sec-Butyl acetate
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.[1] It is a clear flammable liquid with a sweet smell.[2]
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[3] It was experimentally determined and published in 1946 by Rolf Altschul.[4]
Toxicology
The LD50 for rats is 13Script error: No such module "String".g/kg.[5] Exposure in humans to significant quantities of sec-butyl acetate can cause irritation to the eyes, mouth, throat, nose, and skin.[6] Ingestion and inhalation of sec-butyl acetate can cause central nervous system depression producing symptoms of dizziness and disorientation.[6]
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
- ↑ "Acetic acid", Ullman's encyclopedia of industrial chemistry (2003, 6th ed., Vol. 1, pp. 170–171). Weinheim, Germany: Wiley-VCH.
- ↑ 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.
- ↑ 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.
- ↑ Template:Cite Merck Index
- ↑ Canadian Center for Occupational Health and Safety. (1996). 2-Butyl acetate. Retrieved February 20, 2009, from CHEMINFO database.
- ↑ a b International Programme on Chemical Safety. (2003). sec-Butyl acetate. Retrieved February 20, 2009, from INCHEM database.