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ETHYL DIGLYME

CAS NUMBER:  112-36-7

MOLECULAR FORMULA: C8H18O3

MOLECULAR WEIGHT: 162.23

 

 

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 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.

 

 

USAGE AREAS OF ETHYL DIGLYME:


-laboratory chemicals

-pharmaceuticals 

-polymers

-formulation of mixtures and/or re-packaging 

-scientific research and development

-chemicals 

-plastic products and electrical, electronic and optical equipment

 

 

APPLICATION OF ETHYL DIGLYME:


Ethyl diglyme is used as reaction medium for Grignard and similar synthesis.
Ethyl diglymes, with the combination of ether, alcohol and hydrocarbon chain in one molecule, provide versatile solvency characteristics with both polar and non-polar properties. 

The chemical structure of long hydrocarbon chain resist to solubility in water, while ether or alcohol groups introduce the promoted hydrophilic solubility performance.
This surfactant-like structure provides the compatibility between water and a number of organic solvents, and the ability to couple unlike phases. 

Ethyl diglymes are characterized by their wide range of hydrophilic/hydrophobic balances. 
Ethyl diglymes are used as diluents and levelling agents in the manufacture of paints and baking finishes. 

Ethyl diglyme series are used in the manufacture of nitrocellulose and combination lacquers. 
Ethyl diglymes are used as an additive in brake fluid. They are formulated for dying textiles and leathers and for insecticides and herbicides. 

Ethyl diglymes provides performance in cleaners products with oil-water dispersions. 
Ethyl diglymes are used in printing industries as they have a slow evaporation rate. 

Ethyl diglymes are used as a fixative for perfumes, germicides, bactericides, insect repellents and antiseptic. 
Ethyl diglymes are used as an additive for jet fuel to prevent ice buildup. 

The term of cellosolve refers to Ethyl diglyme or a group of glycol ether solvent as below.
Ethyl diglyme, due to being chemically inert and possessing excellent solvent properties, is mainly used as a solvent and an anhydrous reaction medium for organometallic synthesis. 
Ethyl diglyme is also used as a solubilizer.

 

 

PHYSICAL AND CHEMICAL PROPERTIES OF ETHYL DIGLYME:


-Molecular Formula: C8H18O3

-Molar Mass: 162.227 g/mol

-Density: 0.902g/cm3

-Melting Point: -44.3℃

-Boling Point: 190.2°C at 760 mmHg

-Flash Point: 71.1°C

-Solubility: Soluble

-Vapor Presure: 0.758mmHg at 25°C

-Refractive Index: 1.408

 

 

PROPERTIES OF ETHYL DIGLYME:


-Dissolve polar and non-polar contaminants

-Very low odor compared to esters, ketones and monoethers

-Choice of boiling point

-Fully compatible with quats

-Compatible with hydrocarbons AND water!

-Run cleaning hot or cold and match requirements for solvent recovery

-Use of higlyme (non-VOC) for heavy-duty water-based cleaning solutions

-Optimized cleaning by using Ethyl diglyme for more polar impurities

-Use of Ethyl diglyme for non-polar impurities and high temperature

-Maintain ability to remove metal ions

-Reduce surface tension

 

 

SPECIFICATIONS OF ETHYL DIGLYME:


-Appearance (Clarity): Clear

-Appearance (Colour): Colourless    

-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%

 

 

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.

 

 

MANUFACTURE OF ETHYL DIGLYME:

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).

 

 

STORAGE OF ETHYL DIGLYME:

Stored in a cool dry place out of direct sunlight.
Separated from strong oxidants. Ventilation along the floor. 

 

 

SYNONYM:

1,1'-oxybis(2-ethoxyethane)
1-ethoxy-2-(beta-ethoxyethoxy)ethane
2-(2-ethoxyethoxy)-1-ethoxyethane
2,2'-oxybisethanol diethyl ether
2-ethoxyethyl ether
3,6,9-trioxaundecane
Bis-2-ethoxyethyl ether
Diethyl Carbitol
ethyl diglyme
Diethyl diglycol
Diethylenglycoldiethylether
bis-(2-ethoxyethyl) ether
2-ethoxyethyl) ether
bis(2-ethoxyethyl) ether
1-ethoxy-2-(2-ethoxyethoxy)ethane
2-Ethoxyethyl ether
Diethyl carbitol
1-Ethoxy-2-(2-ethoxyethoxy)ethane
Ethyl diglyme
Bis(2-ethoxyethyl) ether
Diethyldiethylene glycol
Ether, bis(2-ethoxyethyl)
3,6,9-Trioxaundecane
DEGDEE
Ethane, 1,1'-oxybis[2-ethoxy-
diethyleneglycoldiethylether
2-(2-Ethoxyethoxy)-1-ethoxyethane
Diethylether diethylenglykolu
1-Ethoxy-2-(beta-ethoxyethoxy)ethane
UNII-ZH086O935Z
Ethanol, 2,2'-oxybis-, diethyl ether

 

 

IUPAC NAME:

1-Ethoxy-2-(2-methoxyethoxy)ethane
1-ethoxy-2-(2-methoxyethoxy)ethane
1-ethoxy-2-(2-methoxyethoxy)ethane
Diethylene Glycol Ethyl Methyl Ether
diethylene glycol methyl ethyl ether
Ethane, 1-ethoxy-2-(2-methoxyethoxy)-
Ethyl diglyme


 

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