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Butyraldehyde

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Title: Butyraldehyde  
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Subject: Aldehyde, Polyvinyl butyral, CARVOC, Hydroformylation, List of UN numbers 1101 to 1200
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Butyraldehyde

Butyraldehyde[1]
Skeletal structure
Flat structure
Ball-and-stick model
Names
IUPAC name
Butanal
Identifiers
 Y
ChEBI  Y
ChemSpider  Y
Jmol-3D images Image
KEGG  Y
PubChem
UNII  Y
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; 348.0 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
3
3
0
Flash point −7 °C (19 °F; 266 K)
230 °C (446 °F; 503 K)
Explosive limits 1.9–12.5%
Lethal dose or concentration (LD, LC):
LD50 (Median dose)
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).
 Y  (: Y/N?)

Butyraldehyde, also known as butanal, is an 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

  • International Chemical Safety Card 0403
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