Carboxylic acid anhydride in the context of Acidic oxide


Carboxylic acid anhydride in the context of Acidic oxide

⭐ Core Definition: Carboxylic acid anhydride

An organic acid anhydride is an acid anhydride that is also an organic compound. An acid anhydride is a compound that has two acyl groups bonded to the same oxygen atom. 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))2O. 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. Thus, (CH3CO)2O is called acetic anhydride. Mixed (or unsymmetrical) acid anhydrides, such as acetic formic anhydride (see below), are known, whereby reaction occurs between two different carboxylic acids. Nomenclature of unsymmetrical acid anhydrides list the names of both of the reacted carboxylic acids before the word "anhydride" (for example, the dehydration reaction between benzoic acid and propanoic acid would yield "benzoic propanoic anhydride").

One or both acyl groups of an acid anhydride may also be derived from another type of organic acid, such as sulfonic acid or a phosphonic acid. One of the acyl groups of an acid anhydride can be derived from an inorganic acid such as phosphoric acid. The mixed anhydride 1,3-bisphosphoglyceric acid, an intermediate in the formation of ATP via glycolysis, is the mixed anhydride of 3-phosphoglyceric acid and phosphoric acid. Acidic oxides are also classified as acid anhydrides.

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Carboxylic acid anhydride in the context of Alkyd

An alkyd is a polyester resin modified by the addition of fatty acids and other components. Alkyds are derived from polyols and organic acids including dicarboxylic acids or carboxylic acid anhydride and triglyceride oils. The term alkyd is a modification of the original name "alcid", reflecting the fact that they are derived from alcohol and organic acids. The inclusion of a fatty acid confers a tendency to form flexible coatings. Alkyds are used in paints, varnishes and in moulds for casting. They are the dominant resin or binder in most commercial oil-based coatings. Approximately 200,000 tons of alkyd resins are produced each year. The original alkyds were compounds of glycerol and phthalic acid sold under the name Glyptal. These were sold as substitutes for the darker-colored copal resins, thus creating alkyd varnishes that were much paler in colour. From these, the alkyds that are known today were developed.

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Carboxylic acid anhydride in the context of Chloroformic acid

Chloroformic acid is a chemical compound with the formula ClCO2H. It is the single acyl-halide derivative of carbonic acid (phosgene is the double acyl-halide derivative). Chloroformic acid is also structurally related to formic acid, in a way that the non-acidic hydrogen of formic acid is replaced by chlorine. Despite the similar name, it is very different from chloroform. It is described as unstable, decomposing into carbon dioxide and hydrogen chloride.

Chloroformic acid itself is too unstable to be handled for chemical reactions. However, many esters of this carboxylic acid are stable and these chloroformates are important reagents in organic chemistry. They are used to prepare mixed carboxylic acid anhydrides used in peptide synthesis.Important chloroformate esters include 4-nitrophenyl chloroformate, fluorenylmethyloxycarbonylchloride, benzyl chloroformate and ethyl chloroformate.

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