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TRIETHYLENE GLYCOL DIMETHYL ETHER

EC / List no.: 203-977-3
CAS no.: 112-49-2
Mol. formula: C8H18O4

Triethylene glycol dimethyl ether (also called triglyme) is a glycol ether used as a solvent.

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 an intermediate step in further manufacturing of another substance (use of intermediates).

Chemical Properties
Water-white liquid; mild ether odor. D 0.9862 (20/20C), refr index 1.4233 (20C), flash p 232F (111C), bp 216.0C (760mmHg), 153.6C (100 mm Hg), fp ?46C. Completely soluble in water and hydrocarbons at 20C. May contain peroxides.
Combustible.

Uses
Labelled Triglyme.
It is used as a solvent.

Definition
ChEBI: A polyether that consists of dodecane in which the carbon atoms at positions 2, 5, 8 and 11 are replaced by oxygen atoms.

It has a role as a solvent.

Triethylene glycol dimethyl ether (also called triglyme) is a glycol ether used as a solvent.

Triethylene glycol dimethyl ether is a clear colorless liquid with a mild ethereal odor.

Uses
Generic lubricants, lubricants for engines, brake fluids, oils, etc (does not include personal care lubricants)
Relatived to the maintenance and repair of automobiles, products for cleaning and caring for automobiles (auto shampoo, polish/wax, undercarriage treatment, brake grease)

Triethylene glycol dimethyl ether is used as a solvent for gases and coupling immiscible liquid.
It is also used to prepare perfluoro-triethyleneglycoldimethylether.

Triethylene glycol dimethyl ether (also called triglyme) is a glycol ether used as a solvent.

Triethylene glycol dimethyl ether. Acts as a high boiling point solvent.
It is a colorless transparent liquid.
Used for organic synthesis, synthesis of ammonia or natural gases and for dyes and resins.

Ozonation of pure aqueous solutions of the polar aliphatic refractory trimethylene glycol dimethyl ether (TEGDME) which is a typical representative of organic solutes of oil reclaiming wastewaters does not lead to effective mineralization unless high ozone doses are applied.
Small doses of UV irradiation do not markedly increase Triethylene glycol dimethyl ether mineralization by ozonation, but the transformation to more oxidized products (mainly carboxylic acids containing methoxy and/or ethoxy groups) which are biodegradable to a higher degree than Triethylene glycol dimethyl ether.
However, adding high concentrations of hydrogen peroxide during ozonation results in an efficient increase of Triethylene glycol dimethyl ether mineralization.
The presence of humic acids - which is a consequence of the biological treatment of wastewaters containing biodegradable organic constituents - has a beneficial effect on the transformation of Triethylene glycol dimethyl ether during ozonation or ozone/UV treatment because hydrogen peroxide is formed during ozonation of humic acid C-C double bonds

Triethylene glycol dimethyl ether is used as a solvent for gases and coupling immiscible liquid. It is also used to prepare perfluoro-triethylene glycol dimethyl ether.

Liquid; Colorless liquid;
Sources/Uses
Used as a solvent;Used as a solvent for gases and coupling immiscible liquid; Not produced commercially in the EU;

Uses
Labelled Triglyme. It is used as a solvent.

Definition
ChEBI: A polyether that consists of dodecane in which the carbon atoms at positions 2, 5, 8 and 11 are replaced by oxygen atoms.

Reactivity Profile
TRIETHYLENE GLYCOL DIMETHYL ETHER forms explosive peroxides on prolonged exposure to air. Its decomposition products may be sensitive to shock. The bulk chemical is stable for 2 weeks at temperatures up to 140° F when protected from light. TRIETHYLENE GLYCOL DIMETHYL ETHER is incompatible with strong oxidizers. TRIETHYLENE GLYCOL DIMETHYL ETHER is also incompatible with strong acids. TRIETHYLENE GLYCOL DIMETHYL ETHER may react with peroxides, oxygen, nitric acid and sulfuric acid. .

Appearance
Clear liquid

Density
0.986g/mL at 25°C

Ignition Point
375°F

Vapor Density
>4.7 (vs air)

Color
Undesignated
Triethylene glycol dimethyl ether could be a useful component for absorption refrigeration based on better environmental, health, and safety properties.

1, Used as solvent, dye, resin, paint, etc
2, As a high boiling solvent , can used in organic synthesis reaction, in some cases, replace DMF AND DMSO
3, Used for synthetic ammonia or natural gas desulfurization and decarbonization agent, aspartame can be prepared by enzymatic reaction in a mixture of triethylene glycol dimethyl ether and water

Triethylene glycol dimethyl ether (also called triglyme) is a glycol ether used as a solvent.

