Cyclododecane

Cyclododecane
Structural formula of cyclododecane
Ball-and-stick model of the cyclododecane molecule
Names
Preferred IUPAC name
Cyclododecane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.005.486
UNII
  • 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 0.79 g/cm3
Melting point 60.4 °C (140.7 °F; 333.5 K)[2]
Boiling point 247.0 °C (476.6 °F; 520.1 K)[2]
Hazards
GHS labelling:
H413[2]
P273, P501[2]
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).
☒N verify (what is checkY☒N ?)
Infobox references

Cyclododecane is an organic compound with the chemical formula (CH2)12.[2] It is a waxy white solid at room temperature,[1]: 17  and is soluble in nonpolar organic solvents.

It is an intermediate of Nylon 12, polyesters, and synthetic lubricating oils.[2]: 8.1  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]: 17 

Synthesis

Cyclododecane is produced industrially through catalytic trimerisation of butadiene to cyclododecatriene, followed by hydrogenation.[3]

Uses

It is a precursor to laurolactam, a precursor to the polymer Nylon 12.[4]

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.[5]

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. "Cyclododecane". PubChem. National Center for Biotechnology Information. Retrieved 1 September 2021.
  3. Arpe, Hans-Jürgen. Industrielle Organische Chemie (in German). p. 291. ISBN 978-3-527-31540-6.
  4. 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.
  5. "Cyclododecane". European Chemicals Agency.
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