Bicyclohexyl, also known as dicyclohexyl or bicyclohexane, is an

organic chemical In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula C₁₂H₂₂ and a molecular mass of 166.303 g mol⁻¹. It is a nonvolatile

liquid A liquid is a nearly incompressible fluid that conforms to the shape of its container but retains a (nearly) constant volume independent of pressure. As such, it is one of the four fundamental states of matter (the others being solid, gas, an ...

at room temperature, with a boiling point of . Its structure consists of two

cyclohexane Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colorless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohex ...

rings joined by a single carbon-carbon bond.

Production

Carbazole Carbazole is an aromatic heterocyclic organic compound. It has a tricyclic structure, consisting of two six-membered benzene rings fused on either side of a five-membered nitrogen-containing ring. The compound's structure is based on the indole st ...

can be denitrogenated by hydrogen to yield bicyclohexyl as the main product. When

is exposed to radiation, bicyclohexyl is produced among other hydrocarbons.

Properties

The molecule is not completely flat, and the two rings are twisted compared to each other. Liquid bicyclohexyl contains a mixture of molecules with C₂ and C_2h symmetry termed ee anti, and ee gauche. The carbon-carbon bond (pivot) between the rings is 1.55 Å, and the carbon-carbon length in the rings is 1.535 Å and carbon-hydrogen bond length is 1.102 Å. The torsion angle between the rings is 74.9°. The C-C-C bond angle ∠ is about 111° and C-C-H angle is 109°. The

speed of sound The speed of sound is the distance travelled per unit of time by a sound wave as it propagates through an elastic medium. At , the speed of sound in air is about , or one kilometre in or one mile in . It depends strongly on temperature as ...

in bicyclohexyl is 1441.51 m/s, higher than many other hydrocarbons. The density is 882.73 kgm⁻¹. The

isothermal compressibility In thermodynamics and fluid mechanics, the compressibility (also known as the coefficient of compressibility or, if the temperature is held constant, the isothermal compressibility) is a measure of the instantaneous relative volume change of a f ...

is 674 TPa⁻¹ and isobaric expansivity is 819 K⁻¹. When bicyclohexyl is heated to around it slowly decomposes to

and

cyclohexene Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkene is a colorless liquid with a sharp smell. It is an intermediate in various industrial processes. Cyclohexene is not very stable upon long term storage with exposure to light a ...

, as the pivot bond joining the two rings is the longest and weakest one. Heat of combustion is 1814.8 kcal/mol.

Use

Bicyclohexyl has uses in

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

as a building block and structural motif, in studying the chemistry of

liquid interfaces A liquid is a nearly incompressible fluid that conforms to the shape of its container but retains a (nearly) constant volume independent of pressure. As such, it is one of the four fundamental states of matter (the others being solid, gas, an ...

, and in surface modification of metal oxides as a solvent.

References

{{reflist Cyclohexyl compounds Hydrocarbons

Production

Properties

Use

See also

References