Ethyl vinyl ether
- CAS No.
- 109-92-2
- Chemical Name:
- Ethyl vinyl ether
- Synonyms
- Ethoxyethene;EVE;VINYL ETHYL ETHER;VINAMAR;ETHOXYETHYLENE;Ethyl Vinyl Ethe;CH2=CHOC2H5;ethoxy-ethen;agrisyntheve;Ethoxythylene
- CBNumber:
- CB0708241
- Molecular Formula:
- C4H8O
- Molecular Weight:
- 72.11
- MOL File:
- 109-92-2.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/7/26 15:15:06
| Melting point | -116 °C (lit.) |
|---|---|
| Boiling point | 33 °C (lit.) |
| Density | 0.753 g/mL at 25 °C (lit.) |
| vapor pressure | 560 hPa (20 °C) |
| refractive index |
n |
| Flash point | −50 °F |
| storage temp. | 2-8°C |
| solubility | 8.3g/l |
| form | Liquid |
| color | Clear colorless |
| Odor | nauseating-ethereal but sweet odor |
| explosive limit | 1.3-12.0%(V) |
| Water Solubility | 7.8 g/L (25 ºC) |
| BRN | 605351 |
| Exposure limits |
ACGIH: Ceiling 2 mg/m3 NIOSH: Ceiling 2 mg/m3 |
| Stability | Stable. Highly flammable. Incompatible with strong oxidizing agents. May form peroxides in storage - check for their formation before use. |
| InChIKey | FJKIXWOMBXYWOQ-UHFFFAOYSA-N |
| LogP | 1.63 at 25℃ |
| CAS DataBase Reference | 109-92-2(CAS DataBase Reference) |
| NIST Chemistry Reference | Ethene, ethoxy-(109-92-2) |
| EPA Substance Registry System | Vinyl ethyl ether (109-92-2) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS02,GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H225-H336-H412 | |||||||||
| Precautionary statements | P210-P233-P240-P241-P242-P273 | |||||||||
| Hazard Codes | F+,Xi,F | |||||||||
| Risk Statements | 12-19-36/37/38-11 | |||||||||
| Safety Statements | 16-23-26-3/7-33-36-9 | |||||||||
| RIDADR | UN 1302 3/PG 1 | |||||||||
| WGK Germany | 1 | |||||||||
| RTECS | KO0710000 | |||||||||
| F | 19 | |||||||||
| Autoignition Temperature | 178 °C | |||||||||
| TSCA | Yes | |||||||||
| HazardClass | 3 | |||||||||
| PackingGroup | I | |||||||||
| HS Code | 29091900 | |||||||||
| Toxicity | LD50 orally in Rabbit: 6120 mg/kg LD50 dermal Rabbit > 15000 mg/kg | |||||||||
| NFPA 704 |
|
Ethyl vinyl ether price More Price(13)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | 8.01391 | Ethyl vinyl ether (stabilised with potassium hydroxide) for synthesis | 109-92-2 | 100ML | ₹4839.99 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.01391 | Ethyl vinyl ether (stabilised with potassium hydroxide) for synthesis | 109-92-2 | 1L | ₹6150 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 422177 | Ethyl vinyl ether contains 0.1% KOH as stabilizer, 99% | 109-92-2 | 250ML | ₹4330 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 422177 | Ethyl vinyl ether contains 0.1% KOH as stabilizer, 99% | 109-92-2 | 1L | ₹5748.08 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 05010 | Ethyl vinyl ether purum, ≥98.0% (GC) | 109-92-2 | 250ML | ₹3574.2 | 2022-06-14 | Buy |
Ethyl vinyl ether Chemical Properties,Uses,Production
Chemical Properties
Colorless liquid. Extremely reactive, can be polymerized in liquid or vapor phase. Slightly soluble in water (0.9% by weight). Commercial material contains inhibitor to prevent premature polymerization. Often stored underground to minimize vapor losses.
Uses
Ethyl vinyl ether is used in fragrances, lubricating oil additives and spices preparation. It acts as an intermediate for sulfadiazine. It finds application in pharmaceuticals as anesthetics and analgesics. Further, it is used as a solvent in organic synthesis.
Preparation
Ethyl vinyl ether (EVE) can be prepared by reacting acetylene with absolute ethanol in the presence of an alkali catalyst. The most commonly used catalyst for vinylation is an alkali metal hydroxide or an alkali metal alkoxide. 
In China, three processes for the manufacture of EVE using the acetylene route were used:
A continuous process with a homogeneous catalyst under high pressure. The advantages of this process are fast reaction rate and high conversion, but the disadvantages include the requirement of high standard equipment, large energy consumption, and easy safety issues.
A process with a solid catalyst (heterogeneous catalyst) under atmospheric pressure is relatively simple in product separation and refining compared with a process with a homogeneous catalyst under high pressure. However, it has the disadvantages of low output, the short service life of catalyst (about 110 h), and a high requirement on the specification of carrier lime.
