Acetone

2008/9 Schools Wikipedia Selection. Related subjects: Chemical compounds

Acetone
Acetone Ball-and-stick model of acetone Space-filling model of acetone
General
Systematic name Propanone
Other names β-ketopropane
Dimethyl ketone,
Molecular formula CH3COCH3
SMILES CC(=O)C
Molar mass 58.09 g/mol
Appearance Colorless liquid
CAS number [67-64-1]
Properties
Density and phase 0.79 g/cm³, liquid
Solubility in Water (molecule)">water miscible
Melting point −94.9 °C (178.2 K)
Boiling point 56.3 °C (329.4 K)
Viscosity 0.32 c P at 20 °C
Structure
Molecular shape trigonal planar at C=O
Dipole moment 2.91 D
Hazards
MSDS External MSDS
EU classification Flammable (F)
Irritant (Xi)
NFPA 704
3
1
0
 
R-phrases R11, R36, R66, R67
S-phrases (S2), S9, S16, S26
Flash point −20 °C
Flammable limits
in air (by volume)
2.55% - 12.80%
Autoignition temperature 465 °C
RTECS number AL31500000
Supplementary data page
Structure & properties n, εr, etc.
Thermodynamic data Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Related ketones Butanone
Related solvents Water
Ethanol
Isopropanol
Toluene
Except where noted otherwise, data are given for
materials in their standard state (at 25°C, 100 kPa)
Infobox disclaimer and references

The chemical compound acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the ketones. Acetone is a colorless, mobile, flammable liquid with melting point of −95.4 °C and boiling point of 56.53 °C. It has a relative density of 0.819 (at 0 °C). It is readily soluble in water, ethanol, ether, etc., and itself serves as an important solvent.

The most familiar household use of acetone is as the active ingredient in nail polish remover. Acetone is also used to make plastic, fibers, drugs, and other chemicals.

Before the invention of the cumene process acetone was produced by the dry distillation of acetates, for example calcium acetate.

In addition to being manufactured as a chemical, acetone is also found naturally in the environment, including in small amounts in the human body.

Uses

An important industrial use for acetone involves its reaction with phenol for the manufacture of bisphenol A. Bisphenol A is an important component of many polymers such as polycarbonates, polyurethanes and epoxy resins. Acetone is also used extensively for the safe transporting and storing of acetylene. Vessels containing a porous material are first filled with acetone followed by acetylene, which dissolves into the acetone. One liter of acetone can dissolve around 250 liters of acetylene.

Acetone is often the primary (or only) component in nail polish remover. Acetonitrile, another organic solvent, is sometimes used as well. Acetone is also used as a superglue remover. It can be used for thinning and cleaning fibreglass resins and epoxies. It is a strong solvent for most plastics and synthetic fibres.

Additionally, acetone is extremely effective when used as a cleaning agent when dealing with permanent markers. Also acetone can be used as an artistic agent; when rubbed on the back of any laser print or laser photocopy it produces a rough ready effect.

Acetone has been used in the manufacture of cordite. During World War I a new process of producing acetone through bacterial fermentation was developed by Chaim Weizmann, the first president of Israel, in order to help the British war effort.

Acetone can also dissolve many plastics, including those used in consumer-targeted Nalgene bottles. Acetone is also used as a drying agent, due to the readiness with which it mixes with water, and its volatility.

In the laboratory, acetone is used as a polar aprotic solvent in a variety of organic reactions, such as SN2 reactions.

Another industrial application is to use it as a general purpose cleaner in paint and ink manufacturing operations.

Use as an automotive fuel additive

Some automotive enthusiasts add acetone at around 1 part in 500 to their fuel, following claims of improved economy. The practice is controversial as acetone may affect fuel system parts, such as rubber seals. Reports of vehicles covering 50,000 miles (80,000 km) without fault would suggest that the percentage 0.2% acetone to fuel ratio will not adversely affect any parts, pipes, seals etc.

Health effects

Acetone is an irritant and inhalation may lead to hepatotoxic effects (causing liver damage). The fumes should be avoided. Always use goggles when handling acetone; it can cause permanent eye damage ( corneal clouding).

Small amounts of acetone are metabolically produced in the body, mainly from fat. In humans, fasting significantly increases its endogenous production (see ketosis). Acetone can be elevated in diabetes. Contamination of water, food (e.g. milk), or the air (acetone is volatile) can lead to chronic exposure to acetone. A number of acute poisoning cases have been described. Relatively speaking, acetone is not a very toxic compound; it can, however, damage the mucosa of the mouth and can irritate and damage skin. Accidental intake of large amounts of acetone may lead to unconsciousness and death.

The effects of long-term exposure to acetone are known mostly from animal studies. Kidney, liver, and nerve damage, increased birth defects, and lowered reproduction ability of males (only) occurred in animals exposed long-term. It is not known if these same effects would be exhibited in humans.

Interestingly, acetone has been shown to have anticonvulsant effects in animal models of epilepsy, in the absence of toxicity, when administered in millimolar concentrations. It has been hypothesized that the high fat low carbohydrate ketogenic diet used clinically to control drug-resistant epilepsy in children works by elevating acetone in the brain.

  • Acetone (data page)

Safety

Due to incompatibilities, it is recommended to keep acetone away from bromine, chlorine, acid">nitric acid, sulfuric acid and Trichloromethane.

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