Chemistry:Isobutyraldehyde
Isobutyraldehyde is the chemical compound with the formula (CH3)2CHCHO. It is an aldehyde, isomeric with n-butyraldehyde (butanal).[1] Isobutyraldehyde is made, often as a side-product, by the hydroformylation of propene. Its odour is described as that of wet cereal or straw. It undergoes the Cannizzaro reaction even though it has alpha hydrogen atom. It is a colorless volatile liquid.
Synthesis
Isobutyraldehyde is produced industrially by the hydroformylation of propene. Several million tons are produced annually.[2]
Biological routes
In the context of butanol fuel, isobutyraldehyde is of interest as a precursor to isobutanol. E. coli as well as several other organisms has been genetically modified to produce isobutanol. α-Ketoisovalerate, derived from oxidative deamination of valine, is prone to decarboxylation to give isobutyraldehyde, which is susceptible to reduction to the alcohol:[3]
- (CH3)2CHC(O)CO2H → (CH3)2CHCHO + CO2
- (CH3)2CHCHO + NADH + H+ → (CH3)2CHCH2OH + NAD+
It can also be produced using engineered bacteria.[4]
Other routes
Strong mineral acids catalyse the rearrangement of methallyl alcohol to isobutyraldehyde.
Reactions
Hydrogenation of the aldehyde gives isobutanol. Oxidation gives methacrolein or methacrylic acid. Condensation with formaldehyde gives hydroxypivaldehyde.[2] The latter is a precursor to vitamin B5.[5]
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Condensation with acetone followed by hydrogenation of the resulting alkene gives the solvent 5-methyl-2-hexanone.[6]
References
- ↑ Isobutyraldehyde is a retained trivial name under the IUPAC rules.Panico, R.; Powell, W. H.; Richer, J. C., eds (1993). "Recommendation R-9.1". A Guide to IUPAC Nomenclature of Organic Compounds. IUPAC/Blackwell Science. ISBN 0-632-03488-2. https://www.acdlabs.com/iupac/nomenclature/.
- ↑ 2.0 2.1 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; Hanai, Taizo; Liao, James C. (January 2008). "Non-fermentative pathways for synthesis of branched-chain higher alcohols as biofuels". Nature 451 (7174): 86–89. doi:10.1038/nature06450. PMID 18172501. Bibcode: 2008Natur.451...86A.
- ↑ 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.
- ↑ Eggersdorfer, Manfred; Laudert, Dietmar; Létinois, Ulla; McClymont, Tom; Medlock, Jonathan; Netscher, Thomas; Bonrath, Werner (2012). "One Hundred Years of Vitamins-A Success Story of the Natural Sciences". Angewandte Chemie International Edition 51 (52): 12975. doi:10.1002/anie.201205886. PMID 23208776. Bibcode: 2012ACIE...5112960E.
- ↑ "Ketones". Ullmann's Encyclopedia of Industrial Chemistry. 2000. doi:10.1002/14356007.a15_077. ISBN 978-3-527-30673-2.
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