ChemicalBook > Product Catalog > Organic Chemistry > Carboxylic acids and derivatives > Carboxylic acid esters and derivatives > Vinyl acetate
- Product Name:Vinyl acetate
- Synonyms: 1-Acetoxyethylene Acetate de vinyle acetatedevinyle acetatedevinyle(french) Acetic acid, ethylene ether Aceticacid,ethenylester aceticacid,ethyleneester aceticacid,ethyleneether
- Product Categories: Vinyl Esters Building Blocks C2 to C5 Carbonyl Compounds Chemical Synthesis Esters Materials Science Monomers Organic Building Blocks Polymer Science VAM
- Mol File:108-05-4.mol
Vinyl acetate Chemical Properties
- Melting point:-93 °C
- Boiling point: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 n
- Flash point:20 °F
- storage temp. 0-6°C
- solubility 20g/l
- form Liquid
- color Clear colorless to almost colorless
- PH7 (20g/l, H2O, 20℃)
- explosive limit2.6-13.4%(V)
- Water Solubility 23 g/L (20 ºC)
- Sensitive Light Sensitive
- Merck 14,9992
- BRN 1209327
- Henry's Law Constant4.81 (calculated, Howard, 1989)
- Exposure limitsNIOSH REL: 15-min ceiling 4 ppm (15 mg/m3); ACGIH TLV: TWA 10 ppm, STEL 15 ppm (adopted).
- 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.
- CAS DataBase Reference108-05-4(CAS DataBase Reference)
- NIST Chemistry ReferenceAcetic acid ethenyl ester(108-05-4)
- EPA Substance Registry SystemAcetic acid ethenyl ester(108-05-4)
- Hazard Codes F,T,Xn
- Risk Statements 11-39/23/24/25-23/24/25-36-20/21/22-40-37-20
- Safety Statements 16-23-29-33-45-36/37-7-9
- RIDADR UN 1301 3/PG 2
- WGK Germany 2
- RTECS AK0875000
- Autoignition Temperature801 °F
- TSCA Yes
- HazardClass 3
- PackingGroup II
- HS Code 29153200
- HS Code 29333999
- Hazardous Substances Data108-05-4(Hazardous Substances Data)
- ToxicityLD50 orally in rats: 2.92 g/kg (Smyth, Carpenter)
Vinyl acetate Usage And Synthesis
- DescriptionVinyl 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.
- Chemical Propertiescolourless mobile liquid with a sweet, irritating odour
- Chemical PropertiesVinyl acetate is a colorless, flammable liquid. The odor threshold is 0.12 ppm 0.3 ppm (NY, NJ).
- Chemical PropertiesVinyl 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 propertiesColorless, 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).
- UsesIn polymerized form for plastic masses, films and lacquers; in plastic film for food packaging. As modifier for food starch.
- Production MethodsThe 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.
- PreparationThe 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.
- ReactionsVinyl 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.
- General DescriptionA 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.
- Air & Water ReactionsHighly flammable. Slightly soluble in water.
- Reactivity ProfileVinyl acetate 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 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].
- Health HazardVinyl 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.
- Fire HazardWhen 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.
- Safety ProfileConfirmed 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.
- Potential ExposureVinyl 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.
- Environmental FateChemical/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).
- ShippingUN1301 Vinyl acetate, stabilized, Hazard Class: 3; Labels: 3-Flammable liquid.
- Purification MethodsInhibitors 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.]
- PolymerizationIt 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 evaluationOn 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.
- IncompatibilitiesVinyl 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.
- Waste DisposalDissolve 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.
Vinyl acetate Preparation Products And Raw materials
- Preparation ProductsPoly(vinyl alcohol)Bromoacetaldehyde diethyl acetal((1R,4S)-2-Azabicyclo[2.2.1]hept-5-en-3-oneMETHYL 5-FORMYL-2-METHYL-3-FUROATETazobactam acid2-Acetylbutyrolactone1,1-Dimethoxy-2-(2-methoxyethoxy)ethane2-TRIFLUOROMETHYLQUINOLINE-7-CARBOXYLIC ACIDPOLY(VINYL ACETATE)Adhesive for nonwoven fabricstiffening agent for synthetic fibre 855VINYL STEARATEPressure sensitive adhesivePALMITIC ACID VINYL ESTERStarch, hydrogen phosphate acetateLT-01 emulsionPR-I retanning agentmaleic acid-vinyl acetate copolymerirradiation initiated starch-g-vinyl acetate water absorbent agentAcetylated Dishtarch Phosphateemulsion used for paper series PCPOLY(ETHYLENE-CO-METHACRYLIC ACID)Vinyl acetate-acrylate copolymer,emulsionSTARCH ACETATEcoating adhensive SSS-855-NORBORNEN-2-YL ACETATEEthylene-vinyl acetate copolymer
- Raw materialsAcetic acid glacialPalladium chlorideAcetylenePlatinum
- ETHYLENE Acrylic acid Megestrol acetate VINYL PROPIONATE Methyl acetate Diethylenetriaminepentaacetic acid POLYVINYL ACEATE Butyl acetate Vinyl chloroacetate Ethylene-vinyl acetate copolymer POLY(VINYL ACETATE) USP Tocopheryl acetate Triacetin Vinyl acetate Benzyl acetate Potassium Acetate PHENYL ACETATE ACETATE
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