Cyclododecane
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Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox headerbarTemplate:Chembox PointGroupTemplate:Chembox CrystalStructVolumeTemplate:Chembox CrystalStructFormulasTemplate:Chembox headerbarTemplate:Chembox GHS (set)Template:Chembox Datapage checkTemplate:Chembox Footer| Template:Longitem | Template:Unbulleted list |
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| Template:Longitem | Template:Chembox Elements/molecular formula |
| Molar mass | Template:Chem molar mass |
| Appearance | White waxy solid[1] |
| Density | 0.855 g/cm3[2] |
| Melting point | Template:Chembox CalcTemperatures |
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| Template:Longitem | Monoclinic |
| Template:Longitem | C2/m |
| Template:Longitem | a = 13.27 Å, b = 8.28 Å, c = 5.44 Å α = 90°, β = 99.5°, γ = 90°
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Cyclododecane is an organic compound with the chemical formula (CH2)12.[4] 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.[4]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.[5]
Uses
It is a precursor to laurolactam, a precursor to the polymer Nylon 12.[6]
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.[7]
Conformation
Cyclododecane has low ring strain. It adopts a chiral [3333] conformation with square (D4) symmetry.[3][8][9]Template:Rp[10]Template:Rp While highly stable, this conformation is not derivable from a diamond lattice,[9] unlike the lowest-energy conformations of cyclohexane, cyclotetradecane, and cyclohexadecane.[8] Monosubstituted cyclododecanes also typically adopt the [3333] conformation,[11]Template:Rp though more highly substituted cyclododecanes may adopt alternative conformations, such as [4332].[12]Template:Rp
References
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External links
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