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109-92-2

Basic Information
CAS No.: 109-92-2
Name: Ethyl vinyl ether
Article Data: 95
Molecular Structure:
Molecular Structure of 109-92-2 (Ethyl vinyl ether)
Formula: C4H8O
Molecular Weight: 72.1069
Synonyms: Ether, vinyl ethyl;1-Ethoxyethylene;Ether, ethyl vinyl (inhibited);Vinamar;Ethoxyethene;Ether, ethyl vinyl;Ethyl ethenyl ether;EVE;Ethene, ethoxy-;Ethene, ethoxy;1-Ethoxyethene;Ethylvinylether;supply ethyl vinyl ether;Ethoxyetylene, ethyl vinyl ether;
EINECS: 203-718-4
Density: 0.751 g/cm3
Melting Point: -116 °C(lit.)
Boiling Point: 32.5 °C at 760 mmHg
Flash Point: ?50°F
Solubility: 7.8 g/L (25 °C) in water
Appearance: colourless liquid with an ether-like odour
Hazard Symbols: HighlyF+,IrritantXi,FlammableF
Risk Codes: 12-19-36/37/38
Safety: 16-23-26-3/7-33-36
Transport Information: UN 1302 3/PG 1
PSA: 9.23000
LogP: 1.16640
Synthetic route
64-17-5

ethanol

74-86-2

acetylene

109-92-2

ethyl vinyl ether

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 120℃; for 1.5h;92%
With sodium ethanolate at 145 - 165℃;
With zinc(II) oxide at 310℃;
64-17-5

ethanol

1112-54-5

vinyltriethylsilane

A

994-49-0

hexaethyl disiloxane

B

109-92-2

ethyl vinyl ether

Conditions
ConditionsYield
With bromine for 4h;A 25%
B 55%
54007-78-2

1-phenyl-4-ethoxy-2,3-dimethylthiobutanone

A

77787-36-1

2,4,4-Trimethyl-3-phenyl-tetrahydro-pyran-3-thiol

B

77787-34-9, 77787-35-0

4-Ethoxy-2,2-dimethyl-1-phenyl-cyclobutanethiol

C

109-92-2

ethyl vinyl ether

Conditions
ConditionsYield
In benzene for 40h; Ambient temperature; Irradiation; through pyrex;A 40%
B 48%
C n/a
With dimethylglyoxal In benzene Quantum yield; Rate constant; Ambient temperature; Irradiation; var. senzitizers and conc. of ones; sev. solvents of different polarities;
925669-95-0

2,3-cis-epoxybutane

A

598-32-3

2-hydroxy-3-butene

B

74-85-1

ethene

C

78-84-2

isobutyraldehyde

D

109-92-2

ethyl vinyl ether

E

78-93-3

butanone

21490-63-1

2,3-trans-epoxybutane

Conditions
ConditionsYield
at 757.9℃; Mechanism; Product distribution; Kinetics; reflected shocks in a pressurized driver single-pulse shock tube ; the temperature range: 900-1150 K.;A 2.62%
B 2.21%
C 4.58%
D 0.902%
E 13.39%
F 5.64%
111-34-2

-butyl vinyl ether

64-17-5

ethanol

A

109-92-2

ethyl vinyl ether

B

71-36-3

butan-1-ol

Conditions
ConditionsYield
(CO)4(palladium)4(acetate)4 for 2h; Product distribution; effect of the catalyst to the production and the selectivity;A 9%
B n/a
110-86-1

pyridine

7081-78-9

1-chloroethyl ethyl ether

109-92-2

ethyl vinyl ether

56-23-5

tetrachloromethane

592-55-2

2-Bromoethyl ethyl ether

A

112-36-7

3,6,9-trioxaundecane

B

109-92-2

ethyl vinyl ether

105-57-7

diethyl acetal

A

64-17-5

ethanol

B

74-85-1

ethene

C

75-07-0

acetaldehyde

D

109-92-2

ethyl vinyl ether

Conditions
ConditionsYield
at 389 - 453℃; Kinetics; Pr.5: Kohlenmonoxid; Pr.6: Methan.Pyrolysis;
105-57-7

diethyl acetal

109-92-2

ethyl vinyl ether

Conditions
ConditionsYield
With sulfuric acid at 350℃;
With sodium hydrogen sulfate
With platinum at 280 - 290℃;
105-57-7

diethyl acetal

A

64-17-5

ethanol

B

109-92-2

ethyl vinyl ether

Conditions
ConditionsYield
at 250℃;
at 300 - 500℃; in Gegenwart von Katalysatoren;
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    Product Name: Ethyl vinyl ether Synonyms: ether,ethylvinyl;ether,vinylethyl;ethoxy-ethen;Ethyl ethenyl ether;Ethyloxyethene;EVE;VINYL ETHYL ETHER;VINAMAR CAS: 109-92-2 MF: C4H8O MW: 72.11 EINECS: 203-718-4

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Chemistry

Structure of Ethyl vinyl ether (CAS NO.109-92-2):

IUPAC Name: ethoxyethene 
Empirical Formula: C4H8O
Molecular Weight: 72.1057 
EINECS: 203-718-4 
Index of Refraction: 1.376
Molar Refractivity: 22.05 cm3
Molar Volume: 96 cm3
Polarizability: 8.74×10-24cm3
Surface Tension: 18.8 dyne/cm
Density: 0.751 g/cm3 
Enthalpy of Vaporization: 26.63 kJ/mol 
Melting Point: −116 °C(lit.)
Boiling Point: 32.5 °C at 760 mmHg
Vapour Pressure: 581 mmHg at 25°C 
Water Solubility: 7.8 g/L (25 ºC) 
Physical Appearance: colourless liquid with an ether-like odour
Stability: Stable. Highly flammable. Incompatible with strong oxidizing agents. May form peroxides in storage - check for their formation before use. 
Product Categories: Pharmaceutical Intermediates 

Uses

In medicine, Ethyl vinyl ether (CAS NO.109-92-2) is used as anesthetics, analgesics, but also as intermediates for fine chemical, intermediates for sulfadiazine. It makes up the monomer of copolymer, organic synthetic materials, spices amd lubricating oil additives.

Production

 Ethyl vinyl ether (CAS NO.109-92-2) was produced by the pressurized reaction of acetylene and ethanol in the presence of potassium hydroxide catalyst.

Toxicity Data With Reference

1.    

skn-rbt 500 mg open MLD

    UCDS**    Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 11/15 ,1971.
2.    

sce-ham:ovr 17,900 ppm

    ANESAV    Anesthesiology. 50 (1979),426.
3.    

orl-rat LD50:6153 mg/kg

    AIHAAP    American Industrial Hygiene Association Journal. 30 (1969),470.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: HighlyF+,IrritantXi,FlammableF
Risk Statements: 12-19-36/37/38 
R12:Extremely flammable. 
R19:May form explosive peroxides. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 16-23-26-3/7-33-36 
S16:Keep away from sources of ignition. 
S23:Do not breathe vapour. 
S3:Keep in a cool place. 
S7:Keep container tightly closed. 
S33:Take precautionary measures against static discharges. 
S36:Wear suitable protective clothing.
RIDADR: UN 1302 3/PG 1
WGK Germany: 1
RTECS: KO0710000
F: 19
HazardClass: 3
PackingGroup: I
HS Code: 29091900
Mildly 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.

Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid