Difference between revisions of "Acetone" - New World Encyclopedia

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! {{chembox header}} | Acetone<ref>''Merck Index'', 11th Edition, '''58'''.</ref>
 
 
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| align="center" colspan="2" | [[Image:Acetone-skeletal.png|100px|Acetone]] [[Image:Acetone-3D-balls.png|100px|Ball-and-stick model of acetone]] [[Image:Acetone-3D-vdW.png|100px|Space-filling model of acetone]]
 
| align="center" colspan="2" | [[Image:Acetone-skeletal.png|100px|Acetone]] [[Image:Acetone-3D-balls.png|100px|Ball-and-stick model of acetone]] [[Image:Acetone-3D-vdW.png|100px|Space-filling model of acetone]]
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| 2.91 [[Debye|D]]
 
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| [[Material safety data sheet|MSDS]]
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| {{S2}}, {{S9}}, {{S16}}, {{S26}}
 
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| −20 °C
 
| −20 °C
 
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| [[Flammable limit]]s<br>in air (by volume)
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| [[Flammable limit]]s<br/>in air (by volume)
 
| 2.55% - 12.80%
 
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| [[Acetone (data page)#Thermodynamic properties|Thermodynamic data]]  
 
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| [[Acetone (data page)#Spectral data|Spectral data]]
 
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| [[water (molecule)|Water]]<br/>[[Ethanol]]<br/>[[Isopropanol]]<br/>[[Toluene]]
 
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| {{chembox header}} | <small>Except where noted otherwise, data are given for<br> materials in their [[standard state|standard state (at 25°C, 100 kPa)]]<br/>[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
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The [[chemical compound]] '''acetone''' (also known as '''propanone''', '''dimethyl ketone''', '''2-propanone''', '''propan-2-one''' and '''β-ketopropane''') is the simplest representative of the [[ketone]]s. Acetone is a colorless, mobile, flammable liquid with melting point of −95.4&nbsp;°C and boiling point of 56.53&nbsp;°C. It has a [[relative density]] of 0.819 (at 0&nbsp;°C). It is readily soluble in [[water (molecule)|water]], [[ethanol]], [[diethyl ether|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.
+
'''Acetone''' (also known as '''propanone''', '''dimethyl ketone''', '''2-propanone''', '''propan-2-one''' and '''β-ketopropane''') is the simplest representative of the group of [[chemical compound]]s known as ''[[ketone]]s''. It is a colorless, volatile, flammable liquid. In addition to being manufactured as a chemical, acetone is also found naturally in the environment, including in small amounts in the human body.
 +
{{toc}}
 +
Acetone is a highly effective [[solvent]] for many organic compounds and is the active ingredient in [[nail polish]] remover. It is also used to make various [[plastic]]s, [[fiber]]s, [[drug]]s, and other chemicals.
  
−
Before the invention of the [[cumene process]] acetone was produced by the dry [[distillation]] of [[acetate]]s, for example [[calcium acetate]].
+
== Occurrence in the human body ==
  
−
In addition to being manufactured as a chemical, acetone is also found naturally in the environment, including in small amounts in the human body.  
+
Small amounts of acetone are metabolically produced in the body, mainly from fat. Fasting significantly increases its endogenous production (see [[ketosis]]). Acetone can be elevated in cases of [[diabetes]].
 +
 
 +
== Chemical synthesis ==
 +
 
 +
Most of the worldwide industrial production of acetone (and [[phenol]]) is currently based on a method called the '''cumene process.''' This process converts two relatively cheap starting materials, [[benzene]] and [[propylene]], into acetone and phenol. Another reactant is [[oxygen]] (from the air).<ref>A small amount of a [[radical initiator]] is added to start the reaction.</ref> The reaction is named after [[cumene]] (isopropyl benzene), the intermediate material formed during the process.
 +
 
 +
The overall reaction may be written as follows:
 +
 
 +
[[Image:Cumene-process-overview-2D-skeletal.png|400px|center|The overall cumene process.]]
 +
 
