Diglyme

Manufactured by Merck Group

Sourced in France

Diglyme is a colorless, polar, aprotic solvent with a high boiling point. It is used as a solvent in various industrial and laboratory applications.

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Lab products found in correlation

Close spelling variants of this product

Bis(2-methoxyethyl) ether (diglyme; Diglyme and dinitrophenylhydrazones of formaldehyde

9 protocols using diglyme

Synthesis of Lanthanide Complexes

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Commercial barium hydroxide [Ba(OH)₂•8H₂O], cerium nitrate [Ce(NO₃)₃•6H₂O] or yttrium acetate hydrate [Y(CH₃COO)₃•xH₂O], and Hhfa (Hhfa = 1,1,1,5,5,5-hexafluoroacetylacetone) were purchased from STREM Chemicals Inc. Bischheim (France), while diglyme and tetraglyme (diglyme = bis(2-methoxyethyl)ether and tetraglyme = 2,5,8,11,14-pentaoxapentadecane) were purchased from Sigma-Aldrich (Merck KGaA, Germany). All chemicals were used without any further purification.
The Ba(hfa)₂tetraglyme, Ce(hfa)₃diglyme and Y(hfa)₃diglyme compounds were synthesized by reacting the barium hydroxide, cerium nitrate hydrate, or yttrium acetate hydrate, respectively, with the ligands Hhfa and polyether, such as tetraglyme (for Ba) and diglyme (for Ce and Y).

Pellegrino A.L., Lo Presti F, & Malandrino G. (2023). Metalorganic Chemical Vapor Deposition Approach to the Synthesis of Perovskite BaCeO3 and BaCe0.8Y0.2O3 Thin Films. Molecules, 28(8), 3303.

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Lithium-Ion Electrochemical Cell Fabrication

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Lithium discs were obtained from MTI Corporation. Diglyme, lithium nitrate were all purchased from Sigma Aldrich. Tris(hexafluoroisopropyl) phosphate was obtained from Synquest Laboratories. Celgard 3501 separator was obtained from Celgard Inc. Lithion solution (LITHion™ dispersion, ~10 wt% in isopropanol) was purchased from Ion Power Inc. The Lithion is composed of a Nafion-type perfluorinated polymer having the sulfonic acid groups (EW ~1100) ion exchanged by lithium ions. Nickel manganese cobalt oxide (NCM) cathodes were obtained from Electrodes and More Co. All the chemicals were used as received in after rigorous drying in a ~0 ppm water level and <0.1 ppm oxygen glove box.

Choudhury S., Tu Z., Nijamudheen A., Zachman M.J., Stalin S., Deng Y., Zhao Q., Vu D., Kourkoutis L.F., Mendoza-Cortes J.L, & Archer L.A. (2019). Stabilizing polymer electrolytes in high-voltage lithium batteries. Nature Communications, 10, 3091.

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Synthesis of Electrolyte Components

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Potassium hydroxide (≥85%), sodium
sulfate (anhydrous), sodium hydride (60%, in mineral oil), 2,2,3,3,3-pentafluoro-1-propanol
(97%), 2,2,2-trifluoroethanol (99%), 1 M LiPF₆ in EC/DMC
(50:50 v/v, battery grade), diethylene glycol (99%), triethylene glycol
(99%), tetraethylene glycol (99%), diglyme (anhydrous), α,α,α-trifluorotoluene
(99%), tetraglyme (anhydrous), and 4 Å molecular sieves were
purchased from Sigma-Aldrich. Acetone (99.5%), tetrahydrofuran (certified
grade, with 0.025% butylated hydroxytoluene as a preservative), dichloromethane
(99.5%), hexanes (98.5%), ethyl acetate (99.5%), and methanol (99.8%)
were purchased from Fisher. Lithium foil (750 μm thick), p-toluenesulfonyl chloride (98%), and triglyme (99%) were
purchased from Alfa Aesar. Lithium perchlorate (99%), lithum bis(fluorosulfonyl)
amide (99%), and pentaethylene glycol (95%) were purchased from Oakwood
Chemical. Deuterated acetonitrile (≥99.8 atom % D) and deuterated
chloroform (≥99.8 atom % D) were purchased from Cambridge Isotope
Laboratories. All solvents used for preparing electrolytes were dried
by 4 Å molecular sieves overnight inside an argon-filled glovebox
(VigorTech, O₂ and H₂O < 1 ppm). LiFSA salt
was vacuum-dried at 120 °C overnight in a heated glovebox antechamber
before use and was not exposed to air at any time. Other chemicals
were used as received.

Ma P., Mirmira P, & Amanchukwu C.V. (2021). Effect of Building Block Connectivity and Ion Solvation on Electrochemical Stability and Ionic Conductivity in Novel Fluoroether Electrolytes. ACS Central Science, 7(7), 1232-1244.

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Synthesis of Organic Intermediates

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All materials were used as received from vendors. ClSO₃H (99%), diethylene glycol dimethyl ether (99%, Diglyme), and acetonitrile (99%) were procured from Sigma Aldrich (St. Louis, MO). The unspecified starting material (>98%) was procured from TCI Chemicals (Tokyo, Japan). Silicon heating oil was procured from Beantown Chemical (Hudson, NH, USA).

Glace M., Armstrong C., Puryear N., Bailey C., Moazeni-Pourasil R.S., Scott D., Abdelwahed S, & Roper T.D. (2023). An Automated Continuous Synthesis and Isolation for the Scalable Production of Aryl Sulfonyl Chlorides. Molecules, 28(10), 4213.

