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 the butyl acetate molecule
Names
IUPAC name
Butyl acetate
Systematic IUPAC name
Butyl ethanoate
Other names
n-Butyl acetate; Butyl ethanoate; Acetic acid, n-butyl ester; Butile;
Identifiers
123-86-4 YesY
Abbreviations BuAcO
ChEBI CHEBI:31328 YesY
ChEMBL ChEMBL284391 YesY
ChemSpider 29012 YesY
EC Number 204-658-1
Jmol 3D model Interactive image
KEGG C12304 YesY
PubChem 31272
RTECS number AF7350000
UNII 464P5N1905 YesY
UN number 1123
  • InChI=1S/C6H12O2/c1-3-4-5-8-6(2)7/h3-5H2,1-2H3 YesY
    Key: DKPFZGUDAPQIHT-UHFFFAOYSA-N YesY
  • InChI=1/C6H12O2/c1-3-4-5-8-6(2)7/h3-5H2,1-2H3
    Key: DKPFZGUDAPQIHT-UHFFFAOYAF
  • CCCCOC(=O)C
Properties
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]
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]
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]
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]
−609.6 kJ/mol[2]
3467 kJ/mol[2]
Vapor pressure {{{value}}}
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).
YesY verify (what is YesYN ?)
Infobox references

n-Butyl acetate, also known as butyl ethanoate, is a soluble 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

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:[3]

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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. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ 2.0 2.1 2.2 2.3 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. ↑ Acetic acid. (2003). In Ullman's encyclopedia of industrial chemistry (6th ed., Vol. 1, pp. 170-171). Weinheim, Germany: Wiley-VCH.

External links

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