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CAS No.: | 108-05-4 |
---|---|
Name: | Vinyl acetate |
Article Data: | 171 |
Molecular Structure: | |
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: | F,T |
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 |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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; |
ethylene glycol divinyl ether
acetyl iodide
A
vinyl acetate
B
vinyliodide
C
2-iodoethyl acetate
Conditions | Yield |
---|---|
In dichloromethane at 10℃; | A 42.8% B 40.5% C 54.9% |
ethene
acetic acid
A
vinyl acetate
B
2-hydroxyethyl acetate
C
ethylene glycol diacetate
Conditions | Yield |
---|---|
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% |
-butyl vinyl ether
acetyl iodide
A
vinyl acetate
B
1-iodo-butane
C
vinyliodide
D
acetic acid butyl ester
Conditions | Yield |
---|---|
In dichloromethane at 10℃; | A 11.8% B 12.8% C 35.8% D 39.8% |
ethene
potassium acetate
acetic acid
A
vinyl acetate
B
carbon dioxide
C
ethyl acetate
Conditions | Yield |
---|---|
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% |
β,β-dichlorovinyl acetate
A
vinyl acetate
B
Z-2-chlorovinyl acetate
C
E-2-chlorovinyl acetate
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride for 0.5h; Ambient temperature; Irradiation; | A 2% B n/a C n/a |
1-acetoxy-2-(ethyl-acetyl-amino)-ethane
A
vinyl acetate
B
N-vinyl-N-ethyl-acetamide
C
N-ethylacetamide
Conditions | Yield |
---|---|
at 490℃; Erhitzung; |
Conditions | Yield |
---|---|
With copper (I) acetate; benzenesulfonic acid |
Conditions | Yield |
---|---|
With sulfuric acid |
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.
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
For occupational chemical analysis use OSHA: #51 or NIOSH: Vinyl Acetate, P&CAM 278.
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%.
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, |