Methyl acrylate

Methyl acrylate
IUPAC name Methyl prop-2-enoate[1]
Other names Methyl acrylate Methyl propenoate Methoxycarbonylethylene Curithane 103[1]
Identifiers
CAS number	96-33-3 Y
PubChem	7294
ChemSpider	7022 Y
KEGG	C19443 N
ChEMBL	CHEMBL9019 Y
Jmol-3D images	Image 1
SMILES C=CC(OC)=O
InChI InChI=1S/C4H6O2/c1-3-4(5)6-2/h3H,1H2,2H3 Y Key: BAPJBEWLBFYGME-UHFFFAOYSA-N Y InChI=1/C4H6O2/c1-3-4(5)6-2/h3H,1H2,2H3 Key: BAPJBEWLBFYGME-UHFFFAOYAO
Properties
Molecular formula	C4H6O2
Molar mass	86.09 g mol−1
Appearance	Colorless liquid
Odor	Acrid[2]
Density	0.95 g/cm³[3]
Melting point	−74 °C; −101 °F; 199 K ([3])
Boiling point	80 °C; 176 °F; 353 K ([3])
Solubility in water	5 g/100 mL
Hazards
MSDS	Oxford MSDS
Main hazards	Harmful (Xn); Highly flammable (F+)
Flash point	−3 °C (27 °F)[3]
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Methyl acrylate is an organic compound with the formula CH₂CHCO₂CH₃. It is 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.^[4] It is also a reagent in the synthesis of various pharmaceutical intermediates.

Production, reactions, and uses

It is produced by acid-catalysed esterification of acrylic acid, which in turn is produced by oxidation of propylene. Owing to its tendency to polymerize, samples typically contain an inhibitor such as hydroquinone.

The compound undergoes transesterification to give a variety of other acrylate esters. The transesterification is facilitated because methanol and methyl acrylate form a low boiling azeotrope (b.p. 62-63 °C).^[5] Several other esters are precursors to useful polymers.

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:^[6]

2 CH₂CHCO₂CH₃ + H₂S → S(CH₂CH₂CO₂CH₃)₂

It is also a good dienophile.

Methyl acrylate is the precursor to fibers that are woven to make carpets. Acrylates are also used in the preparation of polyamidoamine (PAMAM) dendrimers typically by Michael addition with a primary amine.

Safety

It is an acute toxin with an LD₅₀ (rats, oral) of 300 mg/kg and a TLV of 10 ppm.

References