PRODUCTS

Diethylene Glycol Dimethyl Ether

Diethylene glycol dimethyl ether is a hydrophilic[10] electron-donor solvent.

CAS NO:111-96-6

EC NO:203-924-4

IUPAC NAMES:
1-methoxy-2-(2-methoxyethoxy) ethane
1-Methoxy-2-(2-methoxyethoxy)ethane
1-methoxy-2-(2-methoxyethoxy)ethane
Bis(2-methoxyethyl) ether
bis(2-methoxyethyl) ether
Bis(2-methoxyethyl) ether
Bis(2-methoxyethyl)ether
Diethylene Glycol Dimethyl Ether
Diethylene glycol dimethyl ether
Diethylene glycol, dimethyl ether
Diglycol dimethyl ether
Diglyme
diglyme
Diglyme

SYNONYMS:

(2-Methoxyethyl) ether; 1,1'-Oxybis(2-methoxyethane); 2,5,8-Trioxanonane; 2-(2-Methoxyethoxy)-1-methoxyethane; Bis(2-methoxyethyl) ether; Bis(2-methoxyethyl)ether; Di(2-Methoxyethyl) ether; Diethyl glycol dimethyl ether; Diethylene glycol dimethyl ether; Diglycol methyl ether; Diglyme; Dimethyl carbitol; Ethane, 1,1'-oxybis(2-methoxy-; Ethanol, 2,2'-oxybis-, dimethyl ether; Ether, bis(2-methoxyethyl); Glyme 2; Methyldiglyme; Poly-Solv; [ChemIDplus] DEGDME;diglyme, bis 2-methoxyethyl ether, 2-methoxyethyl ether, 1-methoxy-2-2-methoxyethoxy ethane, diethylene glycol dimethyl ether, poly-solv, di 2-methoxyethyl ether, dimethyl carbitol, 2,5,8-trioxanonane
DIMETHYLDIGLYCOL;DIMETHYL DIGOL;DIMETHYL CARBITOL;DIETHYLENE GLYCOL DIMETHYL ETHER;DIGLYME;'DIGLYME';DEDM;BIS(2-METHOXYETHYL) ETHER
111-96-6 [RN]
1736101 [Beilstein]
1-Methoxy-2-(2-methoxyethoxy)ethan [German] [ACD/IUPAC Name]
1-Methoxy-2-(2-methoxyethoxy)ethane [ACD/IUPAC Name]
1-Méthoxy-2-(2-méthoxyéthoxy)éthane [French] [ACD/IUPAC Name]
1O2O2O1 [WLN]
203-924-4 [EINECS]
2-Methoxyethyl ether
Bis(2-methoxyethyl) ether
diethylene glycol dimethyl ether
DIETHYLENE GLYCOL DIMETHYLETHER
diglyme [Wiki]
Diglyme (2-Methoxyethyl Ether)
'Diglyme’
Dimethyldiglycol
ethane, 1-methoxy-2-(2-methoxyethoxy)-
Ethane, 2,2'-oxybis[1-methoxy- [ACD/Index Name]
KN333
di(2-methoxyethyl) ether
diethylene glycol dimethyl ether
diglyme
dimethoxydiglycol
dimethyldiglycol
ethane, 1-methoxy-2-(2-methoxyethoxy)-
ethane, 2,2'-oxybis[1-methoxy-
ether, bis(2-methoxyethyl)
1-methoxy-2-(2-methoxyethoxy)ethane
1,1'-oxybis(2-   methoxyethane)
2,2'-oxybis(1-   methoxyethane)
bis(2-methoxyethyl) ether
2-methoxyethylether
2,2'-oxybis[1-(   methyloxy)ethane]
2,5,8-   trioxanonane

Diethylene Glycol Dimethyl Ether

Application

Diethylene glycol dimethyl ether may be used as a solvent in the following processes:
• Synthesis of 3,5-dinitrobenzaldehyde via reduction of 3,5-dinitrobenzoyl chloride using lithium aluminum tri-tert-butoxyhydride.[9]
• Copper-catalyzed cross-coupling of iodoarenes with 4-[2,2,2-trifluoro-1-(trimethylsilyloxy)ethyl]morpholine to form the corresponding trifluoromethyl arenes.[11]
• Conversion of olefins (for eg: (±)-α-pinene) to primary amines (3-pinanamine) via hydroboration-amination reaction.

Diethylene Glycol Dimethyl Ether, or bis(2-methoxyethyl) ether, is a solvent with a high boiling point. It is an organic compound which is the dimethyl ether of diethylene glycol. (The name "diglyme" is a portmanteau of "diglycol methyl ether.") It is a colorless liquid with a slight ether-like odor. It is miscible with water as well as organic solvents.

