Bicyclohexyl

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 227 °C (441 °F). Its structure consists of two cyclohexane rings joined by a single carbon-carbon bond.

Bicyclohexyl
Structural formula of bicyclohexyl
3D ball-and-stick structure of bicyclohexyl
Names
Preferred IUPAC name
1,1′-Bi(cyclohexane)
Other names
  • 1,1′-Bicyclohexyl
  • Bicyclohexane
  • Dicyclohexyl
  • Cyclohexylcyclohexane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.966
EC Number
  • 202-161-4
UNII
  • InChI=1S/C12H22/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h11-12H,1-10H2
    Key: WVIIMZNLDWSIRH-UHFFFAOYSA-N
  • C1CCC(CC1)C2CCCCC2
Properties
C12H22
Molar mass 166.308 g·mol−1
Appearance Colorless liquid
Density 0.88273 g/cm3
Melting point 4 °C (39 °F; 277 K)
Insoluble
Solubility in other solvents Miscible with organic solvents
1.4796[1]
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H315, H319, H410
P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, P391, P501
Flash point 92 °C (198 °F; 365 K)
245 °C (473 °F; 518 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Production

Carbazole can be denitrogenated by hydrogen to yield bicyclohexyl as the main product.[2]

When cyclohexane is exposed to radiation, bicyclohexyl is produced among other hydrocarbons.[3]

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°.[4]

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.[5]

When bicyclohexyl is heated to around 427 °C (801 °F) it slowly decomposes to cyclohexane and cyclohexene, as the pivot bond joining the two rings is the longest and weakest one.[6]

Heat of combustion is 1814.8 kcal/mol.[7]

Use

Bicyclohexyl has uses in organic synthesis as a building block and structural motif, in studying the chemistry of liquid interfaces,[8] and in surface modification of metal oxides as a solvent.[9]

See also

References
  1. Ferris, S. W. (2013). Handbook of Hydrocarbons. Elsevier. p. 214. ISBN 9781483272856.
  2. Occelli, Mario L. (1996). Hydrotreating Technology for Pollution Control: Catalysts, Catalysis, and Processes. CRC Press. pp. 263–265. ISBN 9780824797560.
  3. Nixon, A. C.; Thorpe, R. E. (May 1958). "Radiation Chemistry of Cyclohexane". The Journal of Chemical Physics. 28 (5): 1004–1005. Bibcode:1958JChPh..28.1004N. doi:10.1063/1.1744261.
  4. Dorofeeva, O.V.; Mastryukov, V.S.; Almenningen, A.; Horn, A.; Klaeboe, P.; Yang, L.; Allinger, N.L. (December 1991). "Molecular structure and conformations of bicyclohexyl, (C6H11)2, as studied by electron diffraction, vibrational spectroscopy and molecular mechanics". Journal of Molecular Structure. 263 (1–2): 281–297. Bibcode:1991JMoSt.263..281D. doi:10.1016/0022-2860(91)80071-B.
  5. Tardajos, G.; Diaz Pena, M.; Lainez, A.; Aicart, E. (October 1986). "Speed of sound in and isothermal compressibility and isobaric expansivity of pure liquids at 298.15 K". Journal of Chemical & Engineering Data. 31 (4): 492–493. doi:10.1021/je00046a031.
  6. Yue, Lei; Qin, Xiaomei; Wu, Xi; Guo, Yongsheng; Xu, Li; Xie, Hujun; Fang, Wenjun (2 July 2014). "Thermal Decomposition Kinetics and Mechanism of 1,1′-Bicyclohexyl". Energy & Fuels. 28 (7): 4523–4531. doi:10.1021/ef501077n.
  7. Good, W.D.; Lee, S.H. (July 1976). "The enthalpies of formation of selected naphthalenes, diphenylmethanes, and bicyclic hydrocarbons". The Journal of Chemical Thermodynamics. 8 (7): 643–650. doi:10.1016/0021-9614(76)90015-X.
  8. Thoma, M; Schwendler, M; Baltes, H; Helm, C. A; Pfohl, T; Riegler, H; Möhwald, H (1996). "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. doi:10.1021/la9508194.
  9. Pujari, Sidharam P; Scheres, Luc; Marcelis, Antonius T. M; Zuilhof, Han (2014). "Covalent Surface Modification of Oxide Surfaces". Angewandte Chemie International Edition. 53 (25): 6322–56. doi:10.1002/anie.201306709. PMID 24849332.
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