Difference between revisions of "Acetone"

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[[File:Sample_of_Acetone.jpg|thumb|200px|Sample of acetone]][[File:800px-Acetone-3D-balls.png|thumb|Acetone chemical structure ]]
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{{Chembox
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| Name = Acetone
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| Reference =
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| IUPACName = Propanone
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| PIN = Propan-2-one
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| SystematicName =
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| OtherNames = 2-Propanone<br>Dimethyl carbonyl<br>Dimethyl formaldehyde<br>Dimethylketal<br>Dimethyl ketone<br>Ketone propane<br>Pyroacetic spirit<br>Spirit of Saturn<br>β-Ketopropane
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| ImageFile1 = Sample_of_Acetone_by_Zyklon-A.jpg
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| ImageSize1 = 200
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| ImageName1 =
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| ImageCaption1 = Sample of acetone
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| ImageFile2 = 800px-Acetone-3D-balls.png
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| ImageSize2 =
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| ImageCaption2 = Acetone chemical structure
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| Section1 = {{Chembox Identifiers
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| 3DMet =
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| Abbreviations =
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| SMILES =
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  }}
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| Section2 = {{Chembox Properties
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| AtmosphericOHRateConstant =
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| Appearance = Colorless volatile liquid
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| BoilingPt =
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| BoilingPtC = 56.05
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| BoilingPt_ref =
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| BoilingPt_notes =
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| Density = 0.7845 g/cm<sup>3</sup> (25 °C)
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| Formula = C<sub>3</sub>H<sub>6</sub>O<br>(CH<sub>3</sub>)<sub>2</sub>CO
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| HenryConstant =
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| LogP = −0.042
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| MolarMass = 58.08 g/mol
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| MeltingPt =
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| MeltingPtC = −94.7
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| MeltingPt_ref =
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| MeltingPt_notes =
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| Odor = Pungent, irritating, floral
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| pKa = 19.2
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| pKb = −5.2 (for conjugate base)
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| Solubility = Miscible
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| SolubleOther = Miscible with almost all organic solvents<br>Immiscible with perfluorocarbons
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| Solvent =
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| VaporPressure = 9.39 kPa (0 °C)<br>30.6 kPa (25 °C)<br>374 kPa (100 °C)<br>2.8 MPa (200 °C)
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  }}
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| Section3 = {{Chembox Structure
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| Coordination = Trigonal planar at C2
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| CrystalStruct = Dihedral at C2
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| MolShape =
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  }}
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| Section4 = {{Chembox Thermochemistry
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| DeltaGf =
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| DeltaHc = −1,772 kJ/mol
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| DeltaHf = −250.03 - −248.77 kJ/mol
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| Entropy = 200.4 J·mol<sup>-1</sup>·K<sup>-1</sup>
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| HeatCapacity = 125.45 J·mol<sup>-1</sup>·K<sup>-1</sup>
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  }}
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| Section5 = {{Chembox Explosive
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| ShockSens =
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| FrictionSens =
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| DetonationV =
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| REFactor =
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| Section6 = {{Chembox Hazards
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| AutoignitionPt = 465 °C (869 °F; 738 K)
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| ExploLimits = 2.6–12.8%
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| ExternalMSDS = [https://www.docdroid.net/XJPMSYc/acetone-sa.pdf.html Sigma-Aldrich]
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| FlashPt = −20 °C (−4 °F; 253 K)
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| LD50 = 5,800 mg/kg (rat, oral)<br>3,000 mg/kg (mouse, oral)<br>5,340 mg/kg (rabbit, oral)
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| LC50 = 20,702 ppm (rat, 8 hr)
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| MainHazards = Flammable<br>Irritant
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| NFPA-F =
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| NFPA-H =
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| NFPA-R =
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| NFPA-S =
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| Section7 = {{Chembox Related
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| OtherAnions =
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| OtherCations =
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| OtherFunction =
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| OtherFunction_label =
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| OtherCompounds = [[Methyl ethyl ketone]]
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  }}
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}}
 
'''Acetone''', also known as '''propanone''' or '''dimethyl ketone''' (chemical formula '''(CH<sub>3</sub>)<sub>2</sub>CO''') is a popular solvent and useful chemical for lots of organic chemistry, being the simplest [[ketone]].
 
