|Jmol-3D images||Image 1|
|Molar mass||86.09 g mol−1|
|Melting point||−74 °C (−101 °F; 199 K)|
|Boiling point||80 °C (176 °F; 353 K)|
|Solubility in water||5 g/100 mL|
|Main hazards||Harmful (Xn); Highly flammable (F+)|
|Flash point||−3 °C (27 °F; 270 K)|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
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. 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). 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:
- 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.
- "methyl acrylate - Compound Summary". PubChem. Retrieved June 30, 2012.
- CDC - NIOSH Pocket Guide to Chemical Hazards
- Record in the GESTIS Substance Database from the IFA
- 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
- Chessie E. Rehberg (1955), n-Butyl acrylate, Org. Synth. 26: 18; Coll. Vol. 3: 146
- Edward A. Fehnel and Marvin Carmack (1950), Methyl-β-dipropionate, Org. Synth. 30: 65; Coll. Vol. 4: 669