Isobutyraldehyde
Names | |
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IUPAC name
2-methylpropanal | |
Other names
2-Methylpropionaldehyde | |
Identifiers | |
78-84-2 | |
3D model (Jmol) | Interactive image |
ChEBI | CHEBI:48943 |
ChemSpider | 6313 |
ECHA InfoCard | 100.001.045 |
PubChem | 6561 |
RTECS number | NQ4025000 |
UNII | C42E28168L |
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Properties | |
C4H8O | |
Molar mass | 72.11 g/mol |
Appearance | colourless liquid |
Density | 0.79 g/cm3 |
Melting point | −65 °C (−85 °F; 208 K) |
Boiling point | 63 °C (145 °F; 336 K) |
moderate | |
Solubility in other solvents | miscible in organic solvents |
Refractive index (nD) |
1.374 |
Hazards | |
Main hazards | flammable |
R-phrases | 11 |
S-phrases | 16 |
Flash point | −19 °C; −2 °F; 254 K |
Related compounds | |
Related alkyl aldehydes |
Lilial |
Related compounds |
Butyraldehyde Propionaldehyde |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
verify (what is ?) | |
Infobox references | |
Isobutyraldehyde is the chemical compound with the formula (CH3)2CHCHO. It is an aldehyde, isomeric with n-butyraldehyde (butanal).[1] Isobutyraldehyde is manufactured, often as a side-product, by the hydroformylation of propene. Its odour is described as that of wet cereal or straw. It undergoes the Cannizaro reaction even though it has alpha hydrogen atom.
Synthesis
Isobutyraldehyde is produced industrially by the hydroformylation of propene. Several million tons are produced annually. [2]
Strong mineral acids catalyse the rearrangement of methallyl alcohol to isobutraldehyde.
It can also be produced using engineered bacteria.[3]
Reactions
Hydrogenation of the aldehyde gives isobutanol. Oxidation gives methacrolein or methacrylic acid. Condensation with formaldehyde gives hydroxypivaldehyde.[2]
References
- ↑ Isobutyraldehyde is a retained trivial name under the IUPAC rules.Panico R, Powell WH, Richer JC, eds. (1993). "Recommendation R-9.1". A Guide to IUPAC Nomenclature of Organic Compounds. IUPAC/Blackwell Science. ISBN 0-632-03488-2.
- 1 2 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
- ↑ Atsumi, Shota; Wendy Higashide; James C. Liao (November 2009). "Direct photosynthetic recycling of carbon dioxide to isobutyraldehyde". Nature Biotechnology. 27 (12): 1177–1180. doi:10.1038/nbt.1586. PMID 19915552.