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Ethyl vinyl ether

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Name

Ethyl vinyl ether

EINECS 203-718-4
CAS No. 109-92-2 Density 0.751 g/cm3
PSA 9.23000 LogP 1.16640
Solubility 7.8 g/L (25 °C) in water Melting Point -116 °C(lit.)
Formula C4H8O Boiling Point 32.5 °C at 760 mmHg
Molecular Weight 72.1069 Flash Point ?50°F
Transport Information UN 1302 3/PG 1 Appearance colourless liquid with an ether-like odour
Safety 16-23-26-3/7-33-36 Risk Codes 12-19-36/37/38
Molecular Structure Molecular Structure of 109-92-2 (Ethyl vinyl ether) Hazard Symbols HighlyF+,IrritantXi,FlammableF
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;

Article Data 95

Ethyl vinyl ether 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;

Ethyl vinyl ether Chemical Properties

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 

Ethyl vinyl ether 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.

Ethyl vinyl ether 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.

Ethyl vinyl ether 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.

Ethyl vinyl ether Consensus Reports

Reported in EPA TSCA Inventory.

Ethyl vinyl ether 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.

Ethyl vinyl ether Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid

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