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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
123-86-4 YesY
3D model (Jmol) Interactive image
Abbreviations BuAcO
ChEBI CHEBI:31328 YesY
ChEMBL ChEMBL284391 YesY
ChemSpider 29012 YesY
ECHA InfoCard 100.004.236
EC Number 204-658-1
KEGG C12304 YesY
PubChem 31272
RTECS number AF7350000
UNII 464P5N1905 YesY
UN number 1123
Properties
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
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)
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)
0.13 W/m·K (50 °C)
0.116 W/m·K (100 °C)
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
1.87 D (24 °C)
Thermochemistry
225.11 J/mol·K
−609.6 kJ/mol
3467 kJ/mol
Hazards
Main hazards Flammable
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)
GHS signal word Warning
H226, H336
P261
R-phrases R10, R66, R67
S-phrases S25
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)
370 °C (698 °F; 643 K)
150 ppm (TWA), 200 ppm (STEL)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 10768 mg/kg (rats, oral)
160 ppm (rat, 4 hr)
2000 ppm (rat, 4 hr)
391 ppm (rat, 4 hr)
1242 ppm (mouse, 2 hr)
14,079 ppm (cat, 72 min)
13,872 ppm (guinea pig, 4 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 150 ppm (710 mg/m3)
REL (Recommended)
 TWA 150 ppm (710 mg/m3) ST 200 ppm (950 mg/m3)
IDLH (Immediate danger)
 1700 ppm
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  (what is YesYN ?)
Infobox references

n-Butyl acetate, also known as butyl ethanoate, is an ester which is a colorless flammable liquid at room temperature. 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. Butyl acetate is often used as a high-boiling solvent of moderate polarity.

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

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:

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.


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