ETHYL DIGLYME
Ethyl diglyme is an organic solvent with a high boiling point, used as a solvent for reactions performed at higher temperatures and involved in the preparation of nitrocellulose, resins, and adhesives.
Ethyl diglyme is utilized as a scrubbing medium to absorb carbonyl sulfide (COS), an impurity in petroleum refineries, and is also used in the production of paints, varnishes, and coatings.
Ethyl diglyme is a glycol ether with excellent solvent properties, used in various applications such as x-ray crystallography, digital ink formulations, and gold extraction from hydrochloric acid media.
CAS Number: 111-96-6
EC Number: 203-920-7
Chemical Formula: C₆H₁₄O₃
Molecular Weight: 118.18 g/mol
Synonyms: 1,1'-Oxybis(2-ethoxy-ethan), Diethyldiethyleneglycol, Diethyldigol, Diethyleneglycoldlethylether, Diethylether diethylenglykolu, Diethyletherdiethylenglykolu, Ethane, 1,1'-oxybis[2-ethoxy-], Ethane, 1,1'-oxybis[2-ethoxy-], DIETHYLENE GLYCOL DIETHYL ETHER, 2-Ethoxyethyl ether, 1-Ethoxy-2-(2-ethoxyethoxy)ethane, Diethyl carbitol, Ethyl diglyme, Bis(2-ethoxyethyl) ether, Diethyldiethylene glycol, Ether, bis(2-ethoxyethyl), 3,6,9-Trioxaundecane, DEGDEE, Diethyleneglycoldiethylether, Ethane, 1,1'-oxybis[2-ethoxy-], Ethyldiglyme, 2-(2-Ethoxyethoxy)-1-ethoxyethane, Diethylether diethylenglykelu, 1-Ethoxy-2-(beta-ethoxyethoxy)ethane, Ethanol, 2,2'-oxybis-, diethyl ether, Ethane, 1,1'-oxybis(2-ethoxy-), Diethyleneglycol diethyl ether, DTXSID3025047, CHEBI:44664, ZH086O935Z, MFCD00009254, Ethanol, 2,2'-oxybis-, diethyl ether, Ethyldiglyme, Hisolve EDE, HSDB 68, P4G, Glycol, diethylene-, diethyl ether, EINECS 203-963-7, Diethylether diethylenglyl [Czech], BRN 1699259, Diethoxydiglycol, UNII-ZH086O935Z, AI3-19428, Ethoxyethyl ether, HISOLVE EDE, (1-Ethoxy)-ethyl ether, EC 203-963-7, Diethyleneglycol diethylether, 1,5-Diethoxy-3-oxapentane, SCHEMBL16596, Diethylene glycol diethylether, DIETHOXYDIGLYCOL [INCI], 1,1'-Oxybis(2-ethoxy)ethane, 1,1'-Oxybis(2-ethoxyethane), DTXCID505047, CHEMBL1235106, Diethyl ene glycol diethyl ether, Ethane, 1,1'-oxybis[2-ethoxy-], Tox21_302050, 1-Ethoxy-2-(2-ethoxyethoxyl)ethane, 1-Ethoxy-2-(2-ethoxyethoxy)-ethane, AKOS015915322, 1-Ethoxy-2-(beta-ethoxyethoxy)ethane, DB08357, 1-Ethoxy-2-(.beta.-ethoxyethoxy)ethane, NCGC00164135-01, NCGC00255128-01, CAS-112-36-7, B0489, DIETHYLENE GLYCOL DIETHYL ETHER [MI], Diethylene glycol diethyl ether, HPLC Grade, NS00004273, DIETHYLENE GLYCOL DIETHYL ETHER [HSDB], A802561, Diethylene glycol diethyl ether, for HPLC, >=99%, J-509308, Q5275148, Diethylene glycol diethyl ether, reagent grade, >=98%, F8881-4182, Z1255402671, 2-Ethoxyethyl ether, Bis(2-ethoxyethyl) ether, Diethyldiglycol, Diethylene glycol diethyl ether, Vetec(TM) reagent grade, 98+ %, InChI=1/C8H18O3/c1-3-9-5-7-11-8-6-10-4-2/h3-8H2,1-2H
Ethyl diglyme is incompatible with strong acids.
Ethyl diglyme is also incompatible with strong oxidizing agents.
Ethyl diglyme is an organic solvent with a high boiling point.
Ethyl diglyme is used as a solvent for reactions performed at higher temperatures.
Ethyl diglyme is involved in the preparation of nitrocellulose, resins and adhesives.
Ethyl diglyme is utilized as a scrubbing medium to absorb carbonyl sulfide (COS), an impurity in petroleum refineries.
