Butyraldehyde

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Butyraldehyde[1]
Skeletal structure
Flat structure
Ball-and-stick model
Identifiers
CAS number 123-72-8 YesY
PubChem 261
ChemSpider 256 YesY
UNII H21352682A YesY
KEGG C01412 YesY
ChEBI CHEBI:15743 YesY
Jmol-3D images Image 1
Properties
Molecular formula 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)
Solubility in water 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
Refractive index (nD) 1.3766
Viscosity 0.45 cP (20 °C)
Dipole moment 2.72 D
Thermochemistry
Std enthalpy of
combustion
ΔcHo298
2470.34 kJ/mol
Hazards
MSDS Sigma-Aldrich
EU Index 605-006-00-2
EU classification 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
Flash point −7 °C (19 °F; 266 K)
Explosive limits 1.9–12.5%
LD50 2490 mg/kg (rat, oral)
Related compounds
Related aldehyde Propionaldehyde
Pentanal
Related compounds Butan-1-ol
Butyric acid, isobutyraldehyde
Except where noted otherwise, 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[edit]

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[edit]

  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[edit]