# Cyclododecatriene
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> Markdown URL: https://mediated.wiki/source/Cyclododecatriene.md
> Source: https://en.wikipedia.org/wiki/Cyclododecatriene
> Source revision: 1347910323
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{Chembox
| Name = ''trans'',''trans'',''cis''-1,5,9-Cyclododecatriene
| ImageFile = Cyclododecatriene.svg
| ImageClass = skin-invert-image
| ImageSize = 120px
| ImageAlt =
| PIN = (1''Z'',5''E'',9''E'')-Cyclododeca-1,5,9-triene
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 706-31-0
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Comment = (''trans'',''trans'',''cis''-1,5,9)
| CASNo1 = 676-22-2
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1_Comment = (''trans'',''trans'',''trans''-1,5,9)
| CASNo2 = 4904-61-4
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2_Comment = (1,5,9; unspecified stereochem)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7K92XVU2C2
| UNII_Comment = (''trans'',''trans'',''cis''-1,5,9)
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1_Comment = (''trans'',''trans'',''trans''-1,5,9)
| UNII1 = PG450K437C
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2_Comment = (1,5,9; unspecified stereochem)
| UNII2 = 6Q5S1IRJ4Q
| SMILES = C1C\C=C\CC\C=C/CC\C=C\1
| PubChem = 6262774
| PubChem_Comment = (''trans'',''trans'',''cis''-1,5,9)
| ChemSpiderID = 4865846
| ChemSpiderID_Comment = (''trans'',''trans'',''cis''-1,5,9)
| InChI = 1/C12H18/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-2,7-10H,3-6,11-12H2/b2-1-,9-7+,10-8+
| InChI_Comment = (''trans'',''trans'',''cis''-1,5,9)
| InChIKey = ZOLLIQAKMYWTBR-RYMQXAEEBC
| StdInChI = 1S/C12H18/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-2,7-10H,3-6,11-12H2/b2-1-,9-7+,10-8+
| StdInChI_Comment = (''trans'',''trans'',''cis''-1,5,9)
| StdInChIKey = ZOLLIQAKMYWTBR-RYMQXAEESA-N
| Abbreviations = CDT; 1,5,9-CDT}}
|Section2={{Chembox Properties
| C=12 | H=18
| Appearance = Colorless liquid
| Density = 0.89 g/mL[{{cite web | url = http://www.sigmaaldrich.com/catalog/product/aldrich/c97482?lang=en | publisher = [Sigma-Aldrich](/source/Sigma-Aldrich) | title = trans,trans,cis-1,5,9-Cyclododecatriene}}]
| MeltingPtC = -18
| MeltingPt_ref = [
| BoilingPtC = 231
| BoilingPt_ref = ][
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
'''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](/source/nylon-12).
:400px|thumb|class=skin-invert-image|left|The four isomers of 1,5,9-cyclododecatriene. Left to right: all-''cis''; all-''trans''; ''cis'',''trans'',''trans''; and ''cis'',''cis'',''trans''{{clear-left}}
==Production==
The ''trans'',''trans'',''cis''-isomer is obtained by cyclotrimerization of [butadiene](/source/butadiene) catalyzed by a mixture of [titanium tetrachloride](/source/titanium_tetrachloride) and an [organoaluminium](/source/organoaluminium) [co-catalyst](/source/co-catalyst). Production capacity in 1995 was 8000 tons.][{{cite book | author = Klaus Weissermel, Hans-Jurgen Arpe | title = Industrial Organic Chemistry | publisher = John Wiley & Sons | edition = 3rd | date = 1997 | isbn = 3-527-28838-4}}]
:thumb|class=skin-invert-image|left|304px|Route to cis,trans,trans-CDT from butadiene{{clear-left}}
As aforementioned, titanium catalysts predominantly 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 [dimer](/source/dimer_(chemistry))s and [oligomers](/source/oligomers) of butadiene.[{{cite book|last1=Oenbrink|first1=G.|last2=Schiffer|first2=T.|title=Ullmann's Encyclopedia of Industrial Chemistry: Cyclododecatriene, Cyclooctadiene, and 4-Vinylcyclohexene|date=2013|publisher=John Wiley & Sons|page=Vol. 2}}]
==Properties==
All of the isomers of 1,5,9-cyclododecatriene are colorless, possess typical [terpene](/source/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](/source/olefins). The all-trans and cis,trans,trans isomers in particular tend to form complexes with [transition metals](/source/transition_metals).[{{cite journal|last1=Wilke|first1=G.|title=COntributions to Organo-NIckel Chemistry.|journal=Angew. Chem. Int. Ed. Engl.|date=1988|volume=27|pages=185–206|doi=10.1002/anie.198801851}}] They also undergo [transannular](/source/transannular) reactions and [isomerization](/source/isomerization).[{{cite web|title=High Performance Building Blocks: 1,5,9-Cyclododecatriene (CDT)|url=http://c8-rings.evonik.com/sites/dc/Downloadcenter/Evonik/Product/C8-Rings/en/Buildingblocks.pdf|website=Evonik Industries|publisher=Evonik Industries|access-date=2014-11-21|archive-date=2014-10-06|archive-url=https://web.archive.org/web/20141006073700/http://c8-rings.evonik.com/sites/dc/Downloadcenter/Evonik/Product/C8-Rings/en/Buildingblocks.pdf|url-status=dead}}]
