Sec-Butyl acetate

sec-Butyl acetate
Sec-butyl acetate
Ball-and-stick model of the sec-butyl acetate molecule
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 Edit this at Wikidata
UNII
  • InChI=1S/C6H12O2/c1-4-5(2)8-6(3)7/h5H,4H2,1-3H3 checkY
    Key: DCKVNWZUADLDEH-UHFFFAOYSA-N checkY
  • InChI=1/C6H12O2/c1-4-5(2)8-6(3)7/h5H,4H2,1-3H3
    Key: DCKVNWZUADLDEH-UHFFFAOYAV
  • O=C(OC(C)CC)C
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
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable
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]
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

sec-Butyl acetate, or s-butyl acetate, is an ester 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 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]

Nomenclature

sec-Butyl acetate is chiral. It has one stereocenter, carbon 2 in the sec-butyl group. The names of the two enantiomers are:

  • [(2S)-butan-2-yl] acetate, (+)-sec-butyl acetate
  • [(2R)-butan-2-yl] acetate, (-)-sec-butyl acetate

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. ^ a b c d e f g 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. ^ "sec-butyl Acetate". The Merck Index. Royal Society of Chemistry. 2013.
  7. ^ Canadian Center for Occupational Health and Safety. (1996). 2-Butyl acetate. Retrieved February 20, 2009, from CHEMINFO database.
  8. ^ a b International Programme on Chemical Safety. (2003). sec-Butyl acetate. Retrieved February 20, 2009, from INCHEM database.

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