Vinyl acetate

Manufactured by Merck Group

Sourced in United States, Italy, Argentina

Vinyl acetate is a chemical compound used in the production of various polymers and resins. It serves as a building block for the synthesis of materials such as polyvinyl acetate, polyvinyl alcohol, and ethylene-vinyl acetate copolymers. The core function of vinyl acetate is to provide a versatile raw material for the manufacturing of these important industrial and commercial products.

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Lab products found in correlation

Preformulated tablets, by Merck Group (4 mentions) Benzyl bromide, by Merck Group (3 mentions) Potassium ethyl xanthate, by Thermo Fisher Scientific (3 mentions) Potassium ethyl xanthate, by Merck Group (2 mentions) Magnesium sulphate, by Thermo Fisher Scientific (2 mentions) Hexane, by Thermo Fisher Scientific (2 mentions) Ethyl acetate, by Thermo Fisher Scientific (2 mentions) Methanol, by Thermo Fisher Scientific (2 mentions) Dimethyl sulfoxide d6, by Merck Group (2 mentions) Deuterated chloroform, by Merck Group (2 mentions) Ethanol, by Merck Group (2 mentions) 4 4 azobis 4 cynaovaleric acid, by Merck Group (2 mentions) Polyvinyl alcohol (pva), by Merck Group (2 mentions) Maleic anhydride, by Merck Group (2 mentions) Isopropyl alcohol, by Merck Group (2 mentions) Tetrahydrofuran, by Thermo Fisher Scientific (1 mentions) Phosphate buffered saline tablet ph 7, by Merck Group (1 mentions) Acetic anhydride, by Merck Group (1 mentions) Dimethylformamide, by Merck Group (1 mentions) Acetone, by Avantor (1 mentions)

29 protocols using vinyl acetate

Synthesis and RAFT Polymerization of Vinyl Acetate

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Vinyl
acetate (99%), 4-bromobutyric acid
(98%), palladium acetate (Pd(OAc)₂, 98%), potassium hydroxide
(KOH, 90%), and sodium azide (NaN₃, 97%) were purchased
from Sigma-Aldrich and used as received, unless otherwise mentioned.
Alumina, activated basic (Al₂O₃: Sigma-Aldrich,
Brockmann I, standard grade, ∼150 mesh, 58 Å), and magnesium
sulfate (MgSO₄: anhydrous, Fisher Scientific, LR grade)
were used as received. The following solvents were used as received;
dichloromethane (CH₂Cl₂: VWR International,
AR grade), N,N-dimethylformamide
(DMF: Sigma-Aldrich, HPLC grade). The following monomers were deinhibited
before use by distillation over CaH₂; vinyl acetate (VAc:
Sigma-Aldrich, >99%; distillation pressure: 0.015 atm, 90–92
°C). 2-Methylene-1,3-dioxepane (MDO) was synthesized using the
previously described method of Bailey et al.³⁸ and the CTA O-hexyl S-methyl 2-propionylxhanthate (1) was synthesized using the procedure described in our previous report.⁴⁹

Hedir G.G., Bell C.A., O’Reilly R.K, & Dove A.P. (2015). Functional Degradable Polymers by Radical Ring-Opening Copolymerization of MDO and Vinyl Bromobutanoate: Synthesis, Degradability and Post-Polymerization Modification. Biomacromolecules, 16(7), 2049-2058.

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Suspension Polymerization of Vinyl Acetate

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EXAMPLE 7

Suspension polymerization using an inorganic emulsifier: To a 2 L flask was added deionized water (691 g), vinyl acetate (259 g, obtained from Sigma-Aldrich Chemical Company; Milwaukee, Wis.), disodium phosphate monohydrate (2.98 g), and Nanoparticle 2 (16.39 g). The mixture was stirred at 350 rpm, and VAZO 52 (2.59 g, obtained form DuPont, Wilmington Del.) was added. The contents were agitated 30 min, then heated to 40° C. while purging with nitrogen. After 90 min at 40° C., the temperature was increased to 50° C., and the held for 3.5 h. The contents of the flask were filtered in a Buchner funnel and washed with deionized water, yielding vinyl acetate beads that ranged from 70 to 250 micrometers in diameter.

US10954318B2. Polymerizable compositions free of organic emulsifier and polymers and methods of making thereof (2021-03-23). None [US], None [US], None [DE], None [US], None [DE], None [DE]. Inventors: Jimmie R. Baran, Jr. [US], Duane D. Fansler [US], Klaus Hintzer [DE], William J. Hunt [US], Harald Kaspar [DE], Tilman C. Zipplies [DE].

