Butyraldehyde
| Skeletal structure | |
| Flat structure | |
| Ball-and-stick model | |
| Names | |
|---|---|
| IUPAC name
Butanal
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| Identifiers | |
123-72-8  |
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| ChEBI | CHEBI:15743 |
| ChemSpider | 256 |
| Jmol 3D model | Interactive image |
| KEGG | C01412 |
| PubChem | 261 |
| UNII | H21352682A |
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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 ethanol, ether, toluene very soluble in acetone, benzene slightly soluble in chloroform |
| log P | 0.88 |
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Refractive index (nD)
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1.3766 |
| Viscosity | 0.45 cP (20 °C) |
| 2.72 D | |
| Thermochemistry | |
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Std enthalpy of
combustion (ΔcH |
2470.34 kJ/mol |
| Vapor pressure | {{{value}}} |
| Related compounds | |
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Related aldehyde
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Propionaldehyde Pentanal |
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Related compounds
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Butan-1-ol Butyric acid, isobutyraldehyde |
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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, 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 acrid 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 aldedyde, which forms a lighter immiscible phase. About 6 billion kilograms are produced annually by hydroformylation.
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.[2]
Upon prolonged exposure to air, butyraldehyde oxidizes to form butyric acid.
References
- ↑ Merck Index, 11th Edition, 1591
- ↑ 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
