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Acryloyl chloride



Acryloyl chloride
IUPAC name 2-propenoyl chloride
Identifiers
CAS number 814-68-6
PubChem 399362
SMILES C=CC(Cl)=O
Properties
Molecular formula C3H3ClO
Molar mass 90.51 g/mol
Density 1.119 g/cm³
Melting point

N/A

Boiling point

75.0 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and 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]

Additional recommended knowledge

Contents

Preparation

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

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.

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 lachrymator.

References

  1. ^ Environmental Chemistry (2007). Acryloyl chloride. Environmental Chemistry.com (J.K. Barbalace, inc).. Retrieved on December 21, 2007.
  2. ^ Physical & Theoretical Chemistry Laboratory (2005). Safety data for acryloyl chloride. Physical & Theoretical Chemistry Laboratory. Retrieved on December 21, 2007.
  3. ^ a b PatentStorm LLC (2006). Process for the manufacture of acryloyl chloride. PatentStorm LLC. Retrieved on December 21, 2007.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Acryloyl_chloride". A list of authors is available in Wikipedia.
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