Acryloyl chloride

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Acryloyl chloride
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Prop-2-enoyl chloride
Other names
2-Propenoyl chloride
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.011.272 Edit this at Wikidata
UNII
  • InChI=1S/C3H3ClO/c1-2-3(4)5/h2H,1H2 checkY
    Key: HFBMWMNUJJDEQZ-UHFFFAOYSA-N checkY
  • InChI=1/C3H3ClO/c1-2-3(4)5/h2H,1H2
    Key: HFBMWMNUJJDEQZ-UHFFFAOYAZ
  • ClC(=O)C=C
Properties
C3H3ClO
Molar mass 90.51 g·mol−1
Density 1.119 g/cm3
Boiling point 75.0 °C (167.0 °F; 348.1 K)
Hazards
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS06: Toxic
Danger
H225, H302, H314, H330
P210, P280, P301+P330+P331, P303+P361+P353, P305+P351+P338, 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).
checkY verify (what is checkY☒N ?)

Acryloyl chloride, also known as 2-propenoyl chloride, acrylyl chloride, or acrylic acid chloride, is the

acid chlorides group of compounds.[1]

Preparation

Acryloyl chloride can be efficiently prepared by treating acrylic acid with benzoyl chloride:[2]

CH2=CHCO2H + C6H5COCl → CH2=CHCOCl + C6H5CO2H

Conventional phosphorus-based chlorinating agents, e.g. 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

organozinc compounds.[4]

Acryloyl chloride is most commonly employed for the introduction of acrylic groups into other compounds, e.g. the preparation of acrylate monomers and polymers.[5]

Toxicity

Acryloyl chloride, like volatile acid chlorides, is a skin irritant, with pulmonary edema in more severe exposures.[6] Other signs and symptoms of acute exposure may include headache, dizziness, and weakness. Gastrointestinal effects may include nausea, vomiting, diarrhea, and stomach ulceration.[7]

References

  1. ^ a b 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. doi:10.1021/ja01161a527
    .
  3. PMID 27325562
    .
  4. doi:10.15227/orgsyn.067.0098.{{cite journal}}: CS1 maint: multiple names: authors list (link
    )
  5. ISBN 978-3527306732
    .
  6. S2CID 251779499
    . Retrieved 8 April 2023.
  7. ^ "ACRYLYL CHLORIDE | CAMEO Chemicals | NOAA".

See also

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