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.
Names | |
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Preferred IUPAC name
Butanal | |
Other names
Butyraldehyde
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Identifiers | |
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3D model (JSmol)
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3DMet |
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ChEBI |
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ChEMBL |
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ChemSpider |
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ECHA InfoCard | 100.004.225 |
EC Number |
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KEGG |
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PubChem CID
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RTECS number |
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UNII |
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UN number | 1129 |
CompTox Dashboard (EPA)
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Properties | |
C4H8O | |
Molar mass | 72.107 g·mol−1 |
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) |
Critical point (T, P) | 537 K (264 °C), 4.32 MPa (42.6 atm) |
7.6 g/100 mL (20 °C) | |
Solubility | Miscible with organic solvents |
log P | 0.88 |
−46.08·10−6 cm3/mol | |
Refractive index (nD)
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1.3766 |
Viscosity | 0.45 cP (20 °C) |
2.72 D | |
Thermochemistry[2] | |
Heat capacity (C)
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163.7 J·mol−1·K−1 (liquid) 103.4 J·mol−1·K−1 (gas) |
Std molar
entropy (S⦵298) |
246.6 J·mol−1·K−1 (liquid) 343.7 J·mol−1·K−1 (gas) |
Std enthalpy of
formation (ΔfH⦵298) |
−239.2 kJ·mol−1 (liquid) −204.8 kJ·mol−1 (gas) |
Std enthalpy of
combustion (ΔcH⦵298) |
2470.34 kJ·mol−1 |
Hazards | |
GHS labelling: | |
[3] | |
Danger | |
H225, H319[3] | |
P210, P280, P302+P352, P304+P340, P305+P351+P338[3] | |
NFPA 704 (fire diamond) | |
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): | |
LD50 (median dose)
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2490 mg/kg (rat, oral) |
Safety data sheet (SDS) | Sigma-Aldrich |
Related compounds | |
Related aldehyde
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Propionaldehyde Pentanal |
Related compounds
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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
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Butyraldehyde is produced almost exclusively by the hydroformylation of propylene:
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.[4]
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.[4]
Butyraldehyde is a component in the two-step synthesis of trimethylolpropane, which is used for the production of alkyd resins.[5]
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