National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-259 ,1986. . Reported in EPA TSCA Inventory. Community Right-To-Know List.

OSHA PEL: TWA 5 ppm; STEL 25 ppm (skin)
ACGIH TLV: TWA 5 ppm; STEL 15 ppm; Suspected Human Carcinogen
DFG MAK: 5 ppm (21 mg/m³)
DOT Classification:  3; Label: Flammable Liquid

For occupational chemical analysis use NIOSH: Esters I, 1450.

Ethyl acrylate, also known as 2-Propenoic acid, ethyl ester, is clear, colorless, flammable liquid with a sharp, acrid odor. It is slightly soluble in water, easily soluble in ethanol, ether, and soluble in chloroform. Ethyl acrylate can easily polymerize upon standing and polymerization is accelerated by heat, light, and peroxides. So this chemical is mainly used in the preparation of various polymers. If you don't want it polymerize spontaneously, you must add an inhibitor to prevent it. The odor threshold for ethyl acrylate ranges from 0.001 to 0.005 part per million (ppm) parts of air. So the human nose is easily detecting this odor.

Preparation: Ethyl acrylate can be obtianed by many methods.

1. Currently, the propylene oxidation method is the most used method. First, oxidize propylene to acrolein, and then further oxidize to acrylic acid. Secondly, go through successive esterification by acrylic acid and ethanol in the presence of ion exchange resin catalyst at the boiling temperature to obtain ethyl acrylate. Equation is as follows:
CH₂=CH-CH₃[O₂]→CH₂=CHCHO[O₂]→CH₂=CHCOOH
CH₂=CHCOOH+C₂H₅OH→CH₂=CHCOOC₂H₅

2. Ethyl acrylate can be obtianed by the reaction of 3-hydroxy propionitrile and ethanol in dilute sulfuric acid solution.

3. Ethyl acrylate can be obtianed by ethylene, carbon monoxide and ethanol in the presence of nickel or cobalt catalyst.

4. Ethyl acrylate can be obtianed by esterification of acrylic acid and acetylene in the presence of hydrochloric acid and Ni (CO)₄ in ethanol solution.

Uses: Ethyl acrylate is mainly used as comonomer in the production of resin which is widely used in paints, textiles, leather, adhesives and other industries. It is the intermediate in the preparation of ethyl carbamate insecticides Benfuracarb. Ethyl acrylate also can be used as raw material of protective coatings, adhesives and paper impregnant. The polymer can be used as anti-cracking agent of leather. And the copolymer with ethylene is a hot-melt adhesives, with 5% chloroethyl vinyl ether is synthetic rubber with good performance of oil resistance and heat resistant, which can replace nitrile rubber in some cases. What's more, ethyl acrylate is used in preparation of food flavor such as rum, pineapple and fruit cocktail allowed by GB 2760-1996.

Safty: The main safety issue of ethyl acrylate arises from its being flammable and highly reactive. So people should keep it away from sources of ignition. It is harmful by inhalation, in contact with skin and if swallowed. The drowsiness, nausea, headache, convulsions, lethargy, and respiratory and gastrointestinal irritation has been reported to be caused by acute exposure of workers to ethyl acrylate vapors. There is a favorable safety aspect which is ethyl acrylate has good warning properties: the odor threshold is much lower than any level of health concern. In other words, before the concentration reaches a level capable of creating a serious health risk, the bad odor warns people of ethyl acrylate's presence long. If you want to contact this product, you must wear suitable protective clothing and gloves.

Other properties: (1)ACD/LogP: 1.30; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.298; (4)ACD/LogD (pH 7.4): 1.298; (5)ACD/BCF (pH 5.5): 5.705; (6)ACD/BCF (pH 7.4): 5.705; (7)ACD/KOC (pH 5.5): 121.04; (8)ACD/KOC (pH 7.4): 121.04; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 26.3 Å²; (13)Index of Refraction: 1.402; (14)Molar Refractivity: 26.713 cm³; (15)Molar Volume: 109.645 cm³; (16)Polarizability: 10.59×10^-24 cm³; (17)Surface Tension: 24.853 dyne/cm; (18)Density: 0.913 g/cm³; (19)Flash Point: 15.556 °C; (20)Enthalpy of Vaporization: 33.885 kJ/mol; (21)Boiling Point: 99.499 °C at 760 mmHg; (22)Vapour Pressure: 38.182 mmHg at 25°C.

Structure Descriptors:
1. Smiles:C(=O)(OCC)C=C
2. InChI:InChI=1/C5H8O2/c1-3-5(6)7-4-2/h3H,1,4H2,2H3

Toxicity: