Cyclododecane

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Cyclododecane
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Names
Preferred IUPAC name
Cyclododecane
Identifiers
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3D model (JSmol)
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  • InChI=1S/C12H24/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-12H2 checkY
    Key: DDTBPAQBQHZRDW-UHFFFAOYSA-N checkY
  • InChI=1/C12H24/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-12H2
    Key: DDTBPAQBQHZRDW-UHFFFAOYAN
  • C1CCCCCCCCCCC1
Properties
C12H24
Molar mass 168.324 g·mol−1
Appearance White waxy solid[1]
Density 0.855 g/cm3[2]
Melting point 60.4 °C (140.7 °F; 333.5 K)[3]
Boiling point 244.0 °C (471.2 °F; 517.1 K)[2]
Structure[5]
Monoclinic
C2/m
D4[4]
a = 13.27 Å, b = 8.28 Å, c = 5.44 Å
α = 90°, β = 99.5°, γ = 90°
589.7 Å3
2
Hazards
Flash point 87.6 °C (189.7 °F; 360.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Template:Chembox Footer/trackingTemplate:Short description

Cyclododecane is an organic compound with the chemical formula (CH2)12.[3] It is a waxy white solid at room temperature,[1]Template:Rp and is soluble in nonpolar organic solvents.

It is an intermediate of Nylon 12, polyesters, and synthetic lubricating oils.[3]Template:Rp It is also used as a temporary binder to stabilise fragile objects or to seal water-sensitive parts; it slowly sublimates over days or weeks without leaving any residue.[1]Template:Rp

Synthesis

Cyclododecane is produced industrially through catalytic trimerisation of butadiene to cyclododecatriene, followed by hydrogenation.[6]

Uses

It is a precursor to laurolactam, a precursor to the polymer Nylon 12.[7]

Formation of laurolactam
Formation of laurolactam

Cyclododecane is also an intermediate in production of flame retardants, detergents, and other chemicals.

Cyclododecane is also used as a volatile binding medium, a temporary binder for sealing and conservation of friable and structurally weak materials, e.g. during excavation and transport of archaeological objects and in art restoration, e.g. to protect water-sensitive parts during cleaning.[1] Due to its relatively slow evaporation in comparison with other volatile binding mediums the layer can last for several weeks. Very pure material has to be used so it does not leave any residue. Cyclododecane can be applied in molten state or dissolved in a nonpolar organic solvent. Other volatile binding mediums in use are camphene, tricyclene and with some limits menthol.

Environmental considerations

Cyclododecane is persistent in the environment, as it does not biodegrade easily. Cyclododecane is lipophilic, usually present in the environment as adsorbed on the surface of soil particles. It has the potential to bioaccumulate. Cyclododecane may cause long lasting harmful effects to aquatic life.[8]

Conformation

Cyclododecane has low ring strain. It adopts a chiral [3333] conformation with square (D4) symmetry.[4][9][10]Template:Rp[11]Template:Rp While highly stable, this conformation is not derivable from a diamond lattice,[10] unlike the lowest-energy conformations of cyclohexane, cyclotetradecane, and cyclohexadecane.[9] Monosubstituted cyclododecanes also typically adopt the [3333] conformation,[12]Template:Rp though more highly substituted cyclododecanes may adopt alternative conformations, such as [4332].[13]Template:Rp

References

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  1. ^ a b c d Page Module:Citation/CS1/styles.css has no content.Rowe, Sophie; Rozeik, Christina (2008). "The uses of cyclododecane in conservation". Studies in Conservation. 53: 17–31. doi:10.1179/sic.2008.53.Supplement-2.17. S2CID 192201300.
  2. ^ a b ECHA REACH
  3. ^ a b c d e Template:Cite PubChem
  4. ^ a b Page Module:Citation/CS1/styles.css has no content.Atavin, EG; Mastryukov, VS; Allinger, NL; Almenningen, A; Seip, R (September 1989). "Molecular structure of cyclododecane, C12H24, as determined by electron diffraction and molecular mechanics". Journal of Molecular Structure. 212: 87–95. doi:10.1016/0022-2860(89)85069-0.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Dunitz, JD; Shearer, HMM (1960). "Die Strukturen der mittleren Ringverbindungen III. Die Struktur des Cyclododecans". Helvetica Chimica Acta. 43 (1): 18–35. doi:10.1002/hlca.19600430104.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Arpe, Hans-Jürgen (12 March 2007). Industrielle Organische Chemie (in Deutsch). John Wiley & Sons. p. 291. ISBN 978-3-527-31540-6.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Schiffer, T.; Oenbrink, G. (2009). "Cyclododecanol, Cyclododecanone, and Laurolactam". Ullman's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a08_201.pub2. ISBN 978-3527306732.
  8. ^ Page Module:Citation/CS1/styles.css has no content."Cyclododecane". European Chemicals Agency.
  9. ^ a b Page Module:Citation/CS1/styles.css has no content.Wilen, Samuel H.; Eliel, Ernest Ludwig; Mander, Lewis N. (1994). Stereochemistry of organic compounds. New York: Wiley. p. 769. ISBN 9780471016700.
  10. ^ a b Page Module:Citation/CS1/styles.css has no content.Dragojlovic, Veljko (September 2015). "Conformational analysis of cycloalkanes". ChemTexts. 1 (3). doi:10.1007/s40828-015-0014-0.
  11. ^ Page Module:Citation/CS1/styles.css has no content.Wunderlich, Bernhard; Möller, Martin; Grebowicz, Janusz; Baur, Herbert (1988). "Condis crystals of cyclic alkanes, silanes and related compounds". Conformational Motion and Disorder in Low and High Molecular Mass Crystals. Berlin, Heidelberg: Springer-Verlag Springer e-books. pp. 26–44. doi:10.1007/BFb0008610. ISBN 978-3-540-38867-8.
  12. ^ Page Module:Citation/CS1/styles.css has no content.Khorasani, Sanaz; Fernandes, Manuel A.; Perry, Christopher B. (5 December 2012). "Do 12-Membered Cycloalkane Rings Only Exist As One Conformation in the Solid-State? A Detailed Solid-State Analysis Involving Polymorphs of N,N'-Biscyclododecyl Pyromellitic Diimide". Crystal Growth & Design. 12 (12): 5908–5916. doi:10.1021/cg300765b.
  13. ^ Page Module:Citation/CS1/styles.css has no content.Skibinski, Maciej; Wang, Yi; Slawin, Alexandra M. Z.; Lebl, Tomas; Kirsch, Peer; O'Hagan, David (4 November 2011). "Alicyclic Ring Structure: Conformational Influence of the CF2 Group in Cyclododecanes". Angewandte Chemie International Edition. 50 (45): 10581–10584. doi:10.1002/anie.201105060.
  • Page Template:Sister-inline/styles.css has no content.Script error: No such module "Sister project logo". Media related to Script error: No such module "Commons link". at Wikimedia Commons

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