4-vinylcyclohexene dioxide

Structural formula
	Complex mixture of stereoisomers - structural formula without stereochemistry
General
Surname	4-vinylcyclohexene dioxide
other names	3-oxiranyl-7-oxabicyclo [4.1.0] heptane; 1,2-epoxy-4- (epoxyethyl) cyclohexane;
Molecular formula	C 8 H 12 O 2
Brief description	colorless liquid
External identifiers / databases
EC number	203-437-7
ECHA InfoCard	100.003.126
PubChem	7833
Wikidata	Q2618250
properties
Molar mass	140.182 g mol −1
Physical state	liquid
density	1.09 g cm −3
Melting point	−108.9 ° C
boiling point	227 ° C
Vapor pressure	13 Pa (20 ° C)
solubility	easily in water
Refractive index	1.4738
safety instructions
H and P phrases	H: 301-311-331-351
	P: 261-280-301 + 310-311
Toxicological data	2130 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

4-vinylcyclohexene dioxide is a cycloaliphatic epoxide that is used industrially as a monomer for the production of crosslinked epoxy resins and as an intermediate for the synthesis of organic compounds.

Manufacturing

4-vinylcyclohexene dioxide by epoxidation of 4-vinylcyclohexene with peracid produced.

properties

4-vinylcyclohexene dioxide has a viscosity of 15 mPas.

Individual evidence

↑ Kam-Piu Ho, Wing-Leung Wong, Kin-Ming Lam, Cheuk-Piu Lai, Tak Hang Chan and Kwok-Yin Wong: A Simple and Effective Catalytic System for Epoxidation of Aliphatic Terminal Alkenes with Manganese (II) as the Catalyst . In: Chemistry - A European Journal . 14, No. 26, September 8, 2008, pp. 7988-7996. doi : 10.1002 / chem.200800759 .
↑ ^a ^b ^c Kh. M. Alimardanov, OA Sadygov, NI Garibov and M. Ya. Abdullaeva: Liquid-phase synthesis of cyclic diene diepoxides using metal halides and hydrogen peroxide . In: Russian Journal of Organic Chemistry . 48, No. 10, November 7, 2012, pp. 1302-1308. doi : 10.1134 / S1070428012100077 .
↑ LA Mukhamedova, G. Kh. Gil'manova, MI Kudryavtseva, FG Nasybullina and AS Kireeva: Synthesis and testing of the antiviral activity of epoxy and triazo derivatives of cyclohexane . In: Pharmaceutical Chemistry Journal . 16, No. 7, July 1982, pp. 510-514. doi : 10.1007 / BF00761540 .
↑ ^a ^b ^c ^d ^e ^f ^g Entry on 1-epoxyethyl-3,4-epoxycyclohexane in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ Entry on 7-oxa-3-oxiranylbicyclo [4.1.0] heptane in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Patent US2555500 : Copolymers of 4-vinylcyclohexene dioxide. Published January 25, 1949 , inventor: Hart Segall Gordon. ‌
^ ^A ^b Ha Q. Pham, Maurice J. Marks: Epoxy Resins . In: Ullmann's Encyclopedia of Industrial Chemistry . September. doi : 10.1002 / 14356007.a09_547.pub2 .

[1] Kam-Piu Ho, Wing-Leung Wong, Kin-Ming Lam, Cheuk-Piu Lai, Tak Hang Chan and Kwok-Yin Wong: A Simple and Effective Catalytic System for Epoxidation of Aliphatic Terminal Alkenes with Manganese (II) as the Catalyst . In: Chemistry - A European Journal . 14, No. 26, September 8, 2008, pp. 7988-7996. doi : 10.1002 / chem.200800759 .

[Alimardanov-2] Kh. M. Alimardanov, OA Sadygov, NI Garibov and M. Ya. Abdullaeva: Liquid-phase synthesis of cyclic diene diepoxides using metal halides and hydrogen peroxide . In: Russian Journal of Organic Chemistry . 48, No. 10, November 7, 2012, pp. 1302-1308. doi : 10.1134 / S1070428012100077 .

[Mukhamedova-3] LA Mukhamedova, G. Kh. Gil'manova, MI Kudryavtseva, FG Nasybullina and AS Kireeva: Synthesis and testing of the antiviral activity of epoxy and triazo derivatives of cyclohexane . In: Pharmaceutical Chemistry Journal . 16, No. 7, July 1982, pp. 510-514. doi : 10.1007 / BF00761540 .

[GESTIS-4] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on 1-epoxyethyl-3,4-epoxycyclohexane in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[CLP_100.003.126-5] Entry on 7-oxa-3-oxiranylbicyclo [4.1.0] heptane in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[6] Patent US2555500 : Copolymers of 4-vinylcyclohexene dioxide. Published January 25, 1949 , inventor: Hart Segall Gordon. ‌

[Ullmann-7] A ^b Ha Q. Pham, Maurice J. Marks: Epoxy Resins . In: Ullmann's Encyclopedia of Industrial Chemistry . September. doi : 10.1002 / 14356007.a09_547.pub2 .