'''Acetone''', also known as '''propanone''' or '''dimethyl ketone''' (chemical formula '''(CH<sub>3</sub>)<sub>2</sub>CO''') is a popular solvent and useful chemical for lots of organic chemistry, being the simplest [[ketone]].
  
 
==Properties==
 
==Properties==
 
===Chemical===
 
===Chemical===
−
Acetone is highly flammable.
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Acetone is highly flammable and will burn in air releasing carbon dioxide and water vapors.
  
−
It will react with [[Halogen|halogens]] to form halogenated organic compounds, i.e. [[iodoacetone]]. Acetone reacts very exothermically with household bleach and other[[Hypochlorite| hypochlorites]] to form [[chloroform]].
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It will react with [[halogen]]s to form halogenated organic compounds, i.e. [[chloroacetone]], [[bromoacetone]], [[iodoacetone]]. Acetone reacts very exothermically with halogens dissolved in basic solutions to give a haloform of the said halogen, process known as [[haloform reaction]]. One example is with household bleach and other [[hypochlorite]]s to form [[chloroform]].
  
 
Acetone will form the unpredictable and dangerous explosive [[acetone peroxide]] when oxidized with [[hydrogen peroxide]] under certain conditions, such as with an acid catalyst.
 
Acetone will form the unpredictable and dangerous explosive [[acetone peroxide]] when oxidized with [[hydrogen peroxide]] under certain conditions, such as with an acid catalyst.
 +
 +
Acetone will react with cold concentrated [[nitric acid]] to yield [[acetic acid]] and [[formic acid]]. The reaction generates lots of heat, which causes the products to evaporate from the reaction flask.
  
 
===Physical===
 
===Physical===
−
Acetone is a clear liquid with very low viscosity that is miscible in water, that boils at 56°C and freezes between −95 to −93 °C. It has a sharp, somewhat sweet, and floral aroma similar to other ketones. It is also miscible in [[benzene]], [[chloroform]], [[ethanol]], [[diethyl ether]] and [[methanol]].
+
Acetone is a clear liquid with very low viscosity that is miscible in water, that boils at 56 °C and freezes between −95 to −93 °C. It has a sharp, somewhat sweet, and floral aroma similar to other ketones. It is also miscible in most organic solvents, like glacial [[acetic acid]], [[benzene]], [[chloroform]], [[diethyl ether]], [[ethanol]], [[heptane]], [[hexane]] and [[methanol]]. Acetone however, is immiscible with [[glycerol]].
  
 
==Availability==
 
==Availability==
−
Acetone can be found at hardware stores as paint thinners of nail polish remover, either pure or mixed with other organic substances (usually esters).
+
Acetone can be found at hardware stores as paint thinners or nail polish remover, either pure or mixed with other organic substances (usually esters). Distillation may be required to purify the acetone.
 +
 
 +
Most technical-grade acetone tends to be fairly pure and has very little if any water. If you want it more pure, you can distill it again.
  
 
==Preparation==
 
==Preparation==
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Because this reaction occurs at around 400-500°C, temperature above the boiling and autoignition temperature of acetone, it must be performed in an oxygen free chamber ([[carbon dioxide]] rich or only atmosphere is sufficient) and because the acetone results as vapors, it must be condensed.
 
Because this reaction occurs at around 400-500°C, temperature above the boiling and autoignition temperature of acetone, it must be performed in an oxygen free chamber ([[carbon dioxide]] rich or only atmosphere is sufficient) and because the acetone results as vapors, it must be condensed.
  
