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CAS NUMBER: 108-05-4
EC NUMBER: 108-05-4
MOLECULAR WEIGHT: 86,090 gr/mol
Vinyl acetate monomer (VAM) is a colourless liquid, immiscible or slightly soluble in water.
Vinyl acetate monomer is a flammable liquid.
Vinyl acetate monomer has a sweet, fruity smell (in small quantities), with sharp, irritating odour at higher levels.
Vinyl acetate monomer is an essential chemical building block used in a wide variety of industrial and consumer products.
Vinyl acetate monomer 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.
Vinyl acetate monomer is an organic compound with the formula CH3CO2CH=CH2.
This colorless liquid is the precursor to polyvinyl acetate, an important industrial polymer.
Vinyl acetate monomer is primarily used as a monomer in the production of other chemicals used in various industrial and consumer product applications.
Vinyl acetate monomer-based polymers, including vinyl chloride-vinyl acetate copolymer, polyvinyl acetate (PVA) and polyvinyl alcohol (PVOH), are used in a variety of applications.
When polymers are made using Vinyl acetate monomer, the vinyl acetate used in their manufacture is completely consumed, which means that there is only residual if any potential exposure to VAM itself in these products.
Vinyl Acetate Monomer (also known as acetic acid ethenyl ester, acetic acid ethylene ether, acetoxyethene, 1-acetoxyethylene, ethenyl ethanoate, ethenyl acetate, and acetic acid vinyl ester) is a colourless mobile liquid with a pungent odour.
Vinyl acetate monomer has the formula CH3COOCH=CH2 and is a key raw material in the production of chemicals which are then used to manufacture a wide variety of consumer and industrial products.
Vinyl acetate monomer (VAM) is a key intermediate used in the making of a number of polymers and resins for adhesives, coatings, paints, films, textiles and other end-products.
Vinyl acetate monomer is used to make barrier resins for plastic bottles (source Carlsberg)
The largest derivative is polyvinyl acetate (PVA) which is mainly used in adhesives as it has good adhesion properties to a number of substrates including paper, wood, plastic films and metals.
Other uses for PVA include paper coatings, paints and industrial coatings.
The second largest consumer of VAM is polyvinyl alcohol (PVOH) which is manufactured from PVA. Main uses for PVOH include textiles, adhesives, packaging films, thickeners and photosensitive coatings.
Vinyl acetate monomer is also used in the manufacture of polyvinyl butyral (PVB), a resin that has strong adhesion, clarity and toughness properties.
PVB is mainly used in laminated glass for automobiles and commercial buildings by providing the protective and transparent interlayer that is bonded between two panes of glass.
Vinyl acetate monomer can also be used in coatings and inks.
Vinyl acetate monomer is consumed in the manufacture of ethylene vinyl acetate (EVA) and vinyl acetate ethylene (VAE).
Vinyl acetate monomer, which has less than 50% vinyl acetate in content, is mainly used for films and wire and cable insulation.
Vinyl acetate monomer, which contains more than 50% vinyl acetate, is primarily used as cement additives, paints and adhesives.
A fast growing use of Vinyl acetate monomer is the manufacture of ethylene vinyl alcohol (EVOH) which is used as a barrier resin in food packaging, plastic bottles and gasoline tanks, and in engineering polymers.
Other Vinyl acetate monomer derivatives include vinyl chloride-vinyl acetate copolymers which have major applications in coatings, paints and adhesives.
Polyvinyl formal is used for wire enamels and magnetic tape.
Vinyl acetate monomer is estimated that approximately 80% of global VAM production is used to make PVA and PVOH, with most of the remaining volume going to PVB, EVA copolymers and EVOH resins.
World growth for Vinyl acetate monomer is expected to be 4%/year with the strongest growth in Asia, particularly China.
In Europe, the economic slowdown has hit Vinyl acetate monomer consumption, notably in the paints and adhesives sectors and construction.
Vinyl acetate monomer (VAM) is an essential chemical building block used to manufacture a variety of consumer and industrial products.
Vinyl acetate is a colorless liquid with a pungent
odor and can be olymerized in mass, solution, suspension or emulsion.
Vinyl acetate appears as 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.
