Revision 7802064 of "Acetone" on enwiki

{| width="300" border="1" cellpadding="2" cellspacing="0" style="float:right; margin-left: 0.5em"
|+ <font size="+1">'''Properties'''</font>
|- colspan=2 align=center
|-
! colspan="2" bgcolor="#FFDEAD" |
'''General'''
|-
| Name || '''Acetone'''
|-
| colspan="2" align=center |
[[Image:2-propanone.png|Acetone (2-propanone)]]
|-
| [[Chemical formula]]
| [[carbon|C]][[hydrogen|H]]<sub>3</sub>[[carbonyl|CO]]CH<sub>3</sub>
|-
| [[Atomic weight|Formula weight]] || 58.08 [[atomic mass unit|amu]]
|-
| Synonyms
| 2-Propanone, &beta;-Ketopropane, Dimethyl ketone
|-
| [[CAS number]] || 67-64-1
|-
| [[UN number]] || 1090
|-
! colspan="2" bgcolor="#FFDEAD" |
'''Phase behavior'''
|-
| [[Melting point]]
| 178.2 [[kelvin|K]] (-94.9[[celsius|°C]])
|-
| [[Boiling point]] || 329.4 K (56.3°C)
|-
| [[Triple point]] || 178.5 K (-94.5°C)
<br>? [[bar (unit)|bar]]
|-
| [[Critical point]] || 508 K (235°C)
<br>48 [[bar (unit)|bar]]
|-
| [[Heat of fusion|&Delta;<sub>fus</sub>H]]
| 5.7 kJ/mol
|-
| [[Entropy of fusion|&Delta;<sub>fus</sub>S]]
| 32.3 J/mol·K
|-
| [[Heat of vaporization|&Delta;<sub>vap</sub>H]]
| 31.3 kJ/mol
|-
| [[Solubility]] || Miscible with water
|-
! colspan="2" bgcolor="#FFDEAD" |
'''Liquid properties'''
|-
| [[Standard enthalpy change of formation|&Delta;<sub>f</sub>H<sup>0</sup><sub>liquid</sub>]]
| -249.4 [[joule|kJ]]/[[mole (unit)|mol]]
|-
| [[Standard molar entropy|S<sup>0</sup><sub>liquid</sub>]]
| 200.4 J/mol·K
|-
| [[Heat capacity|C<sub>p</sub>]] || 125.5 J/mol·K
|-
| [[Density]]
| 0.79 &times;10<sup>3</sup> [[kilogram|kg]]/[[metre|m]]<sup>3</sup>
|-
! colspan="2" bgcolor="#FFDEAD" |
'''Gas properties'''
|-
| [[Standard enthalpy change of formation|&Delta;<sub>f</sub>H<sup>0</sup><sub>gas</sub>]]
| -218.5 [[joule|kJ]]/[[mole (unit)|mol]]
|-
| [[Standard molar entropy|S<sup>0</sup><sub>gas</sub>]]
| J/mol·K
|-
| [[Heat capacity|C<sub>p</sub>]] || 75 J/mol·K
|-
! colspan="2" bgcolor="#FFDEAD" |
'''Safety'''
|-
| Acute effects
| CNS depression. Liver & kidney damage. Respiratory failure.
|-
| Chronic effects || &nbsp;
|-
| [[Flash point]] || < -20°C
|-
| [[Autoignition temperature]] || 540°C
|-
| [[Explosive limit]]s || 2.6-13%
|-
! colspan="2" bgcolor="#FFDEAD" |
'''More info'''
|-
| Properties
| [http://webbook.nist.gov/cgi/cbook.cgi?ID=C67641&Units=SI NIST WebBook]
|-
| [[MSDS]]
| [http://ull.chemistry.uakron.edu/erd/chemicals1/6/5961.html Hazardous Chemical Database]
|-
! colspan="2" bgcolor="#FFDEAD" |
<font size="-1">
[[SI]] units were used where possible. Unless otherwise stated, [[Standard temperature and pressure|standard]] conditions were used.