It is prepared by a reaction of dimethyl ether and ethylene oxide over an acid catalyst.[2]

Because of its resilience to strong bases, Diethylene Glycol Dimethyl Ether
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 diglyme as a solvent.

Diethylene Glycol Dimethyl Ether is also used as a solvent in hydroboration reactions with diborane.

It serves as a chelate for alkali metal cations, leaving anions more active.

Industry Uses
Processing aids, not otherwise listed
Solvents (which become part of product formulation or mixture)
industrial applications

Consumer Uses
Electrical and electronic products
solvent in surface active formulation

Industry Processing Sectors
All other chemical product and preparation manufacturing
Computer and electronic product manufacturing
Solvent for transformer refurbishing
Wholesale and retail trade
Diethylene Glycol Dimethyl Ether can be effectively used as an odor-attractant solvent without reducing the attractiveness of the chemical additive, eg, decanoic acid, trimethylammonium decanoate, and trimethylamine. Odorants dissolved in diglyme can be added to aqueous solutions, such as coyote urine. Also, diglyme has a low freezing point so its use as an odor solvent increases the temperature range in which an odor can be effectively used.

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.

Description
Clear liquid with a pleasant odor;

Sources/Uses
Used as a solvent and chemical intermediate; [Merck Index] Used in the coating industry and in photolithography to make semiconductor chips; Also used in adhesives, sealants, and automotive care products;

Diethylene glycol dimethyl ether is an inert solvent especially well suited for API synthesis.
Benefits
Inert solvent, high solubility for organometallic compounds.

A purified grade of solvent that is certified to meet a particular use. See specifications for details.

Appearance (Clarity)   Clear
Appearance (Colour)   Colourless
Appearance (Form)   Liquid
Assay (GC)   min. 99%
Density (g/ml) @ 20°C   0.942-0.944 g
Refractive Index (20°C)   1.407-1.409
Boiling Range   161-164°C

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
Solvent; reaction medium for Grignard and similar syntheses.

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.

Article service life
Release to the environment of this substance can occur from industrial use: manufacturing of the substance, formulation of mixtures, in processing aids at industrial sites and as processing aid. Other release to the environment of this substance 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). This substance can be found in complex articles, with no release intended: vehicles. This substance can be found in products with material based on: plastic (e.g. food packaging and storage, toys, mobile phones).

Formulation or re-packing
Diethylene Glycol Dimethyl Ether is used in the following products: laboratory chemicals and polymers.
Release to the environment of this substance can occur from industrial use: formulation of mixtures, manufacturing of the substance, 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 this substance 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).

Uses at industrial sites
Diethylene Glycol Dimethyl Ether is used in the following products: laboratory chemicals, pharmaceuticals and polymers.

Diethylene Glycol Dimethyl Ether is used in the following areas: formulation of mixtures and/or re-packaging and scientific research and development.

Diethylene Glycol Dimethyl Ether is used for the manufacture of: chemicals, plastic products and electrical, electronic and optical equipment.

Release to the environment of this substance 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 this substance 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).

Diethylene glycol dimethyl ether (in the following called diglyme) is a colorless liquid with a slight pleasant odor. Due to its dipolar aprotic properties, diglyme is used mainly as a solvent (semiconductor industry chemical synthesis lacquers), as an inert reaction medium in chemical synthesis, and as a separating agent in distillations.

Diethylene Glycol Dimethyl Ether is a neutral, slightly volatile, colorless liquid. Because of the free electron pairs at the oxygen atoms it has high solvating power and is miscible with water and all common solvents in any ratio. As a result of its chemical stability and the absence of reactive groups, Diethylene glycol dimethyl ether can be used as an inert reaction medium for many organic and organometallic reactions and for polymerizations.

Diethylene Glycol Dimethyl Ether, Reagent is more commonly referred to as Diethylene Glycol Dimethyl Ether and is an organic compound that is a clear and colorless liquid with a faint ether-like smell. It is solvent that has a high boiling point and that is miscible with water, alcohol as well as hydrocarbon solvents. Its main use is as a solvent for organic reactions as well as being able to chelate small cations. Its reagent grade means this is the highest quality commercially available for this chemical and that the American Chemical Society has not officially set any specifications for this material.

Diethylene Glycol Dimethyl Ether, or bis(2-methoxyethyl) ether, is a solvent with a high boiling point. It is an organic compound which is the dimethyl ether of diethylene glycol. (The name "diglyme" is a portmanteau of "diglycol methyl ether.") It is a clear, colorless liquid with a slight ether-like odor. It is miscible with water, alcohols, diethyl ether, and hydrocarbon solvents.

