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Butyraldehyde[1]
Butanal-skeletal.png
Flat structure
IUPAC name
Systematic name butanal
Identifiers
CAS number 123-72-8 Yes check.svgY
PubChem 261
SMILES
InChI
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
NFPA 704.svg
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
 Yes check.svgY (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

  1. ^ Merck Index, 11th Edition, 1591
  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

External links

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