Butyl acetate: Difference between revisions
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'''''n''-Butyl acetate''', also known as '''butyl ethanoate''', is a |
'''''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 [[chemical polarity|polarity]]. |
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The other three isomers of butyl acetate are: [[isobutyl acetate]], [[tert-Butyl acetate|''tert''-butyl acetate]], and [[sec-Butyl acetate|''sec''-butyl acetate]]. |
The other three isomers of butyl acetate are: [[isobutyl acetate]], [[tert-Butyl acetate|''tert''-butyl acetate]], and [[sec-Butyl acetate|''sec''-butyl acetate]]. |
Revision as of 10:43, 5 February 2016
Names | |
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IUPAC name
Butyl acetate
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Systematic IUPAC name
Butyl ethanoate | |
Other names
n-Butyl acetate; Butyl ethanoate; Acetic acid, n-butyl ester; Butile;
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Identifiers | |
3D model (JSmol)
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Abbreviations | BuAcO |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.236 |
EC Number |
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KEGG | |
PubChem CID
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RTECS number |
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UNII | |
UN number | 1123 |
CompTox Dashboard (EPA)
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Properties | |
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] |
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 | |
1.87 D (24 °C)[1] | |
Thermochemistry | |
Heat capacity (C)
|
225.11 J/mol·K[2] |
Std enthalpy of
formation (ΔfH⦵298) |
−609.6 kJ/mol[2] |
Std enthalpy of
combustion (ΔcH⦵298) |
3467 kJ/mol[2] |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Flammable |
GHS labelling: | |
[3] | |
Warning | |
H226, H336[3] | |
P261[3] | |
NFPA 704 (fire diamond) | |
Flash point | 22 °C (72 °F; 295 K)[4] |
370 °C (698 °F; 643 K)[4] | |
Threshold limit value (TLV)
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150 ppm[1] (TWA), 200 ppm[1] (STEL) |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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10768 mg/kg (rats, oral)[4] |
LC50 (median concentration)
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160 ppm (rat, 4 hr) 2000 ppm (rat, 4 hr) 391 ppm (rat, 4 hr) 1242 ppm (mouse, 2 hr)[6] |
LCLo (lowest published)
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14,079 ppm (cat, 72 min) 13,872 ppm (guinea pig, 4 hr)[6] |
NIOSH (US health exposure limits): | |
PEL (Permissible)
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TWA 150 ppm (710 mg/m3)[4] |
REL (Recommended)
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TWA 150 ppm (710 mg/m3) ST 200 ppm (950 mg/m3)[5] |
IDLH (Immediate danger)
|
1700 ppm[5] |
Related compounds | |
Related acetates
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Ethyl acetate Propyl acetate Amyl acetate |
Related compounds
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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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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
- ^ 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) (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". https://www.fishersci.ca. Fisher Scientific. Retrieved 2014-06-28.
{{cite web}}
: External link in
(help)|website=
- ^ 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.