Vinyl acetate is an industrial chemical that is produced in large amounts in the United States.
Vinyl acetate monomer is a clear, colorless liquid with a sweet, fruity smell.
Vinyl acetate monomer is very flammable and may be ignited by heat, sparks, or flames. Vinyl acetate is used to make other industrial chemicals.
These chemicals are used mainly to make glues for the packaging and building industries.
They are also used to make paints, textiles, and paper.
Vinyl acetate monomer is also used as a coating in plastic films for food packaging and as a modifier of food starch.
Vinyl acetate monomer is a significant intermediate used in the production of a wide range of resins and polymers for paints & coatings, adhesives, glues & sealants, elastomers, textile finishes, paper coatings, binders, films, and a myriad of other industrial and consumer applications.
Vinyl acetate monomer efficiently homo-polymerizes to polyvinyl acetate (PVA), and VAM can be used in numerous random copolymers and terpolymers such as ethylene-vinyl acetate copolymers, vinyl-acrylic resins, vinyl acetate-acrylic acid copolymers, and vinyl acetate-vinyl chloride copolymers.
With the wide diversity of polymerization options, VAM has allowed the design of products with a wide spectrum of cost and performance profiles.
Vinyl acetate monomer polymerization is easy in all processes, emulsion, bulk, solution, and suspension.
Commercial VAM sources have purities greater than 99.9 percent, with trace levels of water, acetic acid, and acetaldehyde.
Water and acetic acid do not have much of an effect on polymerizations, but acetaldehyde acts as a chain transfer agent and has a significant effect on the viscosity of the final polymers.
Formulators may polymerize hydroquinone-stabilized material without removing the HQ.
Vinyl Acetate Monomer (VAM) is a colorless liquid organic compound that is the precursor to polyvinyl acetate.
Vinyl acetate monomer is an intermediate used in the manufacture of a number of industrial polymers and resins for the production of adhesives, coatings, paints, films and textiles, as well as wire and cable insulation.
The VAM molecular formula is C4H4O2. Its CAS is 108-05-4.
VAM is considered slightly toxic.
The clear, colorless liquid is slightly soluble in water and its vapors are heavier than air.
Vinyl acetate monomer is primarily used as a monomer in the manufacture of polyvinyl acetate and polyvinyl alcohol.
Short-term exposure has resulted in eye and upper respiratory irritation.
Vinyl acetate is an important industrial monomer that is used to make homopolymers and copolymers with a wide variety of applications.
Vinyl acetate monomer is a volatile, flammable liquid that, like many esters, has a pleasant, fruity aroma.
Esters are usually synthesized from an alcohol and an acid; but in the case of vinyl acetate, the starting alcohol would be vinyl alcohol, which is not stable.
To learn how vinyl acetate is made, see “Vinyl acetate synthesis and current production”.
The homopolymer poly(vinyl acetate)1 (PVA or PVAc) is an important polymer used in adhesives, textile sizing, and even chewing gum.
In 1912, German chemist Fritz Klatte discovered PVA when he observed that vinyl acetate easily reacts with itself.
Klatte’s PVA formulations were dense solids; but over the years, researchers developed methods for producing the polymer in other forms.
One of the most common forms of PVA is made by aqueous free-radical emulsion polymerization.
Water, a surfactant, and an initiator (e.g., sodium persulfate) are mixed and heated.
Vinyl acetate monomer (frequently called VAM in the industry) is added slowly, and the system is heated until the reaction is complete.
The product is a milklike latex emulsion.
PVA latices are widely used in adhesives. One of the most familiar is Elmer’s Glue.
PVA adhesives are used in packaging applications such as shipping boxes and bags, food containers, envelopes, tapes, and as binders for paper, plastics, and foils.
In addition to making homopolymers, vinyl acetate is combined with other monomers such as ethylene and acrylates to produce a variety of copolymers.
Ethylene–vinyl acetate copolymers (EVAs) can be made in bulk or by emulsion polymerization.
Emulsion EVAs have many uses, including adhesives that are similar to vinyl acetate homopolymers.
Bulk polymer applications range from large-volume industrial uses to the handy glue sticks you may have at home or in school.