Ethyl diglyme is a glycol ether used as a solvent in the production of paints, varnishes, and other coatings.
Ethyl diglyme has been shown to be chemically stable and non-toxic when used at low concentrations.
Ethyl diglyme can also be used as an alternative solvent for x-ray crystallography experiments because Ethyl diglyme produces high quality crystals of proteins, nucleic acids, and other organic compounds.
The hydroxyl group on its structure makes Ethyl diglyme an excellent substrate for film formation.
Ethyl diglyme is also able to bind to receptors in autoimmune diseases, which may be due to its structural similarity to the natural neurotransmitter acetylcholine.
Ethyl diglyme is a compound that is related to a family of glycol ethers.
Ethyl diglyme's are a group of solvents based on alkylene oxides and alcohols.
Ethyl diglyme's typically have excellent solvent properties for a variety of substances and are used in a wide range of applications.
Ethyl diglyme, or 2-Ethoxyethyl ether, is an organic solvent used to study the activities of enzymes in aqueous organic mixtures.
Ethyl diglyme is a solvent for reactions performed at higher temperatures.
Ethyl diglyme is involved in the preparation of nitrocellulose, resins, and adhesives.
Ethyl diglyme is a scrubbing medium to absorb carbonyl sulfide (COS), an impurity in petroleum refineries.
Ethyl diglyme could be used as an absorbent for CO2.
This absorbent has a high boiling point (462 K, in SciFinder), indicating that energy for absorbent regeneration and loss were saved.
In addition, this absorbent is chemically and thermally stable, non-corrosive, and has low density and viscosity.
Ethyl diglyme is rich in philic-CO2 groups, which makes Diethylene glycol diethyl ether more effective for CO2 capture.
Li et al. found that carbonyl and ether groups in the absorbents improved CO2 solubility, and the carbonyl group was more effective than the ether group.
A polyether that consists of undecane in which the carbon atoms at positions 3, 6 and 9 are replaced by oxygen atoms.
Ethyl diglyme is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 to < 1 000 tonnes per annum.
Ethyl diglyme is used in articles, in formulation or re-packing, at industrial sites and in manufacturing.
Ethyl diglyme (diethylene glycol diethyl ether) is a suitable solvent for emissive applications like digital ink formulations.
This water soluble, low odor aprotic solvent offers high solvency and dispersancy for pigments and dyes, while preventing clogging of printer heads.
Ethyl diglyme is a solvent with a high boiling point.
Ethyl diglyme is an organic compound which is the dimethyl ether of diethylene glycol.
The name " Ethyl diglyme" is a portmanteau of "diglycol methyl ether.".
Ethyl diglyme is a colorless liquid with a slight ether-like odor.
Ethyl diglyme is miscible with water as well as organic solvents.
Ethyl diglyme is prepared by a reaction of dimethyl ether and ethylene oxide over an acid catalyst.
Ethyl diglyme's production and use as a high boiling reaction medium, and as a solvent for nitrocellulose, lacquers, resins, and organic syntheses may result in its release to the environment through various waste streams.
If released to air, a vapor pressure of 0.52 mm Hg at 25 °C indicates Ethyl diglyme will exist solely as a vapor in the atmosphere.
Vapor-phase Ethyl diglyme will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 14 hours.
If released to soil, Ethyl diglyme is expected to have very high mobility based upon an estimated Koc of 39.
Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 1.1X10-7 atm-cu m/mole.
Ethyl diglyme may volatilize from dry soil surfaces based upon its vapor pressure.
Biodegradation of Ethyl diglyme is not expected to be an important fate process in soil or water based on biodegradation studies conducted with sewage seed.
If released into water, Ethyl diglyme is not expected to adsorb to suspended solids and sediment based upon the estimated Koc.
Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant.
An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low.
Occupational exposure to Ethyl diglyme may occur through inhalation and dermal contact with this compound at workplaces where Ethyl diglyme is produced or used.
Monitoring data indicate that the general population may be exposed to Ethyl diglyme via inhalation of ambient air, ingestion of drinking water, and dermal contact with this compound and other products containing Ethyl diglyme.
Ethyl diglyme's production and use as a high boiling reaction medium, and as a solvent for nitrocellulose, lacquers, resins, and organic syntheses may result in its release to the environment through various waste streams(SRC).
Ethyl diglyme, or glymes, are aprotic, saturated polyethers that offer high solvency, high stability in strong bases and moderate stability in acid solutions.
Ethyl diglyme efficiently solvate cations, increasing anion reactivity, and thus can increase both selectivity and reaction rates.
