Cyclododecatriene

Cyclododecatriene is the raw material for the production of dodecanedioic acid (4) through hydrogenation to cyclododecane (2) followed by air oxidation in the presence of boric acid at elevated temperatures to a mixture of the alcohol (3a) and the ketone (3b). In the final step this mixture oxidized further by nitric acid:

The alcohol (3a) and the ketone (3b) can be purified from the alcohol/ketone mixture under different reaction conditions. Pure cyclododecanol (3a) can be produced from the hydrogenation of the mixture in the presence of a copper-chromium catalyst at 30 MPa and 160 °C. Pure cyclododecanone (3b) can be produced through the dehydrogenation of the mixture over copper or copper-chromium catalysts on an active support at a temperature range of 230–245 °C and atmospheric pressure. Pure cyclododecanone can then be converted into cyclododecanone oxime, which yields laurolactam after Beckmann rearrangement. Laurolactam is the precursor to several plastics, such as polyamide 12, which is also known as nylon 12.^[6]

Cyclododecatriene (in its usual trans,trans,cis-isomer) has also been used to produce the flame retardant hexabromocyclododecane (HBCDD).^[7] This use is being curtailed due to environmental concerns.

Cyclododecatriene can serve as a ligand for transition metal complexes, with each of the three alkenes serving as a pi donor. Both the all-cis ^[8] and all-trans nickel(0) complexes^[9] are known.

In March 2012, a fire at the Marl Chemical Park operated by Evonik Industries^[10] in Marl, Germany,^[11] stopped production for an expected duration of several months. The plant produced a substantial proportion of the world's production of CDT, particularly that needed to produce laurolactam, a precursor to the polyamide PA12. This in turn led to concerns for global production of finished goods, particularly in the automotive industry.^[12] Other biobased polyamides, not dependent on laurolactam or CDT, have been put forward as alternative materials.^[11]