Cyclohexene oxide
Cyclohexene oxide
CAS: 286-20-4
Molecular Formula: C6H10O
Cyclohexene oxide - Names and Identifiers
| Name | Cyclohexene oxide |
| Synonyms | Ccho Epoxycyclohexane Cyclohexane Oxide Cyclohexene oxide 1,2-epoxy-cyclohexan cyclohexane,1,2-epoxy- Cyclohexane, 1,2-epoxy- cis-1,2-epoxycyclohexane 2,3-tetramethyleneoxirane 7-Oxabicyclo[4.1.0]heptane 7-oxabicyclo(3.1.0)heptane Bicyclo[4.1.0]heptane, 7-oxa- (1R,6S)-7-oxabicyclo[4.1.0]heptane |
| CAS | 286-20-4 |
| EINECS | 206-007-7 |
| InChI | InChI=1/C6H10O/c1-2-4-6-5(3-1)7-6/h5-6H,1-4H2/t5-,6+ |
Cyclohexene oxide - Physico-chemical Properties
| Molecular Formula | C6H10O |
| Molar Mass | 98.14 |
| Density | 0.97g/mLat 25°C(lit.) |
| Melting Point | -40 °C |
| Boling Point | 129-130°C(lit.) |
| Flash Point | 81°F |
| Water Solubility | INSOLUBLE |
| Vapor Presure | 12 hPa (20 °C) |
| Appearance | Liquid |
| Color | Clear colorless to yellow |
| BRN | 383568 |
| Storage Condition | Store below +30°C. |
| Explosive Limit | 1.2-6.5%(V) |
| Refractive Index | n20/D 1.452(lit.) |
| Physical and Chemical Properties | Epoxy cyclohexane pure colorless to light yellow liquid, B. p.129 ℃, relative density of 0.966,f.p.27.2 ℃, insoluble in water, soluble in alcohol, acetone, ether. |
| Use | It is the main raw material of pesticide acaricide, and also the raw material of surfactant and rubber additive |
Cyclohexene oxide - Risk and Safety
| Hazard Symbols | C - Corrosive |
| Risk Codes | R10 - Flammable R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R34 - Causes burns |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S16 - Keep away from sources of ignition. |
| UN IDs | UN 2924 3/PG 3 |
| WGK Germany | 1 |
| RTECS | RN7175000 |
| TSCA | Yes |
| HS Code | 29109000 |
| Hazard Class | 8 |
| Packing Group | II |
| Toxicity | LD50 orally in Rabbit: 1060 mg/kg LD50 dermal Rabbit 612 mg/kg |
Cyclohexene oxide - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | cyclohexene oxide is a colorless or light yellow liquid with a fragrant smell. It is insoluble in water, soluble in ethanol, ether, acetone and benzene. The ethylene oxide structure of this product is full of reactivity. When it encounters proton compounds such as alcohols and amines or nucleophilic compounds such as Grignard reagents, it is easy to open the ring and generate the corresponding cyclohexanol replacement. Rat oral LD501090mg/kg. |
| application | cyclohexene oxide is a colorless or light yellow liquid, which is mainly used as pesticide raw material and resin modifier. In terms of pesticides, it is used to produce acaricides and tick killers. |
| use | epoxycyclohexane is the raw material for the synthesis of acaricide acaricinite. In addition, trans -1, 2-cyclohexanediol is synthesized from this product for surfactants, rubber additives, and polymer regulators; trans -2-aminocyclohexanol is synthesized from this product, which is used as surfactant, emulsifier, neutralizer, and medicine; 2,2 ′-dihydroxydicyclohexylamine, used in surfactants, rubber additives, medicine, etc. is the main raw material of pesticide acaricide, and also the raw material of surfactant and rubber additive |
