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Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl group 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 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 to form gels used with long-chain acrylates (from C18+ alcohols) as comonomer for comb polymers for reduction of the solidification point of Mineral oil and 2-dimethylaminoethyl acrylate (from dimethylaminoethanol) for the preparation of flocculants for sewage clarification and paper production.
As a reactive monomer, ethyl acrylate is used in homopolymers and copolymers with e.g. Ethylene, acrylic acid and its salts, and esters, , acrylonitrile, , vinyl acetate, vinyl chloride, vinylidene chloride, styrene, butadiene and unsaturated polyesters. Copolymers of acrylic acid ethyl ester with ethene (EPA/ethylene-ethyl acrylate copolymers) are suitable as adhesives and polymer additives, just like ethene vinyl acetate copolymers. Copolymers with acrylic acid increase the cleaning effect of , copolymers with methacrylic acid are used as gastric juices tablet covers (Eudragit).
The large number of possible comonomer units and their combination in copolymers and terpolymers with ethyl acrylate allows the realization of different properties of the acrylate copolymers in a variety of applications in paints and adhesives, paper, textile and leather auxiliaries together with cosmetic and pharmaceutical products.
The nucleophilic addition at ethyl acrylate as an α,β-unsaturated carbonyl compound is a frequent strategy in the synthesis of pharmaceutical intermediates. Examples are the hypnotic glutethimide or the Vasodilation vincamine (obsolete by now) Pharmazeutische Wirkstoffe: Synthesen, Patente, Anwendungen; von A. Kleemann u. J. Engel; 2., neubearb. u. erw. Aufl.; Stuttgart, New York; Thieme; 1982, or more recent therapeutics such as the COPD agent cilomilast or the nootropic leteprinim.D. Lednicer, The Organic Chemistry of Drug Synthesis, Volume 7, J. Wiley & Sons, 2008,
Ethyl 3-bromopropionate is prepared by hydrobromination of ethyl acrylate.
It is possibly carcinogenic and it is toxic in large doses, with an LD50 (rats, oral) of 1020 mg/kg. As of October 2018, the FDA withdrew authorization for its use as a synthetic flavoring substance in food.
One favorable safety aspect is that ethyl acrylate has good warning properties; the odor threshold is much lower than the concentration required to create an atmosphere immediately dangerous to life and health. Reports of the exact levels vary somewhat, but, for example, the EPA reports an odor threshold of 0.0012 parts per million (ppm), but the EPA's lowest level of health concern, the Acute Exposure Guideline Level-1 (AEGL-1) is 8.3 ppm, which is almost 7000 times the odor threshold.
However, as a possible carconigen, NIOSH maintains "that there is no safe level of exposure to a carcinogen. Reduction of worker exposure to chemical carcinogens as much as possible through elimination or substitution and engineering controls is the primary way to prevent occupational cancer."
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