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Acetone can be recovered from an aqueous solution by [[salting out]] with anhydrous [[sodium acetate]], which is conveniently produced from [[Acetic acid|vinegar]] and [[Sodium hydrogen carbonate|baking soda]].
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Acetone can be recovered from an aqueous solution by [[salting out]] with anhydrous [[sodium acetate]], which is conveniently produced from [[Acetic acid|vinegar]] and [[Sodium bicarbonate|baking soda]].
  
 
==Projects==
 
==Projects==
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*[[Chloroform]] synthesis
 
*[[Chloroform]] synthesis
 
*Organic extractions
 
*Organic extractions
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*Make [[ethenone]]
  
 
==Handling==
 
==Handling==
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The main danger of acetone comes from its flammability. Its vapors have a flash point much below room temperature, so air/acetone mixtures can explode or burst into flames easily, even from static shocks.
 
The main danger of acetone comes from its flammability. Its vapors have a flash point much below room temperature, so air/acetone mixtures can explode or burst into flames easily, even from static shocks.
  
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At 486°C acetone will self-ignite.
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At temperatures above 486 °C, acetone will self-ignite.
  
 
===Storage===
 
===Storage===
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===Disposal===
 
===Disposal===
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Acetone can be safely burned. Traces of acetone can be released in open air.
+
Acetone can be safely burned. Traces of acetone can be released in open air. Strongly diluted acetone solutions can be poured down the drain, but do not release large amounts.
  
 
NEVER discard acetone along with [[hydrogen peroxide]] as it will form [[acetone peroxide]], which is a sensible contact explosive.
 
NEVER discard acetone along with [[hydrogen peroxide]] as it will form [[acetone peroxide]], which is a sensible contact explosive.
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<references />
 
<references />
 
===Relevant Sciencemadness threads===
 
===Relevant Sciencemadness threads===
 +
*[http://www.sciencemadness.org/talk/viewthread.php?tid=81799 Technical grade acetone purification]
 
*[http://www.sciencemadness.org/talk/viewthread.php?tid=16216 Acetone from calcium acetate]
 
*[http://www.sciencemadness.org/talk/viewthread.php?tid=16216 Acetone from calcium acetate]
 
*[http://www.sciencemadness.org/talk/viewthread.php?tid=12753 Calcium acetate, other carboxylic salts]
 
*[http://www.sciencemadness.org/talk/viewthread.php?tid=12753 Calcium acetate, other carboxylic salts]
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[[Category:Chemical compounds]]
 
[[Category:Chemical compounds]]
 
[[Category:Organic compounds]]
 
[[Category:Organic compounds]]
−
[[Category:Solvents]]
 
−
[[Category:Readily available chemicals]]
 
 
[[Category:Ketones]]
 
[[Category:Ketones]]
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[[Category:Solvents]]
 
[[Category:Polar solvents]]
 
[[Category:Polar solvents]]
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[[Category:Aprotic solvents]]
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[[Category:Readily available chemicals]]
 
[[Category:DEA List II chemicals]]
 
[[Category:DEA List II chemicals]]
 
[[Category:Volatile chemicals]]
 
[[Category:Volatile chemicals]]
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[[Category:Liquids]]
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[[Category:Essential reagents]]

Latest revision as of 17:44, 1 January 2022

Acetone
Sample of Acetone by Zyklon-A.jpg
Sample of acetone
800px-Acetone-3D-balls.png
Acetone chemical structure
Names
IUPAC name
Propanone
Preferred IUPAC name
Propan-2-one
Other names
2-Propanone
Dimethyl carbonyl
Dimethyl formaldehyde
Dimethylketal
Dimethyl ketone
Ketone propane
Pyroacetic spirit
Spirit of Saturn
β-Ketopropane
Properties
C3H6O
(CH3)2CO
Molar mass 58.08 g/mol
Appearance Colorless volatile liquid
Odor Pungent, irritating, floral
Density 0.7845 g/cm3 (25 °C)
Melting point −94.7 °C (−138.5 °F; 178.5 K)
Boiling point 56.05 °C (132.89 °F; 329.20 K)
Miscible
Solubility Miscible with almost all organic solvents
Immiscible with perfluorocarbons
Vapor pressure 9.39 kPa (0 °C)
30.6 kPa (25 °C)
374 kPa (100 °C)
2.8 MPa (200 °C)
Acidity (pKa) 19.2
Thermochemistry
200.4 J·mol-1·K-1
−250.03 - −248.77 kJ/mol
Hazards
Safety data sheet Sigma-Aldrich
Flash point −20 °C (−4 °F; 253 K)
Lethal dose or concentration (LD, LC):
5,800 mg/kg (rat, oral)
3,000 mg/kg (mouse, oral)
5,340 mg/kg (rabbit, oral)
20,702 ppm (rat, 8 hr)
Related compounds
Related compounds
 Methyl ethyl ketone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Acetone, also known as propanone or dimethyl ketone (chemical formula (CH3)2CO) is a popular solvent and useful chemical for lots of organic chemistry, being the simplest ketone.

