Butyraldehyde
| Butyraldehyde[1] | |
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Butanal |
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| Identifiers | |
| CAS number | 123-72-8  |
| PubChem | 261 |
| ChemSpider | 256 |
| UNII | H21352682A |
| KEGG | C01412 |
| ChEBI | CHEBI:15743 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C4H8O |
| Molar mass | 72.11 g/mol |
| Appearance | colorless flammable liquid |
| Density | 0.8 g/mL |
| Melting point |
-99 °C, 174 K, -146 °F |
| Boiling point |
74.8 °C, 348.0 K, 166.7 °F |
| Solubility in water | 7.6 g/100 mL (20 °C) |
| Hazards | |
| EU Index | 605-006-00-2 |
| EU classification | Flammable (F) |
| R-phrases | R11 |
| S-phrases | (S2), S9, S29, S33 |
| NFPA 704 |
 3
3
0
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| Flash point | −7 °C |
| Autoignition temperature |
230 °C |
| Explosive limits | 2.5–12.5% |
| Related compounds | |
| Related aldehyde | Propionaldehyde Pentanal |
| Related compounds | Butan-1-ol Butyric acid, isobutyraldehyde |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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 [edit]
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 [edit]
- ^ 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
