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.
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 dimers and oligomers of butadiene.[3]
Propertiesedit
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.[4] They also undergo transannular reactions and isomerization.[5]
Applicationedit
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]
2012 Evonik fireedit
In March 2012, a fire at the Marl Chemical Park operated by Evonik Industries[7] in Marl, Germany,[8] 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.[9] Other biobased polyamides, not dependent on laurolactam or CDT, have been put forward as alternative materials.[8]
^Oenbrink, G.; Schiffer, T. (2013). Ullmann's Encyclopedia of Industrial Chemistry: Cyclododecatriene, Cyclooctadiene, and 4-Vinylcyclohexene. John Wiley & Sons. p. Vol. 2.
^Wilke, G. (1988). "COntributions to Organo-NIckel Chemistry". Angew. Chem. Int. Ed. Engl. 27: 185–206. doi:10.1002/anie.198801851.
^ ab"Fire at the CDT plant on the grounds of the Marl Chemicals Park". Press Release. Evonik Industries. 4 April 2012.
^Stephen Evans (19 April 2012). "Fire in small German town could curb world car production". BBC News Online.
November 25, 2023
cyclododecatriene, cyclic, trienes, with, formula, c12h18, four, isomers, known, cyclododecatriene, trans, trans, isomer, precursor, production, nylon, trans, trans, namespreferred, iupac, name, cyclododeca, trieneidentifierscas, number, trans, trans, y676, tr. 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 trans trans cis 1 5 9 Cyclododecatriene NamesPreferred IUPAC name 1Z 5E 9E Cyclododeca 1 5 9 trieneIdentifiersCAS Number 706 31 0 trans trans cis 1 5 9 Y676 22 2 trans trans trans 1 5 9 Y4904 61 4 1 5 9 unspecified stereochem Y3D model JSmol Interactive imageAbbreviations CDT 1 5 9 CDTChemSpider 4865846 trans trans cis 1 5 9 ECHA InfoCard 100 023 212PubChem CID 6262774 trans trans cis 1 5 9 UNII 7K92XVU2C2 trans trans cis 1 5 9 YPG450K437C trans trans trans 1 5 9 Y6Q5S1IRJ4Q 1 5 9 unspecified stereochem YCompTox Dashboard EPA DTXSID8027581InChI InChI 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 Key ZOLLIQAKMYWTBR RYMQXAEESA N 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 Key ZOLLIQAKMYWTBR RYMQXAEEBCSMILES C1C C C CC C C CC C C 1PropertiesChemical formula C 12H 18Molar mass 162 276 g mol 1Appearance Colorless liquidDensity 0 89 g mL 1 Melting point 18 C 0 F 255 K 1 Boiling point 231 C 448 F 504 K 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references The four isomers of 1 5 9 cyclododecatriene Left to right all cis all trans cis trans trans and cis cis transContents 1 Production 2 Properties 3 Application 4 2012 Evonik fire 5 ReferencesProduction editThe 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 2 nbsp 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 dimers and oligomers of butadiene 3 Properties editAll 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 4 They also undergo transannular reactions and isomerization 5 Application editCyclododecatriene 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 nbsp 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 2012 Evonik fire editIn March 2012 a fire at the Marl Chemical Park operated by Evonik Industries 7 in Marl Germany 8 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 9 Other biobased polyamides not dependent on laurolactam or CDT have been put forward as alternative materials 8 References edit a b c trans trans cis 1 5 9 Cyclododecatriene Sigma Aldrich Klaus Weissermel Hans Jurgen Arpe 1997 Industrial Organic Chemistry 3rd ed John Wiley amp Sons ISBN 3 527 28838 4 Oenbrink G Schiffer T 2013 Ullmann s Encyclopedia of Industrial Chemistry Cyclododecatriene Cyclooctadiene and 4 Vinylcyclohexene John Wiley amp Sons p Vol 2 Wilke G 1988 COntributions to Organo NIckel Chemistry Angew Chem Int Ed Engl 27 185 206 doi 10 1002 anie 198801851 High Performance Building Blocks 1 5 9 Cyclododecatriene CDT PDF Evonik Industries Evonik Industries Schiffer T Oenbrink G 2009 Ullmann s Encyclopedia of Industrial Chemistry Cyclododecanol Cyclododecanone and Laurolactam Wiley VCH commercial supplier Degussa a b Fire at the CDT plant on the grounds of the Marl Chemicals Park Press Release Evonik Industries 4 April 2012 Stephen Evans 19 April 2012 Fire in small German town could curb world car production BBC News Online Retrieved from https en wikipedia org w index php title Cyclododecatriene amp oldid 1158005049, wikipedia, wiki, book, books, library,
