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.
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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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| ChEMBL | |||
| ChemSpider |
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| ECHA InfoCard | 100.004.225 | ||
| EC Number |
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| 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 | 72.107ย gยทmolโ1 | ||
| Appearance | Colorless liquid | ||
| Odor | Pungent, aldehyde odor | ||
| Density | 0.8016 g/mL | ||
| Melting point | โ96.86ย ยฐC (โ142.35ย ยฐF; 176.29ย K) | ||
| Boiling point | 74.8ย ยฐC (166.6ย ยฐF; 347.9ย K) | ||
| Criticalย point (T, P) | 537ย K (264ย ยฐC), 4.32ย MPa (42.6ย atm) | ||
| 7.6 g/100 mL (20ย ยฐC) | |||
| Solubility | Miscible with organic solvents | ||
| log P | 0.88 | ||
| โ46.08ยท10โ6ย cm3/mol | |||
Refractive index (nD)
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1.3766 | ||
| Viscosity | 0.45ย cP (20 ยฐC) | ||
| 2.72 D | |||
| Thermochemistry[2] | |||
Heat capacity (C)
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163.7ย Jยทmolโ1ยทKโ1 (liquid) 103.4ย Jยทmolโ1ยทKโ1 (gas) | ||
Std molar
entropy (Sโฆต298) |
246.6ย Jยทmolโ1ยทKโ1 (liquid) 343.7ย Jยทmolโ1ยทKโ1 (gas) | ||
Std enthalpy of
formation (ฮfHโฆต298) |
โ239.2ย kJยทmolโ1 (liquid) โ204.8ย kJยทmolโ1 (gas) | ||
Std enthalpy of
combustion (ฮcHโฆต298) |
2470.34ย kJยทmolโ1 | ||
| Hazards | |||
| GHS labelling: | |||
  [3]
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| Danger | |||
| H225, H319[3] | |||
| P210, P280, P302+P352, P304+P340, P305+P351+P338[3] | |||
| NFPA 704 (fireย diamond) | |||
| Flash point | โ7ย ยฐC (19ย ยฐF; 266ย K) | ||
| 230ย ยฐC (446ย ยฐF; 503ย K) | |||
| Explosive limits | 1.9โ12.5% | ||
| 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 25ย ยฐC [77ย ยฐF], 100ย kPa).
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Production
editButyraldehyde is produced almost exclusively by the hydroformylation of propylene:
- CH3CH=CH2 + H2 + CO โ 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
editButyraldehyde 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]
ย References
edit- ^ Merck Index, 11th Edition, 1591.
- ^ CRC handbook of chemistry and physicsย : a ready-reference book of chemical and physical data. William M. Haynes, David R. Lide, Thomas J. Bruno (2016-2017, 97thย ed.). Boca Raton, Florida. 2016. ISBNย 978-1-4987-5428-6. OCLCย 930681942.
{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: others (link) - ^ 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 Raff, Donald K. (2013). "Butanals". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_447.pub2. ISBNย 978-3-527-30673-2.
- ^ Werle, Peter; Morawietz, Marcus; Lundmark, Stefan; Sรถrensen, Kent; Karvinen, Esko; Lehtonen, Juha (2008). "Alcohols, Polyhydric". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_305.pub2. ISBNย 978-3-527-30673-2.
