Butyraldehyde
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| Names | |||
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| Preferred IUPAC name
Butanal | |||
| Other names
Butyraldehyde
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| Identifiers | |||
3D model (JSmol)
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| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). | ||
| EC Number |
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). | ||
| KEGG | |||
PubChem CID
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| RTECS number |
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| UNII | |||
| 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: | |||
| GHS02: Flammable GHS07: Exclamation mark[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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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
[edit | edit source]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.[4]
Reactions and uses
[edit | edit source]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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References
[edit | edit source]- ^ Merck Index, 11th Edition, 1591.
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ a b c Record of Butyraldehyde in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 13 March 2020.
- ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
External links
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