| Production method | Epoxy cyclohexane is prepared by oxidation of cyclohexene. Preparation Example 1 58g of dioxane, 82g of cyclohexene (1mol) and 0.1g of arsenic trioxide (As2O3) were added to a 250mL reactor, and after heating to 92°C, 23.12g(0.476mol) of 70% hydrogen peroxide solution dissolved in 90g of dioxane was added for 3h to remove water by azeotropic distillation. After addition, the reaction product contains 0.035mol of hydrogen peroxide and 0.432mol of epoxy cyclohexane. The conversion rate of hydrogen peroxide is 92.6%, and the selectivity is 97.9%. Preparation Example 2 The mixture of 35g of n-propanol, 41.4g of cyclohexene (0.505mol), 0.503g of dihydroxytrimethyl antimony (0.0025mol), 0.514g of tungsten hexacarbonyl (0.0015mol) and 121.5mol of hydrogen peroxide (70%,5.92g) was kept at 60 ℃. After 3h of reaction, 10g of cyclohexane (0.102mol) was obtained, the conversion rate of hydrogen peroxide was 90%, and the selectivity of cyclohexane was 92.5%. Preparation Example 3 47g of diethylene glycol dimethyl ether, 82g(1mol) of cyclohexene and 0.2g(0.03mol) of anhydrous boric acid (B2O3) were added to a 300mL reactor with a stirrer and a reflux condenser. After the reaction mixture was heated and refluxed, 20g(0.0485mol) of 70% hydrogen peroxide solution was added to dissolve in 20g of diethylene glycol dimethyl ether for 30min. Water in the reaction medium is continuously removed azeotropic with cyclohexane. After 1h of reaction, the reactant contains 0.0013mol of unreacted hydrogen peroxide, 0.0052mol of hydrogen peroxide in distilled water, and the reactant contains 0.041mol of epoxycyclohexane, with a conversion rate of 86.7% and a selectivity of 97.6%. Preparation Example 4 Add 41g of pentanol, 0.05g of molybdenum oxide, 0.3g of disodium phosphate and 41g(0.5mol) of cyclohexene to a 500mL reactor with a stirrer and a reflux condenser, heat to the boiling point of cyclohexene of 81 ℃, add 5.7g(0.05mol) of an aqueous solution 30% hydrogen peroxide for 12min, react for 2h, remove water by azeotropic with cyclohexene, and keep the reaction temperature at 80-90 ℃. 0.012mol of hydrogen peroxide remained in the reaction product to generate 0.024mol of epoxycyclohexane. The conversion rate of hydrogen peroxide was 76% and the selectivity was 63%. Stir the 2-chlorocyclohexanol and sodium hydroxide solution intensely for 1h. The upper liquid is separated by standing and carefully fractionated with a high-efficiency fractionation column. Cut 1,2-epoxy cyclohexane fraction I (100-129 ℃), remove water, and then fractionate again; Cut 1,2-epoxy cyclohexane fraction II (129-134 ℃), which can be used as a product. Yield 70%-73%. |
| category | flammable liquid |
| toxicity classification | poisoning |
| acute toxicity | oral administration-rat LD50: 1090 mg/kg; Inhalation-rat LCL0: 2000 PPM/ 4 hours |
| flammability hazard characteristics | flammability in case of open flame, high temperature and oxidant; Combustion produces stimulating smoke |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; Store separately from oxidant; Not suitable for long storage to prevent polymerization |
| fire extinguishing agent | dry powder, dry sand, carbon dioxide, foam, 1211 fire extinguishing agent |
| auto-ignition temperature | 703 °F |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:48:19
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View History
Cyclohexene oxide
4-FLUORO-3-(TRIFLUOROMETHYL)CINNAMIC ACID
氰基甲酸苄酯
TIMTEC-BB SBB001309
3-MESITYL-1-METHYL-1H-BENZO[D]IMIDAZOL-3-IUM IODIDE
Aspidofractinine-1-carboxaldehyde, 17-methoxy-3-methylene-, (2α,5α)- (9CI)
2-Naphthalenecarboxylic acid, 6-ethynyl-, methyl ester
Fmoc-NH-ethyl-SS-propionic NHS ester
REL-(1R,2R)-1,2-环戊烷二羧酸
5-Thiazolemethanol, 4-methyl-2-[3-(trifluoromethyl)phenyl]-
4-FLUORO-3-(TRIFLUOROMETHYL)CINNAMIC ACID
氰基甲酸苄酯
TIMTEC-BB SBB001309
3-MESITYL-1-METHYL-1H-BENZO[D]IMIDAZOL-3-IUM IODIDE
Aspidofractinine-1-carboxaldehyde, 17-methoxy-3-methylene-, (2α,5α)- (9CI)
2-Naphthalenecarboxylic acid, 6-ethynyl-, methyl ester
Fmoc-NH-ethyl-SS-propionic NHS ester
REL-(1R,2R)-1,2-环戊烷二羧酸
5-Thiazolemethanol, 4-methyl-2-[3-(trifluoromethyl)phenyl]-