Butyraldehyde

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 unpleasant smell. It is miscible with most organic solvents.

Butyraldehyde[1]
Names
IUPAC name
Butanal
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.225
EC Number
  • 204-646-6
KEGG
RTECS number
  • ES2275000
UNII
UN number 1129
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 organic solvents
log P 0.88
-46,08·10−6 cm3/mol
1.3766
Viscosity 0.45 cP (20 °C)
2.72 D
Thermochemistry
Std enthalpy of
combustion (ΔcH⦵298)
 2470.34 kJ/mol
Hazards
Safety data sheet Sigma-Aldrich
GHS pictograms [2]
GHS Signal word Danger
GHS hazard statements
 H225, H319[2]
P280, P304+340, P302+352, P210, P305+351+338[2]
NFPA 704 (fire diamond)
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. gasolineHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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):
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

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 aldehyde, which forms a lighter immiscible phase. About 6 billion kilograms are produced annually by hydroformylation. A significant application is its conversion to 2-ethylhexanol for production of plasticizers.

A major use of butyraldehyde is in the production of bis(2-ethylhexyl) phthalate, a major plasticizer.

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.[3]

Upon prolonged exposure to air, butyraldehyde oxidizes to form butyric acid.

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References
  1. Merck Index, 11th Edition, 1591
  2. Record of Butyraldehyde in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 13 March 2020.
  3. 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
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