Vinylcyclohexene dioxide

Last updated
Vinylcyclohexene dioxide
Vinylcyclohexendioxid.svg
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)
AbbreviationsVCD
ECHA InfoCard 100.003.126 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • C1CC2C(O2)CC1C3CO3
Properties
C8H12O2
Molar mass 140.182 g·mol−1
AppearanceColorless 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).

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]

Contents

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]

Related Research Articles

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<span class="mw-page-title-main">Epoxide</span> Organic compounds with a carbon-carbon-oxygen ring

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<span class="mw-page-title-main">Johnson–Corey–Chaykovsky reaction</span> Chemical reaction in organic chemistry

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<span class="mw-page-title-main">Epichlorohydrin</span> Chemical compound

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<span class="mw-page-title-main">3,4-Epoxycyclohexylmethyl-3',4'-epoxycyclohexane carboxylate</span> Chemical compound

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SenesTech, Inc. is an agricultural biotechnology life-sciences company, specializing in fertility management as a form of pest control. The company's primary product, ContraPest is designed to make brown and black rats infertile. SenesTech is headquartered in Phoenix, Arizona.

1,4-Butanediol diglycidyl ether (B14DODGE) is an organic chemical in the glycidyl ether family. It is aliphatic and a colorless liquid. It has two epoxide (oxirane) groups per molecule. Its main use is in modifying epoxy resins especially viscosity reduction.

1,6-Hexanediol diglycidyl ether is an organic chemical in the glycidyl ether family. It is an aliphatic compound that is a colorless liquid. It has two epoxide (oxirane) groups per molecule. Its main use is in modifying epoxy resins especially viscosity reduction whilst flexibilizing. It is REACH registered.

<span class="mw-page-title-main">Trimethylolpropane triglycidyl ether</span> Chemical compound

Trimethylolpropane triglycidyl ether (TMPTGE) is an organic chemical in the glycidyl ether family. It has the formula C15H26O6 and the IUPAC name is 2-[2,2-bis(oxiran-2-ylmethoxymethyl)butoxymethyl]oxirane, and the CAS number 3454-29-3. It also has another CAS number of 30499-70-8 A key use is as a modifier for epoxy resins as a reactive diluent.

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<span class="mw-page-title-main">Diethylene glycol diglycidyl ether</span> Chemical compound

Diethylene glycol diglycidyl ether (DEGDGE) is an organic chemical in the glycidyl ether family with the formula C10H18O5.. The oxirane functionality makes it useful as a reactive diluent for epoxy resin viscosity reduction.

<span class="mw-page-title-main">Diglycidyl resorcinol ether</span> Chemical compound

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<span class="mw-page-title-main">Phenyl glycidyl ether</span> Chemical compound

Phenyl glycidyl ether, is a liquid aromatic organic chemical in the glycidyl ether class of compounds. It has the formula C9H10O2. It has the CAS Registry Number 122-60-1 and the IUPAC name of 2-(phenoxymethyl)oxirane. A key use is in the viscosity reduction of epoxy resin systems. It is REACH registered and on EINECS under the name 2,3-epoxypropyl phenyl ether.

<span class="mw-page-title-main">Diglycidyl aniline</span> Chemical compound

Diglycidyl aniline is an aromatic organic chemical in the glycidyl compound family. It is used to reduce the viscosity of epoxy resin systems. It has the empirical formula C12H15NO2 and the IUPAC name is N,N-bis(oxiran-2-ylmethyl)aniline. The CAS number is 2095-06-9. It is REACH registered in Europe with the EC number 218-259-5. A key use is in the viscosity reduction of epoxy resin systems functioning as a reactive diluent.

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. 1 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. 1 2 3 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. 1 2 3 4 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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