Most Ethyl diglymeare water-soluble, but a range of solubility and boiling points are available.
The polyether structure produces only weak associations between glyme molecules, and is responsible for the low viscosity and excellent wetting properties of these solvents.
A further structural feature of Ethyl diglyme that contributes significantly to their usefulness involves the arrangement of oxygen atoms, as ether linkages, at two-carbon intervals.
The model of the Ethyl diglyme molecule (picture above) illustrates this periodic recurrence of oxygen atoms separated by two carbon atoms.
This steric arrangement, analogous to that of crown ethers, gives Ethyl diglyme the ability to form complexes with many cations.
Ethyl diglymes have a wide range of solubilities and boiling points.
Ethyl diglymes are used as reaction solvents and in closed loop applications such as gas scrubbing and in refrigeration systems.
The higher molecular weight Ethyl diglyme beginning with Ethyl diglyme are suitable for emissive applications such as coatings, inks, adhesives and in cleaning compounds.
The lower molecular weight Ethyl diglyme should not be used in emissive applications.
Ethyl diglyme is most commonly utilized as a high-performance solvent for both laboratory and industrial applications.
Ethyl diglyme effectively solvates digital inks and decorative ceramic inks, since Ethyl diglyme is stable enough to withstand the high temperatures of these applications.
Ethyl diglyme is also commonly used on small scales as an extraction solvent for gold from hydrochloric acid media, a process which results in an extremely high concentration of pure gold metal.
Ethyl diglyme can also be used as an intermediate in the production of siloxane-based adjuvants.
Ethyl diglyme is a linear aliphatic diether widely used as a solvent and present as a clear liquid at room temperature with a mild ether odor.
Ethyl diglyme is not known to occur in nature.
Ethyl diglyme is synthesized from ethylene oxide and methanol in the presence of either acidic or basic catalysts.
Ethyl diglyme is a clear colorless viscous liquid.
Uses of Ethyl Diglyme:
Ethyl diglyme is a very useful organic solvent.
Ethyl diglyme has a high boiling point and has been used to study the activities of enzymes in aqueous organic mixtures.
Ethyl diglyme is used to study the activities of enzymes in aqueous organic mixtures.
Ethyl diglyme is used as a mixed solvent of oil and water for printing and dyeing of nitric acid fibers and woolen fabrics, as well as a reaction medium with high boiling point.
Ethyl diglyme is used as an organic synthetic solvent, a nitrospray paint component for brushing, a leveller for fibers and leather, a leveller for photographic printing, etc.
Ethyl diglyme has high boiling point reaction medium.
The stationary phase of gas chromatography (the highest temperature is 30 C, the solvent is ethyl ether) is similar to that of PEG.
Ethyl diglyme is used in the following products: laboratory chemicals, pharmaceuticals and polymers.
Ethyl diglyme is used in the following areas: formulation of mixtures and/or re-packaging and scientific research and development.
Ethyl diglyme is used for the manufacture of: chemicals, plastic products and electrical, electronic and optical equipment.
Ethyl diglyme are also useful as solubilizing agents, extractants and selective solvents.
Methoxyacetaldehyde dimethylacetal can be prepared by electrochemical oxidation in Ethyl diglyme.
Aspartame was prepared by enzymatic catalysis in triglyme-water medium.
Release to the environment of Ethyl diglyme can occur from industrial use: manufacturing of the substance, formulation of mixtures, in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates) and as processing aid.
Other release to the environment of Ethyl diglyme is likely to occur from: indoor use, indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters) and outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials).
Pharma and fine chemicals synthesis of Ethyl diglyme Due to their high stability and solvency, Ethyl diglyme are widely used as reaction media for processes involving alkali metal hydroxides, sodium hydride, and alkali metals.
Grignard reaction yields can be increased and purification costs reduced by using Ethyl diglyme as reaction solvents.
Ethyl diglyme at high temperature can be substituted for lithium aluminum hydride in some reductions.
Carried out in Ethyl diglyme sodium aluminum hydride can be prepared directly from the elements in Ethyl diglyme.
Ethyl diglyme is the solvent of choice when preparing aryl sulfides via use of sodium tetrafluoroborate as a catalyst.
Ethyl diglymes are processed and formulated using Ethyl diglyme to yield isocyanurate and polyisocyanate prepolymers used in various polyurethane applications.
Preparation of urethanes, hydrogenations, condensations, oxidations, olefin insertions, oligomerizations of olefins, and addition reactions can be carried out in Ethyl diglyme as reaction medium.
Ethyl diglyme are useful in formulating rigid polyurethane foams with improved fluidity during molding and with improved bonding strength.
