Propionaldehyde

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Propionaldehyde
Propionaldehyde propanal prepared by NileRed.png
Freshly prepared propionaldehyde
Names
IUPAC name
Propanal
Preferred IUPAC name
Propanal
Other names
1-Propanal
Methylacetaldehyde
Propaldehyde
n-Propanal
Propionic aldehyde
Properties
C3H6O
CH3CH2CHO
Molar mass 58.080 g/mol
Appearance Colorless liquid
Odor Fruity-like, pungent
Density 0.81 g/cm3 (20 °C)
Melting point −81 °C (−114 °F; 192 K)
Boiling point 48 °C (118 °F; 321 K)
30.6 g/100 ml (25 °C)
Solubility Miscible with alcohols, esters, ethers, halocarbons
Vapor pressure 235 mmHg (at 20 °C)
Thermochemistry
Hazards
Safety data sheet Sigma-Aldrich
Flash point −26 °C (−15 °F; 247 K)
Lethal dose or concentration (LD, LC):
1,690 mg/kg (rat, oral)
Related compounds
Related compounds
Acetaldehyde
Butyraldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO.

Properties

Chemical

The condensation reaction between propanal and formaldehyde yields trimethylolethane.

Propanal will polymerize in presence of strong acids acids or bases. Can also occur in contact with methyl methacrylate.

Physical

Propionaldehyde is a colorless volatile liquid, with a strong pungent fruity-like odor. It is partially soluble in water, but miscible with other organic solvents.

Availability

Propionaldehyde is sold by chemical suppliers.

Preparation

Propionaldehyde can be easily produced by oxidizing propanol with a mixture of sulfuric acid and potassium dichromate.

CH3CH2CH2OH + [O] → CH3CH2CHO + H2O

The reflux condenser contains water heated at 60 °C, which condenses unreacted propanol, but allows propionaldehyde to pass. The propionaldehyde vapor is immediately condensed into a suitable receiver. In this arrangement, any propionaldehyde formed is immediately removed from the reactor, thus it does not get over-oxidized to propionic acid.[1]

Industrially, propionaldehyde is produced by hydroformylation of ethylene:

CO + H2 + C2H4 → CH3CH2CHO

Projects

  • Synthesis of n-propyl amine
  • Preparation of trimethylolethane

Handling

Safety

Propanal may be harmful and should be handled with care. With an LD50 of 1690 mg/kg (oral), propionaldehyde exhibits low acute toxicity.

Storage

In closed bottles, away from light, air and bases.

Disposal

Should be mixed with ethanol and incinerated.

References

  1. http://orgsyn.org/demo.aspx?prep=CV2P0541

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