Title: Triglyme
CAS Registry Number: 112-49-2
CAS Name: 2,5,8,11-Tetraoxadodecane
Additional Names: triethylene glycol dimethyl ether
Molecular Formula: C8H18O4
Molecular Weight: 178.23
Percent Composition: C 53.91%, H 10.18%, O 35.91%
Line Formula: CH3O(CH2)2O(CH2)2O(CH2)2OCH3
Literature References: Prepd by high pressure hydrogenation of 1,1,2,2-tetrakis(2-methoxyethoxy)ethane: McNamee, MacDowell, US 2425042 (1947 to Carbide & Carbon Chem.).
Properties: Liquid. d420 0.990. Flash pt 111°C. mp -45°. bp760 216°; bp10 103.5°; bp0.9 20°. nD20 1.4233. Miscible with water, hydrocarbon solvents.
Melting point: mp -45°
Boiling point: bp760 216°; bp10 103.5°; bp0.9 20°
Flash point: Flash pt 111°C
Index of refraction: nD20 1.4233
Density: d420 0.990
Use: Solvent.

1,2-Bis(2-methoxyethoxy) Ethane, Reagent, also known as Triethylene glycol dimethyl ether or triglyme, is a glycol ether with applications as a solvent.
The Reagent grade denotes that this chemical is the highest quality commercially available and that the American Chemical Society has not officially set any specifications for this material.
Spectrum Chemical manufactured Reagent grade products meet the toughest regulatory standards for quality and purity.

Triethylene Glycol Dimethyl Ether forms explosive peroxide on prolonged exposure to air.
The bulk chemical is stable for 2 weeks at temperatures up to 140 ° F when protected from light.
Triethylene Glycol Dimethyl Ether is incompatible with strong oxidizers.
Triethylene Glycol Dimethyl Ether is also incompatible with strong acids.

The highly oxygenated hydrocarbon Triethylene Glycol Dimethyl Ether or triglyme (CH3O– (C2H4O–) 3CH3) was found to efficiently reduce NOx under lean conditions over Ag / Al2O3, but gave a low NOx conversion over Cu-ZSM-5.
Furthermore, Triethylene Glycol Dimethyl Ether showed an extraordinary promoting effect when added together with propene as a reducing agent for NOx over Ag / Al2O3 at low temperature.
Triethylene Glycol Dimethyl Ether is their many favorable properties and specifically balanced amphiphilic nature, glymes (oligomeric ethylene glycol diethers) are of great technological and theoretical interest.
This study focuses on the phase equilibria and energetics of aqueous solutions of two important members of the glyme series, triglyme ( Triethylene Glycol Dimethyl Ether ) and tetraglyme (tetraethylene glycol dimethyl ether).
For these systems, we carried out accurate measurements of water activity at two temperatures (298.15 and 313.15 or 318.15 K) in the whole composition range, boiling temperatures at three pressures (50, 70, and 90 kPa), and freezing temperatures in the water -rich region.

The melting temperature and melting enthalpy of the neat glymes were also determined.
We correlated our water activity data simultaneously with some related thermal data from the literature using an extended SSF-type excess Gibbs energy (GE) model.
The established model descriptions provided not only particularly good fit of the underlying data but, as proven by due comparisons to other results from both the literature and this work, showed a superior performance, extrapolating very well to both higher and lower temperatures.
The high-fidelity global modeling also enabled us to present a clear picture of the energetics of the two aqueous glymes.
At near-ambient temperatures, both systems exhibit non-monotonous activity coefficient courses with composition, large exothermic effects, and remarkably deep drops of the entropy accompanying the mixing, their positive GE being entropy-driven.
On increasing the temperature, the former features gradually decline while GE keeps about the same magnitude and becomes enthalpy-driven.
Although both systems show a great tendency to phase splitting above the normal boiling temperature of water, our model calculations predicted the lower critical solution temperature behavior only for the aqueous solution of Triethylene Glycol Dimethyl Ether .
The observed pattern of the energetic behavior has been well elucidated in terms of competitive water – water and water – ether H-bonding.
most likely due to that Triethylene Glycol Dimethyl Ether promotes the activation of propene.

Since the molecular weight of Triethylene Glycol Dimethyl Ether (178.23 g / mol) is higher than that of diglyme (134.18 g / mol), the substance is expected to be absorbed by the skin in a smaller amount than diglyme.
Glycol ethers in general are readily distributed throughout the body and eliminated through the urine.

