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| Names | |
|---|---|
| Preferred IUPAC name Cyclododecane | |
| Identifiers | |
| |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.005.486 |
| UNII | |
| |
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| 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° | |
Lattice volume (V) | 589.7 Å3 |
Formula units (Z) | 2 |
| Hazards | |
| GHS labelling: | |
| H413[3] | |
| P273,P501[3] | |
| Flash point | 87.6 °C (189.7 °F; 360.8 K) |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Cyclododecane is anorganic compound with thechemical formula (CH2)12.[3] It is a waxy white solid at room temperature,[1]: 17 and is soluble in nonpolar organic solvents.
It is anintermediate ofNylon 12,polyesters, and synthetic lubricating oils.[3]: 8.1 It is also used as a temporarybinder to stabilise fragile objects or to seal water-sensitive parts; it slowlysublimates over days or weeks without leaving any residue.[1]: 17
Cyclododecane is produced industrially through catalytic trimerisation ofbutadiene tocyclododecatriene, followed by hydrogenation.[6]
It is a precursor tolaurolactam, a precursor to the polymerNylon 12.[7]
Cyclododecane is also an intermediate in production offlame retardants,detergents, and other chemicals.
Cyclododecane is also used as avolatile binding medium, a temporary binder for sealing and conservation offriable and structurally weak materials, e.g. duringexcavation and transport ofarchaeological objects and inart 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 nonpolarorganic solvent. Other volatile binding mediums in use arecamphene,tricyclene and with some limitsmenthol.
Cyclododecane is persistent in the environment, as it does not biodegrade easily. Cyclododecane islipophilic, usually present in the environment as adsorbed on the surface of soil particles. It has the potential tobioaccumulate. Cyclododecane may cause long lasting harmful effects to aquatic life.[8]
Cyclododecane has lowring strain. It adopts achiral [3333]conformation with square (D4) symmetry.[4][9][10]: Fig. 70 [11]: 24 While highly stable, this conformation is not derivable from adiamond lattice,[10] unlike the lowest-energy conformations ofcyclohexane,cyclotetradecane, andcyclohexadecane.[9] Monosubstituted cyclododecanes also typically adopt the [3333] conformation,[12]: 5916 though more highly substituted cyclododecanes may adopt alternative conformations, such as [4332].[13]: 10583
Media related toCyclododecane at Wikimedia Commons
