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
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.
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.
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
Production of vinyl acetate polymers
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.
Definition
ChEBI: Vinyl acetate is an acetate ester.
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.
Flammability and Explosibility
Highlyflammable
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.