Vinyl acetate–acrylate emulsion copolymers (“acrylics”) are used primarily in paints and other coatings.
They have largely replaced oil-based coatings for economic and environmental reasons.
Vinyl acetate monomer, also known as VAM, is one of the most essential chemicals used in the manufacture of polymers.
Vinyl acetate monomer is manufactured through catalytic conversion reaction of acetic acid and ethylene with oxygen.
Due to higher reactivity of vinyl acetate monomer, a polymerization inhibitor is required in order to control the degree of polymerization.
Vinyl acetate monomer (VAM) is used as an intermediate in the manufacture of various copolymers and homopolymers such as polyvinyl acetate, polyvinyl alcohol, ethylene-vinyl acetate and ethylene-vinyl alcohol among others.
These copolymers are used in various end-user industries such as adhesives, paints and coatings, textiles, paper and packaging among others.
Vinyl acetate monomer (VAM) is one of the key ingredients used in the manufacture of furniture glue and adhesives.
The industrial preparation of VAM according to the Journal of Catalysis, involves the reaction of ethylene ad acetic acid with oxygen in the presence of a palladium catalyst.
Industry statistics estimate that approximately 80% of global VAM production is used to manufacture PVA and PVOH, with most of the remaining volume being used in the production of PVB, EVA copolymers and EVOH resins.
Vinyl acetate monomer is a colourless liquid with a sweet odour.
Vinyl acetate monomer is made from the raw materials ethylene, acetic acid and oxygen.
VAM has a tendency to polymerise spontaneously.
For this reason, Vinyl acetate monomer is stabilised using hydroquinone in quantities specified by the customer.
Vinyl Acetate Monomer is the basic ingredient in numerous products in our daily lives.
In the form of Polyvinyl Acetate (PVA), Vinyl acetate monomer is used to manufacture dispersions; in the form of polyvinyl alcohol (PVOH), is it found in protective films for mobile phones and LCD televisions; in the form of Polyvinyl butyral (PVB), it plays an important role in the production of composite safety glass for the automotive industry; and in the form of ethylene vinyl acetate (EVA) it is used in the manufacture of flip flop sandals and shower curtains.
Other fields of application include as binding agents in the construction and the paints and varnishes industries.
Vinyl acetate monomer is also an important raw material used in the paper, adhesives and textiles industries.
Vinyl acetate monomers (VAM) are essential building blocks for a large number of water-based polymers.
Vinyl acetate monomer is prepared from ethylene by reacting it with oxygen and acetic acid over a palladium catalyst.
The basic chemical reaction is shown below, along with the chemical structure of vinyl acetate monomer.
Vinyl acetate monomer, a colorless liquid with a pungent odor, is rarely used in its pure form.
Instead, it’s a precursor to other important industrial compounds.
In 2019, the U.S. production volume of vinyl acetate amounted to a total of 1.54 million metric tons.
Vinyl acetate monomer can be polymerized in mass, solution, suspension or emulsion processes.
In the latter process, the monomer of vinyl acetate can be 1200px-PVA.svgpolymerized while dispersed in water to form a milky white emulsion.
When acted upon by free-radical initiators, the vinyl acetate monomers can be linked into long, branched chains of polymers.
The repeating unit of the polymer is shown to the right:
In the emulsion polymerization products, Vinyl acetate monomer emulsion homopolymer and vinyl acetate-based emulsion copolymers have significant industrial importance.
Vinyl acetate monomer emulsion homopolymer was the first synthetic polymer latex to be made on a commercial scale, and today it accounts for 28 percent of the total waterborne synthetic latexes.
Vinyl acetate monomer-based polymers are extremely versatile.
The milky white fluid formed during emulsion polymerization can be processed directly into latex paints, in which the polymer forms a strong, flexible, adherent film.
Vinyl acetate-based polymers also offer excellent adhesion to common substrates one of the most common uses of a vinyl acetate-based polymer is white glue, otherwise known as Elmer’s glue or wood glue.
These polymers have low levels of volatile organic compounds (VOCs), which means less off-gassing, odors and a lower environmental impact.
Additionally, vinyl acetate-based polymers have higher viscosities, which means they are more resistant to flow an important property for adhesives and paints.
