Ethyl acrylate

Ethyl acrylate[1][2]
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
140-88-5 Yes
ChEMBL ChEMBL52084 Yes
ChemSpider 8490 Yes
Jmol-3D images Image
KEGG C19238 
RTECS number AT0700000
UNII 71E6178C9T Yes
Properties
Molecular formula
 C5H8O2
Molar mass 100.12 g·mol−1
Appearance Clear liquid
Odor Acrid[3]
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)[3]
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
3
2
2
Flash point 15 °C (59 °F; 288 K)
Explosive limits 1.4%-14%[3]
US health exposure limits (NIOSH):
TWA 25 ppm (100 mg/m3) [skin][3]
Carcinogen[3]
Ca [300 ppm][3]
Except where noted otherwise, data is 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.[4] 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.[5]

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)."[6] 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."[7] (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),[7] but the E.P.A.'s lowest level of health concern, the Acute Exposure Guideline Level-1 (AEGL-1) is 8.3 ppm,[8] which is almost 7000 times the odor threshold.

References

  1. ↑ Merck Index, 11th Edition, 3715.
  2. ↑ Ethyl acrylate Datasheet at Inchem.org
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 "NIOSH Pocket Guide to Chemical Hazards #0261". National Institute for Occupational Safety and Health (NIOSH).
  4. ↑ Takashi Ohara, Takahisa Sato, Noboru Shimizu, Günter Prescher Helmut Schwind, Otto Weiberg, Klaus Marten, Helmut Greim “Acrylic Acid and Derivatives” in Ullmann's Encyclopedia of Industrial Chemistry 2003, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a01_161.pub2
  5. ↑ Ethyl acrylate Hazardous Substance Fact Sheet, New Jersey Department of Health and Senior Services
  6. ↑ IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Volume 71, International Agency for Research on Cancer (1999)
  7. ↑ 7.0 7.1 EPA Technology Transfer Network, Air Toxics Web Site, United States Environmental Protection Agency (accessed 2008)
  8. ↑ EPA Acute Exposure Guideline Levels, Ethyl acrylate Results, United States Environmental Protection Agency (accessed 2008)

External links