A lithium cation being chelated by a Diethylene Glycol Dimethyl Ether molecule; Diethylene Glycol Dimethyl Ether is mainly used as a solvent in organic reactions. It has the ability to chelate small cations, leaving anions more active. Therefore, reactions involving organometallic reagents, such as Grignard reactions or metal hydride reductions, may have significantly enhanced reaction rates.
Diethylene Glycol Dimethyl Ether is also used as a solvent in hydroboration reactions with diborane.Its stability, even at high pH values, makes it an excellent solvent for reactions with strong bases or reactions that require high temperatures.

Diethylene glycol dimethyl ether is a colorless watery liquid with a pleasant odor. Floats and mixes with water. (USCG, 1999);Liquid;COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.

Diethylene glycol dimethyl ether dissolves vinyl chloride copolymers, post chlorinated poly (vinyl chloride), polymethacrylate, polystyrene, polychloroprene, and cellulose acetate. It does not dissolve rubber and polyethylene, and swells poly(vinyl chloride). It also dissolves sodium borohydride, other covalent inorganic metal compounds, and sodium.;Henry's Law constant = 5.23X10-7 atm-cu m/mol at 25 ℃ (est);Hydroxyl radical reaction rate constant = 1.75X10-11 cu cm/molec-sec at 25 ℃

The chemical has reported non-industrial use in the production of pharmaceuticals.
rubber and plastic products; transport equipment; and fabricated metal products, except machinery and equipment. as an auxiliary solvent in water-based paints, which are industrially applied on automobiles, metal furniture, household appliances, and machines;
as an inert reaction medium in chemical synthesis and as a separating agent in distillations including uses in polymerisation reactions (e.g., of isoprene, styrene), manufacturing perfluorinated organic compounds, and reactions in boron chemistry; and in manufacturing integrated circuit boards, primarily as a solvent for the photoresists. These are used as photosensitive materials to coat the wafer during micro lithographic patterning in the photo/apply process and in producing semiconductors.

Diethylene Glycol Dimethyl Ether, also known as 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. The compound is not known to occur in nature. It is synthesized from ethylene oxide and methanol in the presence of either acidic or basic catalysts.

Diethylene glycol dimethyl ether is an organic compound primarily handled in industrial settings.Diethylene glycol dimethyl ether is used as a solvent, for applications in the semiconductor industry, for circuit boards, and various chemical syntheses.
Diethylene glycol dimethyl ether is also used as a separating agent for distillations. Good manufacturing and industrial hygiene practices should be followed to prevent or reduce exposure.

Diethylene glycol dimethyl ether is a clear colorless liquid with a mild ether-like smell.
Diethylene glycol dimethyl ether is flammable, and vapors may form explosive mixtures with air. In the event of a fire, hazardous byproducts may form such as carbon monoxide and carbon dioxide. In the presence of oxidation agents, Diethylene glycol dimethyl ether may also form peroxide.

Used among others to produce unsaturated polyester resins, thermoplastic polyurethanes and plastifiers, as an additive in producing glass and cement, furniture, shoe polishes, printing inks, plaster boards, emulsifiers and anti-freezes, beauty products, lubricants, brake fluids, wallpaper removers and as an agent heating up or cooling down the fuel High concentrations can cause a slight irritation of the air passages.

There are no known natural sources of Diethylene glycol dimethyl ether. Diethylene glycol dimethyl ether is prepared by the catalytic conversion of dimethyl ether and ethylene oxide under pressure. Diethylene glycol dimethyl ether is readily absorbed by the body through both dermal contact and inhalation. Diethylene glycol dimethyl ether is not highly toxic with a single exposure.

