Cyclododecatriene
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Preferred IUPAC name
(1Z,5E,9E)-Cyclododeca-1,5,9-triene
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3D model (Jmol)
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| Abbreviations | CDT; 1,5,9-CDT |
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| ECHA InfoCard | 100.023.212 |
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PubChem CID
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| Properties | |
| C12H18 | |
| Molar mass | 162.28 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 0.89 g/mL |
| Melting point | −18 °C (0 °F; 255 K) |
| Boiling point | 231 °C (448 °F; 504 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Cyclododecatrienes are cyclic trienes with the formula C12H18. Four isomers are known for 1,5,9-cyclododecatriene. The trans,trans,cis-isomer is a precursor in the production of nylon-12.
The trans,trans,cis-isomer is obtained by cyclotrimerization of butadiene catalyzed by a mixture of titanium tetrachloride and an organoaluminium co-catalyst. Production capacity in 1995 was 8000 tons.
As aforementioned, titanium catalysts predominately produce the important cis,trans,trans- isomer. The all-trans isomer is, however, the product from nickel- and chromium-catalyzed trimerization reactions. The yield of cyclododecatriene through these methods is often greater than 80%. The principal side products are the dimers and oligomers of butadiene.
All of the isomers of 1,5,9-cyclododecatriene are colorless, possess typical terpene-like odors, and have low melting points. The all-trans isomer melts at 34 °C while the other three isomers melt below room temperature. All of the isomers behave like typical olefins. The all-trans and cis,trans,trans isomers in particular tend to form complexes with transition metals. They also undergo transannular reactions and isomerization.
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:
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