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Acetone



Acetone[1]
IUPAC name Propanone
Other names β-ketopropane
Dimethyl ketone,
Identifiers
CAS number 67-64-1
RTECS number AL31500000
SMILES CC(=O)C
InChI InChI=1/C3H6O/c1-3(2)4/h1-2H3
Properties
Molecular formula CH3COCH3
Molar mass 58.09 g/mol
Appearance Colorless liquid
Density 0.79 g/cm³, liquid
Melting point

−94.9 °C (178.2 K)

Boiling point

56.53 °C (329.4 K)

Solubility in water miscible
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
3
1
0
 
R-phrases R11, R36, R66, R67
S-phrases (S2), S9, S16, S26
Flash point -18 °C
Autoignition
temperature
465 °C
Related Compounds
Related solvents Water
Ethanol
Isopropanol
Toluene
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless, mobile, flammable liquid. It is the simplest example of the ketones. Acetone is miscible with 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. In addition to being manufactured as a chemical, acetone is also found naturally in the environment, including in small amounts in the human body.

Additional recommended knowledge

Contents

Production

Acetone is produced primarily in the cumene process. Previously, acetone was produced by the dry distillation of acetates, for example calcium acetate. During World War I a new process of producing acetone through bacterial fermentation was developed by Chaim Weizmann, later the first president of Israel, in order to help the British war effort.

Biosynthesis

See also: ketosis

Small amounts of acetone are produced in the body by the decarboxylation of ketone bodies.

Uses

Cleaning fluid

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.

It is ideal for thinning fiberglass resin, cleaning fiberglass tools and dissolving two-part epoxies and superglue before hardening. A heavy-duty degreaser, it is useful in the preparation of metal prior to painting; it also thins polyester resins, vinyl and adhesives. It easily removes residues from glass and porcelain. In biological research contexts, buffers that contain acetone (such as citrate-buffered formalin) use the acetone to lyse cells for further experimentation.

Additionally, acetone is extremely effective when used as a cleaning agent when dealing with permanent markers.

Solvent

Acetone can also dissolve many plastics, including those used in Nalgene bottles made of polystyrene, polycarbonate and some types of polypropylene.[2]

In the laboratory, acetone is used as a polar aprotic solvent in a variety of organic reactions, such as SN2 reactions. The use of acetone solvent is also critical for the successful Jones oxidation. Technical grade acetone is inexpensive. Because of acetone's medium polarity, it dissolves a wide range of compounds. Thus, it is commonly loaded into squeezebottles and used as a general solvent in rinsing laboratory glassware.

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.

Feedstock

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 has also been used in the manufacture of cordite.

Automotive fuel additive

Some automotive enthusiasts add acetone at around 1 part in 500 to their fuel, following claims of dramatic improvement in fuel economy and engine life.[3] This practice is controversial as there are counterclaims that acetone has no measurable effect or may in fact reduce engine life by adversely affecting fuel system parts.[4][5][6] Debates on this subject and claims of Big Oil cover-up intensified when the practice was addressed on the popular American TV show MythBusters in 2006, and shown to have negative effect in the televised fuel economy test.[7]

Other uses

Acetone is also used as a drying agent, due to the readiness with which it mixes with water, and its volatility.

It can be used as an artistic agent; when rubbed on the back of any laser print or photocopy it produces a roughened effect.

Safety

Acetone peroxide

Main article: acetone peroxide

When oxidized, acetone forms acetone peroxide as a by-product, which is a highly unstable compound. It may be formed accidentally, e.g. when waste hydrogen peroxide is poured into a carboy containing waste acetone solvent.

Toxicology

Acetone is an irritant and inhalation may lead to hepatotoxic effects (causing liver damage). The vapors should be avoided. In no circumstance should it be consumed directly or indirectly. 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. Pregnant women should avoid contact with acetone and acetone fumes in order to avoid the possibility of birth defects, including brain damage.

Interestingly, acetone has been shown to have anticonvulsant effects in animal models of epilepsy, in the absence of toxicity, when administered in millimolar concentrations.[8] 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.[8]

References

  1. ^ Merck Index, 11th Edition, 58.
  2. ^ http://www.nalgenelabware.com/techdata/chemical/
  3. ^ Louis LaPonte (2007-02-13). Acetone in Fuels (A Study of Dimethylketone or Propanone). Smartgas.net. Retrieved on 2007-06-06.
  4. ^ Acetone as a Fuel Additive. Pure Energy Systems Wiki. Retrieved on 2007-06-06.
  5. ^ Tom and Ray Magliozzi (2006-01-21). Click and Clack Talk Cars. Independent Record. Retrieved on 2007-06-06.
  6. ^ Can adding Acetone to fuel increase mpg by 15 to 35%?. Snopes.com Message Board. Retrieved on 2007-06-06.
  7. ^ MythBusters (Season 4, Episode 53)
  8. ^ a b Likhodii SS, Serbanescu I, Cortez MA, Murphy P, Snead OC 3rd, Burnham WM (2003). "Anticonvulsant properties of acetone, a brain ketone elevated by the ketogenic diet". Ann Neurol. 54 (2): 219–226. doi:10.1002/ana.10634.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Acetone". A list of authors is available in Wikipedia.
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