Combine these properties with low cost and ready availability, and you’ll find these polymers in many everyday products.
Vinyl acetate monomer polymerizations are exothermic, requiring provisions for cooling.
In emulsion reactions, polymerization times are about 4 hours at temperatures of 70 °C.
Formulators must maintain the pH at near neutral level during polymerization to minimize VAM hydrolysis.
To ameliorate the hydrolysis reaction, they can use a buffer such as sodium acetate.
Free radical Vinyl acetate monomer copolymerizations occur easily with some monomers and with difficulty with other comonomers.
The method for measuring the tendency of monomer pairs to randomly copolymerize versus a preference for homopolymerization or block polymerization, is based on the measurement of so-called reactivity ratios.
The reactivity ratio for a pair of monomers is the reaction rate constant for propagation of the first monomer in a growing polymer chain to itself versus addition to the second monomer.
When the reactivity ratios of comonomer pairs are similar, random copolymerizations are observed.
Vinyl acetate monomer with a reactivity ratio of r1=0.79 and VAM (r2=1.4) copolymerizes well, affording alternating copolymer compositions closely reflecting the compositions of the monomer feeds.
When the reactivity ratios of two monomers differ significantly, compositions will tend towards that of a homopolymer of the more reactive co-monomer.
As an example, random copolymerization of styrene (r1~50) with VAM (r2=0) cannot be achieved by conventional free-radical polymerizations.
For a thorough explanation of how monomer reactivity ratios can be used to predict copolymer compositions, and a tables of reactivity ratios for comonomer pairs, please see this lecture from Stanford University.
Another unique feature of Vinyl acetate monomer free radical polymerizations is their propensity to undergo chain transfer reactions that afford branched architectures.
This dynamic is due to chain transfer reactions between the growing polymer chain free radical and abstraction of an acetate hydrogen position (predominant mode) or a tertiary hydrogen atom within the polymer chain.
Branching process increases in significance as the conversion proceeds, with decreasing monomer concentrations.
Branching results in PVAs with lower tensile properties, increased ductility, and lower solution and melt viscosities.
The branches are both short and long chain (above the critical entanglement length), with the short chain branches responsible for the lower strength properties.
Vinyl acetate monomer is a key intermediate used in the manufacture of homopolymers, copolymers, and derivatives for adhesives & sealants, paint & coatings, packaging films, construction materials, textile & paper finishes, and a myriad of other applications.
Vinyl acetate monomer is a highly versatile monomer, creating copolymers such as ethylene-co-vinyl acetate, acrylic ester-co-vinyl acetate, vinyl chloride-co-vinyl acetate, etc.
The broad copolymer options allow the design of numerous polymer systems to meet the economics and performance requirements of a multitude of industrial and consumer applications.
The largest use for Vinyl acetate monomer is in polyvinyl acetate homopolymer, which is used in adhesives and paints, offering ease of use and good adhesion properties to paper, fabrics, wood, plastics and many other substrates at a low cost.
USES:
Primarily,
Vinyl acetate monomer is used as a monomer in the production of polyvinyl acetate and polyvinyl alcohol.
Vinyl acetate monomer is also used as a raw material in the production of other chemicals, in adhesives, water-based paints, nonwoven textile fibers, and paper coatings.
Vinyl acetate monomer is mainly used in the production of polyvinyl acetate (PVAc) and polyvinyl alcohol (PVOH or PVA).
In fact, 80 % of all the VAM produced in the world is used to make these two chemicals.
Polyvinyl acetate is used in paints, adhesives, paper coatings and textile treatments, while polyvinyl alcohol is used in the production of adhesives, coatings, and water soluble packaging, and textile warp sizing.
Vinyl acetate monomer is also used to make polyvinyl butyral (PVB) which is used in laminated safety glass for cars and buildings.
Ethylene-vinyl acetate (EVA) resin is also made from VAM and is used in the manufacture of packaging film, heavy-duty bags, extrusion coating, wire and cable jacketing, hot-melt adhesives and cross-linked foam.
Other products made from Vinyl acetate monomer are ethylene-vinyl alcohol (EVOH) resins which are used as a gas barrier in multi-layered food and beverage packages, and as a barrier layer in automobile tanks.
