. J Phys Chem A 121:7641–7654. Cloud Processing of Secondary Organic Aerosol from Isoprene and Methacrolein Photooxidation...

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Keggin structure

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commercialized the use of the compounds in hydration of propene, oxidation of methacrolein, hydration of isobutene and n-butene, and polymerization of THF. 12-Phosphotungstic...

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Takahisa Sato; Noboru Shimizu; Helmut Schwind (2012). "Acrolein and Methacrolein". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH...

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Chiral Lewis acid

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the enantioselective Diels–Alder reaction between cyclopentadiene and methacrolein. The chiral ligand is recovered quantitatively by silica gel chromatography...

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Boranylium ions

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catalyze the enantioselective Diels–Alder reaction of 1,3-dienes with 2-methacrolein or 2-bromoacrolein. This particular borenium ion could be made in situ...

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