Acyl halide

An acyl halide (also known as an acid halide) is a chemical compound derived from an acid by replacing a hydroxyl group with a halide group.^[1]

If the acid is a carboxylic acid, the compound contains a –COX functional group, which consists of a carbonyl group singly bonded to a halogen atom. The general formula for such an acyl halide can be written RCOX, where R may be, for example, an alkyl group, CO is the carbonyl group, and X represents the halogen atom, such as chlorine. Acyl chlorides are the most commonly used acyl halides.

The hydroxyl group of a sulfonic acid may also be replaced by a halogen to produce the corresponding sulfonyl halide. In practical terms this is almost always chlorine to create a sulfonyl chloride.

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Preparation

A common method for the synthesis of acyl halides in the laboratory is by reaction of carboxylic acids with reagents such as thionyl chloride or phosphorus pentachloride for acyl chlorides, phosphorus tribromide for acyl bromides and cyanuric fluoride for acyl fluorides.

Aromatic acyl chlorides can be prepared by chloroformylation, a specific type of Friedel-Crafts acylation using formaldehyde as the reagent.

Reactions

Acyl halides are rather reactive compounds often synthesized to be used as intermediates in the synthesis of other organic compounds. For example, an acyl halide can react with:

• water, to form a carboxylic acid

• an alcohol to form an ester

• an amine to form an amide

• an aromatic compound, using a Lewis acid catalyst such as AlCl₃, to form an aromatic ketone. See Friedel-Crafts acylation.

In the above reactions, HX (hydrogen halide or hydrohalic acid) is also formed. For example, if the acyl halide is an acyl chloride, HCl (hydrogen chloride or hydrochloric acid) is also formed.

Multiple functional groups

  A molecule can have more than one acyl halide functional group. For example, "adipoyl dichloride", usually simply called adipoyl chloride, has two acyl chloride functional groups; see the structure at right. It is the dichloride (i.e., double chloride) of the 6-carbon dicarboxylic acid adipic acid. An important use of adipoyl chloride is polymerization with an organic di-amino compound to form a polyamide called nylon or polymerization with certain other organic compounds to form polyesters.

Phosgene (carbonyl dichloride, Cl–CO–Cl) is a very toxic gas which may be thought of as the dichloride of carbonic acid (HO–CO–OH). Both chloride radicals in phosgene can undergo reactions analogous to the preceding reactions of acyl halides. Phosgene is used a reactant in the production of polycarbonate polymers, among other industrial applications.

General hazards

Volatile acyl halides are lachrymatory because they can react with water at the surface of the eye producing hydrohalic and organic acids irritating to the eye. Similar problems can result if one inhales acyl halide vapors. In general, acyl halides (even non-volatile compounds such as tosyl chloride) are irritants to the eyes, skin and mucous membranes.

References

1. ^ International Union of Pure and Applied Chemistry. "acyl halides". Compendium of Chemical Terminology Internet edition.