Hydroxyacetone

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Hydroxyacetone
Names
IUPAC name
1-Hydroxypropan-2-one
Preferred IUPAC name
1-Hydroxypropan-2-one
Other names
1-Hydroxy-2-propanone
Acetol
Properties
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)
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):
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.[1] 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.[2]

Projects

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.[3]

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

  1. https://onlinelibrary.wiley.com/doi/abs/10.1002/14356007.a22_163.pub2
  2. http://orgsyn.org/demo.aspx?prep=CV2P0005
  3. https://www.sigmaaldrich.com/catalog/product/aldrich/138185

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