108-05-4

Basic information

• Product Name: Vinyl acetate
• Synonyms: Acetic acid vinylester (8CI);1-Acetoxyethylene;Acetic acid, ethenyl ester;Acetoxyethene;Acetoxyethylene;Ethenyl acetate;NSC 8404;SN 12T;Vinyl A monomer;Vinylacetate
• CAS NO: 108-05-4
• Molecular Formula: C₄H₆O₂
• Molecular Weight: 86.0892
• EINECS: 203-545-4
• Product Categories: VAM;Vinyl Esters;Building Blocks;C2 to C5;Carbonyl Compounds;Chemical Synthesis;Esters;Materials Science;Monomers;Organic Building Blocks;Polymer Science
• Mol File: 108-05-4.mol
• Article Data: 171

Chemical Properties

• Melting Point: -93℃
• Boiling Point: 72.499 °C at 760 mmHg
• Flash Point: 20°F
• Appearance: colourless mobile liquid
• Density: 0.93 g/cm³
• Vapor Density: 3 (vs air)
• Vapor Pressure: 118mmHg at 25°C
• Refractive Index: 1.39
• Storage Temp.: 0-6°C
• Solubility: 20g/l
• Water Solubility: 23 g/L (20℃)
• 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.
• Merck: 14,9992
• BRN: 1209327
• CAS DataBase Reference: Vinyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Vinyl acetate(108-05-4)
• EPA Substance Registry System: Vinyl acetate(108-05-4)

Safety Data

• Hazard Codes: F:Flammable
• Statements: R11:
• Safety Statements: S16:; S23:; S29:; S33:
• RIDADR: UN 1301 3/PG 2
• WGK Germany: 2
• RTECS: AK0875000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 108-05-4(Hazardous Substances Data)

Usage

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.

Chemical Properties

Vinyl acetate is a colorless, flammable liquid with a pungent odor. The odor threshold is 0.12 ppm 0.3 ppm (NY, NJ).it is the precursor to polyvinyl acetate, an important polymer in industry.

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.

Uses

In polymerized form for plastic masses, films and lacquers; in plastic film for food packaging. As modifier for food starch.

Production Methods

Vinyl acetate is an industrial chemical that is produced in large amounts in the United States. 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.

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.

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.

General Description

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.

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

Vinyl 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 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.

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.

Flammability and Explosibility

Highlyflammable

Safety Profile

Confirmed 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 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.

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 .

Shipping

UN1301 Vinyl acetate, stabilized, Hazard Class: 3; Labels: 3-Flammable liquid.

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.

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.

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.

InChI:InChI=1/C4H6O2/c1-3-6-4(2)5/h3H,1H2,2H3

Synthetic route

ethylene glycol diacetate (111-55-7) → vinyl acetate (108-05-4)

Conditions	Yield
With acetic anhydride; benzenesulfonic acid at 140℃; under 1875.19 Torr; for 0.75h; Inert atmosphere;	65.05%
With acetic anhydride; benzenesulfonic acid at 142℃; under 3000.3 Torr; for 0.75h; Inert atmosphere;	64.47%
With acetic anhydride; benzenesulfonic acid at 143℃; under 3000.3 Torr; for 0.666667h; Inert atmosphere;	64.57%

ethylidene diacetate (542-10-9) → vinyl acetate (108-05-4)

Conditions	Yield
With acetic anhydride; benzenesulfonic acid at 145℃; under 2850.29 Torr; for 0.75h; Inert atmosphere;	63.51%
With lithium iodide
With acetic anhydride; lithium iodide
at 50 - 200℃; under 11400.8 Torr;

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

Conditions	Yield
In dichloromethane at 10℃;	A 42.8% B 40.5% C 54.9%

ethene (74-85-1) + acetic acid (64-19-7) → vinyl acetate (108-05-4) + 2-hydroxyethyl acetate (542-59-6) + ethylene glycol diacetate (111-55-7)

Conditions	Yield
With Pd(MeCN)2Cl(NO2) at 25℃; under 2068.6 Torr; for 4h; Product distribution; various catalysts, times, additives, O2 atmosphere, with 18O containing complex;	A 20% B 50% C 7%

