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Bicyclohexyl

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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
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.966 Edit this at Wikidata
EC Number
  • 202-161-4
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H22/c1-3-7-11(8-4-1)12-9-5-2-6-10-12/h11-12H,1-10H2Key: WVIIMZNLDWSIRH-UHFFFAOYSA-N
SMILES
  • C1CCC(CC1)C2CCCCC2
Properties
Chemical formula C12H22
Molar mass 166.308 g·mol
Appearance Colorless liquid
Density 0.88273 g/cm
Melting point 4 °C (39 °F; 277 K)
Solubility in water Insoluble
Solubility in other solvents Miscible with organic solvents
Refractive index (nD) 1.4796
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS09: Environmental hazard
Signal word Warning
Hazard statements H315, H319, H410
Precautionary statements P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, P391, P501
Flash point 92 °C (198 °F; 365 K)
Autoignition
temperature 		245 °C (473 °F; 518 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Bicyclohexyl, also known as dicyclohexyl or bicyclohexane, is an organic chemical with the formula C12H22 and a molecular mass of 166.303 g mol. 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.

Production

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

When cyclohexane 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 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°.

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

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.

Heat of combustion is 1814.8 kcal/mol.

Use

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

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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