Ethyl diglyme is also a key to the efficient synthesis.
The viscosity of polyols useful in the manufacture of polyurethanes can be reduced by means of Ethyl diglyme without adversely affecting physical properties.
Polyurethane coatings used to form pinhole-free films with good adhesive strength, applicable to electrical and electronic parts, utilize Ethyl diglyme.
Ethyl diglyme is a very useful organic solvent.
Ethyl diglyme has a high boiling point and has been used to study the activities of enzymes in aqueous organic mixtures.
Uses at industrial sites:
Ethyl diglyme is used in the following products: laboratory chemicals, pharmaceuticals and polymers.
Ethyl diglyme is used in the following areas: formulation of mixtures and/or re-packaging and scientific research and development.
Ethyl diglyme is used for the manufacture of: chemicals, plastic products and electrical, electronic and optical equipment.
Release to the environment of Ethyl diglyme can occur from industrial use: manufacturing of the substance, formulation of mixtures, in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates) and as processing aid.
Other release to the environment of Ethyl diglyme is likely to occur from: indoor use, indoor use in close systems with minimal release (e.g. cooling liquids in refrigerators, oil-based electric heaters) and outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials).
Usage Areas:
Laboratory chemicals
Pharmaceuticals
Polymers
Formulation of mixtures and/or re-packaging
Scientific research and development
Chemicals
Plastic products and electrical, electronic and optical equipment
Solvent of Ethyl Diglyme:
Because of its resiliance to strong bases, Ethyl diglyme is favored as a solvent for reactions of alkali metal reagents even at high temperatures.
Rate enhancements in reactions involving organometallic reagents, such as Grignard reactions or metal hydride reductions, have been observed when using Ethyl diglyme as a solvent.
Ethyl diglyme is also used as a solvent in hydroboration reactions with diborane.
Ethyl diglyme serves as a chelate for alkali metal cations, leaving anions more active.
Preparation of Ethyl Diglyme:
2-Ethoxyethyl ether could be synthesized by reacting 1, 4-dioxane with diethyl ether.
ZSM-5-type zeolite was used as the catalyst.
This reaction is performed in an autoclave.
Purification Methods of Ethyl Diglyme:
Dry the ether with MgSO4, then CaH2 or LiAlH4, under N2.
If sodium is used, the ether should be redistilled alone to remove any products which may be formed by the action of sodium on the ether.
As a preliminary purification, the crude ether (2L) can be refluxed for 12hours with 25mL of conc HCl in 200mL of water, under reduced pressure, with slow passage of N2 to remove aldehydes and other volatile substances.
After cooling, add sufficient solid KOH pellets (slowly and with shaking until no more dissolves) to give two liquid phases.
The upper of these is decanted, dried with fresh KOH pellets, decanted, then refluxed over, and distilled from sodium.
Ethyl diglyme can be passed through (alkaline) alumina prior to purification.
Synthesis Analysis of Ethyl Diglyme:
The synthesis of Ethyl diglyme and its derivatives has been explored through various chemical reactions.
For instance, the synthesis of diethylene glycol ethyl ether can be achieved using diethylene glycol and ethanol with heteropoly acidic salts as catalysts, showing high activity and stability.
Similarly, diethylene glycol monoallyl ether can be synthesized from diethylene glycol, allyl chloride, and sodium hydroxide, using tetrabutylammonium chloride as a phase transfer catalyst.
These methods demonstrate the versatility of diethylene glycol ethers' synthesis, allowing for the production of various derivatives with potential applications in different industries.
Handling and Storage of Ethyl Diglyme:
Handling:
Use in a well-ventilated area to avoid inhalation of vapors.
Avoid contact with skin, eyes, and clothing. Use appropriate personal protective equipment (PPE) such as gloves and safety goggles.
Do not eat, drink, or smoke when using the chemical.
Handle containers carefully to prevent spills and leaks.
Storage:
Store in a cool, dry, and well-ventilated area away from heat sources and direct sunlight.
Keep containers tightly closed and away from incompatible materials such as strong acids and oxidizing agents.
Avoid storage in damp or humid conditions.
Stability and Reactivity of Ethyl Diglyme:
Stability:
Ethyl diglyme is stable under normal conditions of use and storage.
Avoid exposure to high temperatures, flames, and sparks.
Reactivity:
Can react with strong acids and oxidizing agents.
Decomposes at elevated temperatures, which can release hazardous fumes.
May form peroxides if stored improperly for long periods.
First Aid Measures of Ethyl Diglyme:
Inhalation:
Move the affected person to fresh air immediately.
Seek medical attention if symptoms persist or if there is difficulty breathing.
