- Acryloyl chloride
Chembox new
Name = Acryloyl chloride
ImageFile = Acryloyl chloride2.png
ImageName = Acryloyl chloride
IUPACName = 2-propenoyl chloride
Section1 = Chembox Identifiers
PubChem= 399362
CASNo = 814-68-6
SMILES = C=CC(Cl)=O
Section2 = Chembox Properties
C=3|H=3|Cl=1|O=1
MeltingPt = N/A
BoilingPt = 75.0 °C
Density = 1.119 g/cm³Acryloyl chloride, also known as 2-propenoyl chloride or acrylic acid chloride, is a clear, light yellow, flammable liquid with an acrid smell.Cite web|url=http://environmentalchemistry.com/yogi/chemicals/cn/Acryloyl%A0chloride.html|title=Acryloyl chloride|accessyear=2007|accessmonthday=December 21|publisher=Environmental Chemistry.com (J.K. Barbalace, inc).|year=2007|author=Environmental Chemistry] Cite web|url=http://physchem.ox.ac.uk/MSDS/AC/acryloyl_chloride.html|title=Safety data for acryloyl chloride|accessyear=2007|accessmonthday=December 21|publisher=Physical & Theoretical Chemistry Laboratory|year=2005|author=Physical & Theoretical Chemistry Laboratory] It belongs to the
acid chloride s group of compounds and is therefore a derivative ofacrylic acid .Cite web|url=http://www.patentstorm.us/patents/5395966-description.html|title=Process for the manufacture of acryloyl chloride|accessyear=2007|accessmonthday=December 21|publisher=PatentStorm LLC|year=2006|author=PatentStorm LLC]Preparation
Acryloyl chloride can be prepared by reacting acrylic acid with
benzoyl chloride or withthionyl chloride . When preparing this compound adding a small amount of an inhibitor such ashydroquinone can help to avoid light inducedpolymerisation of acryloyl chloride.Reaction
This compound will give the common reactions of acid chlorides: it will react violently with
water producing acrylic acid while it will form anhydrides when reacted with sodium salts of carboxylic acids. Reactions withalcohol s will result in the formation ofester s and reactions with amines will generateamide s.Uses
Acryloyl chloride is most commonly employed in organic synthesis for the introduction of acrylic moieties into other compounds it is also used extensively in the preparation of acrylate monomers and polymers.
afety
Acryloyl chloride is a dangerous compound being both easily flammable and corrosive: contact with skin, inhalation and ingestion should be avoided since it can result in burns. Acryloyl chloride should be handled carefully since it is also a lachrymator.
References
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