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 methyl acrylate
Identifiers
CAS number 96-33-3 YesY
PubChem 7294
ChemSpider 7022 YesY
KEGG C19443 N
ChEMBL CHEMBL9019 YesY
Jmol-3D images Image 1
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; 270 K)[3]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/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.[4] 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).[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[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. ^ CDC - NIOSH Pocket Guide to Chemical Hazards
  3. ^ a b c d Record in the GESTIS Substance Database from the IFA
  4. ^ 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
  5. ^ Chessie E. Rehberg (1955), n-Butyl acrylate, Org. Synth. 26: 18 ; Coll. Vol. 3: 146 
  6. ^ Edward A. Fehnel and Marvin Carmack (1950), Methyl-β-dipropionate, Org. Synth. 30: 65 ; Coll. Vol. 4: 669