Acryloyl chloride

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Acryloyl chloride
Skeletal formula
Ball-and-stick model
Names
IUPAC name
2-propenoyl chloride
Identifiers
814-68-6 YesY
ChemSpider 12588 YesY
Jmol interactive 3D Image
PubChem 399362
Properties
C3H3ClO
Molar mass 90.51 g·mol−1
Density 1.119 g/cm3
Melting point N/A
Boiling point 75.0 °C (167.0 °F; 348.1 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Acryloyl chloride, also known as 2-propenoyl chloride or acrylic acid chloride, is a clear, light yellow, flammable liquid with an acrid smell.[1][2] It belongs to the acid chlorides group of compounds and is therefore a derivative of acrylic acid.[3]

Preparation[edit]

Acryloyl chloride can be prepared by reacting acrylic acid with benzoyl chloride or with thionyl chloride.[3] 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[edit]

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 alcohols will result in the formation of esters and reactions with amines will generate amides.[citation needed]

Uses[edit]

Acryloyl chloride is most commonly employed in organic synthesis for the introduction of acrylic moieties into other compounds and it is also used extensively in the preparation of acrylate monomers and polymers.[citation needed]

References[edit]

  1. ^ Environmental Chemistry (2007). "Acryloyl chloride". Environmental Chemistry.com (J.K. Barbalace, inc). Retrieved December 21, 2007. 
  2. ^ Physical & Theoretical Chemistry Laboratory (2005). "Safety data for acryloyl chloride". Physical & Theoretical Chemistry Laboratory. Retrieved December 21, 2007. 
  3. ^ a b PatentStorm LLC (2006). "Process for the manufacture of acryloyl chloride". PatentStorm LLC. Retrieved December 21, 2007. 

See also[edit]