Sebacoyl chloride (or sebacoyl dichloride) is a di- acyl chloride, with formula (CH₂)₈(COCl)₂. A colorless oily liquid with a pungent odor, it is soluble in hydrocarbons and ethers. Sebacoyl chloride is corrosive; like all acyl chlorides, it hydrolyzes, evolving

hydrogen chloride The compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colourless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hydrogen chloride ga ...

. It is less susceptible to

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolys ...

though than shorter chain aliphatic acyl chlorides.

Preparation

Sebacoyl chloride can be prepared by reacting

sebacic acid Sebacic acid is a naturally occurring dicarboxylic acid with the chemical formula . It is a white flake or powdered solid. ''Sebaceus'' is Latin for tallow candle, ''sebum'' is Latin for tallow, and refers to its use in the manufacture of candles. ...

with an excess of

thionyl chloride Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately per year bein ...

. Residual thionyl chloride can be removed by

distillation Distillation, or classical distillation, is the process of separating the components or substances from a liquid mixture by using selective boiling and condensation, usually inside an apparatus known as a still. Dry distillation is the heat ...

Use

Sebacoyl chloride can be

polymerized In polymer chemistry, polymerization (American English), or polymerisation (British English), is a process of reacting monomer molecules together in a chemical reaction to form polymer chains or three-dimensional networks. There are many for ...

with

hexamethylenediamine Hexamethylenediamine is the organic compound with the formula H2N(CH2)6NH2. The molecule is a diamine, consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups. The colorless solid (yellowish for some commercial sam ...

yielding nylon-6,10.

References

{{Navbox acyl chlorides Acyl chlorides Monomers

Preparation

Use

See also

References