Ethylene oxide

Manufactured by Merck Group

Sourced in Switzerland

Ethylene oxide is a colorless, flammable gas used in the production of various industrial chemicals. It serves as a key intermediate in the manufacturing of various products, including ethylene glycol, which is widely used in the production of polyester fibers and plastics.

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Lab products found in correlation

N butyllithium, by Merck Group (4 mentions) Propylene oxide, by Merck Group (4 mentions) 18 crown 6 ether, by Merck Group (4 mentions) Chloroform d, by Cambridge Isotopes (3 mentions) Naphthalene, by Merck Group (3 mentions) α cyano 4 hydroxycinnamic acid, by Merck Group (3 mentions) Potassium tert butoxide, by Merck Group (3 mentions) Deuterium oxide, by Cambridge Isotopes (3 mentions) Silver trifluoroacetate agtfa, by Merck Group (2 mentions) 1 palmitoyl 2 oleoyl sn glycero 3 phosphocholine, by Avanti Polar Lipids (2 mentions) Sodium chloride (nacl), by Merck Group (2 mentions) Malt extract agar, by Thermo Fisher Scientific (1 mentions) Ethanedithiol, by Merck Group (1 mentions) Eugenol, by Merck Group (1 mentions) Deuterated solvents for nmr, by Cambridge Isotopes (1 mentions) 2 2 dimethoxy 2 phenylacetophenone, by Merck Group (1 mentions) Polyethylene oxide, by Merck Group (1 mentions) Nunc, by Thermo Fisher Scientific (1 mentions) Diphenylhexatriene, by Merck Group (1 mentions) Bioreagent grade buffer salts, by Merck Group (1 mentions)

Close spelling variants of this product

Poly(ethylene oxide) standards (4 citations) Poly(ethylene oxide) average Mw ˜1,000,000 (Aldrich (3 citations) Poly(ethylene oxide) average Mw˜1,000,000 (Aldrich Catalog #372781) (2 citations)

10 protocols using ethylene oxide

Biodeterioration of Balsa Wood by Ganoderma applanatum

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Seventy-five wood samples of O. pyramidale (Balsa) with dimensions of 15 mm (T) by 15 mm (R) by 15 mm (L) were oven dried at 103°C for 24 hours to record initial dry weight. Samples were sterilized with ethylene oxide (Sigma-Aldrich, Buchs, Switzerland) and then placed into Kolle culture flasks containing freshly inoculated G. applanatum (Empa 646) growing on 75 ml of sterilized (20 min at 121°C) 4% Malt Extract Agar (MEA) (Oxoid, Platern, Switzerland). Fifteen biological replicates per incubation conditions were studied. All cultures were maintained in the dark at 22°C and 70% relative humidity. After different incubation periods (4, 6, 8, 10, and 12 weeks), the fungal biomass was carefully removed from the wood surfaces with a brush and the final weight was recorded after drying the samples in the oven at 103°C for 24 hours. It is noteworthy that there is a small shrinkage in the tangential direction of the bulk wood after fungal treatment (fig. S12).

Sun J., Guo H., Schädli G.N., Tu K., Schär S., Schwarze F.W., Panzarasa G., Ribera J, & Burgert I. (2021). Enhanced mechanical energy conversion with selectively decayed wood. Science Advances, 7(11), eabd9138.

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Fungal Biodeterioration of Balsa Wood

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Fifteen wood samples of O. pyramidale (Balsa) with dimensions of 15 mm (T) by 15 mm (R) by 15 mm (L) were oven dried at 103°C for 24 hours to record initial dry weight. Samples were sterilized with ethylene oxide (Sigma-Aldrich, Buchs, Switzerland) and then placed into Kolle culture flasks containing freshly inoculated P. chrysosporium (Empa 605) and G. adspersum (Empa 003) growing on 75 ml of sterilized (20 min at 121°C) 4% MEA (Oxoid, Pratteln, Switzerland). Five biological replicates per incubation conditions were studied. All cultures were maintained in the dark at 22°C and 70% relative humidity. After different incubation periods (4, 8, and 12 weeks), the fungal biomass was carefully removed from the wood surfaces with a brush and the final weight was recorded after drying the samples in the oven at 103°C for 24 hours.