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

Conditions	Yield
In dichloromethane at 10℃;	A 11.8% B 12.8% C 35.8% D 39.8%

ethene (74-85-1) + potassium acetate (127-08-2) + acetic acid (64-19-7) → vinyl acetate (108-05-4) + carbon dioxide (124-38-9) + ethyl acetate (141-78-6)

Conditions	Yield
With oxygen under 9120.61 Torr; for 16h;	A n/a B 11.57% C 0.151%
With oxygen under 9120.61 Torr; for 16h;	A n/a B 9.45% C 0.061%
With oxygen under 9120.61 Torr; for 16h;	A n/a B 9.1% C 0.049%

β,β-dichlorovinyl acetate (36597-97-4) → vinyl acetate (108-05-4) + Z-2-chlorovinyl acetate (103659-54-7) + E-2-chlorovinyl acetate (10138-83-7, 103659-54-7)

Conditions	Yield
With tri-n-butyl-tin hydride for 0.5h; Ambient temperature; Irradiation;	A 2% B n/a C n/a

1-acetoxy-2-(ethyl-acetyl-amino)-ethane (15568-57-7) → vinyl acetate (108-05-4) + N-vinyl-N-ethyl-acetamide (3195-79-7) + N-ethylacetamide (625-50-3)

Conditions	Yield
at 490℃; Erhitzung;

ethylidene diacetate (542-10-9) + acetic anhydride (108-24-7) → vinyl acetate (108-05-4)

Conditions	Yield
With copper (I) acetate; benzenesulfonic acid

acetic anhydride (108-24-7) + acetaldehyde (75-07-0) → vinyl acetate (108-05-4)

Conditions	Yield
With sulfuric acid

ethylidene diacetate (542-10-9) + copper diacetate (142-71-2) + acetic anhydride (108-24-7) + benzenesulfonic acid (98-11-3) → vinyl acetate (108-05-4) + acetaldehyde (75-07-0)

acetic anhydride (108-24-7) → vinyl acetate (108-05-4)

Conditions	Yield
With sodium bei Siedetemperatur;

Ketene (463-51-4) + acetaldehyde (75-07-0) → vinyl acetate (108-05-4) + 3-penten-2-one (625-33-2)

Conditions	Yield
With sulfuric acid

Isopropenyl acetate (108-22-5) + acetoxysulfonic acid (2308-54-5) + acetaldehyde (75-07-0) → vinyl acetate (108-05-4) + acetone (67-64-1)

Conditions	Yield
at 120℃;

Isopropenyl acetate (108-22-5) + acetaldehyde (75-07-0) → vinyl acetate (108-05-4)

Conditions	Yield
With 2-sulfo-acetoacetic acid at 120℃;

acetaldehyde (75-07-0) + acetyl chloride (75-36-5) → vinyl acetate (108-05-4)

Conditions	Yield
With pyridine
With N,N-dimethyl-aniline

ethene (74-85-1) + acetic acid (64-19-7) → vinyl acetate (108-05-4)

acetic acid (64-19-7) + acetylene (74-86-2) → vinyl acetate (108-05-4)

Conditions	Yield
at 200 - 220℃; Leiten ueber mit Zink-Salzen impraegnierter Kohle;
at 200 - 220℃; Leiten ueber mit Cadmium-Salzen impraegnierter Kohle;
With complex salts of BF3; boron trifluoride

acetic acid (64-19-7) + acetylene (74-86-2) → vinyl acetate (108-05-4) + ethylidene diacetate (542-10-9)

Conditions	Yield
With acetic anhydride at 40 - 60℃; under 3800 Torr;

pyridine (110-86-1) + acetyl chloride (75-36-5) + paraldehyde (1499-02-1) → vinyl acetate (108-05-4)

quinoline (91-22-5) + acetic anhydride (108-24-7) + paraldehyde (1499-02-1) → vinyl acetate (108-05-4)

acetylene (74-86-2) → vinyl acetate (108-05-4) + ethylidene diacetate (542-10-9)

Conditions	Yield
With mercury(II) sulfate; acetic acid at 60 - 100℃;

ethene (74-85-1) → vinyl acetate (108-05-4) + 2-hydroxyethyl acetate (542-59-6) + ethylidene diacetate (542-10-9) + ethylene glycol diacetate (111-55-7) + ethylene glycol (107-21-1) + acetaldehyde (75-07-0)