==Applications==
Cyclododecatriene is the raw material for the production of [dodecanedioic acid](/source/dodecanedioic_acid) (4) through [hydrogenation](/source/hydrogenation) to cyclododecane (2) followed by [air oxidation](/source/air_oxidation) in the presence of [boric acid](/source/boric_acid) at elevated temperatures to a mixture of the [alcohol](/source/Alcohol_(chemistry)) (3a) and the [ketone](/source/ketone) (3b). In the final step this mixture oxidized further by [nitric acid](/source/nitric_acid):
:class=skin-invert-image|500px|Dodecanoic acidSynthesis
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](/source/cyclododecanone) (3b) can be produced through the [dehydrogenation](/source/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](/source/oxime), which yields [laurolactam](/source/laurolactam) after [Beckmann rearrangement](/source/Beckmann_rearrangement). Laurolactam is the precursor to several plastics, such as polyamide 12, which is also known as [nylon 12](/source/nylon_12).[{{cite book|last1=Schiffer|first1=T.|last2=Oenbrink|first2=G.|title=Ullmann's Encyclopedia of Industrial Chemistry: Cyclododecanol, Cyclododecanone, and Laurolactam|date=2009|publisher=Wiley-VCH}}]
Cyclododecatriene (in its usual ''trans'',''trans'',''cis''-isomer) has also been used to produce the flame retardant [hexabromocyclododecane](/source/hexabromocyclododecane) (HBCDD).[{{Cite journal |last=Arsenault |first=Gilles |last2=Konstantinov |first2=Alexandre |last3=Marvin |first3=Chris H. |last4=MacInnis |first4=Gordia |last5=McAlees |first5=Alan |last6=McCrindle |first6=Robert |last7=Riddell |first7=Nicole |last8=Tomy |first8=Gregg T. |last9=Yeo |first9=Brian |date=2007-06-01 |title=Synthesis of the two minor isomers, δ- and ε-1,2,5,6,9,10-hexabromocyclododecane, present in commercial hexabromocyclododecane |url=https://linkinghub.elsevier.com/retrieve/pii/S004565350700207X |journal=Chemosphere |volume=68 |issue=5 |pages=887–892 |doi=10.1016/j.chemosphere.2007.02.005 |issn=0045-6535|url-access=subscription }}] This use is being curtailed due to environmental concerns.
Cyclododecatriene can serve as a ligand for [transition metal complex](/source/transition_metal_complex)es, with each of the three alkenes serving as a pi donor. Both the all-''cis'' [{{Cite journal|last1=Jonas|first1=K.|last2=Heimbach|first2=P.|last3=Wilke|first3=G.|year=1968|title=1,5,9-Cyclododecatriene Complexes of Nickel(0)|journal=Angewandte Chemie International Edition|volume=7|issue=12|pages=949–950|doi=10.1002/anie.196809491}}] and [all-''trans'' nickel(0) complex](/source/trans%2Ctrans%2Ctrans-(1%2C5%2C9-Cyclododecatriene)nickel(0))es[{{cite journal | author-link = Günther Wilke | author = Wilke, G. | title = Contributions to Organo-Nickel Chemistry | journal = Angewandte Chemie International Edition | year = 1988 | volume = 27 | issue = 1 | pages = 185–206 | doi = 10.1002/anie.198801851 }}] are known.
== 2012 Evonik fire ==
In March 2012, a fire at the [Marl Chemical Park](/source/Marl_Chemical_Park) operated by [Evonik Industries](/source/Evonik_Industries)[[http://www.degussa-hpp.com/eng/products/synthetic/cyclododecatriene.shtml commercial supplier Degussa]] in [Marl](/source/Marl%2C_North_Rhine-Westphalia), Germany,[{{Cite web
|title=Fire at the CDT plant on the grounds of the Marl Chemicals Park
|work=Press Release
|publisher= [Evonik Industries](/source/Evonik_Industries)
|date=4 April 2012
|url=http://www.vestamid.com/product/vestamid/en/about/downloads/press-releases/pages/details.aspx?newsid=26363
}}] 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.[{{Cite news
|title=Fire in small German town could curb world car production
|url=https://www.bbc.co.uk/news/business-17769466
|date=19 April 2012
|author=Stephen Evans
|journal=[BBC News Online](/source/BBC_News_Online)
}}] Other biobased polyamides, not dependent on laurolactam or CDT, have been put forward as alternative materials.