Methyl acrylate

Methyl acrylate

Names
IUPAC name Methyl prop-2-enoate[1]
Other names Methyl acrylate Methyl propenoate Methoxycarbonylethylene Curithane 103[1]
Identifiers
CAS Registry Number	96-33-3 Y
ChEMBL	ChEMBL9019 Y
ChemSpider	7022 Y
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
Jmol-3D images	Image
KEGG	C19443 N
PubChem	7294
SMILES C=CC(OC)=O
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
Vapor pressure	65 mmHg (20°C)[2]
Hazards
MSDS	Oxford MSDS
Main hazards	Harmful (Xn); Highly flammable (F+)
Flash point	−3 °C (27 °F; 270 K)[3]
Explosive limits	2.8%-25%[2]
LC50 (Median lethal concentration)	3575 ppm (mouse) 1350 ppm (rat, 4 hr) 1000 ppm (rat, 4 hr) 2522 ppm (rabbit, 1 hr)[4]
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 10 ppm (35 mg/m3) [skin][2]
REL (Recommended)	TWA 10 ppm (35 mg/m3) [skin][2]
IDLH (Immediate danger)	250 ppm[2]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
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.^[5] 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).^[6] 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:^[7]

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