Conditions	Yield
With sodium nitrate; oxygen; sodium chloride; palladium dichloride In acetic acid for 1h; Product distribution; Ambient temperature; presence of sodiun acetate; various pressure: 0.1 to 1.0 MPa; various temperature: 50 to 95 deg C;

acetic acid methyl ester (79-20-9) + carbon monoxide (201230-82-2) → vinyl acetate (108-05-4) + ethylidene diacetate (542-10-9) + acetic anhydride (108-24-7) + acetaldehyde (75-07-0) + acetic acid (64-19-7) + methyl iodide (74-88-4)

Conditions	Yield
With ether-phosphane-silyloxy-rhodium; phosphane-silyloxy-platinum at 130℃; under 37503 Torr; for 5h; Product distribution; Mechanism; var. times and temp.; other rhodium complexes;

bromoethyl acetate (927-68-4) → vinyl acetate (108-05-4) + ethylene glycol diacetate (111-55-7) + butane-1,4-diol diacetate (628-67-1) + ethyl acetate (141-78-6)

Conditions	Yield
With nickel(II) salen; tetrabutylammonium tetrafluoroborate In acetonitrile Mechanism; electrolysis; other alkyl bromides also in the presence of activated olefins;	A 10 % Chromat. B 21 % Chromat. C 4 % Chromat. D 10 % Chromat.
With nickel(II) salen; tetrabutylammonium tetrafluoroborate In acetonitrile electrolysis;	A 10 % Chromat. B 21 % Chromat. C 4 % Chromat. D 10 % Chromat.

ethylene glycol diacetate (111-55-7) → vinyl acetate (108-05-4) + acetic acid (64-19-7)

Conditions	Yield
at 682.6℃; Kinetics;

7-acetoxy-2,3:5,6-dibenzobicyclo<2.2.2>octa-2,5-diene (1871-17-6) → vinyl acetate (108-05-4) + anthracene (120-12-7)

Conditions	Yield
In diphenylether at 250℃; Rate constant;

acetic acid (64-19-7) + acetylene (74-86-2) → vinyl acetate (108-05-4) + ethylidene diacetate (542-10-9) + acetaldehyde (75-07-0)

Conditions	Yield
With mercury(II) diacetate; toluene-4-sulfonic acid at 85℃; for 0.233333h; Kinetics; Mechanism; Product distribution;

2-acetoxyethyl propionate → vinyl acetate (108-05-4) + vinyl propionate (105-38-4)

Conditions	Yield
With methanolate In gas
With methanolate In gas Product distribution; also with base F(1-);

vinyl acetate (108-05-4) → 1,2-dibromoethyl acetate (24442-57-7)

Conditions	Yield
With bromine In tetrachloromethane	100%
With propane 3-bromo-1-(triphenylphosphonium) tribromide In dichloromethane at 20℃; for 0.5h;	90%
With bromine for 3h;	62%

vinyl acetate (108-05-4) + cyclohexylamine (108-91-8) → N-cyclohexylacetamide (1124-53-4)

Conditions	Yield
at 90℃; for 1h; microwave irradiation;	100%
With immobilization of Candida cylindracea lipase In hexane at 55℃; for 15h;	99%
With 1-(3-sulfopropyl)pyridinium phosphotungstate In neat (no solvent) at 100℃; for 0.5h; Microwave irradiation;	91%

vinyl acetate (108-05-4) + hexan-1-ol (111-27-3) → 1-hexyl acetate (142-92-7)

Conditions	Yield
With dilithium tetra(tert-butyl)zincate In toluene at 0℃; for 1h; Inert atmosphere;	100%
With pseudomonas fuorescens lipase immobilized on multiwall carbon nano-tubes at 50℃; for 5h; Green chemistry;	99%
With sulfuric acid beim Erhitzen;
With aluminium trichloride at 105℃;
In diethyl ether at 35℃; Candida cylindracea lipase;

vinyl acetate (108-05-4) + (4-hydroxyphenyl)methanol (623-05-2) → 4-hydroxybenzyl acetate (80767-12-0)

