4-Vinylcyclohexene
| 4-Vinylcyclohexene | |
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4-Vinylcyclohexene |
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Other names
Butadiene dimer, 4-ethenylcyclohexene, 1-vinyl-3-cyclohexene; 4-vinyl-1-cyclohexene |
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| Identifiers | |
| CAS number | 100-40-3  |
| PubChem | 7499 |
| ChemSpider | 7218 |
| KEGG | C19310  |
| RTECS number | GW6650000 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C8H12 |
| Molar mass | 108.181 g/mol |
| Appearance | colorless liquid |
| Density | 0.8299 g/cm3 at 20°C |
| Melting point |
-108.9°C |
| Boiling point |
128.9°C |
| Solubility in water | 0.05 g/L[1] |
| Solubility | soluble in benzene, diethyl ether, petroleum ether |
| Vapor pressure | 2 kPa at 25°C |
| Hazards | |
| MSDS | Oxford University |
| EU Index | Harmful (Xn) |
| R-phrases | R20 R22 |
| Flash point | 21.2°C[2] |
| LD50 | 2563 mg/kg (oral, rat)[3] |
| Related compounds | |
| Related compounds | 1,3-Butadiene Cyclohexene |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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 4-vinylcyclohexene diepoxide.
[edit] Reactions
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.
[edit] Safety
4-Vinylcyclohexene is classified as a Group 2B carcinogen by the IARC .[2]
[edit] References
- ^ Lide, David R. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, FL: CRC Press. pp. 8–111. ISBN 0-8493-0594-2.
- ^ a b "4-Vinylcyclohexene". IARC. http://monographs.iarc.fr/ENG/Monographs/vol60/mono60-13.pdf. Retrieved 2009-04-19.
- ^ "Safety (MSDS) data for 4-vinylcyclohexene". Oxford University. http://msds.chem.ox.ac.uk/VI/4-vinylcyclohexene.html. Retrieved 2009-04-19.
- ^ 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. http://books.google.com/?id=4KHzc-nYPNsC&pg=PA236&dq=4-vinylcyclohexene+diels-alder. Retrieved 2009-04-19.
