Butyraldehyde

Butyraldehyde[1]
IUPAC name Butanal
Identifiers
CAS number	123-72-8 Y
PubChem	261
ChemSpider	256 Y
UNII	H21352682A Y
KEGG	C01412 Y
ChEBI	CHEBI:15743 Y
Jmol-3D images	Image 1
SMILES O=CCCC
InChI InChI=1S/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3 Y Key: ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Y InChI=1/C4H8O/c1-2-3-4-5/h4H,2-3H2,1H3 Key: ZTQSAGDEMFDKMZ-UHFFFAOYAZ
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	3 3 0
Flash point	−7 °C; 19 °F; 266 K
Autoignition temperature	230 °C; 446 °F; 503 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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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

External links

• International Chemical Safety Card 0403