Butyl acetate
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Names | |
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Preferred IUPAC name
Butyl acetate | |
Systematic IUPAC name
Butyl ethanoate | |
Other names
n-Butyl acetate
Acetic acid n-butyl ester Butile | |
Identifiers | |
3D model (JSmol)
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Abbreviations | BuAcO |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.236 |
EC Number |
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KEGG | |
PubChem CID
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RTECS number |
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UNII | |
UN number | 1123 |
CompTox Dashboard (EPA)
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Properties | |
CH3CO2(CH2)3CH3 | |
Molar mass | 116.160 g·mol−1 |
Appearance | Colorless liquid |
Odor | Fruity |
Density | 0.8825 g/cm3 (20 °C)[1] |
Melting point | −78 °C (−108 °F; 195 K)[1] |
Boiling point | 126.1 °C (259.0 °F; 399.2 K) at 760 mmHg[1] |
0.68 g/100 mL (20 °C)[1] | |
Solubility | Miscible in EtOH Soluble in acetone, CHCl3[1] |
log P | 1.82[1] |
Vapor pressure | |
Henry's law
constant (kH) |
0.281 L·atm/mol |
−77.47·10−6 cm3/mol | |
Thermal conductivity |
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Refractive index (nD)
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1.3941 (20 °C)[1] |
Viscosity |
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Structure | |
1.87 D (24 °C)[1] | |
Thermochemistry | |
Heat capacity (C)
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225.11 J/mol·K[2] |
Std enthalpy of
formation (ΔfH⦵298) |
−609.6 kJ/mol[2] |
Std enthalpy of
combustion (ΔcH⦵298) |
3467 kJ/mol[2] |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Flammable |
GHS labelling: | |
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Warning | |
H226, H336[3] | |
P261[3] | |
NFPA 704 (fire diamond) | |
Flash point | 22 °C (72 °F; 295 K)[4] |
370 °C (698 °F; 643 K)[4] | |
Threshold limit value (TLV)
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150 ppm[1] (TWA), 200 ppm[1] (STEL) |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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10768 mg/kg (rats, oral)[4] |
LC50 (median concentration)
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160 ppm (rat, 4 hr) 2000 ppm (rat, 4 hr) 391 ppm (rat, 4 hr) 1242 ppm (mouse, 2 hr)[6] |
LCLo (lowest published)
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14,079 ppm (cat, 72 min) 13,872 ppm (guinea pig, 4 hr)[6] |
NIOSH (US health exposure limits): | |
PEL (Permissible)
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TWA 150 ppm (710 mg/m3)[4] |
REL (Recommended)
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TWA 150 ppm (710 mg/m3) ST 200 ppm (950 mg/m3)[5] |
IDLH (Immediate danger)
|
1700 ppm[5] |
Related compounds | |
Related acetates
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Ethyl acetate Propyl acetate Amyl acetate |
Related compounds
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Butanol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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n-Butyl acetate is an organic compound with the formula CH3CO2(CH2)3CH3. A colorless, flammable liquid, it is the ester derived from n-butanol and acetic acid. It is found in many types of fruit, where it imparts characteristic flavors and has a sweet smell of banana or apple. It is used as an industrial solvent.[7]
The other three isomers (four, including stereoisomers) of butyl acetate are isobutyl acetate, tert-butyl acetate, and sec-butyl acetate (two enantiomers).
Production and use
[edit]Butyl acetate is commonly manufactured by the Fischer esterification of butanol (or its isomer to make an isomer of butyl acetate) and acetic acid with the presence of sulfuric acid:[7]
Butyl acetate is mainly used as a solvent for coatings and inks.[7] It is a component of fingernail polish.[8]
Occurrence in nature
[edit]Apples, especially of the 'Red Delicious' variety, are flavored in part by this chemical. The alarm pheromones emitted by the Koschevnikov gland of honey bees contain butyl acetate.
References
[edit]- ^ a b c d e f g h i j k l m Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
- ^ a b c d Acetic acid, butyl ester in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-06-28)
- ^ a b c Sigma-Aldrich Co., Butyl acetate. Retrieved on 2014-06-28.
- ^ a b c d e "MSDS of n-Butyl acetate". fishersci.ca. Fisher Scientific. Retrieved 2014-06-28.
- ^ a b NIOSH Pocket Guide to Chemical Hazards. "#0072". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b "n-Butyl acetate". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ a b c Cheung, Hosea; Tanke, Robin S.; Torrence, G. Paul (2000). "Acetic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_045. ISBN 3527306730.
- ^ Schneider, Günther; Gohla, Sven; Schreiber, Jörg; Kaden, Waltraud; Schönrock, Uwe; Schmidt-Lewerkühne, Hartmut; Kuschel, Annegret; Petsitis, Xenia; Pape, Wolfgang; Ippen, Hellmut; Diembeck, Walter (2001). "Skin Cosmetics". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a24_219. ISBN 3527306730.
External links
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