Acryloyl chloride

Acryloyl chloride
Names
	IUPAC name Prop-2-enoyl chloride
	Other names 2-Propenoyl chloride
Identifiers
CAS Number	814-68-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	12588 ;
ECHA InfoCard	100.011.272
PubChem CID	13140;
UNII	8K23O56TG5 ;
CompTox Dashboard (EPA)	DTXSID1061150 ;
	InChI InChI=1S/C3H3ClO/c1-2-3(4)5/h2H,1H2 Key: HFBMWMNUJJDEQZ-UHFFFAOYSA-N ; InChI=1/C3H3ClO/c1-2-3(4)5/h2H,1H2 Key: HFBMWMNUJJDEQZ-UHFFFAOYAZ;
	SMILES ClC(=O)C=C;
Properties
Chemical formula	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 pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H302, H314, H330
GHS precautionary statements	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

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]

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]

Toxicity

Symptoms of exposure

Symptoms of Acrylyl Chloride Exposure may be high irritation of the skin, eyes, mucous membranes, and respiratory tract. Lacrimation (tearing) is common. Coughing and difficulty in breathing may be noted along with pulmonary edema in more severe exposures. Other signs and symptoms of acute exposure may include headache, dizziness, and weakness. Gastrointestinal effects may include nausea, vomiting, and diarrhea.[5]

References

PatentStorm LLC (2006). "Process for the manufacture of acryloyl chloride". PatentStorm LLC. Archived from the original on January 14, 2013. Retrieved December 21, 2007.
Stempel, Guido H. Jr.; Cross, Robert P.; Mariella, Raymond P. (1950). "Preparation of acrylyl chloride". Journal of the American Chemical Society. 72 (5): 2299–2300. doi:10.1021/ja01161a527.
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. PMID 27325562.
Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus (2003). "Acrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_161.
https://cameochemicals.noaa.gov/chemical/4850