Triethylene Glycol Dimethyl Ether (112-49-2) forms explosive peroxides on prolonged exposure to air.
Triethylene Glycol Dimethyl Ether decomposition products may be sensitive to shock.
The bulk chemical is stable for 2 weeks at temperatures up to 140 ° F when protected from light.
This chemical is incompatible with strong oxidizers.
Triethylene Glycol Dimethyl Ether (112-49-2) is also incompatible with strong acids.
Triethylene Glycol Dimethyl Ether (112-49-2) may react with peroxides, oxygen, nitric acid and sulfuric acid.
Due to the high structural similarity of Triethylene Glycol Dimethyl Ether and diglyme (difference: one ethyl group; but same functional groups) and hence the strong likelihood that both compounds will be metabolized by the same enzymes / metabolic path, a read across from the metabolism data generated with diglyme is used to clarify the toxicokinet ic behavior of triglyme in the registration dossier (dissemination website).
Due to the high structural similarity of Triethylene Glycol Dimethyl Ether and diglyme, a similar skin penetration behavior is expected.
Since the molecular weight of Triethylene Glycol Dimethyl Ether (178.23 g / mol) is higher than that of diglyme (134.18 g / mol), the substance is expected to be absorbed by the skin in a smaller amount than diglyme.

Triethylene Glycol Dimethyl Ether may react with peroxides, oxygen, nitric acid and sulfuric acid.
Glycol ethers are a group of solvents based on alkyl ethers of ethylene glycol or propylene glycol commonly used in paints and cleaners.
These solvents typically have a higher boiling point, together with the favorable solvent properties of lower-molecular weight ethers and alcohols.
The word "Cellosolve'' was registered in 1924 as a United States trademark by Carbide & Carbon Chemicals Corp. (later named Union Carbide Corp.) for "Solvents for Gums, Resins, Cellulose Esters, and the Like".
The first one was ethyl cellosolve (ethylene glycol monoethyl ether), with the name now generic [citation needed] for glycol ethers.
Glycol ethers are either "e-series'' or "p-series" glycol ethers, depending on whether they are made from ethylene oxide or propylene oxide, respectively.
Typically, e-series glycol ethers are found in pharmaceuticals, sunscreens, cosmetics, inks, dyes and water-based paints, while p-series glycol ethers are used in degreasers, cleaners, aerosol paints and adhesives.
Both E-series glycol ethers and P-series glycol ethers can be used as intermediates that undergo further chemical reactions, producing glycol ethers and glycol ether acetates.
P-series glycol ethers are marketed as having lower toxicity than the E-series.
Most glycol ethers are water-soluble, biodegradable and only a few are considered toxic.
One study suggests that occupational exposure to glycol ethers is related to low motile sperm count,a finding disputed by the chemical industry.

Triethylene Glycol Dimethyl Ether is an inert solvent especially well suited for chemical synthesis, particularly for Gr ignard reactions.
Benefits are safe handling, inert solvent, low water solubility .
Stucky et al. 201,317 have also determined structures of complexed alkali metal aryl alkene anion compounds, including (TMED • Li) 2bisfluorenylidene, acenaphthalene (TMED • Li) 2 (cited in Table 14) and the complexes trans-stilbene (Li • L) 2 (L = TMED or PMTD).
The structures of the stilbene complexes, prepared as shown in equation (85), are essentially tip species of amine solvated lithium cations above and below the central carbon – carbon bond of a planar stilbene dianion.
A considerable interaction between the cations and the ethylenic carbon atoms was indicated. This planar configuration of the stilbene dianion contrasts with the conclusions from solution studies.

Triethylene Glycol Dimethyl Ether is often used as a higher boiling alternative to diethyl ether and THF.
Triethylene Glycol Dimethyl Ether acts as a bidentate ligand for some metal cations.
Triethylene Glycol Dimethyl Ether is therefore often used in organometallic chemistry.
Grignard reactions and hydride reductions are typical application.
Triethylene Glycol Dimethyl Ether is also suitable for palladium-catalyzed reactions including Suzuki reactions and Stille couplings.
Triethylene Glycol Dimethyl Ether is also a good solvent for oligo- and polysaccharides.
Triethylene Glycol Dimethyl Ether .
Acts as a high boiling point solvent.

Triethylene Glycol Dimethyl Ether is a colorless transparent liquid.
Used for organic synthesis, synthesis of ammonia or natural gases and for dyes and resins.

Triethylene Glycol Dimethyl Ether complexes with dimethyl sulfide and diethyl ether are so strong that direct hydroboration does not proceed, and the addition of a complexing agent, such as boron trichloride, is necessary for hydroboration.
Dichloroborane-1,4-dioxane complex is readily prepared as a pure, stable 6.3 M liquid by passing diborane into a solution of boron trichloride in 1,4-dioxane or from sodium borohydride and boron trichloride in 1,4-dioxane in the presence of 3% vol Triethylene Glycol Dimethyl Ether.

Triethylene Glycol Dimethyl Ether is the organic compound with the formula CH3OCH3, simplified to C2H6O.
The simplest ether, it is a colorless gas that is a useful precursor to other organic compounds and an aerosol propellant that is currently being demonstrated for use in a variety of fuel applications.
Triethylene Glycol Dimethyl Ether is an isomer of ethanol.

