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108-05-4

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Identification

Name
Vinyl acetate
CAS
108-05-4
Synonyms
ACETIC ACID VINYL ESTER
ACETIC ACID VINYL ESTER MONOMER
Ethenyl ethanoate
VAM
VINYL ACETATE
VINYL ACETATE MONOMER
1-Acetoxyethylene
Acetate de vinyle
acetatedevinyle
acetatedevinyle(french)
Acetic acid, ethylene ether
Aceticacid,ethenylester
aceticacid,ethyleneester
aceticacid,ethyleneether
aceticacidethenylester
acetoxyethene
CH3CO2CH=CH2
Ethanoic acid, ethenyl ester
ethanoicacid,ethenylester
Ethenyl acetate
EINECS(EC#)
203-545-4
Molecular Formula
C4H6O2
MDL Number
MFCD00008713
Molecular Weight
86.09
MOL File
108-05-4.mol

Chemical Properties

Description
Vinyl acetate monomer (VAM) is a colourless liquid, immiscible or slightly soluble in water. VAM is a flammable liquid. VAM has a sweet, fruity smell (in small quantities), with sharp, irritating odour at higher levels. VAM is an essential chemical building block used in a wide variety of industrial and consumer products. VAM is a key ingredient in emulsion polymers, resins, and intermediates used in paints, adhesives, coatings, textiles, wire and cable polyethylene compounds, laminated safety glass, packaging, automotive plastic fuel tanks, and acrylic fibres. Vinyl acetate is used to produce polyvinyl acetate emulsions and resins. Very small residual levels of vinyl acetate have been found present in products manufactured using VAM, such as moulded plastic items, adhesives, paints, food packaging containers, and hairspray.
Appearance
Vinyl acetate is a colorless, flammable liquid. The odor threshold is 0.12 ppm 0.3 ppm (NY, NJ).
Appearance
colourless mobile liquid with a sweet, irritating odour
mp 
-93 °C
Melting point 
-93 °C (lit.)
Boiling point 
72-73 °C (lit.)
bp 
72-73 °C(lit.)

density 
0.934 g/mL at 25 °C(lit.)

vapor density 
3 (vs air)

vapor pressure 
88 mm Hg ( 20 °C)

refractive index 
n20/D 1.395(lit.)

Fp 
20 °F

storage temp. 
0-6°C
solubility 
20g/l
form 
Liquid
color 
Clear colorless to almost colorless
PH
7 (20g/l, H2O, 20℃)
Stability:
Stable. Highly flammable. Incompatible with acids, bases, oxidizing agents, peroxides, chlorosulfonic acid, ethylene imine, hydrochloric acid, oleum, nitric acid, sulfuric acid, 2-aminoethanol, light. Susceptible to polymerization; commercial product may be stabilized by the addition of hydroquinone.
explosive limit
2.6-13.4%(V)
Water Solubility 
23 g/L (20 ºC)
Sensitive 
Light Sensitive
Merck 
14,9992
BRN 
1209327
Henry's Law Constant
4.81 (calculated, Howard, 1989)
Exposure limits
NIOSH REL: 15-min ceiling 4 ppm (15 mg/m3); ACGIH TLV: TWA 10 ppm, STEL 15 ppm (adopted).
CAS DataBase Reference
108-05-4(CAS DataBase Reference)
NIST Chemistry Reference
Acetic acid ethenyl ester(108-05-4)
IARC
2B (Vol. Sup 7, 63) 1995
EPA Substance Registry System
108-05-4(EPA Substance)

Safety Data

Hazard Codes 
F,T
Risk Statements 
R11:Highly Flammable.
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
Safety Statements 
S16:Keep away from sources of ignition-No smoking .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S29:Do not empty into drains .
S33:Take precautionary measures against static discharges .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37:Wear suitable protective clothing and gloves .
S7:Keep container tightly closed .
RIDADR 
UN 1301 3/PG 2

