|3D model (Jmol)||Interactive image|
|Molar mass||86.09 g·mol−1|
|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)|
|Main hazards||Harmful (Xn); Highly flammable (F+)|
|Safety data sheet||Oxford MSDS|
|Flash point||−3 °C (27 °F; 270 K)|
|Lethal dose or concentration (LD, LC):|
LC50 (median concentration)
|3575 ppm (mouse)
1350 ppm (rat, 4 hr)
1000 ppm (rat, 4 hr)
2522 ppm (rabbit, 1 hr)
|US health exposure limits (NIOSH):|
|TWA 10 ppm (35 mg/m3) [skin]|
|TWA 10 ppm (35 mg/m3) [skin]|
IDLH (Immediate danger)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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.
Like ethyl acrylate also methyl acrylate reacts catalysed by Lewis bases in a Michael addition with amines in high yields to β-alanine derivatives which provide amphoteric surfactants when long-chain amines are used and the ester function is hydrolysed subsequently.
Methyl acrylate is used as a comonomer in the polymerization with a variety of acrylic and vinyl monomers. In doing so it has a similar range of uses as ethyl acrylate. When using methyl acrylate as comonomer resulting acrylic paints are harder and more brittle than those with the homologous acrylates. Copolymerizing methyl acrylate with acrylonitrile improves their melt processability to fibers, which could be used as precursors for carbon fibers.
Methyl acrylate is the precursor to fibers that are woven to make carpets.
Owing to its tendency to polymerize, samples typically contain an inhibitor such as hydroquinone.
Methyl acrylate is a classic Michael acceptor, which means that it adds nucleophiles at its terminus. For example, in the presence of a base catalyst, it adds hydrogen sulfide to give the thioether:
- 2 CH2CHCO2CH3 + H2S → S(CH2CH2CO2CH3)2
It is also a good dienophile.
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- Record in the GESTIS Substance Database of the IFA
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