Cyclohexene

Last updated
Cyclohexene
Olefine am Beispiel von Cycloalken-v2.svg
Cyclohexene for highscool.svg
Cyclohexene-conformation-2D-skeletal.png
Cyclohexene-from-xtal-3D-bs-17.png
Names
Preferred IUPAC name
Cyclohexene
Other names
Tetrahydrobenzene, 1,2,3,4-Tetrahydrobenzene, Benzenetetrahydride, Cyclohex-1-ene, Hexanaphthylene, UN 2256
Identifiers
3D model (JSmol)
906737
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.462 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-807-8
1659
PubChem CID
RTECS number
  • GW2500000
UNII
  • InChI=1S/C6H10/c1-2-4-6-5-3-1/h1-2H,3-6H2 Yes check.svgY
    Key: HGCIXCUEYOPUTN-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H10/c1-2-4-6-5-3-1/h1-2H,3-6H2
    Key: HGCIXCUEYOPUTN-UHFFFAOYAQ
  • C1CCC=CC1
Properties
C6H10
Molar mass 82.143 g/mol
Appearancecolorless liquid
Odor sweet
Density 0.8110 g/cm3
Melting point −103.5 °C (−154.3 °F; 169.7 K)
Boiling point 82.98 °C (181.36 °F; 356.13 K)
slightly soluble in water
Solubility miscible with organic solvents
Vapor pressure 8.93 kPa (20 °C)

11.9 kPa (25 °C)

0.022 mol·kg−1·bar−1
-57.5·10−6 cm3/mol
1.4465
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H225, H302, H305, H311, H411
P210, P233, P240, P241, P242, P243, P264, P270, P273, P280, P301+P310, P301+P312, P302+P352, P303+P361+P353, P312, P322, P330, P331, P361, P363, P370+P378, P391, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
3
0
Flash point −12 °C (10 °F; 261 K)
244 °C (471 °F; 517 K)
Explosive limits 0.8–5 %
Lethal dose or concentration (LD, LC):
1407 mg/kg (oral, rat)
13,196 ppm (mouse, 2 hr) [1]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 300 ppm (1015 mg/m3) [2]
REL (Recommended)
TWA 300 ppm (1015 mg/m3) [2]
IDLH (Immediate danger)
2000 ppm [2]
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Cyclohexene is a hydrocarbon with the formula (CH2)4C2H2. It is an example of a cycloalkene. At room temperature, cyclohexene is a colorless liquid with a sharp odor. Among its uses, it is an intermediate in the commercial synthesis of nylon. [3]

Contents

Production and uses

Cyclohexene is produced by the partial hydrogenation of benzene, a process developed by the Asahi Chemical company. [4] The main product of the process is cyclohexane because cyclohexene is more easily hydrogenated than benzene.

In the laboratory, it can be prepared by dehydration of cyclohexanol. [5]

C6H11OH → C6H10 + H2O

Reactions and uses

Benzene is converted to cyclohexylbenzene by acid-catalyzed alkylation with cyclohexene. [6] Cyclohexylbenzene is a precursor to both phenol and cyclohexanone. [7]

Hydration of cyclohexene gives cyclohexanol, which can be dehydrogenated to give cyclohexanone, a precursor to caprolactam. [8]

The oxidative cleavage of cyclohexene gives adipic acid. Hydrogen peroxide is used as the oxidant in the presence of a tungsten catalyst. [9]

1,5-Hexadiene is produced by ethenolysis of cyclohexene. Bromination gives 1,2-dibromocyclohexane. [10]

Structure

Cyclohexene is most stable in a half-chair conformation, [11] unlike the preference for a chair form of cyclohexane. One basis for the cyclohexane conformational preference for a chair is that it allows each bond of the ring to adopt a staggered conformation. For cyclohexene, however, the alkene is planar, equivalent to an eclipsed conformation at that bond.

See also

Related Research Articles

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Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products. Cyclohexane is mainly used for the industrial production of adipic acid and caprolactam, which are precursors to nylon.

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<span class="mw-page-title-main">Cyclohexanol</span> Chemical compound

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<i>o</i>-Xylene Chemical compound

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<span class="mw-page-title-main">4-Nitroaniline</span> Chemical compound

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<span class="mw-page-title-main">Cyclohexylbenzene</span> Chemical compound

Cyclohexylbenzene is the organic compound with the structural formula C6H5−C6H11. It is a derivative of benzene with a cyclohexyl substituent (C6H11). It is a colorless liquid.

References

  1. ↑ "Cyclohexene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 3 NIOSH Pocket Guide to Chemical Hazards. "#0167". National Institute for Occupational Safety and Health (NIOSH).
  3. ↑ Xie, Feng; Chen, Lihang; Cedeño Morales, Eder Moisés; Ullah, Saif; Fu, Yiwen; Thonhauser, Timo; Tan, Kui; Bao, Zongbi; Li, Jing (2024). "Complete separation of benzene-cyclohexene-cyclohexane mixtures via temperature-dependent molecular sieving by a flexible chain-like coordination polymer". Nature Communications. 15 (1): 2240. Bibcode:2024NatCo..15.2240X. doi:10.1038/s41467-024-46556-6. PMC   10933443 . PMID   38472202.
  4. ↑ US 9771313,Narisawa, Naoki&Tanaka, Katsutoshi,"Cyclohexanol, method for producing cyclohexanol, and method for producing adipic acid",published 26 Sep 2017
  5. ↑ G. H. Coleman, H. F. Johnstone (1925). "Cyclohexene". Organic Syntheses. 5: 33. doi:10.15227/orgsyn.005.0033.
  6. ↑ B. B. Corson, V. N. Ipatieff (1939). "Cyclohexylbenzene". Organic Syntheses. 19: 36. doi:10.15227/orgsyn.019.0036.
  7. ↑ Plotkin, Jeffrey S. (2016-03-21). "What's New in Phenol Production?". American Chemical Society. Archived from the original on 2019-10-27. Retrieved 2018-01-02.
  8. ↑ Musser, Michael T. (2005). "Cyclohexanol and Cyclohexanone". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_217. ISBN   978-3527306732.
  9. ↑ Reed, Scott M.; Hutchison, James E. (2000). "Green Chemistry in the Organic Teaching Laboratory: An Environmentally Benign Synthesis of Adipic Acid". J. Chem. Educ. 77 (12): 1627–1629. Bibcode:2000JChEd..77.1627R. doi:10.1021/ed077p1627.
  10. ↑ H. R. Snyder, L. A. Brooks (1932). "1,2-Dibromocyclohexane". Organic Syntheses. 12: 26. doi:10.15227/orgsyn.012.0026.
  11. ↑ Jensen, Frederick R.; Bushweller, C. Hackett (1969). "Conformational preferences and interconversion barriers in cyclohexene and derivatives". J. Am. Chem. Soc. 91 (21): 5774–5782. doi:10.1021/ja01049a013.
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