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Cyclododecane

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Cyclododecane
Structural formula of cyclododecane
Ball-and-stick model of the cyclododecane molecule
Names
Preferred IUPAC name Cyclododecane
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.486 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H24/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-12H2Key: DDTBPAQBQHZRDW-UHFFFAOYSA-N
  • InChI=1/C12H24/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-12H2Key: DDTBPAQBQHZRDW-UHFFFAOYAN
SMILES
  • C1CCCCCCCCCCC1
Properties
Chemical formula C12H24
Molar mass 168.324 g·mol
Appearance White waxy solid
Density 0.855 g/cm
Melting point 60.4 °C (140.7 °F; 333.5 K)
Boiling point 244.0 °C (471.2 °F; 517.1 K)
Structure
Crystal structure Monoclinic
Space group C2/m
Point group D4
Lattice constant a = 13.27 Å, b = 8.28 Å, c = 5.44 Åα = 90°, β = 99.5°, γ = 90°
Lattice volume (V) 589.7 Å
Formula units (Z) 2
Hazards
GHS labelling:
Hazard statements H413
Precautionary statements P273, P501
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

It is an intermediate of Nylon 12, polyesters, and synthetic lubricating oils. 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.

Synthesis

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

Uses

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

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. 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.

Conformation

Cyclododecane has low ring strain. It adopts a chiral conformation with square (D4) symmetry. While highly stable, this conformation is not derivable from a diamond lattice, unlike the lowest-energy conformations of cyclohexane, cyclotetradecane, and cyclohexadecane. Monosubstituted cyclododecanes also typically adopt the conformation, though more highly substituted cyclododecanes may adopt alternative conformations, such as .

References

  1. ^ 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. ^ ECHA REACH
  3. ^ "Cyclododecane". PubChem. National Center for Biotechnology Information. Retrieved 1 September 2021.
  4. ^ 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. 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. Arpe, Hans-Jürgen (12 March 2007). Industrielle Organische Chemie (in German). John Wiley & Sons. p. 291. ISBN 978-3-527-31540-6.
  7. 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. "Cyclododecane". European Chemicals Agency.
  9. ^ Wilen, Samuel H.; Eliel, Ernest Ludwig; Mander, Lewis N. (1994). Stereochemistry of organic compounds. New York: Wiley. p. 769. ISBN 9780471016700.
  10. ^ Dragojlovic, Veljko (September 2015). "Conformational analysis of cycloalkanes". ChemTexts. 1 (3). doi:10.1007/s40828-015-0014-0.
  11. 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. 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. 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.

External links

Cycloalkanes
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