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Solid Polymer Electrolyte Synthesis

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PEGDMA (Mn = 750), Diglyme and Lithium Nitrate were purchased from Sigma Aldrich. All chemicals were thoroughly dried before usage. The PEGDMA and Diglyme were mixed in different ratios as required, however the LiNO₃ content was maintained at Li:EO = 0.1 for all the samples. The mixture was thoroughly mixed to obtain a uniform solution. After addition of 4 wt.% of a photoinitiator methyl benzoylformate (MBF), the solution was casted on a desired substrate and exposed to UV light (VMR UVAC 115 V ∼60 Hz 254/365 nm) for 20 min. After the reaction, the membranes were utilized as is for characterizations.
The solid polymer interphase was formed using the same procedure, however the reaction was carried out on a flat piece of lithium metal anode in an Argon-filled glove-box.

Choudhury S., Stalin S., Vu D., Warren A., Deng Y., Biswal P, & Archer L.A. (2019). Solid-state polymer electrolytes for high-performance lithium metal batteries. Nature Communications, 10, 4398.

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Sodium Metal Electrode Preparation

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Sodium cubes, bromo-propane, chloro-propane, iodo-propane, propylene carbonate (PC), ethylene carbonate (EC), diglyme, dimethoxyethane, sodium hexafluorophosphate, magnesium(II) bis(trifluoromethanesulfonyl)imide, were all purchased from Sigma Aldrich. Celgard 3501 separator was obtained from Celgard Inc. Glass fiber separator was bought from Whatman Inc. All the chemicals were used as received in after rigorous drying in a ~ 0 ppm water level and <5 ppm oxygen glove box; in order to make sure the sodium metal is not oxidized.

Choudhury S., Wei S., Ozhabes Y., Gunceler D., Zachman M.J., Tu Z., Shin J.H., Nath P., Agrawal A., Kourkoutis L.F., Arias T.A, & Archer L.A. (2017). Designing solid-liquid interphases for sodium batteries. Nature Communications, 8, 898.

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Hexafluoroacetylacetone Synthesis and Purification

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Sodium hydroxide (NaOH, >98%) and 1,1,1,5,5,5-hexafluoro-2,4-pentanedione (H-hfa, >98%) were purchased from Strem Chemicals and used without further purification. Monoglyme (1,2-dimethoxyethane, 99.5%), diglyme (bis(2-methoxyethyl)ether, 99.5%), triglyme (2,5,8,11-tetraoxadodecane, >98%), tetraglyme (2,5,8,11,14-pentaoxapentadecane, >99%), dichloromethane (CH₂Cl₂, >99.5%), and n-pentane were purchased from Sigma Aldrich.

Peddagopu N., Pellegrino A.L., Bonaccorso C., Rossi P., Paoli P, & Malandrino G. (2022). Sodium β-Diketonate Glyme Adducts as Precursors for Fluoride Phases: Synthesis, Characterization and Functional Validation. Molecules, 27(19), 6282.

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Cathode and Anode Fabrication for Ca-Ion Batteries

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The active material, carbon
black (Timcal, SUPER C65), and polytetrafluoroethylene (PTFE, DuPont,
Teflon 8A) were mixed inside a glovebox at a weight ratio of 7:2:1
to prepare the cathode films. The anodes were prepared by mixing activated
carbon (AC) (Sigma), carbon black, and PTFE at a weight ratio of 8:1:1
in the glovebox. The mixtures were rolled to form thin film cathodes
and anodes. The coin cells were prepared using these cathode and anode
thin films with a loading density of 3 mg/cm² cathode to
20 mg/cm² anode. The electrolyte was prepared by drying
calcium(II) bis(trifluoromethanesulfonyl)imide [Ca(TFSI)₂, 99.5% Solvionic] salt at 170 °C overnight in an Ar-filled
glovebox. The dried salt was then used to form 0.5 M Ca(TFSI)₂ in diglyme (99.5%, Sigma-Aldrich). The electrolyte and its
components were kept inside the glovebox throughout the process. Coin
cells were assembled using the electrolyte, cathode, and anode thin
films, in addition to the separators (Whatman glass microfiber filter).
Galvanostatic cycling tests were performed at 50 °C by using
an Arbin battery tester. The tests were conducted at a current density
of 2 mA/g, and ex situ samples were collected after washing the cathode
thin films with diglyme in an Ar-filled glovebox.

Kim J., Sari D., Chen Q., Rutt A., Ceder G, & Persson K.A. (2024). First-Principles and Experimental Investigation of ABO4 Zircons as Calcium Intercalation Cathodes. Chemistry of Materials, 36(9), 4444-4455.

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Carbonyl Compound Quantification Protocol

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Acetonitrile (ACN) and hydrochloric acid (12 N HCl) were purchased from Fisher Scientific (Pittsburgh, PA) and used as received. 2,4-Dinitrophenylhydrazine (DNPH) was purchased from BOC Sciences (Shirley, NY) and recrystallized before use to remove water as previously reported.^{31 (link)} Diglyme, phenyl-N-tert-butylnitrone (PBN), 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO), hexane, heptadecane, tertbutylbenzene, and dinitrophenylhydrazones of formaldehyde, acetaldehyde, acrolein, acetone, crotonaldehyde, propionaldehyde, and methyl ethyl ketone (MEK) were all purchased from Sigma-Aldrich (St. Louis, MO) and used as received.

Bitzer Z.T., Goel R., Reilly S.M., Bhangu G., Trushin N., Foulds J., Muscat J, & Richie JP J.r. (2018). Emissions of free radicals, carbonyls, and nicotine from the NIDA Standardized Research Electronic Cigarette and comparison to similar commercial devices. Chemical research in toxicology, 32(1), 130-138.

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