 +
Before the invention of the [[cumene process]], acetone was produced by the dry [[distillation]] of [[acetate]]s, such as [[calcium acetate]].
 +
 
 +
During [[World War I]], a method of producing acetone through [[bacterium|bacterial]] [[Fermentation (biochemistry)|fermentation]] was developed by [[Chaim Weizmann]], (who later became the first president of [[Israel]]), to help the British war effort.
 +
 
 +
== Characteristics ==
 +
 
 +
Acetone has a melting point of −95.4&nbsp;°C and boiling point of 56.53&nbsp;°C. It has a [[relative density]] of 0.819 (at 0&nbsp;°C). It acts as a [[solvent]] and is readily miscible with other solvents, including [[water]], [[ethanol]], and [[ether|diethyl ether]].
  
 
== Uses ==
 
== 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 [[polycarbonate]]s, [[polyurethane]]s and [[epoxy resin]]s. 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.
+
* An important industrial use for acetone involves its reaction with [[phenol]] to produce [[bisphenol A]], which is a valuable component of many polymers, such as [[polycarbonate]]s, [[polyurethane]]s, and [[epoxy resin]]s.
  
−
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.
+
* Another industrial application involves its use as a general purpose cleaner in paint and ink manufacturing operations.
  
−
Additionally, acetone is extremely effective when used as a cleaning agent when dealing with permanent markers.
+
* Acetone is also used extensively for the safe transport and storage 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.
−
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 [[bacterium|bacterial]] [[Fermentation (biochemistry)|fermentation]] was developed by [[Chaim Weizmann]], the first president of [[Israel]], in order to help the British war effort.
+
* It is often the primary (or only) component in [[nail polish]] remover.<ref>[[Acetonitrile]], another organic solvent, is sometimes used as well.</ref> It is also used as a [[superglue]] remover. It can be used for thinning and cleaning [[fiberglass]] [[resin]]s and [[epoxy|epoxies]], and it is highly effective in removing stains by permanent markers.
  
−
Acetone can also dissolve many plastics, including those used in consumer-targeted [[Nalgene]] bottles. Acetone is also used as a [[desiccant|drying agent]], due to the readiness with which it mixes with water, and its volatility.
+
* It can be used as an agent in art work. When rubbed on the back of any laser print or laser photocopy, it produces a rough ready effect.
  
−
In the laboratory, acetone is used as a [[chemical polarity|polar]] [[aprotic solvent]] in a variety of [[organic reaction]]s, such as [[SN2 reaction|S<sub>N</sub>2 reactions]].
+
* It has been used in the manufacture of [[cordite]].
  
−
Another industrial application is to use it as a general purpose cleaner in paint and ink manufacturing operations.
+
* It is a strong solvent for most [[plastic]]s (including those used in consumer-targeted water bottles) and synthetic fibers.
  
−
=== Use as an automotive fuel additive ===
+
* It is used as a [[desiccant|drying agent]], as it is readily miscible with water and is volatile.
−
{{Unreferencedsect|date=April 2007}}
 
−
{{weasel|section}}
 
  
−
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&nbsp;km) without fault{{Fact|date=February 2007}} would suggest that the percentage 0.2% acetone to fuel ratio will not adversely affect any parts, pipes, seals etc.{{Fact|date=February 2007}}
+
* In the laboratory, acetone is used as a [[chemical polarity|polar]] [[aprotic solvent]] (solvent that does not release hydrogen ions) in a variety of [[organic reaction]]s.
  
 
==Health effects==
 
==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]]).
+
At relatively low concentrations, acetone is not very toxic. It can, however, irritate and damage [[skin]] and the [[mucosa]]l lining of the [[mouth]]. Its fumes should be avoided, as inhalation may lead to liver damage. In addition, one should always wear goggles when handling the substance, as it can cause permanent eye damage ([[corneal clouding]]).
 +
 
 +
Contamination of water, food (such as milk), or air (by acetone vapors) can lead to chronic exposure to acetone. A number of acute poisoning cases have been described. Accidental intake of large amounts of acetone may lead to unconsciousness and death.
 +
 
 +
Animal studies have shown that long-term exposure to acetone can damage the [[kidney]]s, [[liver]], and [[nerve]]s, increase [[birth defect]]s, and lower the reproductive capacity of males (only). It is not known if the same effects would occur in humans. Pregnant women should avoid contact with acetone and its fumes, to avoid the possibility of birth defects, including brain damage.
  