Skin Contact:
Wash affected skin with plenty of soap and water.
Remove contaminated clothing.
Seek medical attention if irritation or symptoms persist.
Eye Contact:
Rinse eyes immediately with plenty of water for at least 15 minutes, holding the eyelids open.
Remove contact lenses if present and easy to do.
Seek medical attention if irritation persists.
Ingestion:
Rinse mouth with water.
Do not induce vomiting.
Seek medical attention immediately.
Firefighting Measures of Ethyl Diglyme:
Fire Fighting:
Use foam, dry chemical, or carbon dioxide (CO2) to extinguish fires involving Ethyl diglyme.
Water can be used to cool containers and prevent the spread of fire.
Wear self-contained breathing apparatus (SCBA) and full protective clothing when fighting fires involving Ethyl diglyme.
Fire and Explosion Hazards:
Ethyl diglyme is flammable and can form explosive mixtures with air.
Combustion may produce harmful fumes such as carbon monoxide and carbon dioxide.
Accidental Release Measures of Ethyl Diglyme:
Personal Precautions:
Wear appropriate PPE, including gloves, goggles, and a respirator if needed.
Evacuate non-essential personnel from the area.
Environmental Precautions:
Prevent the chemical from entering drains, waterways, or soil.
Spill Cleanup:
Absorb spills with inert materials such as sand or vermiculite.
Collect the absorbed material in a suitable container for disposal.
Clean the area with soap and water.
Ensure proper disposal of waste in accordance with local regulations.
Exposure Controls/Personal Protective Equipment of Ethyl Diglyme:
Exposure Limits:
There may be specific occupational exposure limits for Ethyl diglyme established by regulatory agencies.
Engineering Controls:
Ensure adequate ventilation in areas where Ethyl diglyme is used.
Use local exhaust ventilation if necessary.
Personal Protective Equipment:
Skin Protection:
Wear chemical-resistant gloves and protective clothing.
Eye Protection:
Use safety goggles or face shields to protect against splashes.
Respiratory Protection:
Use a suitable respirator if ventilation is insufficient or if there is a risk of inhalation.
Hygiene Practices:
Wash hands and face thoroughly after handling.
Remove contaminated clothing and wash before reuse.
Identifiers of Ethyl Diglyme:
Chemical Name: Ethyl diglyme
Other Names: Ethyl Diglycol Ether
Chemical Formula: C₆H₁₄O₃
CAS Number: 111-96-6
Molecular Weight: 118.18 g/mol
EC Number: 203-920-7
PubChem CID: 8228 (Identifier in PubChem database)
Properties of Ethyl Diglyme:
Melting Point: -44.3°C
Boiling Point: 180-190 °C (lit.)
Density: 0.909 g/mL at 25 °C (lit.)
Vapor Density: 5.6 (vs air)
Vapor Pressure: 0.5 mm Hg (20 °C)
Refractive Index: n20/D 1.412 (lit.)
Flash Point: 160 °F
Storage Temp.: Store below +30°C
Solubility: Chloroform (Sparingly), Methanol (Slightly)
Form: Liquid
Color: Clear
Relative Polarity: 3.9
Explosive Limit: 6.2%
Water Solubility: Soluble
λmax λ: 260 nm Amax: 1.00
λ: 300 nm Amax: 0.10
λ: 320 nm Amax: 0.04
λ: 350-400 nm Amax: 0.01
Merck: 14,3118
BRN: 1699259
Dielectric Constant: 5.7
Stability: Stable. Combustible. Incompatible with strong oxidizing agents. May form peroxides on exposure to air - test for their presence before heating.
InChIKey: RRQYJINTUHWNHW-UHFFFAOYSA-N
LogP: 0.39 at 25°C
CAS DataBase Reference: 112-36-7
NIST Chemistry Reference: Ethyl diglyme (112-36-7)
EPA Substance Registry System: Ethyl diglyme (112-36-7)
Molecular Formula: C₈H₁₈O₃
Molar Mass: 162.227 g/mol
Density: 0.902 g/cm³
Melting Point: -44.3°C
Boiling Point: 190.2°C at 760 mmHg
Flash Point: 71.1°C
Solubility: Soluble
Vapor Pressure: 0.758 mmHg at 25°C
Refractive Index: 1.408
Specifications of Ethyl Diglyme:
Appearance (Clarity): Clear
Appearance (Color): Colorless
Appearance (Form): Liquid
Assay (GC): min. 99%
Density (g/ml) @ 20°C: 0.908-0.910
Refractive Index (20°C): 1.411-1.412
Boiling Range: 186-188°C
Water (KF): max. 0.1%