Conditions	Yield
With Candida cylindracea lipase In hexane for 4h;	100%
novozyme 435 In acetonitrile at 20℃; for 6h; Enzymatic reaction;	99%
iodine at 20℃; for 2h;	95%
With porcine pancreatic lipase (PPL, Type II) In tetrahydrofuran at 42 - 45℃; for 48h; Acetylation;	80%
With Pseudomonas cepacia PS lipase In di-isopropyl ether at 25℃; for 0.5h;

vinyl acetate (108-05-4) + p-hydroxyphenethyl alcohol (501-94-0) → 2-(4-hydroxyphenyl)ethyl acetate (58556-55-1)

Conditions	Yield
With Candida cylindracea lipase In hexane for 4h;	100%
With Candida antartica lipase B In tetrahydrofuran at 20℃; for 4h; Enzymatic reaction; chemoselective reaction;	100%
With 1,3-dichlorotetrabutyldistannoxane In tetrahydrofuran at 30℃; for 24h;	99%

vinyl acetate (108-05-4) + salicylic alcohol (90-01-7) → 2-acetoxymethylphenol (6161-96-2)

Conditions	Yield
With Candida cylindracea lipase In hexane for 6h;	100%
With porcine pancreatic lipase (PPL, Type II) In tetrahydrofuran at 42 - 45℃; for 120h; Acetylation;	95%
With Pseudomonas cepacia PS lipase In di-isopropyl ether at 25℃; for 0.25h;

vinyl acetate (108-05-4) + 1,3-dibromoadamantane (876-53-9) → 1-acetyladamantane (1660-04-4)

Conditions	Yield
With Wilkinson's catalyst In dichloromethane at 170℃; for 8h;	100%

vinyl acetate (108-05-4) + 2-benzyl-1,3-propanediol (2612-30-8) → (R)-3-acetoxy-2-benzyl-1-propanol (110270-49-0)

Conditions	Yield
Lipase P;	100%
With Pseudomonas cepacia lipase on epoxysilica at 20℃; for 0.5h; Acetylation;	100%
With 3 A molecular sieve; lipase Amono P supported on Celite In various solvent(s) at 25℃; for 5.7h; Acylation;	95%

vinyl acetate (108-05-4) + 3-Hydroxybenzyl alcohol (620-24-6) → 3-hydroxybenzyl acetate (142784-72-3)

Conditions	Yield
With Candida cylindracea lipase In hexane for 4h;	100%
Y5(OiPr)13O at 20℃; for 18h; Acetylation; transesterification;	93%
With Pseudomonas cepacia PS lipase In di-isopropyl ether at 25℃; for 0.5h;

vinyl acetate (108-05-4) + methyl (2RS,3RS)-2-hydroxy-3-(p-methoxyphenyl)-3-(o-nitrophenylthio)propanoate (30067-00-6, 84056-03-1, 86603-47-6, 125354-93-0, 125354-94-1, 127419-59-4, 131064-04-5, 142926-03-2) → (2R,3R)-2-Acetoxy-3-(4-methoxy-phenyl)-3-(2-nitro-phenylsulfanyl)-propionic acid methyl ester

Conditions	Yield
With dmap In tetrahydrofuran at 22℃; for 48h; lipase from Pseudomonas cepacia;	100%

vinyl acetate (108-05-4) + 2-(<1,1'-biphenyl>-4-ylmethyl)-1,3-propanediol (152961-72-3) → (R)-3-Hydroxy-2-(4-phenylbenzyl)propyl acetate (152961-75-6)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol In di-isopropyl ether; water for 2h; Ambient temperature; lipase PS (Pseudomonas sp.);	100%

vinyl acetate (108-05-4) + benzyl alcohol (100-51-6) → Benzyl acetate (140-11-4) + acetaldehyde (75-07-0)

Conditions	Yield
With 1,3-dicyclohexylimidazolium-2-thiocarboxylate In tetrahydrofuran at 80℃; for 2h; Inert atmosphere;	A 100% B n/a
With lipase from Pseudomonas Cepacia In benzene at 35℃; other ω-substituted-1-alkanols, var. solvents; kinetic parameters of transesterification;

vinyl acetate (108-05-4) + benzyl alcohol (100-51-6) → Benzyl acetate (140-11-4)

