Cyclododecatriene

Cyclododecatriene C₁₂H₁₈ is a cycloalkene with three alkene groups. The 1,3,5-trans-trans-cis isomer has some industrial importance ^[1] and is obtained by cyclotrimerization of butadiene with titanium tetrachloride and an organo-aluminum co-catalyst ^[2]:

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This compound is the raw material for the production of 1,12-dodecanedioic acid through hydrogenation to cyclododecane followed by organic oxidation with boric acid at elevated temperatures to a mixture of the alcohol and the ketone. In the final step this mixture oxidized further by nitric acid:

The acid is used in the production of polyamides.

References

1. ^ 1995 figures for global annual capacity 8000 ton
2. ^ Industrial Organic Chemistry, Klaus Weissermel, Hans-Jurgen Arpe John Wiley & Sons; 3rd 1997 ISBN 3-527-28838-4