Butyl acrylate

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 polybutylacrylate, which is used in paints, sealants, coatings, adhesives, fuel, textiles, plastics, and caulk.[4]

Butyl acrylate
Names
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
EC Number
  • 205-480-7
KEGG
RTECS number
  • UD3150000
UNII
UN number 2348
Properties
C7H12O2
Molar mass 128.171 g·mol−1
Appearance Clear, 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 ethanol, ethyl ether, acetone, carbon tetrachloride (slight)
Vapor pressure 4 mmHg (20°C)[1]
Hazards
GHS pictograms
GHS Signal word Warning
H226, H315, H317, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P271, P272, P280, P302+352, P303+361+353, P304+340, P305+351+338, P312, P321, P332+313, P333+313, P337+313, P362, P363, P370+378, P403+233, P403+235
Flash point 39 °C; 103 °F; 313 K [1]
267 °C (513 °F; 540 K)[2]
Explosive limits 1.5% - 9.9%[1]
Lethal dose or concentration (LD, LC):
1800 mg/kg (dermal, rabbit)[3]
1000 ppm (4 hr)[3]
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).
Infobox references

Production and properties

Butyl acrylate can be produced by the acid-catalyzed esterification acrylic acid with butanol. Since it polymerizes easily, commercial preparations may contain a polymerization inhibitor such as hydroquinone, phenothiazine, or hydroquinone ethyl ether.[2][4]

Safety

Butyl acrylate is of low acute toxicity with an LD50 (rat) of 3730 mg/kg.

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

References
  1. NIOSH Pocket Guide to Chemical Hazards. "#0075". National Institute for Occupational Safety and Health (NIOSH).
  2. "Butyl Acrylate". International Chemical Safety Cards. NIOSH. July 1, 2014.
  3. "N-Butyl Acrylate". OSHA/NIOSH. September 28, 2011.
  4. Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut; Shaffer (2020). "Acrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–21. doi:10.1002/14356007.a01_161.pub4.
  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.
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