ChemicalBook > Product Catalog >Organic Chemistry >Ethers and derivatives >Methoxyethene

Methoxyethene

Methoxyethene Structure
CAS No.
107-25-5
Chemical Name:
Methoxyethene
Synonyms
mve;METHYL VINYL ETHER;VINYL METHYL ETHER;Ethenylmethylether;agrisynthmve;Ethene,methoxy-;1-Methoxyethylene;ether,ethenylmethyl;CH2=CHOCH3;methoxyethene
CBNumber:
CB1428313
Molecular Formula:
C3H6O
Molecular Weight:
58.08
MOL File:
107-25-5.mol
Modify Date:
2024/7/24 13:33:21

Methoxyethene Properties

Melting point -122°C
Boiling point 6°C
Density 0.7440
vapor pressure 169.17kPa at 20℃
refractive index 1.3947
Water Solubility 17.1g/L at 25℃
InChI InChI=1S/C3H6O/c1-3-4-2/h3H,1H2,2H3
InChIKey XJRBAMWJDBPFIM-UHFFFAOYSA-N
SMILES C=COC
LogP 0.42 at 25℃
CAS DataBase Reference 107-25-5(CAS DataBase Reference)
NIST Chemistry Reference Ethene, methoxy-(107-25-5)
EPA Substance Registry System Vinyl methyl ether (107-25-5)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS02,GHS04
Signal word  Danger
Hazard statements  H220
Precautionary statements  P210-P377-P381-P403
Hazard Codes  F+
Risk Statements  12
Safety Statements  9-16-33
RIDADR  UN 1087
HazardClass  2.1
Toxicity rabbit,LD50,skin,> 8gm/kg (8000mg/kg),GAF Material Safety Data Sheet.
NFPA 704
4
2 2

Methoxyethene Chemical Properties,Uses,Production

Description

Methoxyethene (MVE) is a colorless and flammable gas with a sweet and pleasant odor at room temperature. It is heavier than air and can diffuse to a relatively distant place at a lower place. MVE is soluble in ethanol, ether and acetone, but it is only slightly soluble in water. MVE is easily polymerized, so potassium hydroxide is often added as a polymerization inhibitor in the finished product.

Chemical Properties

Colorless compressed gas, or colorless liquid. Slightly soluble in water; soluble in alcohol and ether; easily polymerized. Commercial material contains a small proportion of polymerization inhibitor.

Uses

Copolymers used in coatings and lacquers; modifier for alkyl, polystyrene, and ionomer resins; plasticizer for nitrocellulose and adhesives.

General Description

A colorless gas with a sweet odor. Shipped as a liquefied gas under own vapor pressure. Contact with the liquid may cause frostbite. Easily ignited. Vapors are heavier than air. Leaks may either be liquid or vapor. May asphyxiate by the displacement of air. Under prolonged exposure to fire or intense heat containers may rupture violently and rocket.

Air & Water Reactions

Highly flammable. Reacts slowly with water to form acetaldehyde, reaction is not hazardous unless water is hot or acids are present. Form dangerous peroxides when exposed to air.

Reactivity Profile

Methoxyethene reacts vigorously with oxidizing materials. Explosive in the form of vapor when exposed to heat, flame or strong oxidizing agents. Reacts, possibly explosively with halogens (bromine, chlorine) or hydrogen halides (hydrogen bromide, hydrogen chloride) [Baker, 1980, p. 487]. On contact with dilute acids or even mildly acidic solids (calcium chloride, ceramics) undergoes rapid, exothermic homopolymerization, which cannot be prevented by antioxidants. Must be stored in the presence of base [MVE Brochure, Billingham, ICI, 1962].

Health Hazard

Inhalation causes intoxication, blurring of vision, headache, dizziness, excitation, loss of consciousness. Liquid or concentrated vapor irritates eyes and causes frostbite of skin. Aspiration of the liquid will cause chemical pneumonitis.

Fire Hazard

Behavior in Fire: Containers may explode. Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back.

Safety Profile

Mildly toxic by ingestion. A very dangerous fire hazard when exposed to heat, flame, or oxiduers. Explosive in the form of vapor when exposed to heat or flame. Can react vigorously with oxidizing materials. To fight fire, stop flow of gas. Potentially explosive reaction with halogens (e.g., bromine, chlorine) or hydrogen halides (e.g., hydrogen bromide, hydrogen chloride). Reaction with acids forms acetaldehyde. Weak acids catalyze the exothermic polymerization of the ether. The unstabilized ether can form dangerous peroxides. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthesis

The industrial processes of MVE production include the acetylene route (Reppe process) and the acetal route according to the starting materials.MethoxyetheneA. Acetylene undergoes a nucleophilic addition reaction with methanol in the presence of a strong base to produce MVE. The original Reppe process was carried out at a temperature of 160–165 °C under a 2–2.2 MPa pressure. The most commonly used catalyst for this reaction was an alkali metal hydroxide or an alkali metal alkoxide. Acetylene was usually diluted by nitrogen. However, this process requires high temperature and high pressure, leading to a safety problem in handling acetylene gas under such conditions. Another method is an equimolar mixture of acetylene gas and vaporized methanol, which is introduced into a fixed-bed reactor filled with a ZnO/SiO2 catalyst. The reaction temperature was in the range of 200 to 270 °C. MVE is the main product, and a significant amount of by-product (dimethoxyethane) was also generated by an equilibrium reaction of MVE and methanol to dimethoxyethane.
B. MVE is prepared by pyrolysis of dimethyl acetal at high temperature in the presence of a solid catalyst. In general, the pyrolysis of dimethylacetal is carried out in the vapor phase. Dimethylacetal was vaporized and introduced into a fixed-bed reactor filled with calcium phosphate catalyst. In the reactor, dimethylacetal split into MVE and methanol at 320 °C and under atmospheric pressure. The conversion of dimethylacetal was 95%, and the selectivity to MVE was more than 98%.

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Methoxyethene Spectrum

CH2=CHOCH3 Vinyl methyl ether,inhibited Vinl methyl ether,inhibited methylvinyloxide Metoxyethylene Methyl vinyl ether(DownstreaM Products Cooperation Wanted) Methyl Vinyl Ether ( Vinyl Methyl Ether ) methoxyethene Ether, methyl vinyl ether,methylvinyl etherdemethyleetdevinyle methoxy-ethen Methoxyethylene methylvinylethercyl.withnet~225g Methoxyethene ISO 9001:2015 REACH 1-Methoxyethylene agrisynthmve Ethene,methoxy- VINYL METHYL ETHER METHYL VINYL ETHER mve Ethenylmethylether ether,ethenylmethyl 107-25-5 CH3OCHCH2