Vinylcyclohexene dioxide

{{Chembox

| ImageFile = Vinylcyclohexendioxid.svg

| ImageAlt = Molecular structure of vinylcyclohexene dioxide

| IUPACName = 3-Oxiranyl-7-oxabicyclo[4.1.0]heptane

| OtherNames = 1,2-Epoxy-4-(epoxyethyl)cyclohexane
4-Vinylcyclohexene diepoxide

|Section1={{Chembox Identifiers

| CASNo = 106-87-6

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 596C064IG4

| PubChem = 7833

| SMILES = C1CC2C(O2)CC1C3CO3

| Abbreviations = VCD

}}

|Section2={{Chembox Properties

| C=8 | H=12 | O=2

| Appearance = Colorless liquid{{cite journal |author =Kam-Piu Ho, Wing-Leung Wong, Kin-Ming Lam, Cheuk-Piu Lai, Tak Hang Chan und Kwok-Yin Wong |title=A Simple and Effective Catalytic System for Epoxidation of Aliphatic Terminal Alkenes with Manganese(II) as the Catalyst|journal=Chemistry: A European Journal|date=2008-09-08|volume=14|issue=26|pages=7988–7996|doi=10.1002/chem.200800759|pmid=18618538}}

| Density = 1.09 g·cm−3{{cite journal |author = Kh. M. Alimardanov, O. A. Sadygov, N. I. Garibov und M. Ya. Abdullaeva |title = Liquid-phase synthesis of cyclic diene diepoxides using metal halides and hydrogen peroxide |journal = Russian Journal of Organic Chemistry |date = 2012-11-07|volume = 48|issue = 10|pages = 1302–1308|doi = 10.1134/S1070428012100077|s2cid = 93780572 }}{{cite journal |author = L. A. Mukhamedova, G. Kh. Gil'manova, M. I. Kudryavtseva, F. G. Nasybullina und A. S. Kireeva |title = Synthesis and testing of the antiviral activity of epoxy and triazo derivatives of cyclohexane|journal = Pharmaceutical Chemistry Journal|date = July 1982|volume = 16|issue = 7|pages = 510–514|doi = 10.1007/BF00761540|s2cid = 44566569}}

| MeltingPtC = -108.9

| MeltingPt_ref = {{GESTIS|ZVG=510220 |CAS=106-87-6 |Name= |Date=24 March 2015}}

| BoilingPtC = 227

| BoilingPt_ref =

| Solubility =

| VaporPressure = 13 Pa (20 °C)

}}

|Section3={{Chembox Hazards

| MainHazards = Toxic

| FlashPt =

| AutoignitionPt =

}}

}}

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.{{patent|US|2555500|"Copolymers of 4-vinylcyclohexene dioxide."|Hart Segall Gordon filing date 25.01.1949}} It is a colourless liquid. It is an intermediate for synthesis of organic compounds.

Preparation and properties

4-Vinylcyclohexene dioxide is prepared by epoxidation of 4-vinylcyclohexene with peroxybenzoic acid.{{cite journal|last1=Pham|first1=Ha Q.|last2=Marks|first2=Maurice J.|title=Epoxy Resins|journal=Ullmann's Encyclopedia of Industrial Chemistry|doi=10.1002/14356007.a09_547.pub2|year=2005|isbn=3-527-30673-0}} Its viscosity is 15 mPa·s.

Safety

4-Vinylcyclohexene dioxide, like other volatile epoxides, is classified as an alkylating agent. 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.{{Cite journal|last1=Kappeler|first1=Connie J.|last2=Hoyer|first2=Patricia B.|date=2012-02-01|title=4-vinylcyclohexene diepoxide: a model chemical for ovotoxicity|journal=Systems Biology in Reproductive Medicine|volume=58|issue=1|pages=57–62|doi=10.3109/19396368.2011.648820|issn=1939-6376|pmc=3307534|pmid=22239082}}{{Cite journal|last1=Takai|first1=Yasushi|last2=Canning|first2=Jacqueline|last3=Perez|first3=Gloria I.|last4=Pru|first4=James K.|last5=Schlezinger|first5=Jennifer J.|last6=Sherr|first6=David H.|last7=Kolesnick|first7=Richard N.|last8=Yuan|first8=Junying|last9=Flavell|first9=Richard A.|date=2003-01-01|title=Bax, caspase-2, and caspase-3 are required for ovarian follicle loss caused by 4-vinylcyclohexene diepoxide exposure of female mice in vivo|journal=Endocrinology|volume=144|issue=1|pages=69–74|doi=10.1210/en.2002-220814|issn=0013-7227|pmid=12488331|doi-access=free}}{{Cite journal|last1=Hoyer|first1=P. B.|last2=Devine|first2=P. J.|last3=Hu|first3=X.|last4=Thompson|first4=K. E.|last5=Sipes|first5=I. G.|date=2001-02-01|title=Ovarian toxicity of 4-vinylcyclohexene diepoxide: a mechanistic model|journal=Toxicologic Pathology|volume=29|issue=1|pages=91–99|issn=0192-6233|pmid=11215690|doi=10.1080/019262301301418892|s2cid=33667445}}

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