1,2-Epoxy-4-vinylcyclohexane Chemical Properties

Melting point:

-100°C(lit.)

Boiling point:

169 °C(lit.)

Density 

0.952 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.469(lit.)

Flash point:

115 °F

storage temp. 

2-8°C

form 

clear liquid

color 

Colorless to Almost colorless

Specific Gravity

0.952

InChI

InChI=1S/C8H12O/c1-2-6-3-4-7-8(5-6)9-7/h2,6-8H,1,3-5H2

InChIKey

SLJFKNONPLNAPF-UHFFFAOYSA-N

SMILES

C12C(O1)CCC(C=C)C2

CAS DataBase Reference

106-86-5(CAS DataBase Reference)

NIST Chemistry Reference

7-Oxabicyclo[4.1.0]heptane, 3-ethenyl-(106-86-5)

EPA Substance Registry System

7-Oxabicyclo[4.1.0]heptane, 3-ethenyl- (106-86-5)

Safety Information

Hazard Codes 

T,Xn

Risk Statements 

45-10-20/21/22-40-36-22

Safety Statements 

53-16-23-36/37/39-45-36/37-26

RIDADR 

UN 3271 3/PG 3

WGK Germany 

3

RTECS 

RN8770000

HazardClass 

3.2

PackingGroup 

III

HS Code 

29109000

MSDS

• Language:English Provider:4-Vinyl-1-cyclohexene 1,2-epoxide
• Language:English Provider:SigmaAldrich

1,2-Epoxy-4-vinylcyclohexane Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

Vinylcyclohexene monoxide is a chemical intermediate; it can be copolymerized with other epoxides to yield polyglycols having unsaturation available for further reaction.

Definition

ChEBI: 3-Vinyl-7-oxabicyclo[4.1.0]heptane is an oxacycle.

Synthesis Reference(s)

Tetrahedron Letters, 22, p. 2089, 1981 DOI: 10.1016/S0040-4039(01)93284-8

Synthesis

General Steps: 1. Add known amounts of 4-vinyl-1-cyclohexene and TBHP (tert-butyl hydroperoxide) without co-solvent in a 0.25 L capacity jacketed four-neck glass reactor. Set the feed molar ratio (FMR) of olefin to TBHP from 1:1 to 10:1. 2. Start the stirrer and adjust the stirring rate to 300-600 rpm. Heat the reaction mixture through the water bath and reactor jacket, and monitor the temperature using a digital thermocouple to ensure that the temperature of the reaction mixture stabilizes in the range of 323-353 K, with a fluctuation of no more than ±0.5 K. 3. When the reaction mixture reaches a constant temperature, set the FMR to 1:1 to 10:1, without adding co-solvent. 3. When the reaction mixture reached a constant temperature, a known amount of polymer loaded catalyst (0.15-0.6 mol Mo) was added. The time of catalyst addition was recorded as the reaction onset time (t = 0) and an initial sample was taken immediately. 4. Samples were taken at specific time intervals during the reaction and analyzed using Shimadzu GC-2014 gas chromatography (GC). 5. The experimental results showed that the PBI.Mo and Ps.AMP.Mo catalysts exhibited high selectivity in the epoxidation reaction of 4-vinyl-1-cyclohexene, which predominantly yielded 1,2-epoxy-4-vinylcyclohexane, and the GC analyses did not detect terminal or dicyclic oxide products. Detailed results of the batch experiments are discussed in Sect.

Toxics Screening Level

The initial threshold screening level (ITSL) for 1,2-epoxy-4-vinylcyclohexane is 6.0 μg/m3 based on an annual averaging time.

References

[1] RSC Advances, 2014, vol. 4, # 61, p. 32054 - 32062
[2] Applied Catalysis A: General, 2013, vol. 466, p. 142 - 152
[3] Journal of the American Chemical Society, 2009, vol. 131, # 36, p. 12890 - 12891
[4] Patent: CN108101868, 2018, A. Location in patent: Paragraph 0027-0068
[5] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 21, p. 3115 - 3116

1,2-Epoxy-4-vinylcyclohexane(106-86-5)Related Product Information

• Cyclohexane
• 4-Vinyl-1-cyclohexene
• N-Vinyl-2-pyrrolidone
• Heptane
• VINYL PROPIONATE
• VINYLCYCLOHEXANE
• 2-Cyclohexen-1-one
• Resin epoxy
• NITROCYCLOHEXANE
• Cyclohexylbenzene
• Cyclohexene
• Cyclohexene oxide
• 4-(4-CHLORO-BENZYLOXY)-PHENYLAMINE
• Vinyl acetate
• Ethylcyclohexane
• Methylcyclohexane
• Poly(vinyl alcohol)
• 3,4-Epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate