Bicyclohexyl Explained

Bicyclohexyl, also known as dicyclohexyl or bicyclohexane, is an organic chemical with the formula C12H22 and a molecular mass of 166.303 g mol−1. It is a nonvolatile liquid at room temperature, with a boiling point of . Its structure consists of two cyclohexane rings joined by a single carbon-carbon bond.

Production

Carbazole can be denitrogenated by hydrogen to yield bicyclohexyl as the main product.[1]

When cyclohexane is exposed to radiation, bicyclohexyl is produced among other hydrocarbons.[2]

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 C2h 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°.[3]

The speed of sound in bicyclohexyl is 1441.51 m/s, higher than many other hydrocarbons. The density is 882.73 kgm−1. The isothermal compressibility is 674 TPa−1 and isobaric expansivity is 819 K−1.[4]

When bicyclohexyl is heated to around it slowly decomposes to cyclohexane and cyclohexene, as the pivot bond joining the two rings is the longest and weakest one.[5]

Heat of combustion is 1814.8 kcal/mol.[6]

Use

Bicyclohexyl has uses in organic synthesis as a building block and structural motif, in studying the chemistry of liquid interfaces,[7] and in surface modification of metal oxides as a solvent.[8]

See also

Notes and References

  1. Book: Occelli. Mario L.. Hydrotreating Technology for Pollution Control: Catalysts, Catalysis, and Processes. 1996. CRC Press. 9780824797560. 263–265. en.
  2. Nixon. A. C.. Thorpe. R. E.. Radiation Chemistry of Cyclohexane. The Journal of Chemical Physics. May 1958. 28. 5. 1004–1005. 10.1063/1.1744261. 1958JChPh..28.1004N .
  3. Dorofeeva. O.V.. Mastryukov. V.S.. Almenningen. A.. Horn. A.. Klaeboe. P.. Yang. L.. Allinger. N.L.. Molecular structure and conformations of bicyclohexyl, (C6H11)2, as studied by electron diffraction, vibrational spectroscopy and molecular mechanics. Journal of Molecular Structure. December 1991. 263. 1–2 . 281–297. 10.1016/0022-2860(91)80071-B. 1991JMoSt.263..281D .
  4. Tardajos. G.. Diaz Pena. M.. Lainez. A.. Aicart. E.. Speed of sound in and isothermal compressibility and isobaric expansivity of pure liquids at 298.15 K. Journal of Chemical & Engineering Data. October 1986. 31. 4. 492–493. 10.1021/je00046a031.
  5. Yue. Lei. Qin. Xiaomei. Wu. Xi. Guo. Yongsheng. Xu. Li. Xie. Hujun. Fang. Wenjun. Thermal Decomposition Kinetics and Mechanism of 1,1′-Bicyclohexyl. Energy & Fuels. 2 July 2014. 28. 7. 4523–4531. 10.1021/ef501077n.
  6. Good. W.D.. Lee. S.H.. The enthalpies of formation of selected naphthalenes, diphenylmethanes, and bicyclic hydrocarbons. The Journal of Chemical Thermodynamics. July 1976. 8. 7. 643–650. 10.1016/0021-9614(76)90015-X.
  7. 10.1021/la9508194. Ellipsometry and X-ray Reflectivity Studies on Monolayers of Phosphatidylethanolamine and Phosphatidylcholine in Contact with n-Dodecane,n-Hexadecane, and Bicyclohexyl. Langmuir. 12. 7. 1722. 1996. Thoma. M. Schwendler. M. Baltes. H. Helm. C. A. Pfohl. T. Riegler. H. Möhwald. H.
  8. 10.1002/anie.201306709. 24849332. Covalent Surface Modification of Oxide Surfaces. Angewandte Chemie International Edition. 53. 25. 6322–56. 2014. Pujari. Sidharam P. Scheres. Luc. Marcelis. Antonius T. M. Zuilhof. Han.