Butyl acetate

n-Butyl acetate
Skeletal formula of butyl acetate
Ball-and-stick model of the butyl acetate molecule
Names
Preferred IUPAC name
Butyl acetate
Systematic IUPAC name
Butyl ethanoate
Other names
n-Butyl acetate
Acetic acid n-butyl ester
Butile
Identifiers
CAS Number
  • 123-86-4 checkY
3D model (JSmol)
  • Interactive image
Abbreviations BuAcO
ChEBI
  • CHEBI:31328 checkY
ChEMBL
  • ChEMBL284391 checkY
ChemSpider
  • 29012 checkY
ECHA InfoCard 100.004.236 Edit this at Wikidata
EC Number
  • 204-658-1
KEGG
  • C12304 checkY
PubChem CID
  • 31272
RTECS number
  • AF7350000
UNII
  • 464P5N1905 checkY
UN number 1123
CompTox Dashboard (EPA)
  • DTXSID3021982 Edit this at Wikidata
InChI
  • InChI=1S/C6H12O2/c1-3-4-5-8-6(2)7/h3-5H2,1-2H3 checkY
    Key: DKPFZGUDAPQIHT-UHFFFAOYSA-N checkY
  • InChI=1/C6H12O2/c1-3-4-5-8-6(2)7/h3-5H2,1-2H3
    Key: DKPFZGUDAPQIHT-UHFFFAOYAF
  • CCCCOC(=O)C
Properties
Chemical formula
 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
  • 0.1 kPa (−19 °C)
  • 1.66 kPa (24 °C)[1]
  • 44.5 kPa (100 °C)[2]
Henry's law
constant (kH)
 0.281 L·atm/mol
−77.47·10−6 cm3/mol
Thermal conductivity
  • 0.143 W/m·K (0 °C)
  • 0.136 W/m·K (25 °C)
  • 0.130 W/m·K (50 °C)
  • 0.116 W/m·K (100 °C)[1]
1.3941 (20 °C)[1]
Viscosity
  • 1.002 cP (0 °C)
  • 0.685 cP (25 °C)
  • 0.5 cP (50 °C)
  • 0.305 cP (100 °C)[1]
Structure
1.87 D (24 °C)[1]
Thermochemistry
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
 Flammable
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark[3]
Warning
H226, H336[3]
P261[3]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
Flash point 22 °C (72 °F; 295 K)[4]
Autoignition
temperature
 370 °C (698 °F; 643 K)[4]
150 ppm[1] (TWA), 200 ppm[1] (STEL)
Lethal dose or concentration (LD, LC):
10768 mg/kg (rats, oral)[4]
160 ppm (rat, 4 hr)
2000 ppm (rat, 4 hr)
391 ppm (rat, 4 hr)
1242 ppm (mouse, 2 hr)[6]
14,079 ppm (cat, 72 min)
13,872 ppm (guinea pig, 4 hr)[6]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 150 ppm (710 mg/m3)[4]
REL (Recommended)
 TWA 150 ppm (710 mg/m3) ST 200 ppm (950 mg/m3)[5]
IDLH (Immediate danger)
 1700 ppm[5]
Related compounds
Related acetates
 Ethyl acetate
Propyl acetate
Amyl acetate
Related compounds
 Butanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references
Chemical compound

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

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

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

  1. ^ 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.
  2. ^ 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)
  3. ^ a b c Sigma-Aldrich Co., Butyl acetate. Retrieved on 2014-06-28.
  4. ^ a b c d e "MSDS of n-Butyl acetate". fishersci.ca. Fisher Scientific. Retrieved 2014-06-28.
  5. ^ a b NIOSH Pocket Guide to Chemical Hazards. "#0072". National Institute for Occupational Safety and Health (NIOSH).
  6. ^ a b "n-Butyl acetate". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  7. ^ 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 978-3527306732.
  8. ^ 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

Wikimedia Commons has media related to Butyl acetate.
  • Ethylene and other chemicals in fruit
  • Material Safety Data Sheet
  • CDC - NIOSH Pocket Guide to Chemical Hazards