Butyraldehyde
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Names | |
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IUPAC name
Butyraldehyde | |
Systematic IUPAC name
Butanal | |
Identifiers | |
3D model (JSmol) |
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3DMet | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.225 ![]() |
EC Number |
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KEGG | |
PubChem CID |
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RTECS number |
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UNII | |
UN number | 1129 |
CompTox Dashboard (EPA) |
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Properties | |
C4H8O | |
Molar mass | 72.11 g/mol |
Appearance | colorless liquid |
Odor | pungent, aldehyde odor |
Density | 0.8016 g/mL |
Melting point | −96.86 °C (−142.35 °F; 176.29 K) |
Boiling point | 74.8 °C (166.6 °F; 347.9 K) |
7.6 g/100 mL (20 °C) | |
Solubility | miscible with organic solvents |
log P | 0.88 |
−46,08·10−6 cm3/mol | |
Refractive index (nD) |
1.3766 |
Viscosity | 0.45 cP (20 °C) |
2.72 D | |
Thermochemistry | |
Std enthalpy of combustion (ΔcH⦵298) |
2470.34 kJ/mol |
Hazards | |
Safety data sheet | Sigma-Aldrich |
GHS pictograms | ![]() ![]() |
GHS Signal word | Danger |
H225, H319[2] | |
P280, P304+340, P302+352, P210, P305+351+338[2] | |
NFPA 704 (fire diamond) | |
Flash point | −7 °C (19 °F; 266 K) |
230 °C (446 °F; 503 K) | |
Explosive limits | 1.9–12.5% |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
2490 mg/kg (rat, oral) |
Related compounds | |
Related aldehyde |
Propionaldehyde Pentanal |
Related compounds |
Butan-1-ol Butyric acid, isobutyraldehyde |
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 | |
Butyraldehyde
Butyraldehyde, also known as butanal, is an organic compound with the formula CH3(CH2)2CHO. This compound is the aldehyde derivative of butane. It is a colourless flammable liquid with an unpleasant smell. It is miscible with most organic solvents.
Production
Butyraldehyde is produced almost exclusively by the hydroformylation of propylene:
- CH3CH=CH2 + H2 + CO → CH3CH2CH2CHO
Traditionally, hydroformylation was catalyzed by cobalt carbonyl and later rhodium complexes of triphenylphosphine. The dominant technology involves the use of rhodium catalysts derived from the water-soluble ligand tppts. An aqueous solution of the rhodium catalyst converts the propylene to the aldehyde, which forms a lighter immiscible phase. About 6 billion kilograms are produced annually by hydroformylation. A significant application is its conversion to 2-ethylhexanol for production of plasticizers.
![](../I/Bis(2-ethylhexyl)_phthalate.svg.png.webp)
Butyraldehyde can be produced by the catalytic dehydrogenation of n-butanol. At one time, it was produced industrially by the catalytic hydrogenation of crotonaldehyde, which is derived from acetaldehyde.[3]
Upon prolonged exposure to air, butyraldehyde oxidizes to form butyric acid.
References
- Merck Index, 11th Edition, 1591.
- Record of Butyraldehyde in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 13 March 2020.
- Boy Cornils, Richard W. Fischer, Christian Kohlpaintner "Butanals" in Ullmann's Encyclopedia of Industrial Chemistry, 2000, Wiley-VCH, Weinheim. doi:10.1002/14356007.a04_447.