WGK Germany 
2

RTECS 
AK0875000

Autoignition Temperature
801 °F
TSCA 
Yes
HazardClass 
3
PackingGroup 
II
HS Code 
29153200
HS Code 
29333999
Safety Profile
Confirmed carcinogen with experimental carcinogenic and tumorigenic data. Moderately toxic by ingestion, inhalation, and intraperitoneal routes. A skin and eye irritant. Experimental reproductive effects. Human mutation data reported. Highly dangerous fire hazard when exposed to heat, flame, or oxidzers. A storage hazard, it may undergo spontaneous exothermic polymerization. Reaction with air or water to form peroxides that catalyze an exothermic polymerization reaction has caused several large industrial explosions. Reaction with hydrogen peroxide forms the explosive peracetic acid. Reacts with oxygen above 50℃ to form an unstable explosive peroxide. Reacts with ozone to form the explosive vinyl acetate ozonide. Solution polymerization of the acetate dmolved in toluene has resulted in large industrial explosions. Polymerization reaction with dibenzoyl peroxide + ethyl acetate may release ignitable and explosive vapors. The vapor may react vigorously with desiccants (e.g., sihca gel or alumina). Incompatible (explosive) with 2-amino ethanol, chlorosulfonic acid, ethylenediamine, ethyleneimine, HCl, HF, HNO3, oleum, peroxides, H2SO4. See also ESTERS.
Hazardous Substances Data
108-05-4(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 2.92 g/kg (Smyth, Carpenter)

