4-Vinylcyclohexene dioxide (VCD) is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

that contains two

epoxide In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ...

functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...

s. It is industrially used as a crosslinking agent for the production of epoxy resins. It is a colourless liquid. It is an intermediate for synthesis of

Preparation and properties

4-Vinylcyclohexene dioxide is prepared by

epoxidation In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ...

4-vinylcyclohexene 4-Vinylcyclohexene is an organic compound consisting of a vinyl group attached to the 4-position of the cyclohexene ring. It is a colorless liquid. Although chiral, it is used mainly as the racemate. It is a precursor to vinylcyclohexene dioxide ...

with

peroxybenzoic acid Peroxybenzoic acid is an organic compound with the formula C6H5CO3H. It is the simplest aryl peroxy acid. It may be synthesized from benzoic acid and hydrogen peroxide, or by the treatment of benzoyl peroxide with sodium methoxide, followed by a ...

. Its viscosity is 15 mPa·s.

Safety

4-Vinylcyclohexene dioxide, like other volatile epoxides, is classified as an

alkylating agent Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting ...

. VCD has toxic effects on fertility. It is a killer of

oocyte An oocyte (, oöcyte, or ovocyte) is a female gametocyte or germ cell involved in reproduction. In other words, it is an immature ovum, or egg cell. An oocyte is produced in a female fetus in the ovary during female gametogenesis. The female ger ...

s, eggs in a female's ovaries, in immature

ovarian follicle An ovarian follicle is a roughly spheroid cellular aggregation set found in the ovaries. It secretes hormones that influence stages of the menstrual cycle. In humans, women have approximately 200,000 to 300,000 follicles at the time of puberty, ea ...

s in

mice A mouse (: mice) is a small rodent. Characteristically, mice are known to have a pointed snout, small rounded ears, a body-length scaly tail, and a high breeding rate. The best known mouse species is the common house mouse (''Mus musculus' ...

and

rats Rats are various medium-sized, long-tailed rodents. Species of rats are found throughout the order Rodentia, but stereotypical rats are found in the genus ''Rattus''. Other rat genera include ''Neotoma'' (pack rats), '' Bandicota'' (bandicoot ...

. In pest control, it has been used as an ovotoxic agent for reducing rat fertility.{{cite journal , journal = Toxicol Pathol, date = Jan–Feb 2001, volume = 29, issue = 1, pages = 91–99, title = Ovarian toxicity of 4-vinylcyclohexene diepoxide: a mechanistic model, vauthors = Hoyer PB, Devine PJ, Hu X, Thompson KE, Sipes IG, doi=10.1080/019262301301418892, pmid = 11215690, s2cid = 33667445

References

Epoxides Cyclohexanes Monomers