Butyl acetate

For other uses, see Butyl acetate (disambiguation).

n-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
CAS Number	123-86-4 Y
Abbreviations	BuAcO
ChEBI	CHEBI:31328 Y
ChEMBL	ChEMBL284391 Y
ChemSpider	29012 Y
EC Number	204-658-1
Jmol 3D model	Interactive image
KEGG	C12304 Y
PubChem	31272
RTECS number	AF7350000
UNII	464P5N1905 Y
UN number	1123
InChI InChI=1S/C6H12O2/c1-3-4-5-8-6(2)7/h3-5H2,1-2H3 Y Key: DKPFZGUDAPQIHT-UHFFFAOYSA-N Y InChI=1/C6H12O2/c1-3-4-5-8-6(2)7/h3-5H2,1-2H3 Key: DKPFZGUDAPQIHT-UHFFFAOYAF
SMILES CCCCOC(=O)C
Properties
Chemical formula	C6H12O2
Molar mass	116.16 g·mol−1
Appearance	Colorless liquid
Odor	Fruity
Density	0.8825 g/cm3 (20 °C)
Melting point	−78 °C (−108 °F; 195 K)
Boiling point	126.1 °C (259.0 °F; 399.2 K) at 760 mmHg
Solubility in water	0.68 g/100 mL (20 °C)
Solubility	Miscible in EtOH Soluble in acetone, CHCl3
log P	1.82
Vapor pressure	0.1 kPa (−19 °C) 1.66 kPa (24 °C) 44.5 kPa (100 °C)
Henry's law constant (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)
Refractive index (nD)	1.3941 (20 °C)
Viscosity	1.002 cP (0 °C) 0.685 cP (25 °C) 0.5 cP (50 °C) 0.305 cP (100 °C)
Structure
Dipole moment	1.87 D (24 °C)
Thermochemistry
Specific heat capacity (C)	225.11 J/mol·K
Std enthalpy of formation (ΔfHo298)	−609.6 kJ/mol
Std enthalpy of combustion (ΔcHo298)	3467 kJ/mol
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).
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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:

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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.

External links

• Ethylene and other chemicals in fruit
• Material Safety Data Sheet
• CDC - NIOSH Pocket Guide to Chemical Hazards

• 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)
• Acetic acid. (2003). In Ullman's encyclopedia of industrial chemistry (6th ed., Vol. 1, pp. 170-171). Weinheim, Germany: Wiley-VCH.