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Synthesis and Characterization of Bismuth Complexes

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All chemicals were used as supplied. Ethyl acetate, hexane, methanol, dichloromethane, tetrahydrofuran, and magnesium sulphate were all purchased from Fisher Scientific at laboratory reagent grade. Deuterated chloroform (99.8 atom% D), dimethyl sulfoxide-d6 (99.9 atom% D), vinyl acetate (97%), potassium ethyl xanthate (96%), 2-(methyl bromopropionate) (98%), bismuth(iii) oxide powder (99.999% trace metals basis) hydrazine hydrate 50–60%, phosphate buffered saline tablet pH 7.4 (NaCl = 0.137 M and KCl = 0.0027 M at 25 °C), were purchased from Sigma Aldrich. Dialysis membrane (MWCO = 1000 Da/MWCO: 300–500 Da) was purchased from Spectra/Por.

Kontopoulou I., Congdon T.R., Bassett S., Mair B, & Gibson M.I. (2022). Synthesis of poly(vinyl alcohol) by blue light bismuth oxide photocatalysed RAFT. Evaluation of the impact of freeze/thaw cycling on ice recrystallisation inhibition. Polymer Chemistry, 13(32), 4692-4700.

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Chemical Modification of Japanese Cedar Sapwood

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Japanese cedar (Cryptomeria japonica D. Don) sapwood (20–30 years old) was supplied by the experimental forest of the National Taiwan University. The dimensions of the slicewood samples were 3 mm (R) × 12 mm (T) × 58 mm (L). Oven-dried wood specimens that had straight longitudinal grain, were free of defects, and had modulus of elasticity (MOE) values from 5.5 to 7.0 GPa were selected for this study. All of the samples were used after extraction in a Soxhlet apparatus for 24 h with a 1:2 (v/v) mixture of ethanol and toluene followed by washing with distilled water. The extracted slicewood was dried at 105 °C for 12 h, and the oven-dried weights were measured. Vinyl acetate (VA), acetic anhydride (AA), dimethylformamide (DMF), potassium acetate (PA) (Sigma–Aldrich Chemical Co, St. Louis, MO, USA), potassium carbonate (PC) (Merck Chemical Co., Darmstadt, Germany), and other chemicals and solvents used in this experiment were of the highest quality available.

Hung K.C., Yang C.N., Yang T.C., Wu T.L., Chen Y.L, & Wu J.H. (2017). Characterization and Thermal Stability of Acetylated Slicewood Production by Alkali-Catalyzed Esterification. Materials, 10(4), 393.

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Trehalose Synthesis Protocol

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α-d-Glucose, α,α′-trehalose, allyl bromide, Amberlite IR-120H resin, hydrochloric acid, ethanol, methanol, vinyl acetate, D₂O, CD₃OD and CDCl₃ were purchased from Sigma Aldrich. Potassium hydroxide was purchased from Carlo Erba. Azobisisobutyronitrile (AIBN) was purchased from Fluka. Acetone was purchased from VWR International. All the chemicals were reagent grade and were used without further purification.
Amberlite IR-120H resin (250 mg) was activated by washing with methanol (3 × 10 min, 1.25 ml each time) and standing overnight in methanol (1.25 ml).

Papacchini A., Telaretti Leggieri M.R., Zucchini L., Ortenzi M.A., Ridi F., Giomi D, & Salvini A. (2018). Modified α,α′-trehalose and d-glucose: green monomers for the synthesis of vinyl copolymers. Royal Society Open Science, 5(5), 171313.

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Synthesis of SiO2 Nanoparticles

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Silicon dioxide nanopowder (SiO₂, between 10 and 20 nm size) was purchased from Sigma–Aldrich (Merck, Redox Lab Supplies Com SRL, Bucharest, Romania).
Acrylonitrile, vinyl acetate and dimethyl sulfoxide were supplied by Sigma-Aldrich (Merck KGaA, Darmstadt, Germany) and used without further purification.

Căprărescu S., Modrogan C., Purcar V., Dăncilă A.M, & Orbuleț O.D. (2021). Study of Polyvinyl Alcohol-SiO2 Nanoparticles Polymeric Membrane in Wastewater Treatment Containing Zinc Ions. Polymers, 13(11), 1875.

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Synthesis of Vinyl Acetate Polymers

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Phosphate-buffered saline (PBS) solutions were prepared using preformulated tablets (Sigma-Aldrich) in 200 mL of Milli-Q water (>18.2 Ω mean resistivity) to give [NaCl] = 0.138 M, [KCl] = 0.0027 M, and pH 7.4. Vinyl acetate (>99%), 4,4′azobis(4-cynaovaleric acid) (>98%), and benzyl bromide (98%) were purchased from Sigma-Aldrich. Vinyl acetate was filtered through a plug of basic alumina to remove inhibitors prior to use. The 4,4′azobis(4-cynaovaleric acid) was recrystallized from methanol and stored at −18 °C in the dark. Potassium ethyl xanthate (98%) was purchased from Alfa Aesar. S-benzyl O-ethyl carbondithioate was synthesized as previously described.20 (link)

Stubbs C., Wilkins L.E., Fayter A.E., Walker M, & Gibson M.I. (2018). Multivalent Presentation of Ice Recrystallization Inhibiting Polymers on Nanoparticles Retains Activity. Langmuir : the ACS journal of surfaces and colloids.

