Butyl acrylate

Butyl acrylate
Names
Preferred IUPAC name
Butyl prop-2-enoate
Other names
  • n-Butyl acrylate
  • Butyl ester of acrylic acid
  • Butyl-2-propenoate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.983 Edit this at Wikidata
EC Number
  • 205-480-7
KEGG
RTECS number
  • UD3150000
UNII
UN number 2348
  • InChI=1S/C7H12O2/c1-3-5-6-9-7(8)4-2/h4H, 2-3,5-6H2,1H3
    Key: CQEYYJKEWSMYFG-UHFFFAOYSA-N
  • InChI=1/C7H12O2/c1-3-5-6-9-7(8)4-2/h4H, 2-3,5-6H2,1H3
    Key: CQEYYJKEWSMYFG-UHFFFAOYAL
  • CCCCOC(=O)C=C
Properties
C7H12O2
Molar mass 128.171 g·mol−1
Appearance Colorless liquid[1]
Odor Strong, fruity[1]
Density 0.89 g/mL (20°C)[1]
Melting point −64 °C; −83 °F; 209 K[1]
Boiling point 145 °C; 293 °F; 418 K[1]
0.1% (20°C)[1]
Solubility organic solvents
Vapor pressure 4 mmHg (20°C)[1]
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Warning
H226, H315, H317, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P271, P272, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
Flash point 39 °C; 103 °F; 313 K[1]
267 °C (513 °F; 540 K)[3]
Explosive limits 1.5% - 9.9%[1]
Lethal dose or concentration (LD, LC):
1800 mg/kg (dermal, rabbit)[2]
1000 ppm (4 hr)[2]
NIOSH (US health exposure limits):
REL (Recommended)
 TWA 10 ppm (55 mg/m3)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Butyl acrylate is an organic compound with the formula C4H9O2CCH=CH2. A colorless liquid, it is the butyl ester of acrylic acid. It is used commercially on a large scale as a precursor to poly(butyl acrylate). Especially as copolymers, such materials are used in paints, sealants, coatings, adhesives, fuel, textiles, plastics, and caulk.[4]

Production and properties

Butyl acrylate can be produced by the acid-catalyzed esterification of acrylic acid with butanol. It polymerizes easily, therefore commercial preparations contain polymerization inhibitors such as hydroquinone, phenothiazine, or hydroquinone ethyl ether.[3][4]

Safety

Butyl acrylate is of low acute toxicity with an LD50 (rat) of 3143 mg/kg.[4]

In rodent models, butyl acrylate is metabolized by carboxylesterase or reactions with glutathione; this detoxification produces acrylic acid, butanol, and mercapturic acid waste, which are excreted.[5][6][7]

Exposure can occur through inhalation, skin and/or eye contact absorption, and ingestion.[8] Symptoms may be dependent on exposure route, with skin and eye contact manifesting in redness, pain, and sensitivity; inhalation resulting in burning sensations, cough, shortness of breath, and sore throat; and ingestion resulting in abdominal pain, nausea, vomiting, and diarrhoea.[8]

References

  1. ^ a b c d e f g h i j NIOSH Pocket Guide to Chemical Hazards. "#0075". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b "N-Butyl Acrylate". OSHA/NIOSH. September 28, 2011.
  3. ^ a b "Butyl Acrylate". International Chemical Safety Cards. NIOSH. July 1, 2014.
  4. ^ a b c Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut; Shaffer, Timothy D.; Nandi, Partha (2020). "Acrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–21. doi:10.1002/14356007.a01_161.pub4. ISBN 9783527303854.
  5. ^ "Screening Information Data Set for n-Butyl acrylate, CAS #141-32-2". Organization for Economic Cooperation and Development. October 2002. Archived from the original on 2015-11-07.
  6. ^ Zondlo Fiume M (2002). "Final report on the safety assessment of Acrylates Copolymer and 33 related cosmetic ingredients". Int. J. Toxicol. 21 Suppl 3: 1–50. doi:10.1080/10915810290169800. PMID 12537929.
  7. ^ "Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans". Geneva: World Health Organization: IARC. 1999.
  8. ^ a b PubChem. "Butyl acrylate". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-03-27.