Hydroxyacetone

Hydroxyacetone

Names
IUPAC name 1-Hydroxypropan-2-one
Preferred IUPAC name 1-Hydroxypropan-2-one
Other names 1-Hydroxy-2-propanone Acetol
Properties
Chemical formula	C3H6O2 CH3C(O)CH2OH
Molar mass	74.079 g/mol
Appearance	Colorless liquid
Odor	Sweet
Density	1.082 g/cm3 (25 °C)
Melting point	−17 °C (1 °F; 256 K)
Boiling point	145.5 °C (293.9 °F; 418.6 K)
Solubility in water	Miscible
Solubility	Miscible with alcohols, ethers, ketones
Vapor pressure	56.25 mmHg at 20 °C
Hazards
Safety data sheet	Sigma-Aldrich
Flash point	56 °C (132.8 °F; 329 K) (closed cup)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	2,200 mg/kg (oral, rat)
Related compounds
Related compounds	Acetone Dihydroxyacetone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Hydroxyacetone, also known as acetol, is the organic chemical with the formula CH₃C(O)CH₂OH. It consists of a primary alcohol substituent on acetone. It is an α-hydroxyketone, also called a ketol, and is the simplest hydroxy ketone.

Properties

Chemical

Hydroxyacetone undergoes rapid polymerization, including forming a hemiacetal cyclic dimer.

Under alkaline conditions, it undergoes a rapid aldol condensation.

Physical

Hydroxyacetone is a colorless liquid, though contaminated samples may turn slightly yellow. It has a sweet-like odor and it's miscible with water. It is also hygroscopic.

Availability

Hydroxyacetone is sold by chemical suppliers.

Preparation

Acetol is produced commercially by dehydration of glycerol. Copper chromite has been successfully used as dehydrating agent.

Hydroxyacetone can be easily prepared in the laboratory from a haloacetone (chloroacetone, bromoacetone), via substitution reaction with potassium formate, followed by hydrolysis with methanol.

Projects

• Preparation of pyruvic acid

Handling

Safety

Hydroxyacetone displays moderate to low toxicity. May be irritant to skin and sensitive tissues.

Storage

Hydroxyacetone should be kept in amber glass bottles, away from air and other reagents. Small amounts of pure sodium carbonate is sometimes used as stabilizer, though this doesn't appear to be always necessary.

Disposal

Can be mixed with another solvent and burned in an incinerator. Alternatively, it can be diluted in water and poured down the drain.

References

Relevant Sciencemadness threads

• Hydroxyacetone via dehydration of glycerol