Diglyme CAS 111-96-6
Introduction：Basic information about Diglyme CAS 111-96-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Diglyme Basic information
| Product Name: | Diglyme |
| Synonyms: | DIMETHYLDIGLYCOL;DIMETHYL DIGOL;DIMETHYL CARBITOL;DIETHYLENE GLYCOL DIMETHYL ETHER;DIGLYME;'DIGLYME';DEDM;BIS(2-METHOXYETHYL) ETHER |
| CAS: | 111-96-6 |
| MF: | C6H14O3 |
| MW: | 134.17 |
| EINECS: | 203-924-4 |
| Product Categories: | Carbon Steel Cans with NPT Threads;Functional Materials;Plasticizer;Polyalcohol Ethers, Esters (Plasticizer);Aliphatics;Semi-Bulk Solvents;ACS and Reagent Grade Solvents;Amber Glass Bottles;ReagentPlus;ReagentPlus Solvent Grade Products;Solvent Bottles;Solvent by Application;Solvent Packaging Options;Solvents;Anhydrous Solvents;Sure/Seal Bottles;NMR;Spectrophotometric Grade;Spectrophotometric Solvents;Spectroscopy Solvents (IR;UV/Vis);solvent,metal organic compound synthesis;bc0001 |
| Mol File: | 111-96-6.mol |
Diglyme Chemical Properties
| Melting point | -64 °C (lit.) |
| Boiling point | 162 °C (lit.) |
| density | 0.944 g/mL at 20 °C (lit.)0.939 g/mL at 25 °C (lit.) |
| vapor density | 4.6 (vs air) |
| vapor pressure | 3 mm Hg ( 20 °C) |
| refractive index | n |
| Fp | 134.6 °F |
| storage temp. | Store below +30°C. |
| solubility | Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly) |
| form | Liquid |
| color | ≤10(APHA) |
| Odor | Mild ethereal. |
| PH | 7 (20°C) |
| Relative polarity | 0.244 |
| explosive limit | 1.4-17.4%(V) |
| Water Solubility | Miscible |
| λmax | λ: 225 nm Amax: 1.00 λ: 240 nm Amax: 0.50 λ: 260 nm Amax: 0.20 λ: 280 nm Amax: 0.08 λ: 320-400 nm Amax: 0.01 |
| Sensitive | Hygroscopic |
| Merck | 14,3165 |
| BRN | 1736101 |
| Dielectric constant | 7.2999999999999998 |
| Stability: | Stable. Combustible. Incompatible with strong oxidizing agents. May be air or light sensitive. |
| Cosmetics Ingredients Functions | SOLVENT |
| InChI | 1S/C6H14O3/c1-7-3-5-9-6-4-8-2/h3-6H2,1-2H3 |
| InChIKey | SBZXBUIDTXKZTM-UHFFFAOYSA-N |
| SMILES | COCCOCCOC |
| LogP | -0.36 at 25℃ |
| Surface tension | 24.56mN/m at 298.15K |
| CAS DataBase Reference | 111-96-6(CAS DataBase Reference) |
| NIST Chemistry Reference | Ethane, 1,1'-oxybis[2-methoxy-(111-96-6) |
| EPA Substance Registry System | Diethylene glycol dimethyl ether (111-96-6) |
Safety Information
| Hazard Codes | T |
| Risk Statements | 60-61-10-19 |
| Safety Statements | 53-45 |
| RIDADR | UN 3271 3/PG 3 |
| WGK Germany | 1 |
| RTECS | KN3339000 |
| F | 3-10-23 |
| Autoignition Temperature | 370 °F |
| TSCA | TSCA listed |
| HazardClass | 3 |
| PackingGroup | III |
| HS Code | 29091990 |
| Storage Class | 3 - Flammable liquids |
| Hazard Classifications | Flam. Liq. 3 Repr. 1B |
| Hazardous Substances Data | 111-96-6(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 4760 mg/kg |
| Description | Bis (2-methoxyethyl) ether, also known as diglyme, is a linearaliphatic diether widely used as a solvent and present as a clearliquid at room temperature with a mild ether odor. Thecompound is notknown to occur in nature. It is synthesized fromethylene oxide and methanol in the presence of either acidic orbasic catalysts. The reaction is based on the classic Williamsonether synthesis. It can also be produced from diethylene glycoland dimethyl sulfate. In June 2012, ECHA proposed addition ofdiglyme to the REACH very high concern list. |
| Chemical Properties | Diethylene glycol dimethyl ether is a clear, water-white neutral liquid of faint, pleasant odor. This ether may be used as a solvent for alkali metal hydrides for use in such reactions as reduction, alkylation and condensation. It may also be used as a lacquer solvent. |
| Uses | Solvent; it is used as reaction medium for Grignard and similar synthesis. |
| Uses | Bis (2-methoxyethyl) ether, due to being chemically inert andpossessing excellent solvent properties, is mainly used asa solvent and an anhydrous reaction medium for organometallicsynthesis. It is also used as a solubilizer. |
| Uses | Diethylene glycol dimethyl ether is used as a solvent in organic reactions due to its stability towards higher pH and its high boiling point. It is particularly involved in reactions utilizing organometallic reagents such as Grignard reactions and metal hydride reductions. It is also a solvent for hydroboration reactions with diborane. |
| Definition | ChEBI: A polyether that is the dimethyl ether derivative of diethylene glycol. |
| General Description | Colorless watery liquid with a pleasant odor. Floats and mixes with water. |
| Air & Water Reactions | Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164]. A mixture of liquid air and diethyl ether exploded spontaneously, [MCA Case History 616(1960)]. Water soluble. |
| Reactivity Profile | A violent explosion occurred when lithium aluminum hydride was being used to dry 2-Methoxyethyl ether. The ignition may have occurred due to the presence of large amounts of water or perhaps peroxide formed in the ether. About 75% of the ether had been removed when the explosion occurred, [MCA Case History 1494 (1968)]. |
