4-Vinylcyclohexene

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4-Vinylcyclohexene
4-Vinylcyclohexene
Names
IUPAC name
4-Vinylcyclohexene
Other names
  • Butadiene dimer
  • 4-Ethenylcyclohexene
  • 1-Vinyl-3-cyclohexene
  • 4-Vinyl-1-cyclohexene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.590
EC Number 202-848-9
KEGG
RTECS number GW6650000
UNII
Properties
C8H12
Molar mass 108.18 g·mol−1
Appearance Colorless liquid
Density 0.8299 g/cm3 at 20°C
Melting point −108.9 °C (−164.0 °F; 164.2 K)
Boiling point 128.9 °C (264.0 °F; 402.0 K)
0.05 g/L[1]
Solubility soluble in benzene, diethyl ether, petroleum ether
Vapor pressure 2 kPa
1.4639 (20 °C)
Hazards
Safety data sheet Oxford University
R-phrases (outdated) R20 R22
NFPA 704
Flammability code 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., gasoline Health code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g., sodium chloride Reactivity (yellow): no hazard code Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 21.2 °C (70.2 °F; 294.3 K) [3]
269 °C (516 °F; 542 K)
Lethal dose or concentration (LD, LC):
2563 mg/kg (oral, rat)[2]
Related compounds
Related compounds
1,3-Butadiene
Cyclohexene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

4-Vinylcyclohexene is an organic compound formed when 1,3-butadiene dimerizes in a Diels-Alder reaction.[4] It is found in industrial processes involving 1,3-butadiene, including the manufacture of lauric acid. The 4-vinylcyclohexene formed may be sold as-is or converted to vinylcyclohexene dioxide.

Manufacturing[edit]

Industrially, 4-vinylcyclohexene is manufactured by dimerizing 1,3-butadiene at 110 - 425 °C at pressures of 1.3 - 100 MPa over silicon carbide and salts of copper or chromium.

1,3-Butadiene undergoes a Diels-Alder cycloaddition reaction to form 4-vinylcyclohexane.

Safety[edit]

4-Vinylcyclohexene is classified as a Group 2B carcinogen by the IARC ("possibly carcinogenic to humans").[3]

References[edit]

  1. ^ Lide, David R. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, Florida: CRC Press. pp. 8–111. ISBN 0-8493-0594-2. 
  2. ^ "Safety (MSDS) data for 4-vinylcyclohexene". Oxford University. Retrieved 2009-04-19. 
  3. ^ a b "4-Vinylcyclohexene" (PDF). IARC. Retrieved 2009-04-19. 
  4. ^ Wittcoff, Harold; Reuben, B. G.; Plotkin, Jeffrey S. (1998). Industrial Organic Chemicals (2 ed.). Wiley-Interscience. pp. 236–7. ISBN 978-0-471-44385-8. Retrieved 2009-04-19.