-Adhesives and Glues:
Vinyl acetate monomer has strong adhesion properties for a variety of materials, including paper, wood, plastic films and metals, and is a key ingredient in wood glue, white glue, carpenter’s glue and school glue.
Vinyl acetate monomer is used for adhesive packaging films; it is water-soluble and remains flexible as it ages.
-Paints:
Vinyl acetate monomer-based polymers are used in the production of many interior latex paints as the ingredient that provide adhesion of all the ingredients and the luster of the finish.
-Textiles:
POH is used in textile manufacturing for warp sizing, a process by which textiles are coated with a protective film to minimize breakage during weaving.
-Coatings:
Vinyl acetate monomer is used in photosensitive coatings.
Vinyl acetate monomer is also used in the manufacture of polyvinyl butyral (PVB), a resin that has strong adhesion, clarity and toughness properties.
Vinyl acetate monomer is mainly used in laminated glass for automobiles and commercial buildings; it provides a protective and transparent interlayer that is bonded between two panes of glass.
Vinyl acetate monomer can also be used in coatings and inks.
Vinyl acetate monomer-based derivatives are also used as a coating in plastic films for food packaging.
-Food Starch Modifier:
Vinyl acetate monomer can be used as an ingredient in food starch modifiers.
Modified food starch is typically used as a food additive for the same reasons conventional starches are used: to thicken, stabilize or emulsify food products like soups, sauces and gravy.
-Thickeners:
Vinyl acetate monomer is used as a thickening agent in some liquids.
Thickening agents can be added to some liquids to help treat dysphagia, or swallowing difficulty, and to help the contents of soft drinks to remain evenly distributed.
-Insulation:
Vinyl acetate monomer is consumed in the manufacture of ethylene vinyl acetate (EVA), used in wire and cable insulation due to its flexibility, durability and its flame-retardant properties.
-Barrier Resin:
A growing use of
Vinyl acetate monomer is the manufacture of ethylene vinyl alcohol (EVOH), which is used as a barrier resin in food packaging, plastic bottles, and gasoline tanks, and in engineering polymers.
Barrier resins are plastics used in food packaging to help prevent gas, vapor or liquid penetration and help keep food fresh.
USES:
-Emulsion polymers
-Resins
-Intermediates Used in Paints
-Adhesive
-Coatings
-Textiles
-Wire and Cable
-Polyethylene Compounds
-Laminated Safety Glass
-Packaging
-Automotive Plastic Fuel Tanks
-Acrylic Fibers
-Chewing Gum Base
APPLICATIONS:
Vinyl acetate monomer is the key raw material used for the production of polyvinyl acetate (PVAc), vinyl acetate ethylene (VAE) emulsions and polyvinyl alcohol (PVOH), a precursor to PvB films.
Vinyl acetate monomer is also used to make ethylene vinyl alcohol (EVOH) resins and ethylenevinyl acetate copolymers (EVA).
In addition, VAM is an intermediate used to produce paints and coatings, adhesives, textile finishes, water-soluble films and fibers, and laminated safety glass.
The largest end-use for VAM is in the production of polyvinyl acetate resins as a base for adhesives and coatings, as well as a feedstock for derivative resins like polyvinyl alcohol (PVOH).
Vinyl acetate monomer emulsions and resins are low in cost and convenient to use, and they have a wide application range.
Vinyl acetate monomer is likely best known as the base component of household white glues used for bonding paper, fabrics, wood, and plastic.
Worldwide consumption of VAM measures over 4 million metric tons, with an annual growth rate of about 4.7 percent.
Vinyl acetate monomer represents over half of the total usage of VAM.
In addition to uses in paints, coatings, adhesives, and binders, PVAs are feedstocks for other large-volume systems such as polyvinyl alcohol (PVOH), polyvinyl butyral (PVB,) and polyvinyl formal (PVF).
Vinyl acetate monomer is the largest use for PVAs, followed by adhesives and paints & coatings.
Vinyl acetate is polymerized as to yield polyvinyl acetate (PVA) and polyvinyl alcohol (PVA).
80% of vinyl acetate production is for this purpose. Other monomers are used to prepare copolymers such as EVA, PVCA.