| Health Hazard | INGESTION (severe cases): nausea, vomiting, abdominal cramps, weakness progressing to coma. |
| Fire Hazard | 2-Methoxyethyl ether is combustible. |
| Flammability and Explosibility | Flammable |
| Chemical Reactivity | Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent. |
| Synthesis | 265 g (2.5 mol) of diethylene glycol, 320 g (10.0 mol) of methanol, and 14.3 g (0.0125 equivalents) of NAFION 1100 EW Polymer (H+ form) were charged to a one-liter autoclave. After sealing and pressure testing, the contents of the autoclave were agitated, and the autoclave was pressurized to 100 psi with nitrogen. After 5 minutes of agitation, the autoclave was depressurized. This process was repeated two more times to ensure complete deoxygenation. After deoxygenation, the autoclave was heated to a temperature of 198 ℃, and the contents of the autoclave were agitated at 1900 rpm for 5 hours at temperature (198-200 ℃). A pressure of 810 psi was obtained. After 5 hours, the autoclave was cooled and sampled. By analysis, a total of 77.2% by weight of the diethylene glycol (1.93 moles) was converted in the reaction, producing 0.335 mol of Diglyme. The co-product includes 1,4 dioxane and the intermediate diethylene glycol monomethyl ether. |
| Environmental Fate | The metabolite 2-methoxyacetic acid, which is generated from2-methroxyethanol by the reaction of alcohol dehydrogenase,may be important for the toxic effects. It can undergo activationto methoxyacetyl coenzyme A and enter the Krebs cycle or fattyacid biosynthesis. Several metabolites of 2-methoxyethanol,such as 2-methoxy-N-acetyl glycine, have been identified thatsupport this pathway. Thus, 2-methoxyacetic acid may interferewith essential metabolic pathways of the cell, and it washypothesized that this causes the testicular lesions and malformationsin experimental animals. |
| Purification Methods | Dry diglyme with NaOH pellets or CaH2, then reflux with, and distil (under reduced pressure) it from Na, CaH2, LiAlH4, NaBH4 or NaH. These operations are carried out under N2. The amine-like odour of diglyme has been removed by shaking with a weakly acidic ion-exchange resin (Amberlite IR-120) before drying and distilling. Addition of 0.01% NaBH4 to the distillate inhibits peroxidation. Purify it also as for dioxane. It has been passed through a 12-in column of molecular sieves to remove water and peroxides. [Beilstein 1 IV 2393.] |
| Properties and Applications | Diglyme is also known as Diethylene Glycol Dimethyl Ether. The IUPAC name of this compound is 1-Methoxy-2-(2-methoxyethoxy)ethane. This compound belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups. In addition, it is an aprotic polar solvent with a high boiling point that is stable at high pH levels. Therefore, it is a suitable solvent for organic reactions conducted under strongly alkaline conditions[1]. Some researchers have already used diglyme as a physical absorbent of CO2. |
| Toxicity evaluation | Bis (2-methoxyethyl) ether will present asa vapor, when released to air, at a vapor pressure of2.96 mmHg at 25°C. The vapor phase is easily degraded inthe atmosphere by reaction with photochemically producedhydroxyl radicals. The half-life for the reaction is estimatedto be 22 h. Bis (2-methoxyethyl) ether does not containchromophores that will absorb at wavelengths >290 nmand therefore is not expected to be susceptible to directphotolysis by sunlight. Bis (2-methoxyethyl) ether has very highmobility in soil based on the estimated Koc of 15, when released to soil. It may volatilize from dry soil surfacesbased upon its vapor pressure.Aquatic fate: Bis (2-methoxyethyl) ether does not absorb tosuspended solids and sediments when released into water.Hydrolysis is not an important environmental matterbecause bis (2-methoxyethyl) ether does not containa functional group that can hydrolyze under environmentalconditions. |
| References | [1] Weijia Huang. “An Aprotic Polar Solvent, Diglyme, Combined with Monoethanolamine to Form CO2 Capture Material: Solubility Measurement, Model Correlation, and Effect Evaluation.” Industrial & Engineering Chemistry Research 54 13 (2015): 3430–3437. |
Diglyme Preparation Products And Raw materials
| Raw materials | Sodium hydroxide-->Dimethyl sulfate-->Diethylene glycol monomethyl ether-->Ethane, 1,1,1-trifluoro-2-(2-methoxyethoxy)--->BIS(2,2,2-TRIFLUOROETHYL) ETHER-->2-METHOXYETHYL P-TOLUENESULFONATE-->2,2,2-TRIFLUOROETHYL P-TOLUENESULFONATE-->2-Iodo-1,1,1-trifluoroethane |
| Preparation Products | 2,5-DIMETHYL-1,3-OXAZOLE-4-CARBALDEHYDE-->(2,5-DIMETHYL-1,3-OXAZOL-4-YL)METHANOL-->6,6'-Dimethyl-2,2'-dipyridyl-->3-CYCLOPENTENE-1-OL-->Cyclohexene oxide-->2-METHYLCYCLOPROPANECARBOXYLIC ACID-->5-AMINOMETHYL-PYRROLIDIN-2-ONE-->1-(2-Methoxyphenyl)piperazine hydrobromide-->5,5'-DIMETHYL-2,2'-DIPYRIDYL-->2-BROMO-6-(1H-PYRAZOL-1-YL)PYRIDINE-->1-(1-NAPHTHYL)PIPERAZINE HYDROCHLORIDE-->Methanol-->Pentacene |
