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Ethyl methacrylate

From Wikipedia, the free encyclopedia
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 100.002.362Edit 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 114.144g·mol−1
Appearance colorless liquid
Density 0.9135 g/cm3
Boiling point 117 °C (243 °F; 390 K)
Hazards
GHSlabelling:
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 theirstandard state(at 25 °C [77 °F], 100 kPa).

Ethyl methacrylateis the organic compound with the formula C2H5O2CC(CH3)=CH2.A colorless liquid, it is a commonmonomerfor the preparation ofacrylate polymers.[1]It is typically polymerized underfree-radicalconditions.[2]

Ethyl methacrylate was first obtained by treatingethyl 2-hydroxyisobutyratewithphosphorus pentachloridein an apparent dehydration reaction.[3]

Environmental issues and health hazards[edit]

The relatedmethylandbutyl methacrylateshave respective acuteLD50s10 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[edit]

References[edit]

  1. ^abcBauer, Jr., William (2002). "Methacrylic Acid and Derivatives".Ullmann's Encyclopedia of Industrial Chemistry.Weinheim: Wiley-VCH.doi:10.1002/14356007.a16_441.ISBN978-3527306732..
  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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