Vinyl acetate monomer (VAM) is a colorless liquid that is immiscible or slightly soluble in water. VAM is a flammable liquid. VAM has a sweet, fruity odor (in small amounts) and a sharp, pungent odor at higher levels.
describe | Vinyl acetate monomer (VAM) is a colorless liquid that is immiscible or slightly soluble in water. VAM is a flammable liquid. VAM has a sweet, fruity odor (in small amounts) and a sharp, pungent odor at higher levels. VAM is an important chemical building block used in a wide variety of industrial and consumer products. VAM is a key ingredient in emulsion polymers, resins and intermediates for paints, adhesives, coatings, textiles, polyvinyl compounds for wire and cable, laminated safety glass, packaging, automotive plastic fuel tanks and acrylic fibers. Vinyl acetate is used in the production of polyvinyl acetate emulsions and resins. Very small amounts of vinyl acetate residues can be found in products made with VAM, such as molded plastic articles, adhesives, paints, food packaging containers, and hairspray. |
chemical properties | Vinyl acetate is a colorless, flammable liquid with a pungent odor. Odor threshold is 0.12 ppm 0.3 ppm (New York, New Jersey). It is a precursor to polyvinyl acetate, an industrially important polymer. |
physical properties | Colorless, watery liquid with a pleasant fruity aroma. The experimentally determined threshold concentrations for detection and identification of odors are 400 μg/m 3 (120 ppb v ) and 1.4 mg/m 3 (400 ppb v ) respectively (Hellman and Small, 1974). |
use | Vinyl acetate is mainly used in the production of polyvinyl acetate emulsion and polyvinyl alcohol. The main uses for these emulsions are in adhesives, paints, textiles, and paper products. |
use | Polymeric form used in plastic blocks, films and lacquers; plastic films used in food packaging. As a modifier of food starch. |
production method | Vinyl acetate is an industrial chemical produced in large quantities in the United States. Global vinyl acetate monomer (VAM) production capacity in 2007 was estimated at 6,154,000 tons/year, with most capacity concentrated in the United States (1,585,000 tons/year), China (1,261,000 tons), Japan (725,000 tons) and Taiwan (650,000 tons). The average bid price in 2008 was $1,600/ton. Celanese is the largest producer (approximately 25% of global capacity), and other important producers include Sinopec (7%), Changchun Group (6%) and LyondellBasell (5%). It is a key ingredient in furniture glue. |
Prepare | The main industrial route involves the reaction of ethylene and acetic acid with oxygen in the presence of a palladium catalyst. Ethylene + acetic acid + 1/2 O 2 → vinyl acetate + H 2 O but also produce by-products: ethylene + 3 O 2 → 2CO 2 + 2H 2 O Vinyl acetate can also be prepared by gas phase addition of acetic acid to acetylene. |
definition | ChEBI: Vinyl acetate is an acetate ester. |
reaction | Vinyl acetate undergoes reactions expected of many alkenes and esters. Addition of bromine gives the dibromide. Addition of hydrogen halides yields ethyl 1-haloacetates, which cannot be produced by other means due to the unavailability of the corresponding halohydrins. Addition of acetic acid in the presence of a palladium catalyst affords ethylene diacetate CH3CH ( OAc) 2 . It undergoes transesterification reactions with various carboxylic acids. Alkenes also undergo Diels-Alder addition and 2+2 cycloaddition. |
general instructions | Vinyl acetate is a clear, colorless liquid. Flash point 18°F. Density 7.8 lbs/gallon. Slightly soluble in water. Vapor is heavier than air. Vapor is irritating to eyes and respiratory system. May polymerize if heated or contaminated. If polymerization occurs inside the container, the container may burst violently. Used in the manufacture of adhesives, paints and plastics. |
air and water reaction | Highly flammable. Slightly soluble in water. |
reactive profile | Vinyl acetate may undergo spontaneous thermal polymerization when exposed to light. Reacts with air or water to form peroxide, triggering violent polymerization. Reacts with hydrogen peroxide to form explosive peracetic acid. Reacts with oxygen to form explosive peroxides. Contact with ozone forms explosive vinyl acetate ozone. Reacts violently or explosively with 2-aminoethanol, chlorosulfonic acid, ethylenediamine, inorganic acids (hydrochloric, hydrofluoric, nitric, sulfuric, oleum) and peroxides [Lewis, 3rd ed., 1993, page 17] 1311]. The polymerization reaction initiated by dibenzoyl peroxide in ethyl acetate accelerated out of control, ignited and exploded [Vervalin, 1973, p. 11]. 81]. Polymerization in toluene solutions has caused several large industrial explosions [MCA Case History No. 2087]. |
health hazard | Vinyl acetate has been linked to reproductive abnormalities. It is a skin and upper respiratory tract irritant and central nervous system depressant. Exposure resulted in progressive deterioration of the heart muscle. |
