Bis(2-methoxyethyl)ether

Bezeichnung:Bis(2-methoxyethyl)ether

CAS-Nr111-96-6

Englisch Name:Diglyme

CBNumberCB4302276

SummenformelC6H14O3

Molgewicht134.17

MOL-Datei111-96-6.mol

Synonyma

Bis(2-methoxyethyl)ether

Diglyme

1,1'-Oxybis(2-methoxyethan)

Bis(2-methoxyethyl)ether physikalisch-chemischer Eigenschaften

Schmelzpunkt	-64 °C (lit.)
Siedepunkt	162 °C (lit.)
Dichte	0.944 g/mL at 20 °C (lit.) 0.939 g/mL at 25 °C (lit.)
Dampfdichte	4.6 (vs air)
Dampfdruck	3 mm Hg ( 20 °C)
Brechungsindex	n20/D 1.408(lit.)
Flammpunkt	134.6 °F
storage temp.	Store below +30°C.
Löslichkeit	Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
Aggregatzustand	Liquid
Farbe	≤10(APHA)
Geruch (Odor)	Mild ethereal.
Relative polarity	0.244
Explosionsgrenze	1.4-17.4%(V)
Wasserlöslichkeit	Miscible
Sensitive	Hygroscopic
maximale Wellenlänge (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
Stabilität	Stable. Combustible. Incompatible with strong oxidizing agents. May be air or light sensitive.
InChIKey	SBZXBUIDTXKZTM-UHFFFAOYSA-N
LogP	-0.36 at 25℃
CAS Datenbank	111-96-6(CAS DataBase Reference)
NIST chemische Informationen	Ethane, 1,1'-oxybis[2-methoxy-(111-96-6)
EPA chemische Informationen	Diethylene glycol dimethyl ether (111-96-6)

Sicherheit

Kennzeichnung gefährlicher	T
R-Sätze:	60-61-10-19
S-Sätze:	53-45
RIDADR	UN 3271 3/PG 3
WGK Germany	1
RTECS-Nr.	KN3339000
F	3-10-23
Selbstentzündungstemperatur	370 °F
TSCA	Yes
HazardClass	3
PackingGroup	III
HS Code	29091990
Giftige Stoffe Daten	111-96-6(Hazardous Substances Data)
Toxizität	LD50 orally in Rabbit: 4760 mg/kg

Gefahreninformationscode (GHS)

Diglyme Chemische Eigenschaften,Einsatz,Produktion Methoden

ERSCHEINUNGSBILD
FARBLOSE FLüSSIGKEIT MIT CHARAKTERISTISCHEM GERUCH.
CHEMISCHE GEFAHREN
Bildung explosionsfähiger Peroxide wahrscheinlich. Reagiert sehr heftig mit starken Oxidationsmitteln.
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt (ACGIH 2005).
MAK: 5 ppm, 28 mg/m? Hautresorption; Spitzenbegrenzung: überschreitungsfaktor II(8); Schwangerschaft: Gruppe B; (DFG 2005).
AUFNAHMEWEGE
Aufnahme in den Körper durch Inhalation der Dämpfe, durch Verschlucken und über die Haut.
INHALATIONSGEFAHREN
Beim Verdampfen bei 20°C kann schnell eine gesundheitsschädliche Kontamination der Luft eintreten.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION:
Die Substanz reizt leicht die Augen, die Haut und die Atemwege.
WIRKUNGEN NACH WIEDERHOLTER ODER LANGZEITEXPOSITION
Tierversuche zeigen, dass die Substanz möglicherweise fruchtbarkeitsschädigend oder entwicklungsschädigend wirken kann.
LECKAGE
Zündquellen entfernen. Belüftung. Ausgelaufene Flüssigkeit in abdichtbaren Behältern sammeln. Reste mit Sand oder inertem Absorptionsmittel aufnehmen und an einen sicheren Ort bringen. Persönliche Schutzausrüstung: Atemschutzfilter für organische Gase und Dämpfe.
R-Sätze Betriebsanweisung:
R60:Kann die Fortpflanzungsfähigkeit beeinträchtigen.
R61:Kann das Kind im Mutterleib schädigen.
R10:Entzündlich.
R19:Kann explosionsfähige Peroxide bilden.
S-Sätze Betriebsanweisung:
S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Aussehen Eigenschaften
C6H14O3; Diglyme, Bis(2-methoxyethyl)-ether, Dimethyldiglycol. Farblose Flüssigkeit mit schwachem Eigengeruch.
Gefahren für Mensch und Umwelt
Kann die Fortpflanzungsfähigkeit beeinträchtigen. Kann das Kind im Mutterleib schädigen.
Reizt die Atmungsorgane und die Haut.
Entzündlich. Kann explosionsfähige Peroxide bilden. Im dampf-/gasförmigen Zustand explosionsfähig.
LD₅₀ (oral, Ratte) > 4000 mg/kg.
Schutzmaßnahmen und Verhaltensregeln
Unter Lichtschutz lagern.
Schutzhandschuhe als kurzzeitiger Spritzschutz.
Verhalten im Gefahrfall
Dämpfe nicht einatmen.
Mit flüssigkeitsbindendem Material z.B. Rench Rapid aufnehmen. Der Entsorgung zuführen. Nachreinigen.
Kohlendioxid, Wasser, Schaum, Pulver.
Brennbar. Dämpfe schwerer als Luft. Mit Luft Bildung explosionsfähiger Gemische möglich.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: Mit reichlich Wasser bei geöffnetem Lidspalt mindestens 10 Minuten ausspülen. Augenarzt hinzuziehen.
Nach Einatmen: Frischluft.
Nach Verschlucken: Reichlich Wasser trinken lassen. Erbrechen auslösen. Arzt hinzuziehen.
Nach Kleidungskontakt: Kontaminierte Kleidung entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Als halogenfreie, organische Lösemittelabfälle.
Beschreibung
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.
Chemische Eigenschaften
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.
Verwenden
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.
Verwenden
Solvent; it is used as reaction medium for Grignard and similar synthesis.
Verwenden
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.
Definition
ChEBI: A polyether that is the dimethyl ether derivative of diethylene glycol.
Allgemeine Beschreibung
Colorless watery liquid with a pleasant odor. Floats and mixes with water.
Air & Water Reaktionen
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.
Reaktivität anzeigen
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.
Brandgefahr
2-Methoxyethyl ether is combustible.
Flammability and Explosibility
Flammable
Chemische Reaktivität
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.
Synthese
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.
läuterung methode
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.
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte

Bis(2-methoxyethyl)ether Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

111-96-6, Diglyme Verwandte Suche:

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