Butyl acetate

n-Butyl acetate
Names
	Preferred IUPAC name Butyl acetate
	Systematic IUPAC name Butyl ethanoate
	Other names n-Butyl acetate; Acetic acid n-butyl ester; Butile
Identifiers
CAS Number	123-86-4 ;
3D model (JSmol)	Interactive image;
Abbreviations	BuAcO
ChEBI	CHEBI:31328 ;
ChEMBL	ChEMBL284391 ;
ChemSpider	29012 ;
ECHA InfoCard	100.004.236
EC Number	204-658-1;
KEGG	C12304 ;
PubChem CID	31272;
RTECS number	AF7350000;
UNII	464P5N1905 ;
UN number	1123
CompTox Dashboard (EPA)	DTXSID3021982 ;
	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	116.160 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
Magnetic susceptibility (χ)	−77.47·10−6 cm3/mol
Thermal conductivity	0.143 W/m·K (0 °C); 0.136 W/m·K (25 °C); 0.130 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
Heat capacity (C)	225.11 J/mol·K
Std enthalpy of; formation (ΔfH⦵298)	−609.6 kJ/mol
Std enthalpy of; combustion (ΔcH⦵298)	3467 kJ/mol
Hazards
Main hazards	Flammable
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H336
Precautionary statements	P261
NFPA 704 (fire diamond)	2 3 0
Flash point	22 °C (72 °F; 295 K)
Autoignition; temperature	370 °C (698 °F; 643 K)
Threshold limit value (TLV)	150 ppm (TWA), 200 ppm (STEL)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	10768 mg/kg (rats, oral)
LC50 (median concentration)	160 ppm (rat, 4 hr); 2000 ppm (rat, 4 hr); 391 ppm (rat, 4 hr); 1242 ppm (mouse, 2 hr)
LCLo (lowest published)	14,079 ppm (cat, 72 min); 13,872 ppm (guinea pig, 4 hr)
	NIOSH (US health exposure limits):
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).
	(what is ?)
	Infobox references

n-Butyl acetate, also known as butyl ethanoate, is an ester that is a colorless, flammable liquid at room temperature. It 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. It is also used as a solvent in nail polish along with ethyl acetate.

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

Production[]

Butyl acetate is 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 this 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[]

^ ^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.
^ ^a ^b ^c ^d Acetic acid, butyl ester in Linstrom, Peter J.; Mallard, William 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)
^ ^a ^b ^c Sigma-Aldrich Co., Butyl acetate. Retrieved on 2014-06-28.
^ ^a ^b ^c ^d ^e "MSDS of n-Butyl acetate". fishersci.ca. Fisher Scientific. Retrieved 2014-06-28.
^ ^a ^b NIOSH Pocket Guide to Chemical Hazards. "#0072". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b "n-Butyl acetate". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Acetic acid. (2003). In Ullman's encyclopedia of industrial chemistry (6th ed., Vol. 1, pp. 170-171). Weinheim, Germany: Wiley-VCH.

External links[]

[crc-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.

[nist-2] Acetic acid, butyl ester in Linstrom, Peter J.; Mallard, William 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)

[sigma-3] Sigma-Aldrich Co., Butyl acetate. Retrieved on 2014-06-28.

[fca-4] "MSDS of n-Butyl acetate". fishersci.ca. Fisher Scientific. Retrieved 2014-06-28.

[PGCH-5] NIOSH Pocket Guide to Chemical Hazards. "#0072". National Institute for Occupational Safety and Health (NIOSH).

[IDLH-6] "n-Butyl acetate". Immediately Dangerous to Life or Health Concentrations (IDLH). 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.

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v t Esters
Methyl esters	Methyl formate Methyl acetate Methyl propionate Methyl butyrate Methyl pentanoate
Ethyl esters	Ethyl formate Ethyl acetate Ethyl propionate Ethyl butyrate Ethyl pentanoate Ethyl hexanoate Ethyl heptanoate Ethyl octanoate Ethyl decanoate
Propyl esters	Propyl acetate Propyl propanoate Isopropyl acetate Isopropyl palmitate
Butyl esters	Butyl acetate Butyl butyrate Isobutyl acetate
Amyl esters	Amyl acetate Pentyl propanoate Pentyl butyrate Pentyl pentanoate Pentyl hexanoate Isoamyl acetate Sec-Amyl acetate

Names


Preferred IUPAC name Butyl acetate
Systematic IUPAC name Butyl ethanoate
Other names n-Butyl acetate Acetic acid n-butyl ester Butile
Identifiers
CAS Number	123-86-4^Y
3D model (JSmol)	Interactive image
Abbreviations	BuAcO
ChEBI	CHEBI:31328^Y
ChEMBL	ChEMBL284391^Y
ChemSpider	29012^Y
ECHA InfoCard	100.004.236
EC Number	204-658-1
KEGG	C12304^Y
PubChem CID	31272
RTECS number	AF7350000
UNII	464P5N1905^Y
UN number	1123
CompTox Dashboard (EPA)	DTXSID3021982
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	116.160 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]
Henry's law constant (k_H)	0.281 L·atm/mol
Magnetic susceptibility (χ)	−77.47·10⁻⁶ cm³/mol
Thermal conductivity	0.143 W/m·K (0 °C) 0.136 W/m·K (25 °C) 0.130 W/m·K (50 °C) 0.116 W/m·K (100 °C)^[1]
Refractive index (n_D)	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
Heat capacity (C)	225.11 J/mol·K^[2]
Std enthalpy of formation (Δ_fH^⦵₂₉₈)	−609.6 kJ/mol^[2]
Std enthalpy of combustion (Δ_cH^⦵₂₉₈)	3467 kJ/mol^[2]
Hazards
Main hazards	Flammable
GHS labelling:
Pictograms	^[3]
Signal word	Warning
Hazard statements	H226, H336^[3]
Precautionary statements	P261^[3]
NFPA 704 (fire diamond)	^[4] 2 3 0
Flash point	22 °C (72 °F; 295 K)^[4]
Autoignition temperature	370 °C (698 °F; 643 K)^[4]
Threshold limit value (TLV)	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)^[6]
LC_Lo (lowest published)	14,079 ppm (cat, 72 min) 13,872 ppm (guinea pig, 4 hr)^[6]
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 150 ppm (710 mg/m³)^[4]
REL (Recommended)	TWA 150 ppm (710 mg/m³) ST 200 ppm (950 mg/m³)^[5]
IDLH (Immediate danger)	1700 ppm^[5]
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).
Y (what is ^YN ?)
Infobox references