fire hazard | When decomposed by heat, vinyl acetate burns and releases a pungent odor. Highly hazardous when exposed to heat, flame or oxidizing agents; Explosive hazard with strong acids and strong oxidizing agents. Incompatible with alumina, oxidizing materials, 2-aminoethanol, chlorosulfonic acid; ethyleneimine; 36% hydrochloric acid; 48.7% hydrofluoric acid; 70% nitric acid; oleum; 96% sulfuric acid; ethylenediamine; oxides and silica gels. Avoid light or any polymerization initiators. Hazardous polymerization reactions may be initiated by organic and inorganic peroxides; azo compounds; redox systems (including organometallic components); light; and high-energy radiation. |
Flammability and explosiveness | Highly flammable |
Security overview | Confirmation of carcinogens through experimental carcinogenicity and tumorigenicity data. Moderately toxic by ingestion, inhalation and intraperitoneal routes. Irritating to skin and eyes. Experimental reproductive effects. Human mutation data are reported. There is a high risk of fire hazard when exposed to heat, flame or oxidizing agents. Storage hazard exists, spontaneous exothermic polymerization may occur. Reacts with air or water to form peroxides, which catalyze exothermic polymerization reactions and have caused several large industrial explosions. Reacts with hydrogen peroxide to form explosive peracetic acid. It reacts with oxygen above 50℃ to form unstable and explosive peroxide. Reacts with ozone to form explosive vinyl acetate ozone. Solution polymerization of acetate dissolved in toluene resulted in large-scale industrial explosions. Polymerization reaction with dibenzoyl peroxide + ethyl acetate may release flammable and explosive vapors. Vapors may react violently with desiccants such as silica gel or alumina. Incompatible (explosive) with 2-aminoethanol, chlorosulfonic acid, ethylenediamine, ethyleneimine, HCl, HF, HNO3, fuming sulfuric acid, peroxide, and H2SO4. See also ester. |
potential contact | Vinyl acetate is mainly used in the polymerization process to produce polyvinyl acetate; a copolymer of polyvinyl alcohol and vinyl acetate. These polymers are often formulated as emulsions, suspensions, solutions or resins and are used in the preparation of adhesives, paints, paper coatings and textile finishes. Low molecular weight vinyl acetate is used as a chewing gum base. |
Carcinogenicity | There is insufficient evidence that vinyl acetate is carcinogenic to humans. There is limited experimental animal evidence regarding the carcinogenicity of vinyl acetate. Therefore, IARC classifies vinyl acetate as possibly carcinogenic to humans (Group 2B). This conclusion is based on the following evidence: vinyl acetate is rapidly converted into acetaldehyde in human blood and animal tissues, there is sufficient evidence in experimental animals to prove that acetaldehyde is carcinogenic, and both vinyl acetate and acetaldehyde can induce toxicity after inhalation. Murine nasal cancer, vinyl acetate and acetaldehyde are genotoxic to human cells in vitro and in animals. |
Shipping | UN1301 Vinyl Acetate, Stable, Hazard Class: 3; Label: 3 - Flammable Liquid. |
Purification method | Inhibitors such as hydroquinone and other impurities were removed by drying over CaCl2 and fractional distillation under nitrogen, followed by brief reflux with a small amount of benzoyl peroxide and redistillation under nitrogen. Store it in the dark at 0o. Add inhibitor (~0.004%) for storage. [Berstein 2 IV 176. ] |
polymerization | It can be polymerized alone to prepare polyvinyl acetate, and can also be polymerized 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). Attempts to control polymerization through most "living/controlled" radical processes have proven problematic due to the instability of free radicals. However, RAFT (or more specifically MADIX) polymerization provides a convenient method to control PVA synthesis by adding xanthate or dithiocarbamate chain transfer agents. |
Toxicity evaluation | On January 31, 2009, the Canadian government's final assessment concluded that exposure to vinyl acetate is not considered harmful to human health. This decision under the Canadian Environmental Protection Act (CEPA) is based on new information received during the public comment period, as well as updated information from a risk assessment conducted by the European Union. |
Incompatibility | Vinyl acetate may undergo spontaneous thermal polymerization when exposed to light. Vapors may form explosive mixtures with air. Incompatible with oxidizing agents (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fire or explosion. Keep away from alkaline substances, strong bases, strong acids, oxygen-containing acids, epoxides, strong light and ultraviolet rays. Steam can react violently with silica gel or aluminum, acid, alkali, silica gel; alumina, oxidants, azo compounds. Ozone polymerizes easily at high temperatures, under the influence of light or peroxides. Stabilizers are often included to prevent polymerization. |
waste disposal | The material is dissolved or mixed with a flammable solvent and burned in a chemical incinerator equipped with an afterburner and scrubber. All federal, state and local environmental regulations must be followed. |
Vinyl acetate upstream and downstream product information |