Acryloyl chloride

Acryloyl chloride, also known as 2-propenoyl chloride or acrylic acid chloride, is the organic compound with the formula CH2=CHCO(Cl). It is a colorless liquid, although aged samples appear yellow. Although it belongs to the acid chlorides group of compounds, its synthesis and reactivity are somewhat different.[1]

Acryloyl chloride
Names
IUPAC name
Prop-2-enoyl chloride
Other names
2-Propenoyl chloride
Acryloyl chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.272
UNII
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)
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H225, H302, H314, H330
P210, P280, P301+330+331, P303+361+353, P305+351+338, P310
Flash point −4 °C (25 °F; 269 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

Preparation

Acryloyl chloride can be prepared by treating acrylic acid with acid chlorides, originally benzoyl chloride.[2] Conventional one-pot chlorinating agents, e.g. thionyl chloride, phosphorus trichloride, are ineffective. Flow conditions allows use of a broadened range of chlorinating agents including oxalyl chloride and thionyl chloride.[1] [3]

Reactions

This compound undergoes the reactions common for acid chlorides. For example, it reacts readily with water, producing acrylic acid. When treated with sodium salts of carboxylic acids, the anhydride is formed. Reactions with alcohols and amines gives esters and amides, respectively. Acryloyl chloride is most commonly employed for the introduction of acrylic groups into other compounds, e.g. the preparation of acrylate monomers and polymers.[4]

References
  1. PatentStorm LLC (2006). "Process for the manufacture of acryloyl chloride". PatentStorm LLC. Archived from the original on January 14, 2013. Retrieved December 21, 2007.
  2. Stempel, Guido H., Jr.; Cross, Robert P.; Mariella, Raymond P. (1950). "Preparation of acrylyl chloride". Journal of the American Chemical Society. 72: 2299–2300. doi:10.1021/ja01161a527.CS1 maint: multiple names: authors list (link)
  3. Movsisyan, Marine; Heugebaert, Thomas S. A.; Dams, Rudy; Stevens, Christian V. (9 August 2016). "Safe, Selective, and High-Yielding Synthesis of Acryloyl Chloride in a Continuous-Flow System". ChemSusChem. 9 (15): 1945–1952. doi:10.1002/cssc.201600348.
  4. Takashi Ohara, Takahisa Sato, Noboru Shimizu, Günter Prescher Helmut Schwind, Otto Weiberg, Klaus Marten, Helmut Greim (2003). "Acrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_161.pub2.CS1 maint: multiple names: authors list (link)

See also
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