Ethyl acrylate

Ethyl acrylate

Skeletal structure of ethyl acrylate
Ball-and-stick model of the ethyl acrylate molecule
Names
IUPAC name Ethyl propenoate
Other names Acrylic acid ethyl ester Ethyl propenoate Ethyl ester of acrylic acid
Identifiers
CAS Number	140-88-5 Y
ChEMBL	ChEMBL52084 Y
ChemSpider	8490 Y
Jmol 3D model	Interactive image
KEGG	C19238 N
RTECS number	AT0700000
UNII	71E6178C9T Y
InChI InChI=1S/C5H8O2/c1-3-5(6)7-4-2/h3H,1,4H2,2H3 Y Key: JIGUQPWFLRLWPJ-UHFFFAOYSA-N Y InChI=1/C5H8O2/c1-3-5(6)7-4-2/h3H,1,4H2,2H3 Key: JIGUQPWFLRLWPJ-UHFFFAOYAN
SMILES CCOC(=O)C=C
Properties
Chemical formula	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)
Solubility in water	1.5 g/100 mL
Vapor pressure	29 mmHg (20°C)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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.

Production, reactions, and uses

It 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."

Owing to its tendency to polymerize, samples typically contain an inhibitor such as hydroquinone. Ethyl acrylate is a Michael acceptor and a good dienophile.

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

Safety

It is an acute toxin with an LD50 (rats, oral) of 1020 mg/kg and a TLV of 5 ppm. The International Agency for Research on Cancer stated, "Overall evaluation, Ethyl acrylate is possibly carcinogenic to humans (Group 2B)." The United States Environmental Protection Agency (EPA) states, "Human studies on occupational exposure to ethyl acrylate... have suggested a relationship between exposure to the chemical(s) and colorectal cancer, but the evidence is conflicting and inconclusive. In a study by the National Toxicology Program (NTP), increased incidences of squamous cell papillomas and carcinomas of the forestomach were observed in rats and mice exposed via gavage (experimentally placing the chemical in the stomach). However, the NTP recently determined that these data were not relevant to human carcinogenicity since humans do not have a forestomach, and removed ethyl acrylate from its list of carcinogens." (Occupational exposure generally involves exposure that occurs regularly, over an extended period of time.)

One favorable safety aspect is that ethyl acrylate has good warning properties; the odor threshold is much lower than any level of health concern. In other words, the bad odor warns people of ethyl acrylate's presence long before the concentration reaches a level capable of creating a serious health risk. Reports of the exact levels vary somewhat, but, for example, the U.S. E.P.A. reports an odor threshold of 0.0012 parts per million (ppm), but the E.P.A.'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.

External links

• CDC - NIOSH Pocket Guide to Chemical Hazards - Ethyl Acrylate