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108-05-4

Basic Information
CAS No.: 108-05-4
Name: Vinyl acetate
Article Data: 171
Cas Database
Molecular Structure:
Molecular Structure of 108-05-4 (Vinyl acetate)
Formula: C4H6O2
Molecular Weight: 86.0904
Synonyms: Acetic acid vinylester (8CI);1-Acetoxyethylene;Acetic acid, ethenyl ester;Acetoxyethene;Acetoxyethylene;Ethenyl acetate;NSC 8404;SN 12T;Vinyl A monomer;Vinylacetate;
EINECS: 203-545-4
Density: 0.93 g/cm3
Melting Point: -93 °C
Boiling Point: 72.499 °C at 760 mmHg
Flash Point: 20°F
Solubility: 23 g/L (20 °C) in water
Appearance: colourless mobile liquid
Hazard Symbols: FlammableF,ToxicT
Risk Codes: 11-39/23/24/25
Safety: 16-23-29-33-45-36/37-7
Transport Information: UN 1301 3/PG 2
PSA: 26.30000
LogP: 0.69300
Synthetic route
111-55-7

ethylene glycol diacetate

108-05-4

vinyl acetate

Conditions
ConditionsYield
With acetic anhydride; benzenesulfonic acid at 140℃; under 1875.19 Torr; for 0.75h; Inert atmosphere;65.05%
With acetic anhydride; benzenesulfonic acid at 142℃; under 3000.3 Torr; for 0.75h; Inert atmosphere;64.47%
With acetic anhydride; benzenesulfonic acid at 143℃; under 3000.3 Torr; for 0.666667h; Inert atmosphere;64.57%
542-10-9

ethylidene diacetate

108-05-4

vinyl acetate

Conditions
ConditionsYield
With acetic anhydride; benzenesulfonic acid at 145℃; under 2850.29 Torr; for 0.75h; Inert atmosphere;63.51%
With lithium iodide
With acetic anhydride; lithium iodide
at 50 - 200℃; under 11400.8 Torr;
764-78-3

ethylene glycol divinyl ether

507-02-8

acetyl iodide

A

108-05-4

vinyl acetate

B

593-66-8

vinyliodide

C

627-10-1

2-iodoethyl acetate

Conditions
ConditionsYield
In dichloromethane at 10℃;A 42.8%
B 40.5%
C 54.9%
74-85-1

ethene

64-19-7

acetic acid

A

108-05-4

vinyl acetate

B

542-59-6

2-hydroxyethyl acetate

C

111-55-7

ethylene glycol diacetate

Conditions
ConditionsYield
With Pd(MeCN)2Cl(NO2) at 25℃; under 2068.6 Torr; for 4h; Product distribution; various catalysts, times, additives, O2 atmosphere, with 18O containing complex;A 20%
B 50%
C 7%
111-34-2

-butyl vinyl ether

507-02-8

acetyl iodide

A

108-05-4

vinyl acetate

B

542-69-8

1-iodo-butane

C

593-66-8

vinyliodide

D

123-86-4

acetic acid butyl ester

Conditions
ConditionsYield
In dichloromethane at 10℃;A 11.8%
B 12.8%
C 35.8%
D 39.8%
74-85-1

ethene

127-08-2

potassium acetate

64-19-7

acetic acid

A

108-05-4

vinyl acetate

B

124-38-9

carbon dioxide

C

141-78-6

ethyl acetate

Conditions
ConditionsYield
With oxygen under 9120.61 Torr; for 16h;A n/a
B 11.57%
C 0.151%
With oxygen under 9120.61 Torr; for 16h;A n/a
B 9.45%
C 0.061%
With oxygen under 9120.61 Torr; for 16h;A n/a
B 9.1%
C 0.049%
36597-97-4

β,β-dichlorovinyl acetate

A

108-05-4

vinyl acetate

B

103659-54-7

Z-2-chlorovinyl acetate

C

10138-83-7, 103659-54-7

E-2-chlorovinyl acetate

Conditions
ConditionsYield
With tri-n-butyl-tin hydride for 0.5h; Ambient temperature; Irradiation;A 2%
B n/a
C n/a
15568-57-7

1-acetoxy-2-(ethyl-acetyl-amino)-ethane

A

108-05-4

vinyl acetate

B

3195-79-7

N-vinyl-N-ethyl-acetamide

C

625-50-3

N-ethylacetamide

Conditions
ConditionsYield
at 490℃; Erhitzung;
542-10-9

ethylidene diacetate

108-24-7

acetic anhydride

108-05-4

vinyl acetate

Conditions
ConditionsYield
With copper (I) acetate; benzenesulfonic acid
108-24-7

acetic anhydride

75-07-0

acetaldehyde

108-05-4

vinyl acetate

Conditions
ConditionsYield
With sulfuric acid
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Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 19 ,1979,p. 341.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 39 ,1986,p. 113.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 39 ,1986,p. 113.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. Community Right-To-Know List. EPA Extremely Hazardous Substances List.

