Butyl acetate

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For other uses, see Butyl acetate (disambiguation).
n-Butyl acetate
Skeletal formula of butyl acetate
Ball-and-stick model of butyl acetate
Identifiers
CAS number 123-86-4 YesY
PubChem 31272
ChemSpider 29012 YesY
UNII 464P5N1905 YesY
EC number 204-658-1
UN number 1123
KEGG C12304 YesY
ChEBI CHEBI:31328 YesY
ChEMBL CHEMBL284391 YesY
RTECS number AF7350000
Jmol-3D images Image 1
Properties
Molecular formula C6H12O2
Molar mass 116.16 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]
Solubility in water 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]
kH 0.281 L·atm/mol
Thermal conductivity 0.143 W/m·K (0 °C)
0.136 W/m·K (25 °C)
0.13 W/m·K (50 °C)
0.116 W/m·K (100 °C)[1]
Refractive index (nD) 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
Dipole moment 1.87 D (24 °C)[1]
Thermochemistry
Specific
heat capacity
C
225.11 J/mol·K[2]
Std enthalpy of
formation
ΔfHo298
−609.6 kJ/mol[2]
Std enthalpy of
combustion
ΔcHo298
3467 kJ/mol[2]
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)[3]
GHS signal word Warning
GHS hazard statements H226, H336[3]
GHS precautionary statements P261[3]
EU Index 607-025-00-1
R-phrases R10, R66, R67
S-phrases S25
Main hazards Flammable
NFPA 704
Flammability code 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., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 22 °C (72 °F; 295 K)[4]
Autoignition temperature 370 °C (698 °F; 643 K)[4]
U.S. Permissible
exposure limit (PEL)
150 ppm (OSHA)[4]
Threshold Limit Value 150 ppm[1] (TWA), 200 ppm[1] (STEL)
LD50 10768 mg/kg (rats, oral)[4]
Related compounds
Related acetates Ethyl acetate
Propyl acetate
Amyl acetate
Related compounds Butanol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

n-Butyl acetate, also known as butyl ethanoate, is an organic compound commonly used as a solvent in the production of lacquers and other products. It is a colorless flammable liquid. Butyl acetate is found in many types of fruit, where along with other chemicals it imparts characteristic flavors and has a sweet smell of banana or apple. It is used as a synthetic fruit flavoring in foods such as candy, ice cream, cheeses, and baked goods.

The other three isomers of butyl acetate are: isobutyl acetate, tert-butyl acetate, and sec-butyl acetate.

Production[edit]

Butyl acetates are 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 catalytic sulfuric acid under reflux conditions with the following reaction:[5]

Synthesis Butyl acetate.svg

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]

  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, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (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". https://www.fishersci.ca. Fisher Scientific. Retrieved 2014-06-28. 
  5. ^ Acetic acid. (2003). In Ullman's encyclopedia of industrial chemistry (6th ed., Vol. 1, pp. 170-171). Weinheim, Germany: Wiley-VCH.

External links[edit]