Acetyl chloride
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Names | |||
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Preferred IUPAC name
Acetyl chloride[2] | |||
Systematic IUPAC name
Ethanoyl chloride | |||
Other names
Acyl chloride
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Identifiers | |||
3D model (
JSmol ) |
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605303 | |||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard
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100.000.787 | ||
EC Number |
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1611 | |||
PubChem CID
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RTECS number
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UNII | |||
UN number | 1717 | ||
CompTox Dashboard (EPA)
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Properties | |||
CH3COCl | |||
Molar mass | 78.49 g/mol | ||
Appearance | Colorless liquid | ||
Density | 1.104 g/ml, liquid | ||
Melting point | −112 °C (−170 °F; 161 K) | ||
Boiling point | 52 °C (126 °F; 325 K) | ||
Reacts with water | |||
-38.9·10−6 cm3/mol | |||
Structure | |||
2.45 D | |||
Hazards | |||
GHS labelling: | |||
Danger | |||
H225, H302, H314, H335, H412 | |||
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P370+P378, P403+P233, P403+P235, P405, P501 | |||
NFPA 704 (fire diamond) | |||
Flash point | 4 °C (39 °F; 277 K) | ||
390 °C (734 °F; 663 K) | |||
Explosive limits
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7.3–19% | ||
Related compounds | |||
Related acyl chlorides
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Propionyl chloride Butyryl chloride | ||
Related compounds
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Acetic acid Acetic anhydride Acetyl bromide | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Acetyl chloride (CH3COCl) is an
Synthesis
On an industrial scale, the reaction of acetic anhydride with hydrogen chloride produces a mixture of acetyl chloride and acetic acid:[3]
Laboratory routes
Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by treating potassium acetate with phosphoryl chloride.[4]
Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as phosphorus trichloride (PCl3), phosphorus pentachloride (PCl5), sulfuryl chloride (SO2Cl2), phosgene, or thionyl chloride (SOCl2). However, these methods usually give acetyl chloride contaminated by phosphorus or sulfur impurities, which may interfere with the organic reactions.[5]
Other methods
When heated, a mixture of
Occurrence
Acetyl chloride is not expected to exist in nature, because contact with
Uses
Acetyl chloride is used for acetylation reactions, i.e., the introduction of an acetyl group. Acetyl is an
Acetic acid esters and amide
Acetyl chloride is a reagent for the preparation of esters and amides of acetic acid, used in the
Frequently such acylations are carried out in the presence of a base such as
Friedel-Crafts acetylations
A second major class of acetylation reactions are the
See also
References
- ^ Merck Index, 11th Edition, 79.
- ISBN 978-0-85404-182-4.
- ISBN 978-3527306732.
- ^ See:
- Gerhardt, Charles (1852) "Ueber wasserfreie organische Säuren" (On anhydrous organic acids), Annalen der Chemie und Pharmacie, 83 : 112–116.
- Gerhardt, Charles (1853) "Untersuchungen über die wasserfreien organischen Säuren" (Investigations into anhydrous organic acids), Annalen der Chemie und Pharmacie, 87 : 57–84 ; see especially pp. 68–71.
- ^ ISBN 978-0-471-97927-2.
- ^ US 4352761, Erpenbach, Heinz; Gehrmann, Klaus & Lork, Winfried et al., "Production of acetyl chloride", published 1982-10-05, assigned to Hoechst AG