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Ethyl acrylate

Ethyl acrylate
Skeletal structure of ethyl acrylate
Ball-and-stick model of the ethyl acrylate molecule
Names
Preferred IUPAC name
Ethyl prop-2-enoate
Other names
Ethyl propenoate
Ethyl acrylate
Acrylic acid ethyl ester
Ethyl propenoate
Ethyl ester of acrylic acid
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.004.945
KEGG
RTECS number AT0700000
UNII
Properties
C5H8O2
Molar mass 100.12 g·mol−1
Appearance Clear liquid
Odor Acrid
Density 0.9405 g/mL
Melting point −71 °C (−96 °F; 202 K)
Boiling point 99.4 °C (210.9 °F; 372.5 K)
1.5 g/100 mL
Vapor pressure 29 mmHg (20°C)
Hazards
Main hazards Carcinogenic
R-phrases R11 R20/21/22 R36/37/38 R43
S-phrases (S2) S9 S16 S33 S36/37
NFPA 704
Flammability code 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., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g., phosphorus Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 15 °C (59 °F; 288 K)
Explosive limits 1.4%-14%
Lethal dose or concentration (LD, LC):
2180 ppm (rat, 4 hr)
3894 ppm (mouse)
1204 ppm (rabbit, 7 hr)
1204 ppm (guinea pig, 7 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 25 ppm (100 mg/m3) [skin]
REL (Recommended)
 Carcinogen
IDLH (Immediate danger)
 Ca [300 ppm]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is also a reagent in the synthesis of various pharmaceutical intermediates.

Ethyl acrylate is produced by acid-catalysed esterification of acrylic acid, which in turn is produced by oxidation of propylene. It may also be prepared from acetylene, carbon monoxide and ethanol by a Reppe reaction.

Ethyl acrylate is used in the production of polymers including resins, plastics, rubber, and denture material.

Ethyl acrylate is a reactant for homologous alkyl acrylates (acrylic esters) by transesterification with higher alcohols through acidic or basic catalysis. In that way speciality acrylates are made accessible, e.g. 2-ethylhexyl acrylate (from 2-ethylhexanol) used for pressure-sensitive adhesives, cyclohexyl acrylate (from cyclohexanol) used for automotive clear lacquers, 2-hydroxyethyl acrylate (from ethylene glycol) which is crosslinkable with diisocyanates to form gels used with long-chain acrylates (from C18+ alcohols) as comonomer for comb polymers for reduction of the solidification point of paraffin oils and 2-dimethylaminoethyl acrylate (from dimethylaminoethanol) for the preparation of flocculants for sewage clarification and paper production.


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