A process with a homogeneous catalyst under atmospheric pressure has the advantages of high output and good safety but disadvantages of low conversion.
In the process with solid catalyst under atmospheric pressure, acetylene, and ethanol vapor were introduced into a fixed-bed reactor, and the vinylation reaction was carried out at a temperature as high as about 180 °C. EVE was produced with a concentration of about 70% in the outlet gas stream from the reactor. The fixed-bed reactor was charged with 4–5 mesh catalyst particles of potassium hydroxide supported on lime.
General Description
A clear colorless low-boiling liquid (35-36°C) with an ether-like odor. Flash point below -50°F. May polymerize exothermically if heated or contaminated. If polymerization takes place inside a container, the container may rupture violently. Less dense than water and slightly soluble in water. Hence floats on water. Vapors are heavier than air.
Air & Water Reactions
Highly flammable. Slightly soluble in water. Tends to form explosively unstable peroxides when exposed to oxygen.
Reactivity Profile
Ethyl vinyl ether is a very dangerous fire and explosion hazard when exposed to heat or flame. Undergoes autooxidation with formation of peroxides in the air. Can react vigorously with oxidizing materials. Undergoes explosive polymerization in contact with methanesulfonic acid [Eaton, P. E. et al., J. Org. Chem., 1972, 37, p. 1947].
Hazard
Carcinogen.
Health Hazard
INHALATION OR INGESTION: Excitement followed by unconsciousness and respiratory paralysis. CNS depression. EYES: May cause irritation and transient injury to cornea. SKIN: Prolonged contact can cause tissue defatting and dehydration leading to dermatitis.
Fire Hazard
Behavior in Fire: Explosive hazard
Safety Profile
Mddly toxic by ingestion. Mutation data reported. A skin irritant. A very dangerous fire and explosion hazard when exposed to heat or flame; can react vigorously with oxidizing materials. To fight fire, use alcohol foam, foam, CO2, dry chemical. Explosive polymerization is catalyzed by methane sulfonic acid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ETHERS.
Synthesis
Ethyl vinyl ether is synthesized by bubbling Acetylene through Ethylalcohol in presence of Sodium ethoxide.
Purification Methods
It usually contains polymerization inhibitors (usually amines, e.g. triethanolamine) which can be removed by fractional distillation. Redistil it from sodium. [Beilstein 1 IV 2049.] LACHRYMATORY.
Purification Methods
Ethyl vinyl ether (EVE) mainly contains impurities such as ethanol, acetaldehyde, and acetal and triethanolamine, which are added to prevent hydrolysis and must be refined before use. The purification is done by extensive washing with water or diluting potassium hydroxide solution. Peroxide may be generated in EVE if the latter has been stored for a long time. In this case, potassium iodide dissolved in dioxane can be applied to check if the ether contains peroxide. The peroxide in the ether can be washed by reducing agent solution of ferrous sulfate, sodium sulfite, stannous chloride, and the like, dried by potassium hydroxide and calcium chloride, and finally refined by distillation in the presence of potassium hydroxide or metallic sodium.
Ethyl vinyl ether Preparation Products And Raw materials
Raw materials
Preparation Products
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chevron_right| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| JSK Chemicals | +919879767970 | Gujarat, India | 3756 | 58 | Inquiry |
| Otto Chemie Pvt Ltd | +91-2222070099 +91-2266382599 | Maharashtra, India | 429 | 58 | Inquiry |
| BASF India Limited | +91-2262785600 +91-2262785600 | Maharashtra, India | 209 | 58 | Inquiry |
| Spectrochem Private Limited | 08048372608Ext 246 | Maharashtra, India | 1056 | 58 | Inquiry |
| CHEMSWORTH | +91-261-2397244 | New Delhi, India | 6707 | 30 | Inquiry |
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
| Alfa Aesar | 1 800 209 7001 | Maharashtra, India | 6913 | 58 | Inquiry |
| Sisco Research Laboratories Pvt. Ltd. | +91-22-4268 5800 | Mumbai, India | 4317 | 58 | Inquiry |
| Triveni chemicals | 08048762458 | New Delhi, India | 6093 | 58 | Inquiry |
| Avra Synthesis Pvt Ltd | +914027175796 | New Delhi, India | 1606 | 30 | Inquiry |
| Supplier | Advantage |
|---|---|
| JSK Chemicals | 58 |
| Otto Chemie Pvt Ltd | 58 |
| BASF India Limited | 58 |
| Spectrochem Private Limited | 58 |
| CHEMSWORTH | 30 |
| TCI Chemicals (India) Pvt. Ltd. | 58 |
| Alfa Aesar | 58 |
| Sisco Research Laboratories Pvt. Ltd. | 58 |
| Triveni chemicals | 58 |
| Avra Synthesis Pvt Ltd | 30 |
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