Acryloyl chloride explained

Acryloyl chloride, also known as 2-propenoyl chloride, acrylyl 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. It belongs to the acid chlorides group of compounds.^[1]

Preparation

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

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 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. It acylates 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.

Toxicity

Acryloyl chloride, like volatile acid chlorides, is a skin irritant, with pulmonary edema in more severe exposures.^[5] Other signs and symptoms of acute exposure may include headache, dizziness, and weakness. Gastrointestinal effects may include nausea, vomiting, diarrhea, and stomach ulceration.^[6]

See also

• Methacryloyl chloride
• List of extremely hazardous substances

Notes and References

1. Web site: Process for the manufacture of acryloyl chloride . https://archive.today/20130114073014/http://www.patentstorm.us/patents/5395966-description.html . dead . January 14, 2013 . December 21, 2007 . PatentStorm LLC . 2006 . PatentStorm LLC .
2. Preparation of acrylyl chloride. Stempel, Guido H. Jr. . Cross, Robert P. . Mariella, Raymond P. . Journal of the American Chemical Society. 1950. 72. 5 . 2299–2300. 10.1021/ja01161a527.
3. Movsisyan. Marine. Heugebaert. Thomas S. A.. Dams. Rudy. Stevens. Christian V.. Safe, Selective, and High-Yielding Synthesis of Acryloyl Chloride in a Continuous-Flow System. ChemSusChem. 9 August 2016. 9. 15. 1945–1952. 10.1002/cssc.201600348. 27325562. 2016ChSCh...9.1945M .
4. 10.15227/orgsyn.067.0098. Ethyl 5-Oxo-6-Methyl-6-Heptenoate from Methacryloyl Chloride and Ethyl 4-Iodobutyrate . Organic Syntheses . 1989 . 67 . 98. Yoshinao Tamaru, Hirofumi Ochiai, Tatsuya Nakamura, Zen-ichi Yoshida.
5. Pathan . Asama . Ahmad . Iqrar . Girase . Rukaiyya . Jagatap . Vilas . Patel . Harun . A Laboratory Accident of Acryloyl Chloride, Its Consequences, Treatment, and Safety Measures: An Arduous Lesson to All Researchers . ACS Chemical Health & Safety . August 23, 2022 . 29 . 5 . 405-420 . 10.1021/acs.chas.2c00036 . 251779499 . 8 April 2023.
6. Web site: ACRYLYL CHLORIDE | CAMEO Chemicals | NOAA.