Butyraldehyde

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Butyraldehyde

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UN number	1129
Template:Longitem	Template:Chembox Elements/molecular formula
Molar mass	Template:Chem molar mass
Appearance	Colorless liquid
Odor	Pungent, aldehyde odor
Density	0.8016 g/mL
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Solubility	Miscible with organic solvents
log P	0.88
Template:Longitem	−46.08·10−6 cm3/mol
Template:Longitem	1.3766
Viscosity	0.45 cP (20 °C)
Template:Longitem	2.72 D
Template:Longitem	163.7 J·mol−1·K−1 (liquid) 103.4 J·mol−1·K−1 (gas)
Template:Longitem	246.6 J·mol−1·K−1 (liquid) 343.7 J·mol−1·K−1 (gas)
Template:Longitem	−239.2 kJ·mol−1 (liquid) −204.8 kJ·mol−1 (gas)
Template:Longitem	2470.34 kJ·mol−1
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Flash point	Template:Chembox CalcTemperatures
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Explosive limits	1.9–12.5%
Template:Longitem	Propionaldehyde Pentanal
Template:Longitem	Butan-1-ol Butyric acid, isobutyraldehyde

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 colorless flammable liquid with an unpleasant 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 but rhodium complexes are more common. 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 (less dense) immiscible phase. About 6 billion kilograms are produced annually in this manner. 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.

Reactions and uses

Butyraldehyde undergoes reactions typical of alkyl aldehydes, and these define many of the uses of this compound. Important reactions include hydrogenation to the alcohol, oxidation to the acid, and base-catalyzed condensation. In the presence of a base, two equivalents of butyraldehyde undergoe aldol condensation to give 2-ethylhexenal. This unsaturated aldehyde is then partially hydrogenated to form 2-ethylhexanal, a precursor to plasticizers such as bis(2-ethylhexyl) phthalate.

Butyraldehyde is a component in the two-step synthesis of trimethylolpropane, which is used for the production of alkyd resins.

File:Bis(2-ethylhexyl) phthalate.svg

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

External links

• International Chemical Safety Card 0403