Butyraldehyde

Butyraldehyde[1]
Names
IUPAC name
Butanal
Identifiers
123-72-8 YesY
ChEBI CHEBI:15743 YesY
ChemSpider 256 YesY
Jmol interactive 3D Image
KEGG C01412 YesY
PubChem 261
UNII H21352682A YesY
Properties
C4H8O
Molar mass 72.11 g/mol
Appearance colorless liquid
Odor pungent, aldehyde odor
Density 0.8016 g/mL
Melting point −96.86 °C (−142.35 °F; 176.29 K)
Boiling point 74.8 °C (166.6 °F; 347.9 K)
7.6 g/100 mL (20 °C)
Solubility miscible with ethanol, ether, toluene
very soluble in acetone, benzene
slightly soluble in chloroform
log P 0.88
1.3766
Viscosity 0.45 cP (20 °C)
2.72 D
Thermochemistry
2470.34 kJ/mol
Hazards
Safety data sheet Sigma-Aldrich
Flammable (F)
R-phrases R11
S-phrases (S2), S9, S29, S33
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
3
3
0
Flash point −7 °C (19 °F; 266 K)
230 °C (446 °F; 503 K)
Explosive limits 1.912.5%
Lethal dose or concentration (LD, LC):
2490 mg/kg (rat, oral)
Related compounds
Related aldehyde
Propionaldehyde
Pentanal
Related compounds
Butan-1-ol
Butyric acid, isobutyraldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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

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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