−
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.
+
Interestingly, acetone has been shown to have [[anticonvulsant]] effects in animal models of [[epilepsy]], in the absence of toxicity, when administered at low (millimolar) concentrations.<ref name="Likhodii">Likhodii et al., [https://www.ncbi.nlm.nih.gov/pubmed/12891674 Anticonvulsant properties of acetone, a brain ketone elevated by the ketogenic diet] ''Ann Neurol.'', 54(2) (2003): 219–226. Retrieved April 3, 2018.</ref> 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.<ref name="Likhodii"/>
  
−
The effects of long-term exposure to acetone are known mostly from animal studies. [[Kidney]], [[liver]], and [[nerve]] damage, increased [[birth defect]]s, 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 increased brain damage.
+
== Chemical safety measures ==
  
−
Interestingly, acetone has been shown to have [[anticonvulsant]] effects in animal models of [[epilepsy]], in the absence of toxicity, when administered in millimolar concentrations.<ref name="Likhodii">Likhodii et al., ''Ann Neurol.'' 2003, 54(2):219–226)</ref> 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.<ref name="Likhodii"/>
+
Due to chemical incompatibilities, it is recommended that acetone should be kept away from [[bromine]], [[chlorine]], [[nitric acid]], [[sulfuric acid]] and [[trichloromethane]].
  
−
*[[Acetone (data page)]]
+
== See also ==
  
−
==Safety==
+
* [[Ketone]]
−
Due to incompatibilities, it is recommended to keep acetone away from [[bromine]], [[chlorine]], [[nitric acid]], [[sulfuric acid]] and  [[Trichloromethane]].
+
* [[Solvent]]
 +
 
 +
== Notes ==
 +
<references/>
  
 
==References==
 
==References==
−
<references/>
+
 
 +
* McMurry, John. ''Organic Chemistry'', 6th ed. Belmont, CA: Brooks/Cole, 2004. ISBN 0534420052.
 +
* Morrison, Robert T., and Robert N. Boyd. ''Organic Chemistry'', 6th ed. Englewood Cliffs, NJ: Prentice Hall, 1992. ISBN 0136436692.
 +
* Solomons, T. W. Graham, and Craig B. Fryhle. ''Organic Chemistry'', 8th ed. Hoboken, NJ: John Wiley, 2004. ISBN 0471417998.
  
 
==External links==
 
==External links==
−
*[http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc00/icsc0087.htm International Chemical Safety Card 0087]
+
All links retrieved June 14, 2023.
−
* [http://www.npi.gov.au/database/substance-info/profiles/3.html National Pollutant Inventory – Acetone]
+
* [http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/aldket1.htm#aknom Aldehydes and Ketones] ''Virtual Textbook of Organic Chemistry''.
−
*[http://www.cdc.gov/niosh/npg/npgd0004.html NIOSH Pocket Guide to Chemical Hazards]
+
* [http://www.cdc.gov/niosh/npg/npgd0004.html Acetone.] ''NIOSH Pocket Guide to Chemical Hazards''.
−
{{ChemicalSources}}
+
* [http://webbook.nist.gov/cgi/cbook.cgi?Name=acetone&Units=SI Acetone] ''NIST Chemistry WebBook''.
  
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[[Category:Household chemicals]]
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[[Category:Physical sciences]]
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[[Category:Cosmetic chemicals]]
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[[Category:Chemistry]]
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[[Category:Biotechnology products]]
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[[Category:Organic chemistry]]
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[[Category:Ketones]]
 
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[[Category:Solvents]]
 
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[[Category:Fuel additives]]
 
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[[Category:DEA List II chemicals]]
 
  
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Latest revision as of 07:34, 14 June 2023


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 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

NFPA 704.svg

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)

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

Acetone is a highly effective solvent for many organic compounds and is the active ingredient in nail polish remover. It is also used to make various plastics, fibers, drugs, and other chemicals.

