3759. Ethyl Acrylate

Nomenclature

CAS number: 140-88-5
2-Propenoic acid ethyl ester; acrylic acid ethyl ester.
C5H8O2; mol wt 100.12.
C 59.98%, H 8.05%, O 31.96%.

Description and references

Prepd from ethylene chlorohydrin or acrylonitrile, ethanol, and sulfuric acid; also by an oxo reaction from acetylene, carbon monoxide, and ethanol in the presence of suitable catalysts. See the refs under Methyl Acrylate.

Chemical structure

Derivative

Monomer.

Properties

Liquid, acrid, penetrating odor, retained by clothing. Lacrimator. d420 0.9405. fp below -72°. bp760 99.4°; bp39.2 20° (polymerizes on distn). nD20 1.404. Specific heat at -60°: 0.442 cal/g/°C. Heat of vaporization 8.27 kcal/mol; heat of combustion 655.49 kcal/mol. Flash pt, open cup: 60°F (15°C). Vapor density 3.45 (air = 1). Flammable. Soly in water at 20°: 2 g/100 ml. Soly of water in ethyl acrylate at 20°: 1.5 g/100 g. Sol in alcohol, ether. Azeotropes: 45.0% water = bp 81°; 56.8% ethanol = bp 76°. Easily polymerizes on standing; polymerization process speeded up by heat, light, and peroxides. If pure, the monomer can be stored below +10° without incurring polymerization.

Derivative

Polymer.

Properties

Transparent, elastic substance. Practically no odor. Little adhesive power. Resists the usual solvents.

Caution

Potential symptoms of overexposure to the monomer are irritation of eyes, respiratory system and skin. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 132. See also Patty's Industrial Hygiene and Toxicology vol. 2A, G. D. Clayton, F. E. Clayton, Eds. (Wiley-Interscience, New York, 3rd ed., 1981) p 2292-2296. This substance was formerly listed as reasonably anticipated to be a human carcinogen: Eighth Report on Carcinogens (PB99-128746, 1998) p III-627; delisted because the relevant data are not sufficient to meet the current criteria for this listing: Ninth Report on Carcinogens (PB2000-107509, 2000) p B-2.

Use

The monomer in the manuf of water emulsion paint vehicles; in production of emulsion-based polymers used in textile and paper coatings, leather finish resins and adhesives. Imparts flexibility to hard films.