Conditions	Yield
Y5(OiPr)13O at 20℃; for 42h; Acetylation; transesterification;	100%
With dilithium tetra(tert-butyl)zincate In tetrahydrofuran at 25℃; for 1h; Reagent/catalyst; Solvent; Time; Temperature; Inert atmosphere;	100%
With P(MeNCH2CH2)3N In tetrahydrofuran for 2h; Ambient temperature;	99%

vinyl acetate (108-05-4) + Geraniol (106-24-1) → 3,7-dimethyl-2E,6-octadien-1-yl acetate (105-87-3)

Conditions	Yield
With dilithium tetra(tert-butyl)zincate In toluene at 0℃; for 1h; Inert atmosphere;	100%
With N,N'-bismesityl-imidazol-2-ylidene In tetrahydrofuran at 20℃; for 1h;	99%
1,3-bis(2,4,6-trimethyl-phenyl)imidazol-2-ylidene In tetrahydrofuran at 20℃; for 1h;	99%

vinyl acetate (108-05-4) + (E)-(S)-6-(4-Methoxy-benzyloxy)-2-methyl-hex-2-ene-1,4-diol (208586-48-5) → Acetic acid (E)-(S)-4-hydroxy-6-(4-methoxy-benzyloxy)-2-methyl-hex-2-enyl ester (208586-60-1)

Conditions	Yield
In tetrahydrofuran at 0℃; for 24h; PFL enzyme;	100%

vinyl acetate (108-05-4) + (3S,3aS,5aS,8S,9aS,9bS)-8-Hydroxy-3,5a,9-trimethyl-decahydro-naphtho[1,2-b]furan-2-one → (11S)-3β,6α-dihydroxy-eudesman-12-oic acid-6-lactone (6089-71-0) + (11S)-3β-acetoxy-6α-hydroxy-4βH-eudesman-12-oic acid-lactone (74493-56-4)

Conditions	Yield
With Candida antarctica lipase at 40℃; for 24h; Heating;	A 70 mg B 100%

vinyl acetate (108-05-4) + 2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin (3663-82-9) → acetic acid 2,3-dihydro-1,4-benzodioxin-2-ylmethyl ester (64179-44-8)

Conditions	Yield
With N,N'-bismesityl-imidazol-2-ylidene In tetrahydrofuran at 20℃; for 0.25h;	100%
1,3-bis(2,4,6-trimethyl-phenyl)imidazol-2-ylidene In tetrahydrofuran at 20℃; for 0.25h;	100%
With P(MeNCH2CH2)3N In tetrahydrofuran for 2h; Ambient temperature;	99%

vinyl acetate (108-05-4) + benzyl (1R,2S)-1-hydroxy-2,3-dihydro-1H-inden-2-ylcarbamate → benzyl (1R,2S)-N-(2-acetoxyindan-1-yl)carbamate

Conditions	Yield
With Pseudomonas cepacia lipase In 1,4-dioxane at 30℃; for 120h;	100%

vinyl acetate (108-05-4) + (+/-)-trans-benzyl N-(1-hydroxyindan-2-yl)carbamate → benzyl (1R,2R)-N-(1-acetoxyindan-2-yl)carbamate

Conditions	Yield
With Pseudomonas cepacia lipase In 1,4-dioxane at 30℃; for 48h;	100%

vinyl acetate (108-05-4) + (1R,2S)-(2-hydroxymethylcyclobutyl)methanol (54445-64-6) → [(1S,2R)-2-(hydroxymethyl)cyclobutyl]methyl acetate (123809-78-9)

Conditions	Yield
With pseudomonas fluorescens lipase at -2℃; for 13.75h; Acetylation;	100%
With Amano lipase AK at -2℃; for 14h; Enzymatic reaction; optical yield given as %ee;	99%

vinyl acetate (108-05-4) + all-cis-5-(tert-butyldimethyl-silanyloxy)-cyclohexane-1,3-diol (187266-42-8, 327189-66-2) → (1R,3S,5S)-1-acetoxy-3-hydroxy-5-(tert-butyldimethylsilanyloxy)-cyclohexane (327189-67-3)

