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Organic compound (CH ₃COCl)
Acetyl chloride[1]
Skeletal formula of acetyl chloride Ball-and-stick model of acetyl chloride
Names
Preferred IUPAC name
Systematic IUPAC name
Other names
Acyl chloride
Identifiers
CAS Number
3D model (JSmol )
Beilstein Reference
605303
ChEBI
ChemSpider
ECHA InfoCard 100.000.787
EC Number
Gmelin Reference
1611
PubChem CID
RTECS number
UNII
UN number
1717
CompTox Dashboard (EPA )
InChI=1S/C2H3ClO/c1-2(3 )4/h1H3 Y
Key: WETWJCDKMRHUPV-UHFFFAOYSA-N Y
InChI=1/C2H3ClO/c1-2(3 )4/h1H3
Key: WETWJCDKMRHUPV-UHFFFAOYAQ
Properties
Chemical formula
CH 3
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 )
Solubility in water
Reacts with water
Magnetic susceptibility (χ)
-38.9·10−6 cm 3
Structure
Dipole moment
2.45 D
Hazards
GHS labelling
Pictograms
Signal word
Danger
Hazard statements
H225 , H302 , H314 , H335 , H412
Precautionary statements
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
Flash point
4 °C (39 °F; 277 K )
Autoignition
390 °C (734 °F; 663 K )
Explosive limits
7.3–19%
Related compounds
Related acyl chlorides
Propionyl chloride Butyryl chloride
Related compounds
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).
Infobox references
Chemical compound
Acetyl chloride (CH 3 acyl chloride derived from acetic acid (CH 3 organic compounds called acid halides . It is a colorless, corrosive, volatile liquid . Its formula is commonly abbreviated to AcCl.
Synthesis [ edit ]
On an industrial scale, the reaction of acetic anhydride with hydrogen chloride produces a mixture of acetyl chloride and acetic acid:[3]
(
CH
3
CO )
2
O +
HCl
⟶
CH
3
COCl
+
CH
3
CO
2
H
{\displaystyle {\ce {(CH3CO)2O + HCl -> CH3COCl + CH3CO2H}}}
Laboratory routes [ edit ]
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 (SO 2 Cl 2 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 [ edit ]
When heated, a mixture of dichloroacetyl chloride and acetic acid gives acetyl chloride.[5] carbonylation of methyl chloride .[6] acetonitrile , and hydrogen chloride .[citation needed
Occurrence [ edit ]
Acetyl chloride is not expected to exist in nature, because contact with water would hydrolyze it into acetic acid and hydrogen chloride . In fact, if handled in open air it releases white "smoke" resulting from hydrolysis due to the moisture in the air. The smoke is actually small droplets of hydrochloric acid and acetic acid formed by hydrolysis.
Acetyl chloride is used for acetylation reactions, i.e., the introduction of an acetyl group. Acetyl is an acyl group having the formula −C(=O)−CH3 ). For further information on the types of chemical reactions compounds such as acetyl chloride can undergo, see acyl halide . Two major classes of acetylations include esterification and the Friedel-Crafts reaction .
Acetic acid esters and amide [ edit ]
Acetyl chloride is a reagent for the preparation of esters and amides of acetic acid, used in the derivatization of alcohols and amines . One class of acetylation reactions are esterification , for example the reaction with ethanol to produce ethyl acetate and hydrogen chloride :
CH
3
COCl
+
HO
−
CH
2
−
CH
3
⟶
CH
3
−
COO
−
CH
2
−
CH
3
+
HCl
{\displaystyle {\ce {CH3COCl + HO-CH2-CH3 -> CH3-COO-CH2-CH3 + HCl}}}
Frequently such acylations are carried out in the presence of a base such as pyridine , triethylamine , or DMAP , which act as catalysts to help promote the reaction and as bases neutralize the resulting HCl . Such reactions will often proceed via ketene .
Friedel-Crafts acetylations [ edit ]
A second major class of acetylation reactions are the Friedel-Crafts reactions .[7]
See also [ edit ]
References [ edit ]
^ Cheung, Hosea; Tanke, Robin S.; Torrence, G. Paul (2000). "Acetic Acid". Ullmann's Encyclopedia of Industrial Chemistry doi :10.1002/14356007.a01_045 . ISBN 978-3527306732
^ See:
^ a b Leo A. Paquette (2005). "Acetyl chloride". Handbook of Reagents for Organic Synthesis, Activating Agents and Protective Groups . John Wiley & Sons. p. 16. 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
^ Charles Merritt, Jr and Charles E. Braun "9-Acetylanthracene" Org. Synth. 1950, 30, 2. doi :10.15227/orgsyn.030.0001
External links [ edit ]
t
e
Acetyl halides and salts of the
acetate ion
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Acetyl_chloride&oldid=1178257527 " C a t e g o r i e s : ● A c y l c h l o r i d e s ● A c e t y l a t i n g a g e n t s ● O r g a n i c c o m p o u n d s w i t h 2 c a r b o n a t o m s H i d d e n c a t e g o r i e s : ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n i s d i f f e r e n t f r o m W i k i d a t a ● A r t i c l e s w i t h o u t K E G G s o u r c e ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● C h e m b o x h a v i n g G H S d a t a ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● C h e m b o x i m a g e s i z e s e t ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a ● A l l a r t i c l e s w i t h u n s o u r c e d s t a t e m e n t s ● A r t i c l e s w i t h u n s o u r c e d s t a t e m e n t s f r o m M a y 2 0 1 8 ● A r t i c l e s w i t h G N D i d e n t i f i e r s
● T h i s p a g e w a s l a s t e d i t e d o n 2 O c t o b e r 2 0 2 3 , a t 1 4 : 4 1 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w ●
T o g g l e l i m i t e d c o n t e n t w i d t h
