sec-Butyl acetate

sec-Butyl acetate, or s-butyl acetate, is a solvent commonly used as a solvent in lacquers and enamels, where it is used in the production of acyclic polymers, vinyl resins, and nitrocellulose.[3] It is a clear flammable liquid with a sweet smell.[4]

sec-Butyl acetate
Names
Preferred IUPAC name
Butan-2-yl acetate[1]
Other names
  • 2-Butyl acetate
  • sec-Butyl ester
  • s-Butyl acetate
  • sec-Butyl ester of acetic acid
  • 1-Methylpropyl acetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.001
UNII
Properties
C6H12O2
Molar mass 116.160 g·mol−1
Appearance Clear, liquid
Odor Fruity[2]
Density 0.87 g/cm3, liquid
Melting point −99 °C (−146 °F; 174 K)
Boiling point 112 °C (234 °F; 385 K)
0.80 g/100 mL
Vapor pressure 10 mmHg[2]
Hazards
Main hazards Flammable
Safety data sheet External MSDS
Flash point 17 °C; 62 °F; 290 K[2]
Explosive limits 1.7–9.8%[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 200 ppm (950 mg/m3)[2]
REL (Recommended)
 TWA 200 ppm (950 mg/m3)[2]
IDLH (Immediate danger)
 1700 ppm[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

sec-Butyl acetate has three isomers that are also acetate esters: n-butyl acetate, isobutyl acetate, and tert-butyl acetate.

History

The first method of production of sec-butyl acetate was the esterification of sec-butanol and acetic anhydride[5] It was experimentally determined and published in 1946 by Rolf Altschul.[6]

Toxicology

The LD50 for rats is 13 g/kg.[7] Exposure in humans to significant quantities of sec-butyl acetate can cause irritation to the eyes, mouth, throat, nose, and skin.[8] Ingestion and inhalation of sec-butyl acetate can cause central nervous system depression producing symptoms of dizziness and disorientation.[8]

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References
  1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 370. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. NIOSH Pocket Guide to Chemical Hazards. "#0073". National Institute for Occupational Safety and Health (NIOSH).
  3. "Acetic acid", Ullman's encyclopedia of industrial chemistry (2003, 6th ed., Vol. 1, pp. 170–171). Weinheim, Germany: Wiley-VCH.
  4. Howard, H. H. (1993). sec-Butyl acetate. In Handbook of environmental fate and exposure data for organic chemists (Vol. 5, pp. 60–65). Chelsea, MI: Lewis.
  5. Altschul, R. (1946). "The Reversible Esterification of Carboxylic Acids with Isobutene and Trimethylethylene. Quantitative Studies and Synthetic Applications", Journal of the American Chemical Society, 68(12), 2605–2609.
  6. O'Neil, M. J. (Ed.) (2001). sec-Butyl Acetate. In The Merck index: An encyclopedia of chemicals, drugs, and biologicals (13th ed., pg. 1539). Whitehouse Stations, NJ: Merck.
  7. Canadian Center for Occupational Health and Safety. (1996). 2-Butyl acetate. Retrieved February 20, 2009, from CHEMINFO database.
  8. International Programme on Chemical Safety. (2003). sec-Butyl acetate. Retrieved February 20, 2009, from INCHEM database.
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