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Methyl acrylate

Methyl acrylate
Skeletal formula of methyl Acrylate
Ball-and-stick model of the methyl acrylate molecule
Names
IUPAC name
Methyl prop-2-enoate
Other names
Methyl acrylate
Methyl propenoate
Methoxycarbonylethylene
Curithane 103
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.002.274
KEGG
PubChem CID
Properties
C4H6O2
Molar mass 86.09 g·mol−1
Appearance Colorless liquid
Odor Acrid
Density 0.95 g/cm3
Melting point −74 °C (−101 °F; 199 K)
Boiling point 80 °C (176 °F; 353 K)
5 g/100 mL
Vapor pressure 65 mmHg (20°C)
Hazards
Main hazards Harmful (Xn); Highly flammable (F+)
Safety data sheet Oxford MSDS
Flash point −3 °C (27 °F; 270 K)
Explosive limits 2.8%-25%
Lethal dose or concentration (LD, LC):
3575 ppm (mouse)
1350 ppm (rat, 4 hr)
1000 ppm (rat, 4 hr)
2522 ppm (rabbit, 1 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 10 ppm (35 mg/m3) [skin]
REL (Recommended)
TWA 10 ppm (35 mg/m3) [skin]
IDLH (Immediate danger)
250 ppm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced to make acrylate fiber, which is used to weave synthetic carpets. It is also a reagent in the synthesis of various pharmaceutical intermediates.

The standard industrial reaction for producing methyl acrylate is esterification with methanol under acid catalysis (sulfuric acid, p-toluene sulfonic acid, acidic ion exchangers.). The transesterification is facilitated because methanol and methyl acrylate form a low boiling azeotrope (b.p. 62-63 °C).

The patent literature describes a one-pot route involving vapor-phase oxidation of propene or 2-propenal with oxygen in the presence of methanol.

Methyl acrylate can be prepared by debromination of methyl 2,3-dibromopropanoate with zinc. Methyl acrylate is formed in good yield on pyrolysis of methyl lactate in the presence of ethenone (ketene). Methyl lactate is a renewable "green chemical". Another patent describes the dehydration of methyl lactate over zeolites.

The nickel tetracarbonyl-catalyzed hydrocarboxylation of acetylene with carbon monoxide in the presence of methanol also yields methyl acrylate. The reaction of methyl formate with acetylene in the presence of transition metal catalysts also leads to methyl acrylate. Both, the alcoholysis of propiolactone with methanol as well as the methanolysis of acrylonitrile via intermediately formed acrylamide sulfate are also proven but obsolete processes.


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