Preparation and application of capryloyl chloride

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Octanoyl chloride is a colorless, transparent liquid at room temperature and pressure. It has a pungent odor and is soluble in most organic solvents, but it is easily deliquesced when exposed to water.

Octanoyl chloride, a clear, colorless liquid at room temperature and pressure, has a pungent odor and is soluble in most organic solvents but readily hydrolyzes in water. Octanoyl chloride is an alkyl acyl chloride, prepared from octanoic acid via chlorination. It is primarily used as a basic chemical reagent in organic synthesis, undergoing acylation reactions with alcohols or amines, commonly used in the preparation of octanamide and octanoate derivatives.

Physicochemical Properties

Octanoyl chloride possesses high chemical reactivity, primarily due to its acyl chloride moiety. This renders it valuable in organic synthesis. It undergoes condensation reactions with alcohols or amines under alkaline conditions. Octanoyl chloride is chemically unstable and readily decomposes upon heating or contact with water. This decomposition releases toxic hydrogen chloride gas, necessitating careful handling.

Preparation Method

Figure 1 Preparation Method of Octanoyl Chloride

In a dry reaction flask, octanoic acid (2.5 g) is dissolved in thionyl chloride (15 mL). The reaction mixture is heated to reflux and stirred for approximately 10 hours. Avoid contact with water and air during the reaction to prevent hydrolysis of the product. After the reaction, the mixture is cooled to room temperature and concentrated under reduced pressure to remove thionyl chloride. The residue is concentrated under high vacuum (oil pump) to yield a pale yellow/brown oil, the pure target product, octanoyl chloride. [1]

Industrial Applications

Octanoyl chloride undergoes condensation reactions with alcohols or amines under alkaline conditions to form the corresponding esters or amides. This is one of its most widespread applications. Octanamides are widely used in pharmaceuticals and pesticide synthesis, while octanoates are commonly used in lubricants and coatings. In rubber industry, it is used in the production of adhesives, which play a bonding and processing role in rubber products. Octanoyl chloride, as one of its raw materials, provides the necessary chemical properties and bonding performance.

References

[1] Pal, Mohan; et al Organic & Biomolecular Chemistry (2014), 12(48), 9760-9763.

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