Butyraldehyde

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Butyraldehyde[1]
Structural formula of Butyraldehyde
Flat structure
Ball-and-stick model
Names
IUPAC name
Butanal
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.004.225 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3 checkY
    Key: ZTQSAGDEMFDKMZ-UHFFFAOYSA-N checkY
  • InChI=1/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3
    Key: ZTQSAGDEMFDKMZ-UHFFFAOYAZ
  • O=CCCC
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
2470.34 kJ/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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. gasolineInstability 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)
Safety data sheet (SDS) Sigma-Aldrich
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).
checkY verify (what is checkY☒N ?)

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 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.[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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