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Characterization of Pluronic and POPC Compounds

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Pluronics F68, F108, F87, F127, P103, P104, P105, L35, P65 and P84 were provided by BASF. Ethylene oxide (EO, ≥ 99.5%), propylene oxide (PO, ≥ 99%), methoxy-terminated polyethylene glycol (methoxy-PEO, 2000 g/mol), potassium tert-butoxide, n-butyllithium, potassium, naphthalene, and 18-crown-6 ether for anionic polymerization were purchased from Sigma-Aldrich and used as received, unless otherwise noted. PEO-8 (8000 g/mol) was purchased from EMD Millipore (Billerica, MA). 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC, PC (16:0–18:1 PC)) in chloroform was purchased from Avanti Polar Lipids (Alabaster, AL) and used as received. Silver trifluoroacetate (AgTFA) and α-cyano-4-hydroxycinnamic acid (CHCA, ≥ 98%) for MALDI characterization were also purchased from Sigma-Aldrich. Deuterium oxide (D₂O, 99.9 atom % D) and chloroform-d (CDCl₃, 99.8 atom % D + 0.05% V/V TMS) were purchased from Cambridge Isotope Laboratories, Inc.

Zhang W., Haman K.J., Metzger J.M., Hackel B.J., Bates F.S, & Lodge T.P. (2017). Quantifying Binding of Ethylene Oxide - Propylene Oxide Block Copolymers with Lipid Bilayers. Langmuir : the ACS journal of surfaces and colloids, 33(44), 12624-12634.

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Synthesis and Characterization of Functionalized Polymers

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Unless otherwise stated, ACS reagent grade chemicals and solvents were purchased from Sigma-Aldrich and used without further purification. Tetrahydrofuran was collected from a dry solvent system and used immediately thereafter. Allyl glycidyl ether was purchased from TCI-America, Inc., degassed by freeze–pump–thaw, and distilled onto butylmagnesium chloride (Sigma-Aldrich), where it was stirred for 10 min at 0 °C and distilled to a buret for use. Potassium naphthalenide was prepared from potassium metal and recrystallized naphthalene in dry THF and allowed to stir with a glass-coated stir bar for 24 h at room temperature before use. Triethylsilane and tris(pentafluorophenyl)borane were purchased from Gelest. 2,2-Dimethoxy-2-phenylacetophenone (99%), eugenol, ethane dithiol, ethylene oxide (99.5%+), and poly(ethylene oxide) were purchased from Sigma-Aldrich. Deuterated solvents for NMR were purchased from Cambridge Isotope Laboratories, Inc.

Kang T., Banquy X., Heo J., Lim C., Lynd N.A., Lundberg P., Oh D.X., Lee H.K., Hong Y.K., Hwang D.S., Waite J.H., Israelachvili J.N, & Hawker C.J. (2016). Mussel-Inspired Anchoring of Polymer Loops That Provide Superior Surface Lubrication and Antifouling Properties. ACS nano, 10(1), 930-937.

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Porous Titanium Implants with Growth Factors

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In the in vitro experiments, titanium samples were used as follows: three types of porous titanium samples were employed: (a) simple, uncoated, as controls; (b) coated samples, containing IGF1; (c) coated samples, containing BMP2.
To study the influence of the growth factors, the implants were coated with chitosan layers (Sigma Aldrich, Saint Louis, MO, USA) containing microcapsules (3 × 10⁶/implant) loaded with BMP2 and IGF1 respectively. After sterilization with ethylene oxide (Sigma Aldrich, Saint Louis, MO, USA) to avoid titanium denaturation and the inactivation of growth factors), the samples were placed in 96-well plates (Nunc^TM, ThermoFisher Scientific, Waltham, MA, USA) with culture medium containing the cells (5 × 10⁴ cells/implant).

Dindelegan G.C., Caziuc A., Brie I., Soritau O., Dindelegan M.G., Bintintan V., Pascalau V., Mihu C, & Popa C. (2021). Multilayered Porous Titanium-Based 3rd Generation Biomaterial Designed for Endosseous Implants. Materials, 14(7), 1727.

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Synthesis and Characterization of Lipid Membranes

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Ethylene oxide, propylene oxide, 1,2-epoxybutane, potassium tert-butoxide, tetrahydrofuran, 18-crown-6 ether, methanol, naphthalene, potassium metal, α-cyano-4-hydroxycinnamic acid (CHCA), sodium trifluoroacetate (NaTFA), and diphenylhexatriene (DPH), bioreagent grade buffer salts (sodium chloride, potassium chloride, calcium chloride, magnesium chloride, and HEPES) and Triton X-100 were purchased from Sigma Aldrich and used without further purification. 1-palmitoyl-2-oleoyl-glycero-3-phosphocholine (POPC) was purchased from Avanti Polar Lipids as a 10 mg/mL solution in chloroform.

Van Zee N.J., Peroutka A.S., Crabtree A., Hillmyer M.A, & Lodge T.P. (2022). Lipid Membrane Binding and Cell Protection Efficacy of Poly(1,2-butylene oxide)-b-poly(ethylene oxide) Copolymers. Biomacromolecules, 23(3), 1433-1442.

