| Butyraldehyde[1] | |
|---|---|
 |
|
 |
|
| IUPAC name |
butyraldehyde
|
| Systematic name | butanal |
| Identifiers | |
| CAS number | 123-72-8  |
| PubChem | 261 |
| SMILES |
O=CCCC
|
| InChI |
1/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3
|
| InChI key | ZTQSAGDEMFDKMZ-UHFFFAOYAZ |
| ChemSpider ID | 256 |
| Properties | |
| Molecular formula | C4H8O |
| Molar mass | 72.11 g/mol |
| Density | 0.8 g/ml |
| Melting point |
−99 °C |
| Boiling point |
74.8 °C |
| 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
|
| 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 |
| (what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
|
| 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 that smells like sweaty feet. 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
External links
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