Properties

Chemical

Acetone is highly flammable and will burn in air releasing carbon dioxide and water vapors.

It will react with halogens to form halogenated organic compounds, i.e. chloroacetone, bromoacetone, iodoacetone. Acetone reacts very exothermically with halogens dissolved in basic solutions to give a haloform of the said halogen, process known as haloform reaction. One example is with household bleach and other hypochlorites to form chloroform.

Acetone will form the unpredictable and dangerous explosive acetone peroxide when oxidized with hydrogen peroxide under certain conditions, such as with an acid catalyst.

Acetone will react with cold concentrated nitric acid to yield acetic acid and formic acid. The reaction generates lots of heat, which causes the products to evaporate from the reaction flask.

Physical

Acetone is a clear liquid with very low viscosity that is miscible in water, that boils at 56 °C and freezes between −95 to −93 °C. It has a sharp, somewhat sweet, and floral aroma similar to other ketones. It is also miscible in most organic solvents, like glacial acetic acid, benzene, chloroform, diethyl ether, ethanol, heptane, hexane and methanol. Acetone however, is immiscible with glycerol.

Availability

Acetone can be found at hardware stores as paint thinners or nail polish remover, either pure or mixed with other organic substances (usually esters). Distillation may be required to purify the acetone.

Most technical-grade acetone tends to be fairly pure and has very little if any water. If you want it more pure, you can distill it again.

Preparation

Industrially, acetone is made via the cumene process, where benzene is alkylated with propylene to produce cumene, which is oxidized by air to produce phenol and acetone.

Before that method, acetone was produced via dry distillation of an acetate salt, usually calcium acetate or sodium acetate.

2 Na(CH3COO) → Na2CO3 + (CH3)2CO
Ca(CH3COO)2 → CaCO3 + (CH3)2CO

Because this reaction occurs at around 400-500°C, temperature above the boiling and autoignition temperature of acetone, it must be performed in an oxygen free chamber (carbon dioxide rich or only atmosphere is sufficient) and because the acetone results as vapors, it must be condensed.

Acetone can be recovered from an aqueous solution by salting out with anhydrous sodium acetate, which is conveniently produced from vinegar and baking soda.

Projects

Handling

Safety

Skin contact with acetone is not recommended, as prolonged exposure can cause defatting of the skin. Acetone's low boiling point of requires work in a ventilated area. While acetone is volatile and while its fumes are not particularly toxic, they can be irritating in large amounts. Acetone however is among the least toxic solvents, and as many studies have shown there are no long term risks in case of repeated exposure.

The main danger of acetone comes from its flammability. Its vapors have a flash point much below room temperature, so air/acetone mixtures can explode or burst into flames easily, even from static shocks.

At temperatures above 486 °C, acetone will self-ignite.

Storage

Acetone is best stored in closed bottles, away from any source of heat.

Disposal

Acetone can be safely burned. Traces of acetone can be released in open air. Strongly diluted acetone solutions can be poured down the drain, but do not release large amounts.

NEVER discard acetone along with hydrogen peroxide as it will form acetone peroxide, which is a sensible contact explosive.

See also

References

Relevant Sciencemadness threads

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