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Synthesis and Characterization of Pluronic Surfactants

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Pluronics F68, P84, P103, P105, F108, and F127 were provided by BASF. Ethylene oxide (EO, ≥99.5%), propylene oxide (PO, ≥99%), potassium, naphthalene, potassium tert-butoxide, n-butyllithium, 18-crown-6 ether, sodium chloride (NaCl, ≥99.0%), silver trifluoroacetate (AgTFA), and α-cyano-4-hydroxycinnamic acid (≥98%), were purchased from Sigma-Aldrich and used as received. POPC and POPG in chloroform were purchased from Avanti Polar Lipids (Alabaster, AL) and used as received. Deuterium oxide (D₂O, 99.9 atom % D) and chloroform-d (CDCl₃, 99.8 atom % D + 0.05% V/V TMS) were purchased from Cambridge Isotope Laboratories, Inc. Ultrapure water with a resistivity of 18.2 MΩ·cm was obtained from a Millipore Direct Q-3 water system (EMD Millipore, Billerica, MA).

Zhang W., Metzger J.M., Hackel B.J., Bates F.S, & Lodge T.P. (2020). Influence of the Headgroup on the Interaction of Poly(ethylene oxide)-Poly(propylene oxide) Block Copolymers with Lipid Bilayers. The journal of physical chemistry. B, 124(12), 2417-2424.

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Synthetic Protocols for Complex Molecules

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All solvents were purchased in the highest available quality required for their application in this study. The reactions requiring anhydrous conditions were carried out under argon atmosphere using anhydrous solvents treated with activated molecular sieves for at least 24 h. molecular sieves (4Å and 3Å) were purchased from Alfa Aesar (Karlsruhe, Germany) and heat-activated under vacuum before use. Triethylamine, trityl chloride, toluene-sulfonyl chloride, NaHCO₃, Na₂SO₄, 1,4-butanediol, P₂O₅, sodium hydride, n-butyllithium (1.6 M solution in hexane), (3-bromopropoxy)-tert-butyldimethylsilane, (4) and ethylene oxide (2.9–3.1 M solution in THF) were purchased from Sigma Aldrich (Steinheim, Germany). Cobalt bis(1,2-dicarbollide) was purchased from Katchem Ltd., Prague, Czech Republic.

Śmiałkowski K., Sardo C, & Leśnikowski Z.J. (2023). Metallacarborane Synthons for Molecular Construction—Oligofunctionalization of Cobalt Bis(1,2-dicarbollide) on Boron and Carbon Atoms with Extendable Ligands. Molecules, 28(10), 4118.

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Chemical Synthesis Protocol Supplies

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Ethylene oxide, styrene oxide, terfenadine, Pluronic F127 were purchased from Sigma-Aldrich (UK).
HPLC grade THF and methanol were obtained from Fisher Scientific Ltd. UK. NMR grade chloroform-d and methanol-d were from Cambridge Isotope Laboratories (USA).

Zhou Z., Chhabria V., D'Emanuele A, & Forbes R.T. (2020). Worm-like micelles of triblock copolymer of ethylene oxide and styrene oxide characterised using light scattering and Taylor dispersion analysis. International journal of pharmaceutics, 588.

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Anionic Polymerization of Pluronic Copolymers

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Pluronics F68, F127, and P103 were provided by BASF. The materials used for anionic polymerization, including ethylene oxide (EO, ≥99.5%), propylene oxide (PO, ≥99%), potassium tert-butoxide, n-butyllithium, naphthalene, potassium, and 18-crown-6 ether, were purchased from Sigma-Aldrich and used as received. 1Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) and 1,2dioleoyl-sn-glycero-3-phosphocholine (DOPC) in chloroform were purchased from Avanti Polar Lipids (Alabaster, AL) and used as received. Cholesterol (≥99%) and the chemicals used for matrix-assisted laser desorption ionization (MALDI) characterization, including silver trifluoroacetate (AgTFA) and α-cyano-4-hydroxycinnamic acid (CHCA, ≥98%), were also purchased from Sigma-Aldrich. Deuterium oxide (D₂O, 99.9 atom % D) and chloroform-d (CDCl₃, 99.8 atom % D + 0.05% v/v tetramethylsilane) were purchased from Cambridge Isotope Laboratories, Inc.

Zhang W., Coughlin M.L., Metzger J.M., Hackel B.J., Bates F.S, & Lodge T.P. (2019). Influence of Cholesterol and Bilayer Curvature on the Interaction of PPO–PEO Block Copolymers with Liposomes. Langmuir : the ACS journal of surfaces and colloids, 35(22), 7231-7241.

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