ChemicalBook > CAS DataBase List > Diglyme

Diglyme

Product Name
Diglyme
CAS No.
111-96-6
Chemical Name
Diglyme
Synonyms
DIGLYME;2-METHOXYETHYL ETHER;DEDM;BIS(2-METHOXYETHYL) ETHER;1-Methoxy-2-(2-methoxyethoxy)ethane;DIMETHYLDIGLYCOL;iglyme;Di(2-Methoxyethyl) ether;glyme2;Glyme-2
CBNumber
CB4302276
Molecular Formula
C6H14O3
Formula Weight
134.17
MOL File
111-96-6.mol
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Diglyme Property

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 
n20/D 1.408(lit.)
Flash point:
134.6 °F
storage temp. 
Store below +30°C.
solubility 
Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
form 
Liquid
color 
≤10(APHA)
Relative polarity
0.244
Odor
Mild ethereal.
PH
7 (20°C)
explosive limit
1.4-17.4%(V)
Water Solubility 
Miscible
Sensitive 
Hygroscopic
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
Merck 
14,3165
BRN 
1736101
Dielectric constant
7.2999999999999998
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents. May be air or light sensitive.
InChIKey
SBZXBUIDTXKZTM-UHFFFAOYSA-N
LogP
-0.36 at 25℃
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)
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Safety

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 
Yes
HazardClass 
3
PackingGroup 
III
HS Code 
29091990
Hazardous Substances Data
111-96-6(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 4760 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H226Flammable liquid and vapour

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.02934
Product name
Diethylene glycol dimethyl ether
Purity
(stabilised) for synthesis
Packaging
250ML
Price
$47.8
Updated
2024/03/01
Sigma-Aldrich
Product number
8.02934
Product name
Diethylene glycol dimethyl ether
Purity
(stabilised) for synthesis
Packaging
1L
Price
$160
Updated
2024/03/01
Sigma-Aldrich
Product number
8.02934
Product name
Diethylene glycol dimethyl ether
Purity
(stabilised) for synthesis
Packaging
2.5L
Price
$352
Updated
2024/03/01
Sigma-Aldrich
Product number
M14102
Product name
Diethylene glycol dimethyl ether
Purity
ReagentPlus?, 99%
Packaging
20L
Price
$1290
Updated
2023/06/20
Sigma-Aldrich
Product number
04143
Product name
Diethylene glycol dimethyl ether
Purity
analytical standard
Packaging
1mL
Price
$28.5
Updated
2022/05/15
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Diglyme Chemical Properties,Usage,Production

Description

Bis (2-methoxyethyl) 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 notknown to occur in nature. It 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. It can also be produced from diethylene glycol and dimethyl sulfate. In June 2012, ECHA proposed addition of diglyme 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

Bis (2-methoxyethyl) ether, due to being chemically inert and possessing excellent solvent properties, is mainly used as a solvent and an anhydrous reaction medium for organometallic synthesis. 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.

Uses

Solvent; it is used as reaction medium for Grignard and similar synthesis.

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 from 2-methroxyethanol by the reaction of alcohol dehydrogenase, may be important for the toxic effects. It can undergo activation to methoxyacetyl coenzyme A and enter the Krebs cycle or fatty acid biosynthesis. Several metabolites of 2-methoxyethanol, such as 2-methoxy-N-acetyl glycine, have been identified that support this pathway. Thus, 2-methoxyacetic acid may interfere with essential metabolic pathways of the cell, and it was hypothesized that this causes the testicular lesions and malformations in 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 as a vapor, when released to air, at a vapor pressure of 2.96 mmHg at 25°C. The vapor phase is easily degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals. The half-life for the reaction is estimated to be 22 h. Bis (2-methoxyethyl) ether does not contain chromophores that will absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight.
Bis (2-methoxyethyl) ether has very high mobility in soil based on the estimated Koc of 15, when released to soil. It may volatilize from dry soil surfaces based upon its vapor pressure. Aquatic fate: Bis (2-methoxyethyl) ether does not absorb to suspended solids and sediments when released into water. Hydrolysis is not an important environmental matter because bis (2-methoxyethyl) ether does not contain a functional group that can hydrolyze under environmental conditions.

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

Diethylene glycol monomethyl ether Diethanol Sodium hydroxide Dimethyl sulfate

Preparation Products

5-AMINOMETHYL-PYRROLIDIN-2-ONE 2-BROMO-6-(1H-PYRAZOL-1-YL)PYRIDINE 1-(2-Methoxyphenyl)piperazine hydrobromide (2,5-DIMETHYL-1,3-OXAZOL-4-YL)METHANOL 6,6'-Dimethyl-2,2'-dipyridyl 5,5'-DIMETHYL-2,2'-DIPYRIDYL 2-METHYLCYCLOPROPANECARBOXYLIC ACID 2,5-DIMETHYL-1,3-OXAZOLE-4-CARBALDEHYDE 3-CYCLOPENTENE-1-OL Cyclohexene oxide 1-(1-NAPHTHYL)PIPERAZINE HYDROCHLORIDE
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View Lastest Price from Diglyme manufacturers

Hebei Mujin Biotechnology Co.,Ltd
Product
Diethylene Glycol Dimethyl Ether 111-96-6
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-07-25
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Diglyme 111-96-6
Price
US $990.00-800.00/ton
Min. Order
1ton
Purity
99%
Supply Ability
5000
Release date
2024-08-19
Hebei Weibang Biotechnology Co., Ltd
Product
Diethylene Glycol Dimethyl Ether 111-96-6
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-10-29

111-96-6, DiglymeRelated Search:

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