Conditions	Yield
With Lipase QL In ethyl acetate at 20℃; for 46h; Acetylation;	100%
With Lipase QLM In ethyl acetate at 20℃; Enzymatic reaction;	100%
With Lipase QL In ethyl acetate at 22℃; for 46h;	99%
With amano lipase SP, from burkholderia cepacia In ethyl acetate at 20℃; Enzymatic reaction;	2.356 g

vinyl acetate (108-05-4) + 3-Azido-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (247025-10-1) → 3-azido-5-O-acetyl-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-ribofuranose (551934-06-6)

Conditions	Yield
With Novozyme-435 In toluene at 25 - 28℃; Enzymatic reaction; regioselective reaction;	100%
With Candida antarctica lipase In toluene at 25 - 28℃;	98%

vinyl acetate (108-05-4) + 3,6-bis(3,4-dimethoxybenzoyl)-1,2,4,5-tetrazine (534619-54-0) → 3,6-bis(3,4-dimethoxybenzoyl)pyridazine

Conditions	Yield
In toluene at 110℃; for 17h;	100%

vinyl acetate (108-05-4) + benzyl azide (622-79-7) → 1-benzyl-1H-[1,2,3]triazole (4368-68-7)

Conditions	Yield
With trimethyl orthoformate at 120℃; for 30h;	100%
at 120℃; for 5h; Microwave irradiation; Sealed vial;	99%
at 120℃; Sealed tube; Large scale;

(3S,5S,7R,9S,11S,13S)-3,13-Bis-benzyloxymethoxy-pentadecane-1,5,7,9,11,15-hexaol + vinyl acetate (108-05-4) → Acetic acid (3S,5S,7R,9S,11S,13S)-15-acetoxy-3,13-bis-benzyloxymethoxy-5,7,9,11-tetrahydroxy-pentadecyl ester

Conditions	Yield
With lipase from Candida cylindracea at 25℃; for 6h;	100%

(3S,5S,7S)-3-Benzyloxymethoxy-8-[(4S,6R)-6-((S)-2-benzyloxymethoxy-4-hydroxy-butyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-octane-1,5,7-triol + vinyl acetate (108-05-4) → Acetic acid (S)-4-[(4R,6S)-6-((2S,4S,6S)-8-acetoxy-6-benzyloxymethoxy-2,4-dihydroxy-octyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-benzyloxymethoxy-butyl ester

Conditions	Yield
With lipase from Candida cylindracea at 25℃; for 6h;	100%

(3R,5R,7S,9S,11S,13R)-3,13-Bis-benzyloxymethoxy-9-(tert-butyl-dimethyl-silanyloxy)-pentadecane-1,5,7,11,15-pentaol (914803-06-8) + vinyl acetate (108-05-4) → Acetic acid (3R,5S,7S,9S,11R,13R)-15-acetoxy-3,13-bis-benzyloxymethoxy-7-(tert-butyl-dimethyl-silanyloxy)-5,9,11-trihydroxy-pentadecyl ester (914803-10-4)

Conditions	Yield
With lipase from Candida cylindracea at 25℃; for 6h;	100%

vinyl acetate (108-05-4) + 4-hydroxy-2-sulfolene (6211-59-2) → 4-acetoxy-2-thiolene 1,1-dioxide (86597-94-6)

Conditions	Yield
With Novozym 435(R) In acetonitrile at 30℃; for 16h;	100%

(4R,5R)-4-acetoxy-7-chloro-5-methoxymethoxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (926035-11-2) + vinyl acetate (108-05-4) → (4R,5R)-7-chloro-4-hydroxy-5-methoxymethoxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine (926035-13-4)

Conditions	Yield
Stage #1: (4R,5R)-4-acetoxy-7-chloro-5-methoxymethoxy-1-(p-toluenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepine With sodium hydroxide In ethanol at 20℃; for 0.5h; Stage #2: vinyl acetate With Lipase QLM In acetonitrile at 65℃; for 1h; Stage #3: With sodium hydroxide In ethanol at 20℃; for 0.5h; Further stages.;	100%

vinyl acetate (108-05-4) + 3-hexyn-2,5-diol (3031-66-1) → C8H12O3 + Acetic acid (1R,4R)-4-acetoxy-1-methyl-pent-2-ynyl ester (152694-53-6) + (2S,5S)-hex-3-yne-2,5-diol (152694-52-5)

