The Synthetic Routes of 4,4′-Diaminodicyclohexylmethane

4,4′-Diaminodicyclohexylmethane, also known as DCDM, is a versatile chemical compound commonly used in various applications in the chemical industry.
The most common synthetic routes for DCDM include the reduction of bis-chloromethyl-diamine and the reduction of N,N-dichloroacetamide.

The first step in the synthesis of DCDM via the reduction of bis-chloromethyl-diamine involves the reaction of sodium cyanide and chloroform to produce hydrogen cyanide and sodium chloride.
The resulting hydrogen cyanide is then treated with a molar excess of sodium amide in the presence of a polar solvent such as dimethylformamide or dimethyl sulfoxide to produce the bis-chloromethyl-diamine.
The bis-chloromethyl-diamine is then reduced using hydrogen in the presence of a transition metal catalyst such as palladium on barium carbonate to produce DCDM.

The second synthetic route for DCDM involves the reduction of N,N-dichloroacetamide.
This process involves the reaction of sodium nitrite and N,N-dichloroacetamide in the presence of a solvent such as acetonitrile or dimethylformamide.
The resulting product is then treated with lithium aluminum hydride in the presence of a polar solvent such as dimethylformamide to reduce the N,N-dichloroacetamide and produce DCDM.

Both of these synthetic routes have their advantages and disadvantages.
The first route involves the use of cheaper and more readily available reagents, but it also produces a higher yield of byproduct carbon disulfide.
The second route uses more expensive reagents, but it produces a lower yield of byproduct carbon disulfide.

One critical aspect of the synthesis of DCDM is the removal of impurities such as metal ions, chloride ions, and excess moisture, which can interfere with downstream applications.
This can be accomplished through a variety of methods, such as filtration, distillation, and crystallization.

DCDM is widely used in a variety of applications in the chemical industry, including as a building block for the production of polymers and as a catalyst for the production of polyethylene terephthalate (PET).
It is also used as a curing agent for the production of unsaturated polyester resins and as a hardener for the production of epoxy resins.

In conclusion, the synthetic routes for 4,4′-diaminodicyclohexylmethane have been well studied and are commonly used in the chemical industry.
The choice of synthetic route will depend on the specific requirements of the application and the availability and cost of the reagents.
The final product must be carefully purified to remove impurities that can interfere with downstream applications.
DCDM is an important building block in the production of a wide range of chemicals and materials.