Diethylene glycol dimethyl ether is used as a building block in organic synthesis, e.g. morpholine and 1,4-dioxane. Diethylene glycol dimethyl ether is a solvent for nitrocellulose, resins, dyes, oils, and other organic compounds.Diethylene glycol dimethyl ether is a humectant for cigarettes, cork, ink, and glue.Diethylene glycol dimethyl ether is also a component of brake fluid, lubricants, decorative detergents, artificial fog solutions, and hot / cooking fuel.
In personal care products (e.g. lotions and lotions, deodorants), the Diethylene glycol dimethyl ether is often replaced with selected diethylene glycol ethers. Diluents of diethylene glycol can also be used as a cryoprotectant; However, ethylene glycol is more commonly used. Most polyethylene glycol antifreeze contains a few percent diethylene glycol, currently as a byproduct of ethylene glycol production. The solutions for artificial fog and fuel heating / cooking.
Diethylene glycol dimethyl ether is used by Bracco Imaging s.p.a as a processing aid in the purification of 5-amino-2,4,6-triiodoisophthalic acid dichloride, which is an intermediate in the multi-step synthesis of Iopamidol, an x-ray contrast imaging agent. Diethylene glycol dimethyl ether is used as a co-solvent in the solubilisation of the N-sulfinyl derivative of the acid chloride followed byDiethylene glycol dimethyl ether is subsequent hydrolysis and crystallisation to yield 5-amino-2,4,6-triiodoisophthalic acid dichloride.
Diethylene glycol dimethyl ether is subsequently recovered by vacuum distillation and recycled. Contaminated Diethylene glycol dimethyl ether that cannot be recycled (part of the bottom fraction of the distillate, a mixture of water, Diethylene glycol dimethyl ether and NaOH) is treated in an on-site biological wastewater treatment plant.

Diethylene glycol dimethyl ether " forms unstable peroxides on exposure to air, heat, or sunlight or UV light (peroxides may be removed by stirring with a suspension of iron oxide in aqueous alcohol). " reacts violently with oxidisers, metal halides, permanganates, peroxides, ammonium persulfate, bromine dioxide, sulfuric acid, nitric acid, perchloric acid, and other string acids " is incompatible with acyl halides, aliphatic amines, alkalis, boranes, isocyanates.

Glycol ethers may form peroxides under certain conditions; the potential for peroxide formation is enhanced when these substances are used in processes such as distillation where they are concentrated or even evaporated to near-dryness or dryness; storage under a nitrogen atmosphere is recommended to minimise the possible formation of highly reactive peroxides " Nitrogen blanketing is recommended if transported in containers at temperatures within.

Diethylene glycol dimethyl ether C of the flash-point and at or above the flash-point - large containers may first need to be purged and inerted with nitrogen prior to loading " In the presence of strong bases or the salts of strong bases, at elevated temperatures, the potential exists for runaway reactions. " Contact with aluminium should be avoided; release of hydrogen gas may result- glycol ethers will corrode scratched aluminium surfaces.

May discolour in mild steel/ copper; lined containers, glass or stainless steel is preferred " Diethylene glycol dimethyl ether and their ethers undergo violent decomposition in contact with 70% perchloric acid. This seems likely to involve formation of the glycol perchlorate esters (after scission of ethers) which are explosive, those of ethylene glycol and 3-chloro-1,2-propanediol being more powerful than glyceryl nitrate, and the former so sensitive that Diethylene glycol dimethyl ether explodes on addition of water.

Diethylene glycol dimethyl ether is one of the heavier ethylene oxide based glymes available commercially. Butyl Diethylene glycol dimethyl ether is most commonly utilized as a high-performance solvent for both laboratory and industrial applications.Diethylene glycol dimethyl ether effectively solvates digital inks and decorative ceramic inks, since Diethylene glycol dimethyl ether is stable enough to withstand the high temperatures of these applications.

Diethylene glycol dimethyl ether 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. Butyl Diethylene glycol dimethyl ether can also be used as an intermediate in the production of siloxane-based adjuvants.

Bis (2-methoxyethyl) ether, also known as Diethylene glycol dimethyl ether, is a linear aliphatic diether widely used as a solvent and present as a clear liquid at room temperature with a mild ether odor. The compound is not known to occur in nature.Diethylene glycol dimethyl ether is synthesized from ethylene oxide and methanol in the presence of either acidic or basic catalysts. The reaction is based on the classic Williamson ether synthesis.Diethylene glycol dimethyl ether can also be produced from diethylene glycol and dimethyl sulfate.

Diethylene glycol dimethyl ether or glymes have several unique properties that make them attractive solvents for electrochemical energy storage. Diethylene glycol dimethyl ether has the general formula CH3(OCH2CH2)nOCH3, and physical properties such as freezing point, boiling point, and viscosity can be tuned over a wide range by varying the chain length. They are typically chemically and thermally stable with a large electrochemical window.

Solubility   (20 °C) soluble
Melting Point   -64 °C
Molar Mass   134.17 g/mol
Boiling Point   155 - 165 °C (1013 hPa)
Vapor Pressure   2 hPa (20 °C)
Flash Point   70 °C
Refractive Index   1.4097 (20 °C, 589 nm)
Explosion Limit   1.4 - 17.4 %(V)
Density   0.944 g/cm3 (20 °C)
pH   (H2O, 20 °C) neutral
Ignition Point   190 °C
Evaporation number   90
Hazard Class   3
Hazard Class Description   Flammable Liquid