Conditions	Yield
With lipase AK at 32℃; for 16h; Enzymatic reaction;	A n/a B 100% C n/a

Upstream product

• 108052-76-2 4-(BROMOMETHYL)-BENZOIC ACID, 1,1-DIMETHYLETHYL ESTER 
• 1080-52-0 1-(2,4-DIMETHYL-PHENYL)-PYRROLE-2,5-DIONE 
• 108051-94-1 N-Deformyl-N-benzyloxycarbonyl Orlistat 
• 108051-48-5 2-PHENYLTHIO-5-PROPIONYLPHENYLACETICACIDMETHYLESTER 
• 108051-45-2 5-(2-hydroxyethyl)-4-methyl-3-[(2-methyl-6-oxo-1,6-dihydropyrimidin-5-yl)methyl]-1,3-thiazol-3-ium bromide hydrobromide 
• 108051-44-1 (2E)-1-[5-chloro-2-hydroxy-3-(hydroxymethyl)phenyl]-3-[4-(dimethylamino)phenyl]prop-2-en-1-one 
• 108051-43-0 (2E)-1-[5-chloro-2-hydroxy-3-(hydroxymethyl)phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one 
• 108051-41-8 (2E)-1-[5-chloro-2-hydroxy-3-(hydroxymethyl)phenyl]-3-phenylprop-2-en-1-one 
• 108051-40-7 2,4-dihydroxy-5-[(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoyl]benzoic acid 
• 108051-36-1 (2E)-1-(2-hydroxy-5-iodophenyl)-3-(4-nitrophenyl)prop-2-en-1-one 
• 108051-34-9 (2E)-1-(5-bromo-2,4-dihydroxyphenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one 
• 108051-33-8 (2E)-1-(5-bromo-2,4-dihydroxyphenyl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one 
• 108051-32-7 (2E)-1-(5-bromo-2,4-dihydroxyphenyl)-3-(2-methoxyphenyl)prop-2-en-1-one 
• 108051-30-5 (2E)-1-(5-acetyl-2,4-dihydroxyphenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one 

Downstream Products

• 108055-42-1 diethoxymethoxyethane 
• 108055-90-9 3-Bromocyclohexene 
• 1080573-28-9 5-BOC-AMino-2-chlorophenylboronic acid pinacol ester 
• 108059-85-4 2-(2-ETHYLBENZOYL)BENZOIC ACID 
• 108060-84-0 O6-Benzyl-N2,3-etheno Guanosine 
• 108061-47-8 7-Bromo-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 108061-77-4 2-(6-bromo-1H-indol-3-yl)ethanamine hydrochloride 
• 108062-05-1 5-nitro-2-{2-nitrobenzyl}-1H-isoindole-1,3(2H)-dione 
• 1080-62-2 1-hydroxy-7-methyl-8-(methylsulfanyl)-3,7-dihydro-1H-purine-2,6-dione 
• 108062-27-7 2-(4-phenylcyclohexyl)acetic acid 
• 1080622-86-1 CP466722 
• 108063-02-1 2,5-Dimethyl-1-undecylpiperazine dihydrochloride 
• 1080632-76-3 p-Terphenyl, 4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)- 
• 1080636-31-2 3-(2-fluorophenyl)cyclobutanone 

Recommend Products

• 98272-73-2  (+/-)-trans-2-acetoxy-cyclopropanecarboxylic acid methyl ester 
• 108-05-4  vinyl acetate 
• 6832-16-2  methyl diazoacetate 
• 5578-41-6  (2-acetoxy-ethyl)-dichloro-methyl-silane 
• 75-54-7  Dichloromethylsilane 
• 2653-43-2  vinyl 2-methylbenzoate 
• 118-90-1  ortho-methylbenzoic acid 
• 7252-83-7  1-bromo-2,2-dimethoxyethane 
• 67-56-1  methanol 
• 534-15-6  1,1-dimethoxyethane 
• 97-97-2  chloroacetaldehyde dimethyl acetal 
• 3234-54-6  vinyl crotonate 
• 3724-65-0  2-butenoic acid 
• 7064-07-5  3-phenyl-5-acetoxy-4,5-dihydroisoxazole 

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