[[Organic table information|Disclaimer and references]]
</font>
|}

In [[chemistry]], '''acetone''' (also known as '''dimethyl ketone''', '''2-propanone''', '''propan-2-one''' and '''beta-ketopropane''') is the simplest representative of the [[ketone]]s. 

Acetone is a colourless mobile flammable liquid with a pleasant, somewhat fruity odor, melting at -95.4&nbsp;°[[Celsius|C]] and boiling at 56.53&nbsp;°C. It has a [[specific gravity]] of 0.819 (at 0&nbsp;°C). It is readily soluble in [[water (molecule)|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.

As a member of the [[ketone bodies]] it is present in very small quantity in normal [[urine]] and in the [[blood]]. Larger quantities can be found after starvation and in [[diabetes|diabetic]] patients with severe [[insulin]] deficiency (that is untreated or inadequately treated persons); a fruity smell of the breath caused by acetone is one symptom of [[diabetic ketoacidosis]]. See [[ketone bodies]] for more information.

Acetone occurs naturally in plants, trees, volcanic gases, forest fires, and as a product of the breakdown of body fat. It is present in vehicle exhaust, tobacco smoke, and landfill sites. Industrial processes contribute more acetone to the environment than natural processes.
It is found among the products formed in destructive distillation of [[wood]], [[sugar]], [[cellulose]], etc., and for this reason it is always present in crude wood [[alcohol|spirit]], from which the greater portion of it may be recovered by [[fractional distillation]].  

It forms a [[hydrazone]] with [[phenyl]] [[hydrazine]] and an [[oxime]] with [[hydroxylamine]]. Reduction by [[sodium amalgam]] converts it into [[isopropyl alcohol]]; oxidation by [[chromic acid]] gives [[carbon dioxide]] and acetic acid. It reacts with [[ammonia]] to form di- and triacetoneamines. It also unites directly with [[hydrogen cyanide|hydrocyanic acid]] to form the [[nitrile]] of &alpha;-oxyiso[[butyric acid]]. 

By the action of various reagents, such as [[calcium oxide|lime]], caustic [[potash]], [[hydrochloric acid]], etc., acetone is converted into [[condensation]] products, [[mesityl]] oxide C<sub>6</sub>H<sub>10</sub>O, phorone C<sub>9</sub>H<sub>14</sub>O, etc., being formed. On distillation with sulphuric acid (H<sub>2</sub>SO<sub>4</sub>), it is converted into [[mesitylene]] C<sub>9</sub>H<sub>12</sub> (symmetrical trimethyl benzene). Acetone has also been used in the artificial production of [[indigo dye|indigo]]. In the presence of [[iodine]] and an [[alkali]] it gives [[iodoform]].

==Health effects==

After inhaling acetone fumes or ingesting acetone, it enters the [[blood]], which then carries it to all the organs in the body. If it is a small amount, the [[liver]] breaks it down to chemicals that are not harmful and uses these chemicals to make energy for normal body functions. Breathing moderate- to-high levels of acetone for short periods of time, however, can cause [[nose]], [[throat]], [[lung]], and [[eye]] [[irritation]]; [[headache]]s; light-headedness; confusion; increased pulse rate; effects on blood; [[nausea]]; vomiting; [[unconsciousness]] and possibly [[coma]]; and shortening of the [[menstruation|menstrual]] cycle in women.

Swallowing very high levels of acetone can result in unconsciousness and damage to the [[skin]] in the [[mouth]]. Skin contact can result in irritation and damage to the skin.

The smell and respiratory irritation or burning eyes that occur from moderate exposure levels are excellent warning signs that can help avoid breathing damaging levels of acetone.

Health effects from long-term exposures 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.

[[Category:Ketones]]
[[Category:Household chemicals]]

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