Vinylcyclohexene dioxide

4-Vinylcyclohexene dioxide (VCD) is an organic compound that contains two epoxide functional groups. It is industrially used as a crosslinking agent for the production of epoxy resins.[5][6] It is a colourless liquid. It is an intermediate for synthesis of organic compounds.[2]

Vinylcyclohexene dioxide
Molecular structure of vinylcyclohexene dioxide
Names
IUPAC name
3-Oxiranyl-7-oxabicyclo[4.1.0]heptane
Other names
1,2-Epoxy-4-(epoxyethyl)cyclohexane
4-Vinylcyclohexene diepoxide
Identifiers
3D model (JSmol)
Abbreviations VCD
ECHA InfoCard 100.003.126
UNII
  • C1CC2C(O2)CC1C3CO3
Properties
C8H12O2
Molar mass 140.182 g·mol−1
Appearance Colorless liquid[1]
Density 1.09 g·cm−3[2][3]
Melting point −108.9 °C (−164.0 °F; 164.2 K)[4]
Boiling point 227 °C (441 °F; 500 K)[4]
Vapor pressure 13 Pa (20 °C)[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation and properties

4-Vinylcyclohexene dioxide is prepared by epoxidation of 4-vinylcyclohexene with peroxybenzoic acid.[5] Its viscosity is 15 mPa·s.[5]

Safety

4-Vinylcyclohexene dioxide, like other volatile epoxides, is classified as an alkylating agent.[5] VCD has toxic effects on fertility. It is a killer of oocytes, eggs in a female's ovaries, in immature ovarian follicles in mice and rats.[7][8][9]

In pest control, it has been used as an ovotoxic agent for reducing rat fertility.[10]

References
  1. Kam-Piu Ho, Wing-Leung Wong, Kin-Ming Lam, Cheuk-Piu Lai, Tak Hang Chan und Kwok-Yin Wong (2008-09-08). "A Simple and Effective Catalytic System for Epoxidation of Aliphatic Terminal Alkenes with Manganese(II) as the Catalyst". Chemistry: A European Journal. 14 (26): 7988–7996. doi:10.1002/chem.200800759. PMID 18618538.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. Kh. M. Alimardanov, O. A. Sadygov, N. I. Garibov und M. Ya. Abdullaeva (2012-11-07). "Liquid-phase synthesis of cyclic diene diepoxides using metal halides and hydrogen peroxide". Russian Journal of Organic Chemistry. 48 (10): 1302–1308. doi:10.1134/S1070428012100077. S2CID 93780572.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. L. A. Mukhamedova, G. Kh. Gil'manova, M. I. Kudryavtseva, F. G. Nasybullina und A. S. Kireeva (July 1982). "Synthesis and testing of the antiviral activity of epoxy and triazo derivatives of cyclohexane". Pharmaceutical Chemistry Journal. 16 (7): 510–514. doi:10.1007/BF00761540. S2CID 44566569.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. Record of CAS RN 106-87-6 in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 24 March 2015.
  5. Pham, Ha Q.; Marks, Maurice J. (2005). "Epoxy Resins". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a09_547.pub2. ISBN 3-527-30673-0.
  6. US 2555500 "Copolymers of 4-vinylcyclohexene dioxide."
  7. Kappeler, Connie J.; Hoyer, Patricia B. (2012-02-01). "4-vinylcyclohexene diepoxide: a model chemical for ovotoxicity". Systems Biology in Reproductive Medicine. 58 (1): 57–62. doi:10.3109/19396368.2011.648820. ISSN 1939-6376. PMC 3307534. PMID 22239082.
  8. Takai, Yasushi; Canning, Jacqueline; Perez, Gloria I.; Pru, James K.; Schlezinger, Jennifer J.; Sherr, David H.; Kolesnick, Richard N.; Yuan, Junying; Flavell, Richard A. (2003-01-01). "Bax, caspase-2, and caspase-3 are required for ovarian follicle loss caused by 4-vinylcyclohexene diepoxide exposure of female mice in vivo". Endocrinology. 144 (1): 69–74. doi:10.1210/en.2002-220814. ISSN 0013-7227. PMID 12488331.
  9. Hoyer, P. B.; Devine, P. J.; Hu, X.; Thompson, K. E.; Sipes, I. G. (2001-02-01). "Ovarian toxicity of 4-vinylcyclohexene diepoxide: a mechanistic model". Toxicologic Pathology. 29 (1): 91–99. doi:10.1080/019262301301418892. ISSN 0192-6233. PMID 11215690. S2CID 33667445.
  10. Hoyer PB, Devine PJ, Hu X, Thompson KE, Sipes IG (Jan–Feb 2001). "Ovarian toxicity of 4-vinylcyclohexene diepoxide: a mechanistic model". Toxicol Pathol. 29 (1): 91–99. doi:10.1080/019262301301418892. PMID 11215690. S2CID 33667445.
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