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Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH 3 CO) 2 O. Commonly abbreviated Ac 2 O , it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis .
The worldwide production of acetic anhydride is a major application, and uses approximately 25% to 30% of the global production of acetic acid. The main process involves dehydration of acetic acid to give ketene at 700–750 °C. Ketene is thereafter reacted with acetic acid to obtain the anhydride: [50] CH 3 CO 2 H → CH 2 =C=O + H 2 O
A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O)) 2 O. Symmetrical acid anhydrides of this type are named by replacing the word acid in the name of the parent carboxylic acid by the word anhydride. [2] Thus, (CH 3 CO) 2 O is called acetic ...
Acetyl hypochlorite is reported to be produced by the reaction of acetic anhydride and dichlorine monoxide at very low temperatures: [2]. Cl 2 O + (CH3CO) 2 O → 2CH 3 COOCl. The liquid can be distilled at reduced pressure, however it cannot be heated, as it violently decomposes at 100 °C to acetic anhydride, oxygen, and chlorine gas, and reacts with water and alcohols.
Acetylacetone is an organic compound with the chemical formula CH 3 −C(=O)−CH 2 −C ... In the gas phase, ... Acetone and acetic anhydride ...
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 (PCl 3), phosphorus pentachloride (PCl 5), sulfuryl chloride (SO 2 Cl 2), phosgene, or thionyl chloride (SOCl 2).
For example, it reacts with water to form acetic acid; [23] with acetic acid to form acetic anhydride; with ammonia and amines to form ethanamides; [24] and with dry hydrogen halides to form acetyl halides. [25] The formation of acetic acid likely occurs by an initial formation of 1,1-dihydroxyethene, which then tautomerizes to give the final ...
Trifluoroacetic anhydride has various uses in organic synthesis. It may be used to introduce the corresponding trifluoroacetyl group, for which it is more convenient than the corresponding acyl chloride , trifluoroacetyl chloride , which is a gas.