Raw materials And Preparation Products

Hazard Information

General Description
A clear colorless liquid. Flash point 18°F. Density 7.8 lb/gal. Slightly soluble in water. Vapors are heavier than air. Vapors irritate the eyes and respiratory system. May polymerize if heated or contaminated. If polymerization occurs inside a container, the container may violently rupture. Used to make adhesives, paints, and plastics.
Reactivity Profile
VINYL ACETATE(108-05-4) may undergo spontaneous exothermic polymerization on exposure to light. Reacts with air or water to produces peroxides that initiate explosively violent polymerization. Reacts with hydrogen peroxide to form explosive peracetic acid. Reacts with oxygen to form explosive peroxides. Forms explosive VINYL ACETATE(108-05-4) ozonide on contact with ozone. Undergoes violent or explosive reactions with 2-aminoethanol, chlorosulfonic acid, ethylenediamine, mineral acids (hydrochloric acid, hydrofluoric acid, nitric acid, sulfuric acid, oleum), and peroxides [Lewis, 3rd ed., 1993, p. 1311]. Polymerization initiated by dibenzoyl peroxide in ethyl acetate accelerated out of control, ignited and exploded [Vervalin, 1973, p. 81]. Polymerization in toluene solution has caused several large industrial explosions [MCA Case History No. 2087].
Air & Water Reactions
Highly flammable. Slightly soluble in water.
Health Hazard
Vinyl acetate has been related to reproductive abnormalities. It is a skin and upper respiratory tract irritantand a central nervous system depressant. Exposure caused gradual deterioration of heart muscles.
Potential Exposure
Vinyl acetate is used primarily in polymerization processes to produce polyvinyl acetate; polyvinyl alcohol, and vinyl acetate copolymer. The polymers, usually made as emulsions, suspensions, solutions, or resins, are used to prepare adhesives, paints, paper coatings, and textile finishes. Low molecular weight vinyl acetate is used as a chewing gum base.
Fire Hazard
When heated to decomposition, VINYL ACETATE burns and emits acrid fumes. Highly dangerous when exposed to heat, flames or oxidizers; explosion hazard with strong acids and strong oxidizers. Incompatible with alumina, oxidizing materials, 2-aminoethanol, chlorosulfonic acid; ethyleneimine; 36% hydrochloric acid; 48.7% hydrofluoric acid; 70% nitric acid; oleum; 96% sulfuric acid; ethylene diamine; peroxides and silica gel. Avoid light or any polymerizing initiator. Hazardous polymerization can be initiated by organic and inorganic peroxides; azo compounds; redox systems (including organometallic components); light; and high energy radiation.
First aid
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
Shipping
UN1301 Vinyl acetate, stabilized, Hazard Class: 3; Labels: 3-Flammable liquid.
Incompatibilities
Vinyl acetate may undergo spontaneous exothermic polymerization on exposure to light. Vapors may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, strong light and UV. The vapor may react vigorously with silica gel or aluminum, acids, bases, silica gel; alumina, oxidizers, azo compounds. Ozone readily polymerizes in elevated temperatures, under the influence of light, or peroxides. Usually contains a stabilizer to prevent polymerization.
Chemical Properties
colourless mobile liquid with a sweet, irritating odour
Waste Disposal
Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.
Chemical Properties
Vinyl acetate is a colorless, flammable liquid. The odor threshold is 0.12 ppm 0.3 ppm (NY, NJ).
Chemical Properties
Vinyl acetate is an organic compound with the formula CH3COOCH = CH2. A colorless liquid with a pungent odor, it is the precursor to polyvinyl acetate, an important polymer in industry.
Physical properties
Colorless, watery liquid with a pleasant, fruity odor. Experimentally determined detection and recognition odor threshold concentrations were 400 μg/m3 (120 ppbv) and 1.4 mg/m3 (400 ppbv), respectively (Hellman and Small, 1974).
Uses
In polymerized form for plastic masses, films and lacquers; in plastic film for food packaging. As modifier for food starch.
Uses
Vinyl acetate is primarily used to produce polyvinyl acetate emulsions and polyvinyl alcohol. The principal use of these emulsions has been in adhesives, paints, textiles, and paper products.
Uses
Production of vinyl acetate polymers
Preparation
The major industrial route involves the reaction of ethylene and acetic acid with oxygen in the presence of a palladium catalyst.
Ethylene + acetic acid + 1/2 O2 → Vinyl acetate +H2O
But by products are also generated:
Ethylene + 3 O2 → 2CO2 + 2H2O
Vinyl acetate is also prepared by the gas-phase addition of acetic acid to acetylene.
Production Methods
The worldwide production capacity of vinyl acetate monomer (VAM) was estimated at 6,154,000 tonnes/annum in 2007, with most capacity concentrated in the United States (1,585,000 all in Texas), China (1,261,000), Japan (725,000) and Taiwan (650,000) . The average list price for 2008 was $1600/tonne. Celanese is the largest producer (ca 25% of the worldwide capacity), while other significant producers include China Petrochemical Corporation (7 %), Chang Chun Group (6%) and LyondellBasell (5%).
It is a key ingredient in furniture - glue.
Reactions
Vinyl acetate undergoes many of the reactions anticipated for an alkene and an ester. Bromine adds to give the dibromide. Hydrogen halides add to give 1-haloethyl acetates, which cannot be generated by other methods because of the non - availability of the corresponding halo-alcohols. Acetic acid adds in the presence of palladium catalysts to give ethylidene diacetate, CH3CH(OAc)2. It undergoes transesterification with a variety of carboxylic acids.The alkene also undergoes Diels - Alder and 2 + 2 cycloadditions.
Carcinogenicity
There is inadequate evidence in humans for the carcinogenicity of vinyl acetate. There is limited evidence in experimental animals for the carcinogenicity of vinyl acetate. Therefore, IARC has classified vinyl acetate as possibly carcinogenic to humans (Group 2B). This conclusion was based on the following evidence: vinyl acetate is rapidly transformed into acetaldehyde in human blood and animal tissues, there is sufficient evidence in experimental animals for the carcinogenicity of acetaldehyde, both vinyl acetate and acetaldehyde induce nasal cancer in rats after administration by inhalation, and vinyl acetate and acetaldehyde are genotoxic in human cells in vitro and in animals in vivo .
Environmental Fate
Chemical/Physical. Anticipated hydrolysis products would include acetic acid and vinyl alcohol. Slowly polymerizes in light to a colorless, transparent mass.
At an influent concentration of 1,000 mg/L, treatment with GAC resulted in an effluent concentration of 357 mg/L. The adsorbability of the carbon used was 129 mg/g carbon (Guisti et al., 1974).
Purification Methods
Inhibitors such as hydroquinone and other impurities are removed by drying with CaCl2 and fractionally distilling under nitrogen, then refluxing briefly with a small amount of benzoyl peroxide and redistilling it under nitrogen. Store it in the dark at 0o. Add inhibitor (~0.004%) for storage. [Beilstein 2 IV 176.]
Polymerization
It can be polymerized, either by itself to make polyvinyl acetate or with other monomers to prepare copolymers such as ethylene-vinyl acetate (EVA), vinyl acetate-acrylic acid (VA / AA), polyvinyl chloride acetate (PVCA), and polyvinylpyrrolidone (Vp / Va Copolymer, used in hair gels). Due to the instability of the radical, attempts to control the polymerization via most 'living/controlled' radical processes have proved problematic. However, RAFT (or more specifically MADIX) polymerization offers a convenient method of controlling the synthesis of PVA by the addition of a xanthate or a dithiocarbamate chain transfer agent.
Toxicity evaluation
On January 31, 2009, the Government of Canada's final assessment concluded that exposure to vinyl acetate is not considered to be harmful to human health . This decision under the Canadian Environmental Protection Act (CEPA) was based on new information received during the public comment period, as well as more recent information from the risk assessment conducted by the European Union.

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