Adiponitrile

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Adiponitrile

Structural formula of adiponitrile
3D ball model of adiponitrile

Adiponitrile is an organic compound with the formula (CH_)_(CN)_. It is a nitrile, which is a type of organic compound containing a cyano group (_C_N). Adiponitrile is a key intermediate in the production of nylon, specifically nylon 6,6.

Structure and Properties

Adiponitrile is a colorless liquid with a faint odor. It is composed of a six-carbon chain with nitrile groups at each end. The chemical structure can be represented as NC(CH_)_CN. The presence of the nitrile groups makes adiponitrile a polar molecule, which affects its solubility and reactivity.

Synthesis

Adiponitrile is primarily produced through the hydrocyanation of butadiene. This process involves the addition of hydrogen cyanide (HCN) to butadiene to form adiponitrile. The reaction is catalyzed by nickel complexes. The overall reaction can be summarized as follows:

Hydrocyanation of butadiene to adiponitrile

Another method of synthesis involves the electrochemical hydrodimerization of acrylonitrile.

Synthesis of adiponitrile from acrylonitrile

Applications

The primary use of adiponitrile is in the production of hexamethylenediamine, which is a precursor to nylon 6,6. Nylon 6,6 is a widely used synthetic polymer with applications in textiles, automotive parts, and various consumer goods.

Safety and Handling

Adiponitrile is classified as a hazardous material. It is important to handle it with care, using appropriate personal protective equipment. It can cause irritation to the skin, eyes, and respiratory tract. In case of exposure, it is advised to seek medical attention immediately.

Related pages

Gallery

  • Structural formula of adiponitrile

  • 3D ball model of adiponitrile

  • Hydrocyanation of butadiene to adiponitrile

  • Synthesis of adiponitrile from acrylonitrile

  • Structural formula of Adiponitrile

  • 3D ball model of Adiponitrile

  • Butadiene Hydrocyanation process

  • Synthesis of Adiponitrile

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Contributors: Prab R. Tumpati, MD