Standards and Recommendations

OSHA PEL: TWA 10 ppm; STEL 20 ppm
ACGIH TLV: 10 ppm, STEL: 15 ppm; Animal Carcinogen
DFG MAK: 10 ppm (35 mg/m3); Confirmed Animal Carcinogen with Unknown Relevance to Humans
NIOSH REL: (Vinyl Acetate) CL 15 mg/m3/15M
DOT Classification:  3; Label: Flammable Liquid

Analytical Methods

For occupational chemical analysis use OSHA: #51 or NIOSH: Vinyl Acetate, P&CAM 278.

Specification

The CAS registry number of Vinyl acetate is 108-05-4. The IUPAC name is ethenyl acetate. In addition, the molecular formula is C4H6O2. What's more, it is a colorless liquid with a pungent odor. And it is the precursor to polyvinyl acetate. It can be polymerized, either by itself to make polyvinyl acetate or with other monomers to prepare copolymers such as ethylene-vinyl acetate. 

Physical properties about this chemical are: (1)ACD/LogP: 0.63; (2)ACD/LogD (pH 5.5): 0.629; (3)ACD/LogD (pH 7.4): 0.629; (4)ACD/BCF (pH 5.5): 1.77; (5)ACD/BCF (pH 7.4): 1.77; (6)ACD/KOC (pH 5.5): 52.382; (7)ACD/KOC (pH 7.4): 52.382; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 26.3 Å2; (11)Index of Refraction: 1.39; (12)Molar Refractivity: 22.081 cm3; (13)Molar Volume: 93.138 cm3; (14)Polarizability: 8.753 ×10-24cm3; (15)Surface Tension: 23.482 dyne/cm; (16)Density: 0.924 g/cm3; (17)Flash Point: °C; (18)Enthalpy of Vaporization: 31.389 kJ/mol; (19)Boiling Point: 72.499 °C at 760 mmHg; (20)Vapour Pressure: 118.484 mmHg at 25°C.

Preparation of Vinyl acetate: the major industrial route involves the reaction of ethylene and acetic acid with oxygen in the presence of a palladium catalyst. The reaction temperature is 160-180 °C and the reaction pressure is below 1MPa. The equation is as follows: 2CH2=CH2 + 2CH3CO2H + O2 → 2CH2=CHOCOCH3. In addition, acetylene can react with acetic acid in the presence of zinc amalgam to give this chemical. The equation is as follows: CH≡CH + CH3CO2H → CH2=CHOCOCH3.

Uses of Vinyl acetate: it is mainly used for organic synthesis. In addition, it can react with 1-phenyl-ethanol to get (R)-1-acetoxy-1-phenyl-ethane. This reaction will need reagents Pseudomonas fluorescens Lipase, o-phenantroline and acetophenone, catalyst Rh2(OAc)4 and solvent CH2Cl2. The reaction time is 72 hours at reaction temperature of 20 °C. The yield is about 60%.

Vinyl acetate can react with 1-phenyl-ethanol to get (R)-1-acetoxy-1-phenyl-ethane

When you are using this chemical, please be cautious about it as the following:
This chemical is highly flammable. And it has danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. During using it, wear suitable protective clothing, gloves and eye/face protection. You can not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer). And in case of accident or if you feel unwell, seek medical advice immediately (show label where possible). What's more, you should keep away from sources of ignition and no smoking. In addition, you should not empty into drains. Keep container tightly closed after using it. Besides, you can take precautionary measures against static discharges.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(=O)OC=C
(2)InChI: InChI=1/C4H6O2/c1-3-6-4(2)5/h3H,1H2,2H3
(3)InChIKey: XTXRWKRVRITETP-UHFFFAOYAB

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LC50 inhalation 6200ppm/4H (6200ppm)   National Technical Information Service. Vol. OTS0521596,
guinea pig LDLo intraperitoneal 500mg/kg (500mg/kg) LIVER: FATTY LIVER DEGERATION American Industrial Hygiene Association Journal. Vol. 35, Pg. 21, 1974.
mouse LC50 inhalation 1550ppm/4H (1550ppm)   E.I. Dupont de Nemours and Company, Technical Sheet. Vol. ES-3574, Pg. 1975,
mouse LD50 oral 1600mg/kg (1600mg/kg)   National Technical Information Service. Vol. OTS0521596,
rabbit LC50 inhalation 2500ppm/4H (2500ppm)   "Documentation of the Threshold Limit Values and Biological Exposure Indices," 5th ed., Cincinnati, OH, American Conference of Governmental Industrial Hygienists, Inc., 1986Vol. 5, Pg. 621, 1986.
rabbit LD50 skin 2335mg/kg (2335mg/kg)   E.I. Dupont de Nemours and Company, Technical Sheet. Vol. ES-3574, Pg. 1975,
rat LC50 inhalation 11400mg/m3/4H (11400mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(11), Pg. 57, 1981.
rat LD50 oral 2900mg/kg (2900mg/kg)   National Technical Information Service. Vol. OTS0521596,