Vinyl acetate monomer is difficult to control the reaction due to instability of radicals.
While polyvinyl acetate is used in dyes, glues, paper coatings and textile processes, polyvinyl alcohol is used in glues, packings and warping dimentions.
Vinyl acetate monomer is used for producing polyvinyl butyral which is used in laminated safety glass production which are used in automobiles and buildings.
Vinyl acetate monomer is also used as ethylene alcohol resins in gas barriers and barrier coats for automobile tanks.
A fast-growing use of Vinyl acetate monomer is the manufacture of vinyl acetate-ethylene (VAE) and ethylene-vinyl acetate (EVA) copolymers.
As the Vinyl acetate monomer content increases in an ethylene-vinyl acetate copolymer, crystallinity decreases and tensile properties decrease.
However, flexibility, toughness and adhesive strength increase. At a level of 50 percent, EVAs are amorphous.
Vinyl acetate monomers with more than 60 percent VAM content are used in coatings, adhesives, cements, and plasters.
Vinyl acetate monomers produce low-VOC emulsion systems, because the ethylene monomer serves as a plasticizing monomer and reduces the need for coalescing agents or plasticizers.
Commercial Vinyl acetate monomer emulsions exhibit Tgs between -15 °C and +15 °C.
Formulators may freeze-dry VAE emulsions to produce redispersible powders (RDPs), often referred to as “solid latexes.”
Vinyl acetate monomers with less than 40 percent VAM content are thermoplastics used for elastomeric films, extrusion coating, and adhesives.
Vinyl acetate monomers are further employed in the production of ethylene vinyl alcohol (EVOH) copolymers with excellent gas barrier properties useful in multi-layer food packaging and agricultural films, beverage & cosmetic bottles, and barrier layers of plastic gasoline tanks.
A wide variety of Vinyl acetate monomer options are available.
Vinyl acetate monomers are economical products that find extensive usage in interior architectural paints & caulks, adhesives & sealants, paper & textile binders, engineered fabrics, and pigment dispersions.
Vinyl acetate monomer like ethyl, butyl and 2-ethylhexyl acrylates enhance the performance of copolymers by improving flexibility, water resistance, adhesion, and scrub & stain resistance.
Ter-monomers are also used like ethylene and acrylic acid in these systems.
BENEFITS:
Frequently used as a co-monomer with acrylic monomers.
Vinyl acetate monomer copolymers are making inroads in low VOC coating applications.
For film packaging, Vinyl acetate monomer increases cling, toughness, clarity.
Vinyl acetate monomer resins have high barriers to O2, flavor, aroma – excellent for food packaging.
Vinyl acetate monomer paper coatings increase brightness, resistant to contamination, improve eye appeal, provide printable surface.
Vinyl acetate monomer hot melt adhesives improve adhesion, paper penetration, and dry quickly.
-Hydrophilic backbone – tunable when combined with acrylic monomers for increase exterior durability and non-yellowing.
-High affinity for cellulosic substrates
-High mechanical stability
-Good adhesion to LSE substrates
-Easily blended with aminoplast resins
-Good plasticizer response
-Low cost
PHYSICAL PROPERTIES:
-General Properties: colorless liquid
-Odor: strawberry-like, sweet, strong
-Intensity: 0.934 g/cm3
-Boiling point: 72,7 °C
-Melting point: -93,5 °C
-Flash point: -8 °C
-Vapor pressure: 100 mmHg (20 °C)
-Refraction index: 1,3941 nD
-Solubility (aqueous) 2 gr/100 mL (20 °C)
PROPERTIES:
Vinyl acetate monomer, or VAM, is a colorless monomer which has a strong odor.
Vinyl acetate monomer is precessor for polyvinyl acetate which is an important polymer in industry.
Vinyl acetate monomer is an important raw material for many industrial products.
Vinyl acetate monomer can go into many reactions which are expected for an alkene and ester.
