Acetyl chloride
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2008-06-02T11:26:58Z
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{{Chembox new
| Name = Acetyl chloride
| ImageFileL1 = Acetyl-chloride.png
| ImageSizeL1 = 100px
| ImageNameL1 = Skeletal formula of acetyl chloride
| ImageFileR1 = Acetyl-chloride-3D-balls.png
| ImageSizeR1 = 100px
| ImageNameR1 = Ball-and-stick model of acetyl chloride
| ImageFile2 = Acetyl-chloride-3D-vdW.png
| ImageSize2 = 120px
| ImageName2 = Space-filling model of acetyl chloride
| IUPACName = Ethanoyl chloride
| OtherNames = Acetyl chloride
| Section1 = {{Chembox Identifiers
| SMILES = CC(=O)Cl
| CASNo = 75-36-5
| RTECS = AO6390000
}}
| Section2 = {{Chembox Properties
| Formula = CH<sub>3</sub>COCl
| MolarMass = 78.5 g/mol
| Appearance = colorless liquid
| Density = 1.11 g/ml, liquid
| Solubility = Reacts
| MeltingPt = −112 °C
| BoilingPt = 51 °C
| Viscosity =
}}
| Section3 = {{Chembox Structure
| Dipole = 2.45 [[Debye|D]]
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS =
| EUClass = Flammable ('''F''')<br />Corrosive ('''C''')
| RPhrases = {{R11}}, {{R14}}, {{R34}}
| SPhrases = {{S1/2}}, {{S9}}, {{S16}}, {{S26}}, {{S45}}
| FlashPt = 5 °C
| Autoignition = 390 °C
| ExploLimits = 7.3–19%
}}
| Section8 = {{Chembox Related
| Function = [[acyl chloride]]s
| OtherFunctn = [[Propionyl chloride]]<br />[[Butyryl chloride]]
| OtherCpds = [[Acetic acid]]<br />[[Acetic anhydride]]
}}
}}
'''Acetyl chloride''', also known as '''ethanoyl chloride''', is an [[acid chloride]] (also known as an [[acyl chloride]]) derived from [[acetic acid]] ([[ethanoic acid]]). It has the formula CH<sub>3</sub>COCl and it belongs to the class of [[organic compound]]s called [[acyl halide]]s. At room temperature and pressure, it is a clear colorless [[liquid]]. Acetyl chloride does not exist in nature, because contact with [[water (molecule)|water]] would hydrolyze it into acetic acid and [[hydrogen chloride]]. In fact, if handled in open air it gives of white [[smoke]] owing to the hydrolysis from the moisture in the air. The smoke is actually [[gas]]eous hydrogen chloride which forms small droplets in the air with water vapour.
==Synthesis==
Acetyl chloride is [[Chemical synthesis|synthesized]] by the reaction of [[acetic acid]] (CH<sub>3</sub>COO-H) with [[thionyl chloride]] (O=SCl<sub>2</sub>) under liberation of [[sulfur dioxide]] (SO<sub>2</sub>).
:CH<sub>3</sub>COO-H + O=SCl<sub>2</sub> → CH<sub>3</sub>COCl + SO<sub>2</sub> + [[Hydrogen chloride|H-Cl]]
==Uses==
It is a reagent for '''[[acetylation]]''' in the [[synthesis]] or derivatization of [[chemical compound]]s. Examples of acetylation reactions include [[acylation]] processes such as [[esterification]] (see below) and the [[Friedel-Crafts reaction]]).
:CH<sub>3</sub>COCl + [[Ethanol|HO-CH<sub>2</sub>-CH<sub>3</sub>]] → [[Ethyl acetate|CH<sub>3</sub>-COO-CH<sub>2</sub>-CH<sub>3</sub>]] + [[Hydrogen chloride|H-Cl]]
Frequently such acylations are carried out in the presence of a base such as [[pyridine]], [[triethylamine]], or [[4-Dimethylaminopyridine|DMAP]], which as [[catalyst]]s help to promote the reaction and as [[base (chemistry)|base]]s [[neutralization|neutralize]] the resulting HCl.
Acetylation is the introduction of an [[acetyl]] group via [[acylation]] using a [[reactant]] such as acetyl chloride or [[acetic anhydride]]. An acetyl group is an [[acyl]] group having the formula
:-C(=O)-CH<sub>3</sub>
For further information on the types of chemical reactions compounds such as acetyl chloride can undergo, see [[acyl halide]].
==References==
{{Unreferenced|date =September 2007}}
<references/>
==External links==
*[http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc02/icsc0210.htm International Chemical Safety Card 0210]
[[Category:Acyl chlorides]]
[[de:Essigsäurechlorid]]
[[es:Cloruro de etanoilo]]
[[fr:Chlorure d'éthanoyle]]
[[id:Asetil klorida]]
[[it:Cloruro di acetile]]
[[ja:塩化アセチル]]
[[pl:Chlorek acetylu]]
[[pt:Cloreto de acetila]]
[[ru:Ацетилхлорид]]
[[zh:乙酰氯]]