Butyl acetate

n-Butyl acetate

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
Abbreviations	BuAcO
ChEBI	CHEBI:31328
ChEMBL	ChEMBL284391
ChemSpider	29012
EC Number	204-658-1
Jmol interactive 3D	Image
KEGG	C12304
PubChem	31272
RTECS number	AF7350000
UNII	464P5N1905
UN number	1123
InChI InChI=1S/C6H12O2/c1-3-4-5-8-6(2)7/h3-5H2,1-2H3 Key: DKPFZGUDAPQIHT-UHFFFAOYSA-N 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/cm^3 (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]
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)[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 (ΔfH^o298)	−609.6 kJ/mol[2]
Std enthalpy of combustion (ΔcH^o298)	3467 kJ/mol[2]
Hazards
Main hazards	Flammable
GHS pictograms	[3]
GHS signal word	Warning
GHS hazard statements	H226, H336[3]
GHS precautionary statements	P261[3]
R-phrases	R10, R66, R67
S-phrases	S25
NFPA 704	[4] 3 2 0
Flash point	22 °C (72 °F; 295 K)[4]
Autoignition temperature	370 °C (698 °F; 643 K)[4]
Threshold Limit Value	150 ppm[1] (TWA), 200 ppm[1] (STEL)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	10768 mg/kg (rats, oral)[4]
LC50 (Median concentration)	160 ppm (rat, 4 hr) 2000 ppm (rat, 4 hr) 391 ppm (rat, 4 hr) 1242 ppm (mouse, 2 hr)[5]
LCLo (Lowest published)	14,079 ppm (cat, 72 min) 13,872 ppm (guinea pig, 4 hr)[5]
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 150 ppm (710 mg/m^3)[4]
REL (Recommended)	TWA 150 ppm (710 mg/m^3) ST 200 ppm (950 mg/m^3)[6]
IDLH (Immediate danger	1700 ppm[6]
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 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.

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:^[7]

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. 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. 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. Sigma-Aldrich Co., Butyl acetate. Retrieved on 2014-06-28.
4. "MSDS of n-Butyl acetate". https://www.fishersci.ca. Fisher Scientific. Retrieved 2014-06-28. External link in |website= (help)
5. "n-Butyl acetate". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
6. "NIOSH Pocket Guide to Chemical Hazards #0072". National Institute for Occupational Safety and Health (NIOSH).
7. Acetic acid. (2003). In Ullman's encyclopedia of industrial chemistry (6th ed., Vol. 1, pp. 170-171). Weinheim, Germany: Wiley-VCH.

External links

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