-Molar mass: 86.09
-Boiling temperature at 1013 hPa: 72.7
-Melting temperature: -93.2
-Vapor pressure at 20°: 113
-Vapor density (air = 1): 3.0
-Density at 20°C: 0.932
-Solubility in water at 20°C: 20
-Evaporation number (n-butyl acetate = 1): 8.9
PRODUCTION:
The worldwide production capacity of vinyl acetate was estimated at 6,969,000 tonnes/year 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).[4] 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%).[4]
Vinyl acetate monomer is a key ingredient in furniture glue.
The main production method for vinyl acetate monomer is the reaction of ethylene and acetic acid with oxygen, in the presence of a palladium catalyst.
The Vinyl acetate monomer is recovered by condensation and scrubbing and is then purified by distillation.
A new manufacturing process, dubbed Leap, could offer large capital cost savings as a more efficient fluidised bed system replaces the fixed bed reactors currently in use.
The oldest means of manufacturing VAM is the addition of acetic acid to acetylene and this process is still used but not on a large scale.
POLYMERIZATION:
Vinyl acetate monomer can be polymerized to give polyvinyl acetate (PVA).
With other monomers it can be used to prepare various 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 by 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.
OTHER REACTIONS:
Vinyl acetate monomer 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.
Vinyl acetate monomer adds in the presence of palladium catalysts to give ethylidene diacetate, CH3CH(OAc)2.
Vinyl acetate monomer undergoes transesterification with a variety of carboxylic acids.
The alkene also undergoes Diels–Alder and 2+2 cycloadditions.
POTENTIAL EXPOSURE:
Vinyl acetate monomer 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 monomer is used as a chewing gum base.
CONSUMER EXPOSURE:
Consumers may come into contact with some of the polymers made from Vinyl acetate monomer noted in the “Uses and Benefits” section above, such as glues and paints, but exposures are expected to be very low.
The U.S. Food and Drug Administration (FDA) has determined that vinyl acetate may be safely used as a coating in plastic films for food packaging, and as a food starch modifier.
The Centers for Disease Control and Prevention’s Agency for Toxic Substances and Disease Registry states that studies have shown that once ingested by nose or mouth, vinyl acetate is quickly distributed through the body and removed.
Vinyl acetate monomer breaks down quickly and leaves the body through the breath.
Small amounts will also leave the body through urine and waste.
INDUSTRIAL EXPOSURE:
In industrial settings workers are protected from exposure to vinyl acetate with equipment design, protective gear and monitoring.
The U.S. Occupational Safety and Health Administration (OSHA) has set specific limits for worker exposure to vinyl acetate that manufacturers must abide by.
Acute (short-term) inhalation exposure of workers to vinyl acetate in facilities where it is manufactured can result in eye irritation and upper respiratory tract irritation.
Chronic (long-term) occupational exposure has not been shown to result in any severe adverse effects in workers; some instances of upper respiratory tract irritation, cough and/or hoarseness were reported.
The U.S. Environmental Protection Agency (EPA) has not classified vinyl acetate for carcinogenicity in humans.
PREPARATION:
Vinyl acetate monomer is the acetate ester of vinyl alcohol.
Since vinyl alcohol is highly unstable (with respect to acetaldehyde), the preparation of vinyl acetate is more complex than the synthesis of other acetate esters.
The major industrial route involves the reaction of ethylene and Vinyl acetate monomer with oxygen in the presence of a palladium catalyst.
STORAGE:
Vinyl acetate monomer is stored in mild steel storage tanks and/or new or reconditioned steel drums and can be transported by bulk vessels or tank trucks.
Vinyl acetate monomer has a specific gravity of 0.933 and a flash point of -8° C (closed cup) and is highly flammable.
Vinyl acetate monomer should therefore be stored in a cool, dry, well-ventilated area that is free from the risk of ignition.
For transportation purposes, Vinyl acetate monomer is classified as packing group II and hazard class 3 and it is an irritant.
SYNONYM:
108-05-4
Ethenyl acetate
Acetic acid ethenyl ester
Acetic acid vinyl ester
Ethenyl ethanoate
1-Acetoxyethylene
Vinyl ethanoate
Vinyl acetate monomer
Acetoxyethene
Acetoxyethylene
Vinylacetat
Vinyl A monomer
Zeset T
Vinylacetaat
Octan winylu
Acetic acid, ethenyl ester
Acetate de vinyle
