Acrolein

Acrolein

Names
IUPAC name Prop-2-enal
Other names Acraldehyde Acrylaldehyde Acrylic aldehyde Allyl Aldehyde Ethylene aldehyde
Properties
Chemical formula	C3H4O
Molar mass	56.06 g/mol
Appearance	Colorless to yellowish liquid
Odor	Acrid, burnt fat-like
Density	0.839 g/cm3
Melting point	−88 °C (−126 °F; 185 K)
Boiling point	53 °C (127 °F; 326 K)
Solubility in water	20 g/100 ml (20 °C)
Solubility	Miscible in acetone, benzene, diethyl ether, ethanol, methylcyclohexane Slightly soluble in chloroform
Vapor pressure	210 mmHg
Thermochemistry
Std enthalpy of formation (ΔfHo298)	-65.314 kJ/mol
Hazards
Safety data sheet	Sigma-Aldrich
Flash point	−26 °C
Lethal dose or concentration (LD, LC):
LC50 (Median concentration)	875 ppm (mouse, 1 min) 175 ppm (mouse, 10 min) 150 ppm (dog, 30 min) 8 ppm (rat, 4 hr) 375 ppm (rat, 10 min) 25.4 ppm (hamster, 4 hr) 131 ppm (rat, 30 min)
Related compounds
Related compounds	Propionaldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Acrolein or propenal (C₃H₄O) is the simplest unsaturated aldehyde. It is a colourless liquid with a piercing, disagreeable, acrid smell reminiscent of burnt fat.

Properties

Chemical

Acrolein will polymerize in contact with light or a strong base.

Physical

Acrolein is a colorless to slight yellowish liquid, with a strong unpleasant odor, reminiscent of burnt fat.

Availability

While some chemical suppliers will sell acrolein, it is extremely difficult to get hold of.

Preparation

Can be prepared by dehydration of glycerol.

Oxidation of propene will also give acrolein.

Projects

• Make 1-octen-3-ol
• Make propanol

Handling

Safety

Acrolein is highly toxic and irritant. Wear proper protection and work in a well ventilated place or in a fumehood. Normal respirators do not block it, so you'll have to use a different type of breathing mask.

Storage

Acrolein should be stored in amber bottles, away from light or bases. Hydroquinone is added as a stabilizer. However, it should be noted that acrolein will polymerize in several days.

Disposal

Acrolein can be neutralized with a base, such as sodium hydroxide.

References

Relevant Sciencemadness threads

• Glycerol to Propionic Acid: A Chemical Safari Tour.
• Valorizing the Glycerol from Biodiesel Production