Vinyl acetate

Base Information

• Chemical Name: Vinyl acetate
• CAS No.: 108-05-4
• Deprecated CAS: 220713-36-0,61891-42-7,82041-23-4,85306-26-9,172702-77-1,58162-13-3,172702-77-1,61891-42-7,85306-26-9
• Molecular Formula: C4H6O2
• Molecular Weight: 86.0904
• Hs Code.: 29333999
• European Community (EC) Number: 203-545-4,617-699-9,686-890-7
• ICSC Number: 0347
• NSC Number: 8404
• UN Number: 1301
• UNII: L9MK238N77
• DSSTox Substance ID: DTXSID3021431
• Nikkaji Number: J2.860F
• Wikipedia: Vinyl acetate
• Wikidata: Q377339
• RXCUI: 1368177
• Metabolomics Workbench ID: 44752
• ChEMBL ID: CHEMBL1470323
• Mol file: 108-05-4.mol

Synonyms:vinyl acetate

Chemical Property of Vinyl acetate

Chemical Property:

• Appearance/Colour: colourless mobile liquid
• Vapor Pressure: 118mmHg at 25°C
• Melting Point: -93 °C
• Refractive Index: 1.39
• Boiling Point: 72.499 °C at 760 mmHg
• Flash Point: 20°F
• PSA: 26.30000
• Density: 0.93 g/cm³
• LogP: 0.69300
• Storage Temp.: 0-6°C
• Solubility.: 20g/l
• Water Solubility.: 23 g/L (20℃)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 86.036779430
• Heavy Atom Count: 6
• Complexity: 65.9
• Transport DOT Label: Flammable Liquid

Purity/Quality:

98% ^*data from raw suppliers

VinylAcetate(Stabilizedwith8-12ppmHydroquinone) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F:Flammable
• Statements: R11:
• Safety Statements: S16:; S23:; S29:; S33:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CC(=O)OC=C
• Recent ClinicalTrials: Assessment of VAC-3S Therapeutic Properties When Combined With Standard ART in the Course of HIV-1 Infection
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the respiratory tract. The substance is mildly irritating to the eyes and skin.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dryness and cracking. This substance is possibly carcinogenic to humans.
• 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.
• 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: 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. In polymerized form for plastic masses, films and lacquers; in plastic film for food packaging. As modifier for food starch.

Technology Process of Vinyl acetate

There total 67 articles about Vinyl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 54.9%

ethylene glycol divinyl ether (764-78-3,50856-26-3) + acetyl iodide (507-02-8) → vinyl acetate (108-05-4,9003-20-7) + vinyliodide (593-66-8) + 2-iodoethyl acetate (627-10-1)

Guidance literature:

In dichloromethane; at 10 ℃;

DOI:10.1023/B:RUJO.0000036063.58577.17

Reference yield: 39.8%

-butyl vinyl ether (111-34-2,92680-80-3) + acetyl iodide (507-02-8) → vinyl acetate (108-05-4,9003-20-7) + 1-iodo-butane (542-69-8) + vinyliodide (593-66-8) + acetic acid butyl ester (123-86-4)

Guidance literature:

In dichloromethane; at 10 ℃;

DOI:10.1023/B:RUJO.0000036063.58577.17

Reference yield: 20.0%

ethene (74-85-1) + acetic acid (64-19-7,77671-22-8) → vinyl acetate (108-05-4,9003-20-7) + 2-hydroxyethyl acetate (542-59-6) + ethylene glycol diacetate (111-55-7,27252-83-1)

Guidance literature:

With Pd(MeCN)2Cl(NO₂); at 25 ℃; for 4h; under 2068.6 Torr; Product distribution; various catalysts, times, additives, O₂ atmosphere, with 18O containing complex;

DOI:10.1021/ja00298a024

upstream raw materials:

ethylene glycol diacetate

1-acetoxy-2-(ethyl-acetyl-amino)-ethane

ethylidene diacetate

acetic anhydride

Downstream raw materials:

(2-acetoxy-ethyl)-dichloro-methyl-silane

bromoacetaldehyde dipropyl acetal

3-phenyl-5-acetoxy-4,5-dihydroisoxazole

vinyl formate

Refernces

• 1、 Calaza, Florencia,Stacchiola, Dario,Neurock, Matthew,Tysoe, Wilfred T.. "Kinetic parameters for the elementary steps in the palladium-catalyzed synthesis of vinyl acetate". . p. 135 - 142. Retrieved 2010.
• 2、 Samanos et al.. "". . p. 19,22, 23, 24. Retrieved 1971.
• 3、 Pitha,Ts'o. "N-vinyl derivatives of substituted pyrimidines and purines.". . p. 1341 - 1344. Retrieved 1968.
• 4、 Tovrog, Benjamin S.,Mares, Frank,Diamond, Steven E.. "Cobalt-Nitro Complexes as Oxygen Transfer Agents: Oxidation of Olefins". . p. 6616 - 6618. Retrieved 1980.
• 5、 Voronkov,Trukhina,Vlasova. "Acyl iodides in organic synthesis: VI. Reactions with vinyl ethers". . p. 467 - 469. Retrieved 2004.
• 6、 Taylor, Roger. "The Mechanism of Thermal Elimination. Part 17. Rate Data for Pyrolysis of Vinyl Acetate and 1,2-Diacetoxyethane". . p. 1157 - 1160. Retrieved 1983.
• 7、 Calaza, Florencia,Stacchiola, Dario,Neurock, Matthew,Tysoe, Wilfred T.. "Coverage effects on the palladium-catalyzed synthesis of vinyl acetate: Comparison between theory and experiment". . p. 2202 - 2207. Retrieved 2010.
• 8、 Brady. "". . p. 434. Retrieved 1970.
• 9、 Stacchiola, Dario,Calaza, Florencia,Burkholder, Luke,Tysoe, Wilfred T.. "Vinyl acetate formation by the reaction of ethylene with acetate species on oxygen-covered Pd(111)". . p. 15384 - 15385. Retrieved 2004.
• 10、 -. "PROCESS TO PRODUCE ETHYLENE AND VINYL ACETATE MONOMER AND DERIVATIVES THEREOF". Page/Page column 57-59. . Retrieved 2019/10/04.