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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 .
In the laboratory, it can be easily synthesized from anthranilic acid and acetic anhydride. N -Acetylanthranilic acid exhibits triboluminescence when crushed. [ 5 ] The fractured crystals have large electrical potentials between areas of high and low charge.
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
Other electrophilic aromatic substitution reactions can also be promoted with trifluoroacetic anhydride, including nitration, sulfonation and nitrosylation. [2] Similar to acetic anhydride, trifluoroacetic anhydride can be used as a dehydrating agent and as an activator for the Pummerer rearrangement. [4]
Sigma Advanced Genetic Engineering (SAGE) Labs is a division within Sigma-Aldrich that specializes in genetic manipulation of in vivo systems for special research and development applications. It was formed in 2008 to investigate zinc finger nuclease technology and its application for disease research models.
Acetylferrocene is prepared by Friedel-Crafts acylation of ferrocene, usually with acetic anhydride (Ac 2 O): . Fe(C 5 H 5) 2 + Ac 2 O → (C 5 H 5)Fe(C 5 H 4 Ac) + HOAc. The experiment is often conducted in the instructional laboratory to illustrate acylation as well as chromatographic separations.
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 ...
Acetone and acetic anhydride ((CH 3 C(O)) 2 O) upon the addition of boron trifluoride (BF 3) catalyst: [11] (CH 3 C(O)) 2 O + CH 3 C(O)CH 3 → CH 3 C(O)CH 2 C(O)CH 3 A second synthesis involves the base-catalyzed condensation (e.g., by sodium ethoxide CH 3 CH 2 O − Na + ) of acetone and ethyl acetate , followed by acidification of the sodium ...