Methyl acrylate

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Not to be confused with methyl methacrylate.
Methyl acrylate
Skeletal formula of methyl Acrylate
Ball-and-stick model of the methyl acrylate molecule
Names
IUPAC name
Methyl prop-2-enoate[1]
Other names
Methyl acrylate
Methyl propenoate
Methoxycarbonylethylene
Curithane 103[1]
Identifiers
96-33-3 YesY
ChEMBL ChEMBL9019 YesY
ChemSpider 7022 YesY
Jmol-3D images Image
KEGG C19443 N
PubChem 7294
Properties
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]
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]
3575 ppm (mouse)
1350 ppm (rat, 4 hr)
1000 ppm (rat, 4 hr)
2522 ppm (rabbit, 1 hr)[4]
US health exposure limits (NIOSH):
TWA 10 ppm (35 mg/m3) [skin][2]
TWA 10 ppm (35 mg/m3) [skin][2]
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 isYesY/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[edit]

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[edit]

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

References[edit]

  1. ^ a b "methyl acrylate - Compound Summary". PubChem. Retrieved June 30, 2012. 
  2. ^ a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0394". National Institute for Occupational Safety and Health (NIOSH). 
  3. ^ a b c d Record in the GESTIS Substance Database of the IFA
  4. ^ "Methyl acrylate". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH). 
  5. ^ Takashi Ohara, Takahisa Sato, Noboru Shimizu, Günter Prescher Helmut Schwind, Otto Weiberg, Klaus Marten, Helmut Greim “Acrylic Acid and Derivatives” in Ullmann's Encyclopedia of Industrial Chemistry 2003, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a01_161.pub2
  6. ^ Chessie E. Rehberg (1955). "n-Butyl acrylate". Org. Synth. 26: 18. ; Coll. Vol. 3, p. 146 
  7. ^ Edward A. Fehnel and Marvin Carmack (1950). "Methyl-β-dipropionate". Org. Synth. 30: 65. ; Coll. Vol. 4, p. 669