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Synthesis of Ethylene-Based Terpolymer

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EXAMPLE 5

In this example, an Ethylene-based polymer was produced by incorporating vinyl acetate and trimethylsilyl-protected methyl vinyl glycolate to assay a number of polymer properties for the resulting compositions.

Ethylene (99.95%, Air Liquide, 1200 psi) and azobisisobutyronitrile (AIBN, 98% Sigma Aldrich) were used as received. Dimethyl carbonate (DMC, anhydrous 99%, Sigma Aldrich) and vinyl acetate (99%, Sigma Aldrich) were distilled before use and stored under nitrogen.

Synthesis of terpolymer with Ethylene, vinyl acetate and trimethylsilyl-protected methyl vinyl glycolate (Sample E2)

5 g trimethylsilyl-protected methyl vinyl glycolate, 15 g vinyl acetate, 80 g dimethyl carbonate and 0.1 g of azobisisobutyronitrile were added to a 300 mL Parr reactor. The reactor was sealed and flushed three times with 1000 psi pressure of nitrogen while stirring. The system was then heated, at 70° C. at an Ethylene pressure of 1200 psi and allowed to stir for the desired time. The reaction mixture was collected and the reactor was washed with THF at 60° C. The solvent in the reaction mixture and wash was removed by rotary evaporation. The resulting polymer was dissolved in THF and precipitated into cold methanol, then vacuum filtered.

US11453732B2. Polyethylene copolymers and products and methods thereof (2022-09-27). Braskem S.A. [BR]. Inventors: Ashley Hanlon [BR], Jonas Alves Fernandes [BR], Mauro Alfredo Soto Oviedo [BR], Hadi Mohammadi [BR], Nei Sebastiao Domingues Junior [BR], Adriane Gomes Simanke [BR], Manoela Ellwanger Cangussu [BR], Markus Busch [BR], Sascha Hintenlang [BR].

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Synthesis of Gold Nanoparticles and Nitrophenol Reduction

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2-2′-Azo-bis-isobutyronitrile (AIBN), vinyl acetate (>99%), tetrachlorauric acid (HAuCl₄·3H₂O), sodium borohydride (NaBH₄, 99%), activated carbon NORIT SX1G, sulfuric acid (H₂SO₄, 96%), 4-nitrophenol (>99%), 3-nitrophenol (>99%), 2-nitrophenol (>99%), polyvinyl alcohol 88 (Mw: 13,000–23,000, 88–89% hydrolyzed), polyvinyl alcohol 2 (Mw: 13,000–23,000, 98–99% hydrolyzed), polyvinyl alcohol 3 (Mw: 31,000–50,000, 98–99% hydrolyzed), and polyvinyl alcohol 4 (Mw: 146,000–186,000, 98–99% hydrolyzed) were purchased from Sigma Aldrich (Italy). The other polymers were properly synthesized in the laboratory and experimental protocols are presented below. The solvents were used without further processes of purification.

Scurti S., Monti E., Rodríguez-Aguado E., Caretti D., Cecilia J.A, & Dimitratos N. (2021). Effect of Polyvinyl Alcohol Ligands on Supported Gold Nano-Catalysts: Morphological and Kinetics Studies. Nanomaterials, 11(4), 879.

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Preparation of Magnetite-Containing Materials

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Iron(III)
pentahydrate
sulphate (Fe₂(SO₄)₃·5H₂O, 97%), ammonia (NH₃, 28–30 wt %, d = 0.9 g/cm³), diethyl ether, ethyl acetate, dichloromethane,
toluene, ethanol (95%), vinyl acetate, and lipase acrylic resin from Candida antarctica 10,000 U/g (Novozyme 435) were
purchased from Sigma-Aldrich. CDCl₃ was from Euriso-top
(Saint-Aubin, France), iron(II) heptahydrate sulphate (Fe₂SO₄·7H₂O, 95%) and triethylamine (TEA,
99%) were from Carlo Erba (Italy), and oxalyl chloride was from Alfa
Aesar, Thermo Fisher Scientific (Karlsruhe, Germany). Ultrapure UPP
water used for magnetite synthesis was obtained with a Milli-Q plus
system (Millipore Co., resistivity 18MΩcm). (R)-9-Hydroxystearic acid was synthesized from Dimorphotheca
sinuata L. seeds, as previously described.^{27 (link)} CH₂Cl₂ was dried by distillation
over P₂O₅ and stored under an argon atmosphere.
toluene was dehydrated by distillation under nitrogen on Na/K amalgam
and stored under nitrogen on 4 Å molecular sieves.

Micheletti G., Boga C., Telese D., Cassani M.C., Boanini E., Nitti P., Ballarin B., Ghirri A., Barucca G, & Rinaldi D. (2020). Magnetic Nanoparticles Coated with (R)-9-Acetoxystearic Acid for Biomedical Applications. ACS Omega, 5(22), 12707-12715.

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