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Ethyl methacrylate

Ethyl methacrylate is the organic compound with the formula C2H5O2CC(CH3)=CH2. A colorless liquid, it is a common monomer for the preparation of acrylate polymers.[1] It is typically polymerized under free-radical conditions.[2]

Ethyl methacrylate
Names
Preferred IUPAC name
Ethyl 2-methylprop-2-enoate
Other names
Ethyl 2-methylpropenoate, Acryester E, Acryester BMA
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.362 Edit this at Wikidata
EC Number
  • 202-597-5
RTECS number
  • OZ4550000
UNII
UN number 2277
  • InChI=1S/C6H10O2/c1-4-8-6(7)5(2)3/h2,4H2,1,3H3
    Key: SUPCQIBBMFXVTL-UHFFFAOYSA-N
  • CCOC(=O)C(=C)C
Properties
C6H10O2
Molar mass 114.144 g·mol−1
Appearance colorless liquid
Density 0.9135 g/cm3
Boiling point 117 °C (243 °F; 390 K)
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Warning
H225, H315, H317, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P271, P272, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
2
3
2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ethyl methacrylate was first obtained by treating ethyl 2-hydroxyisobutyrate with phosphorus pentachloride in an apparent dehydration reaction.[3]

Environmental issues and health hazards

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The related methyl and butyl methacrylates have respective acute LD50s 10 and 20 g/kg (oral, rat);[1] a linear extrapolation suggests that ethyl methacrylate would have LD50 approximately 13 g/kg.

Acrylate esters irritate the eyes and can cause blindness.[1]

See also

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References

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  1. ^ a b c Bauer, Jr., William (2002). "Methacrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_441. ISBN 978-3527306732..
  2. ^ Granel, C.; Dubois, Ph.; Jérôme, R.; Teyssié, Ph. (1996). "Controlled Radical Polymerization of Methacrylic Monomers in the Presence of a Bis(ortho-chelated) Arylnickel(II) Complex and Different Activated Alkyl Halides". Macromolecules. 29 (27): 8576–8582. Bibcode:1996MaMol..29.8576G. doi:10.1021/ma9608380.
  3. ^ E. Frankland, B. F. Duppa (1865). "Untersuchungen über Säuren aus der Acrylsäure-Reihe; 1) Umwandlung der Säuren aus der Milchsäure-Reihe in die der Acrylsäure-Reihe". Justus Liebigs Annalen der Chemie. 136: 12. doi:10.1002/jlac.18651360102.
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