Adipoyl chloride

Adipoyl chloride‏‎ is an organic compound with the formula (CH₂)₄(COCl)₂. It is a colorless liquid that is used primarily in the production of nylon-6,6, a type of polyamide that is widely used in the manufacture of textiles, plastics, and other materials. Adipoyl chloride is an acid chloride derived from adipic acid, a dicarboxylic acid that is a key intermediate in the industrial production of nylon.

The synthesis of adipoyl chloride typically involves the reaction of adipic acid with thionyl chloride (SOCl₂) or other chlorinating agents. This process converts the carboxylic acid groups (-COOH) of adipic acid into acyl chloride groups (-COCl), making it more reactive and suitable for further chemical transformations.

In the production of nylon-6,6, adipoyl chloride is reacted with hexamethylenediamine (HMDA), a diamine, in a process known as polycondensation. This reaction forms nylon-6,6 and hydrochloric acid (HCl) as a byproduct. The polycondensation process requires careful control of reaction conditions, including temperature and the removal of HCl, to ensure the production of high-quality nylon.

Adipoyl chloride is also used in the synthesis of other polymers and as a reagent in organic synthesis, where its reactivity towards nucleophiles can be exploited in various coupling reactions.

Due to its reactive nature, adipoyl chloride must be handled with caution. It is corrosive and can cause severe burns upon contact with skin or eyes. Additionally, its vapors can irritate the respiratory system. Proper safety measures, including the use of personal protective equipment (PPE) and adequate ventilation, are essential when working with this chemical.