The largest use of Triethylene Glycol Dimethyl Ether is as the feedstock for the production of the methylating agent, dimethyl sulfate, which entails its reaction with sulfur trioxide: CH3OCH3 + SO3 → (CH3) 2SO4 Triethylene Glycol Dimethyl Ether can also be converted into acetic acid using carbonylation technology related to the Monsanto acetic acid process: (CH3) 2O + 2 CO + H2O → 2 CH3CO2H.
Laboratory reagent and solvent; Triethylene Glycol Dimethyl Ether is a low-temperature solvent and extraction agent, applicable to specialized laboratory procedures.
Its usefulness is limited by Triethylene Glycol Dimethyl Ether is low boiling point (−23 ° C (−9 ° F)), but the same property facilitates its removal from reaction mixtures.
Triethylene Glycol Dimethyl Ether is the precursor to the useful alkylating agent, trimethyloxonium tetrafluoroborate.
Niche applications; A mixture of Triethylene Glycol Dimethyl Ether and propane is used in some over-the-counter "freeze spray" products to treat warts, by freezing them.
In this role, Triethylene Glycol Dimethyl Ether has supplanted halocarbon compounds (Freon).
Triethylene Glycol Dimethyl Ether is also a component of certain high temperature "MAP-plus" blowtorch gas blends, supplanting the use of methyl acetylene and propadiene mixtures.
Triethylene Glycol Dimethyl Ether is also used as a propellant in aerosol products.
Such products include hair spray, bug spray and some aerosol glue products.

IUPAC NAMES:
1,2-Bis(2-methoxyethoxy)ethane
1,2-bis(2-methoxyethoxy)ethane
1-methoxy-2-[2-(2-methoxyethoxy)ethoxy]ethane
2,5,8,11-Tetraoxadodecane
2,5,8,11-tetraoxadodecane
TRIETHYLENE GLYCOL DIMETHYL ETHER
Triethylene Glycol Dimethyl Ether
Triglyme

SYNONYMS:
(CH3O(CH2)2OCH2)2
Ansul Ether 161
Triethylene Glycol DiMethyl Ether (stabilized with BHT)
1,2-Bis(2-methoxyethoxy)ethane 2,5,8,11-Tetraoxadodecane Triglyme
TRIETHYLENE GLYCOL DIMETHYL ETHER FOR SY
1,2-Bis(2-Methoxyethoxy) Ethane, Reagent
Triethylene glycol diMethyl et
Triethylene glycol dimethyl ether ReagentPlus(R), 99%
Triethylene glycol dimethyl ether Vetec(TM) reagent grade, 98%
Ttiethylene Glycol Dimethyl Ether
DIMETHYLTRIGLYCOL
2,5,8,11-TETRAOXADODECANE
1,2-BIS(METHOXYETHOXY)ETHANE
1,2-BIS(2-METHOXYETHOXY)ETHANE
TRIETHYLENE GLYCOL DIMETHYL ETHER
TRIGLYME
TRIETHYLENE GLYCOL DIMETHYL ETHER, ABS., OVER MOL. SIEVE
2-(2-Methoxyethoxy)ethyl 2-methoxyethyl ether
Triethylene glycol dimethyl ether, stabilized, 99%
dimethyltrigol
acetic acid 3-acetyloxybutyl ester
ansulether161
Dimethyl ether of triethylene glycol
Ethane, 1,2-bis(2-methoxyethoxy)-
ethane,1,2-bis(2-methoxyethoxy)-
Glyme-3
glyme4
methyltriglyme
triglyme (triethylene glycol dimethyl ether)
Triethylene glycol dimethyl ether, stabilized, extra pure, 99%
Tetraoxa dodecane
Triethylene glycol diMethyl ether, 99%, extra pure, stabilized
Triethylene glycol diMethyl ether, stabilized, 99% 1LT
Triethylene glycol diMethyl ether, stabilized, 99% 250ML
Triethylene Glycol DiMethyl Ether(1,2-Di(2-Methoxy ethoxy)ethane)
1,2-Bis(2-methoxyethoxy)ethan
Triethylene glycol dimethyl ether, 99%, stabilized
1,1'-(Ethylenebisoxy)bis(2-methoxyethane)
1,8-Dimethoxy-3,6-dioxaoctane
1,2-bis(2-methoxyethoxy)ethane TEGDME triethylene glycol dimethyl ether triglyme
1,2-Bis(2-methoxyethoxy)ethane, Dimethyltriglycol, Triglyme
1-Methoxy-2-[2-(2-methoxy-ethoxy)-ethoxy]-ethane
Triethylene glycol d
Triethylene Glycol Dimethyl Ether (stabilized with BHT)>
Triethylene glycol dimethyl ether,>99%
riglyme