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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. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with ...
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 ...
A base anhydride is an oxide of a chemical element from group 1 or 2 (the alkali metals and alkaline earth metals, respectively). They are obtained by removing water from the corresponding hydroxide base. If water is added to a base anhydride, a corresponding hydroxide salt can be [re]-formed.
An acid anhydride is a type of chemical compound derived by the removal of water molecules from an acid. In organic chemistry, organic acid anhydrides contain the functional group −C(=O)−O−C(=O)−. Organic acid anhydrides often form when one equivalent of water is removed from two equivalents of an organic acid in a dehydration reaction.
Unlike acid-catalyzed processes, both the nucleophile and the leaving group exist as anions under basic conditions. This mechanism is supported by isotope labeling experiments. When ethyl propionate with an oxygen-18 -labeled ethoxy group is treated with sodium hydroxide (NaOH), the oxygen-18 label is completely absent from propionic acid and ...
The naphthalene route (the Gibbs phthalic anhydride process or the Gibbs–Wohl naphthalene oxidation reaction) has declined relative to the o-xylene route. Proposed early steps in vanadium -catalyzed oxidation of naphthalene to phthalic anhydride, with V 2 O 5 represented as a molecule versus its true extended structure.
The condensation produces water, however, which can hydrolyze the anhydride back to the starting carboxylic acids. Thus, the formation of the anhydride via condensation is an equilibrium process. Under acid-catalyzed conditions, carboxylic acids will react with alcohols to form esters via the Fischer esterification reaction, which is also an ...
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