Propionaldehyde
From Wikipedia, the free encyclopedia
| Propionaldehyde | ||
|---|---|---|
 |
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| Common name | propionaldehyde | |
| IUPAC name | propionaldehyde | |
| Systematic name | propanal | |
| Synonyms |
Methylacetaldehyde |
|
| Chemical formula | C3H6O | |
| SMILES | CCC=O | |
| Molecular mass | 58.080 g mol−1 | |
| Appearance | Colorless liquid Pungent, fruity odor |
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| CAS number | [123-38-6] | |
| UN number | 1275 | |
| Properties | ||
| Density | 0.81 g cm−3 | |
| Solubility in water | 20 g/100 mL | |
| Melting point | −81 °C (192 K) | |
| Boiling point | 46-50 °C (321 K) | |
| Viscosity | 0.6 cP at 20°C | |
| Structure | ||
| Molecular shape | C1, O: sp2
C2, C3: sp3 |
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| Dipole moment | 2.52 D | |
| Hazards | ||
| MSDS | External MSDS | |
| EU classification | Highly flammable (F) Irritant (Xi) |
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| NFPA 704 |
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| R-phrases | R11, R36/37/38 | |
| S-phrases | S9, S16, S29 | |
| Flash point | −26 °C | |
| Autoignition temperature | 175 °C | |
| RTECS number | ? | |
| Supplementary data page | ||
| Structure and properties |
n, εr, etc. | |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
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| Spectral data | UV, IR, NMR, MS | |
| Related compounds | ||
| Related aldehydes | Formaldehyde Acetaldehyde Butyraldehyde |
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| Disclaimer and references | ||
- Note that propanol is a different compound.
Propionaldehyde is the the organic compound with the formula CH3CH2CHO. It is the only 3-carbon aldehyde and is a structural isomer of acetone. It is a colourless liquid with a slightly irritating, fruity odour.
Propanal is mainly produced through the hydroformylation, by combining synthesis gas (carbon monoxide and hydrogen) with ethylene using a metal catalyst:
- CO + H2 + C2H4 → CH3CH2CHO
[edit] Uses
It is principally used to make trimethylolethane through a condensation reaction with methanol; this process is important in the production of alkyd resins.
Condensation of propionaldehyde with tert-butylamine gives CH3CH2CH=N-t-Bu, a useful three-carbon building block in organic synthesis. Deprotonation of this imine with LDA affords CH3CHLi2CH=N-t-Bu, which in turn condenses with aldehydes.[1]
[edit] References
- ^ Peralta, M. M. "Propionaldehyde t-Butylimine" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.