Occurrence in the human body

Small amounts of acetone are metabolically produced in the body, mainly from fat. Fasting significantly increases its endogenous production (see ketosis). Acetone can be elevated in cases of diabetes.

Chemical synthesis

Most of the worldwide industrial production of acetone (and phenol) is currently based on a method called the cumene process. This process converts two relatively cheap starting materials, benzene and propylene, into acetone and phenol. Another reactant is oxygen (from the air).[1] The reaction is named after cumene (isopropyl benzene), the intermediate material formed during the process.

The overall reaction may be written as follows:

The overall cumene process.

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

During World War I, a method of producing acetone through bacterial fermentation was developed by Chaim Weizmann, (who later became the first president of Israel), to help the British war effort.

Characteristics

Acetone has a 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 acts as a solvent and is readily miscible with other solvents, including water, ethanol, and diethyl ether.

Uses

  • An important industrial use for acetone involves its reaction with phenol to produce bisphenol A, which is a valuable component of many polymers, such as polycarbonates, polyurethanes, and epoxy resins.
  • Another industrial application involves its use as a general purpose cleaner in paint and ink manufacturing operations.
  • Acetone is also used extensively for the safe transport and storage 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.
  • It is often the primary (or only) component in nail polish remover.[2] It is also used as a superglue remover. It can be used for thinning and cleaning fiberglass resins and epoxies, and it is highly effective in removing stains by permanent markers.
  • It can be used as an agent in art work. When rubbed on the back of any laser print or laser photocopy, it produces a rough ready effect.
  • It has been used in the manufacture of cordite.
  • It is a strong solvent for most plastics (including those used in consumer-targeted water bottles) and synthetic fibers.
  • It is used as a drying agent, as it is readily miscible with water and is volatile.
  • In the laboratory, acetone is used as a polar aprotic solvent (solvent that does not release hydrogen ions) in a variety of organic reactions.

Health effects

At relatively low concentrations, acetone is not very toxic. It can, however, irritate and damage skin and the mucosal lining of the mouth. Its fumes should be avoided, as inhalation may lead to liver damage. In addition, one should always wear goggles when handling the substance, as it can cause permanent eye damage (corneal clouding).

Contamination of water, food (such as milk), or air (by acetone vapors) can lead to chronic exposure to acetone. A number of acute poisoning cases have been described. Accidental intake of large amounts of acetone may lead to unconsciousness and death.

Animal studies have shown that long-term exposure to acetone can damage the kidneys, liver, and nerves, increase birth defects, and lower the reproductive capacity of males (only). It is not known if the same effects would occur in humans. Pregnant women should avoid contact with acetone and its fumes, 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 at low (millimolar) concentrations.[3] 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.[3]

Chemical safety measures

Due to chemical incompatibilities, it is recommended that acetone should be kept away from bromine, chlorine, nitric acid, sulfuric acid and trichloromethane.

See also

Notes

  1. ↑ A small amount of a radical initiator is added to start the reaction.
  2. ↑ Acetonitrile, another organic solvent, is sometimes used as well.
  3. ↑ 3.0 3.1 Likhodii et al., Anticonvulsant properties of acetone, a brain ketone elevated by the ketogenic diet Ann Neurol., 54(2) (2003): 219–226. Retrieved April 3, 2018.

References
ISBN links support NWE through referral fees

  • McMurry, John. Organic Chemistry, 6th ed. Belmont, CA: Brooks/Cole, 2004. ISBN 0534420052.
  • Morrison, Robert T., and Robert N. Boyd. Organic Chemistry, 6th ed. Englewood Cliffs, NJ: Prentice Hall, 1992. ISBN 0136436692.
  • Solomons, T. W. Graham, and Craig B. Fryhle. Organic Chemistry, 8th ed. Hoboken, NJ: John Wiley, 2004. ISBN 0471417998.

External links

All links retrieved June 14, 2023.

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