Acetone

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For other uses, see Acetone (disambiguation).

Acetone
Image:Acetone-skeletal.png Image:Acetone-3D-vdW.png
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	miscible
Melting point	−94.9 °C (178.2 K)
Boiling point	56.3 °C (329.4 K)
Viscosity	0.32 cP 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	Image:NFPA 704.svg 3 1 0
R-phrases	R11, R36, R66, R67
S-phrases	S2, S9, S16, S26
Flash point	−20 °C
Autoignition temperature	465 °C
RTECS number	AL31500000
Supplementary data page
Structure & properties	n, ε_r, 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

In chemistry, 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 at −95.4 °C and boiling point at 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.

1 Production
2 Uses
- 2.1 Use as a cleaning solvent
3 Health effects
4 See also
5 External links

[edit] Production

This section is a stub. You can help by expanding it.

[edit] 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 litres 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 fiberglass resins and epoxies. It is a strong solvent for most plastics and synthetic fibres.

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, 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 binds to water, and its volatility. Acetone can also be used on the hair. It can be used as a rinse before shampooing to remove build up, oil and hard water minerals.^{[citation needed]}

[edit] Use as a cleaning solvent

Due to the relatively polar properties of acetone and its high rate of vaporization, it has been used in many university labs as a cleanser for substances in test tubes after working with all manner of organic substances (e.g. cyclohexane, cyclohexene). Acetone is squirted directly from a bottle containing the substance onto the glassware and is (usually) drained into a specially marked organic waste bucket. Acetone is particularly useful because it is inexpensive, is moderately polar allowing it to dissolve a wide range of organic substances, and evaporates quickly.

However, care should be used when cleaning test tubes with acetone as acetone is readily absorbed through vinyl or latex gloves and will come in contact with skin where it is absorbed into the skin. If an excessive amount of acetone is splashed onto gloves, remove gloves immediately and wash hands with water before donning a new pair of gloves.

Due to its high volatility, acetone evaporates quickly. A quick way of drying wet glassware is to rinse the inside surfaces of the freshly washed item with acetone. Since acetone is miscible with water, any water present will be removed as the acetone is poured out. The remaining film of acetone (containing traces of water) will evaporate quickly on the bench or inside an oven.

[edit] 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 (see: Likhodii et. al., Ann Neurol. 2003, 54(2):219–226). 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 (see Ibid, p. 219). It can cause many damages to the body(following paragraph)