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Acetic anhydride
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Acetic anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is one the simplest anhydrides of a carboxylic acid and is widely used in the production of cellulose acetate as well as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.
Acetic anhydride, like most organic acid anhydrides, is a flexible molecule with a nonplanar structure. The C=O and C-O distances are 1.19 and 1.39 Å. The pi system linkage through the central oxygen offers very weak resonance stabilization compared to the dipole-dipole repulsion between the two carbonyl oxygens. The energy barriers to bond rotation between each of the optimal aplanar conformations are quite low.
Acetic anhydride was first synthesized in 1852 by the French chemist Charles Frédéric Gerhardt (1816-1856) by heating potassium acetate with benzoyl chloride.
Acetic anhydride is produced by carbonylation of methyl acetate:
The Tennessee Eastman acetic anhydride process involves the conversion of methyl acetate to methyl iodide. Carbonylation of the methyl iodide produces acetyl iodide, which reacts with acetate source to give the desired anhydride. Rhodium chloride in the presence of lithium iodide is employed as the catalyst. Because acetic anhydride is not stable in water, the conversion is conducted under anhydrous conditions.
To a decreasing extent, acetic anhydride is also prepared by the reaction of ketene (ethenone) with acetic acid at 45–55 °C and low pressure (0.05–0.2 bar).
The route from acetic acid to acetic anhydride via ketene was developed by Wacker Chemie in 1922, when the demand for acetic anhydride increased due to the production of cellulose acetate.
Due to its low cost, acetic anhydride is usually purchased, not prepared, for use in research laboratories.
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Acetic anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is one the simplest anhydrides of a carboxylic acid and is widely used in the production of cellulose acetate as well as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.
Acetic anhydride, like most organic acid anhydrides, is a flexible molecule with a nonplanar structure. The C=O and C-O distances are 1.19 and 1.39 Å. The pi system linkage through the central oxygen offers very weak resonance stabilization compared to the dipole-dipole repulsion between the two carbonyl oxygens. The energy barriers to bond rotation between each of the optimal aplanar conformations are quite low.
Acetic anhydride was first synthesized in 1852 by the French chemist Charles Frédéric Gerhardt (1816-1856) by heating potassium acetate with benzoyl chloride.
Acetic anhydride is produced by carbonylation of methyl acetate:
The Tennessee Eastman acetic anhydride process involves the conversion of methyl acetate to methyl iodide. Carbonylation of the methyl iodide produces acetyl iodide, which reacts with acetate source to give the desired anhydride. Rhodium chloride in the presence of lithium iodide is employed as the catalyst. Because acetic anhydride is not stable in water, the conversion is conducted under anhydrous conditions.
To a decreasing extent, acetic anhydride is also prepared by the reaction of ketene (ethenone) with acetic acid at 45–55 °C and low pressure (0.05–0.2 bar).
The route from acetic acid to acetic anhydride via ketene was developed by Wacker Chemie in 1922, when the demand for acetic anhydride increased due to the production of cellulose acetate.
Due to its low cost, acetic anhydride is usually purchased, not prepared, for use in research laboratories.