Acryloyl chloride 2318557 210039598 2008-05-04T04:12:31Z Akane700 5630131 [[ja:塩化アクリル]] {{Chembox new | Name = Acryloyl chloride | ImageFile = Acryloyl chloride2.png | ImageSize = 120px | ImageName = Acryloyl chloride | IUPACName = 2-propenoyl chloride | Section1 = {{Chembox Identifiers | PubChem= 399362 | CASNo = 814-68-6 | SMILES = C=CC(Cl)=O }} | Section2 = {{Chembox Properties | Formula = C<sub>3</sub>H<sub>3</sub>ClO | MolarMass = 90.51 g/mol | MeltingPt = N/A | BoilingPt = 75.0 °C | Density = 1.119 g/cm³ }} }} '''Acryloyl chloride''', also known as 2-propenoyl chloride or acrylic acid chloride, is a clear, light yellow, flammable liquid with an acrid smell.<ref name="database">{{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}}</ref><ref name="lab">{{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}}</ref> It belongs to the [[acid chloride]]s group of compounds and is therefore a derivative of [[acrylic acid]].<ref name="patent">{{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}}</ref> ==Preparation== Acryloyl chloride can be prepared by reacting acrylic acid with [[benzoyl chloride]] or with [[thionyl chloride]].<ref name="patent"/> When preparing this compound adding a small amount of an inhibitor such as [[hydroquinone]] can help to avoid light induced [[polymerisation]] 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 with [[alcohol]]s will result in the formation of [[ester]]s and reactions with amines will generate [[amide]]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. ==Safety== 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 [[lachrymatory agent|lachrymator]]. ==References== {{reflist}} [[Category:Acyl chlorides]] [[Category:Monomers]] [[Category:lachrymatory agents]] [[ja:塩化アクリル]]